Query Query
Results
Date
126 substances in Reaxys
2016-06-21 14h:35m:59s (EST)
2 substances in Reaxys
2016-06-21 14h:38m:07s (EST)
NH 2
1. Query NH
Search as: As drawn, No mixtures, No charges, No radicals 2. Query
(1. Query) AND itemno in (2,1)
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Reaxys ID 125513 View in Reaxys
1/2 CAS Registry Number: 61-54-1 Chemical Name: tryptamine; 1H-indole-3-ethanamine; Tryptamine Linear Structure Formula: NC8H6CH2CH2NH2 Molecular Formula: C10H12N2 Molecular Weight: 160.219 Type of Substance: heterocyclic InChI Key: APJYDQYYACXCRM-UHFFFAOYSA-N Note:
NH
NH 2
Substance Label (167) Label References 9
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7
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13
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1
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6
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s6
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8
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4a
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Steven C.; Hayter, Barry R.; Hussain, Syeed; Karoutchi, Galith; Lamont, Scott G.; MacFaul, Philip; Moss, Thomas A.; Pearson, Stuart E.; Tonge, Michael; Walker, Graeme E.; Weir, Hazel M.; Wilson, Zena; Journal of Medicinal Chemistry; vol. 58; nb. 20; (2015); p. 8128 - 8140, View in Reaxys 15
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2j
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Kalaitzakis, Dimitris; Montagnon, Tamsyn; Antonatou, Eirini; Bardaji, Nuria; Vassilikogiannakis, Georgios; Chemistry - A European Journal; vol. 19; nb. 31; (2013); p. 10119 - 10123, View in Reaxys
21a
Mori, Mattia; Tintori, Cristina; Christopher, Robert Selwyne Arul; Radi, Marco; Schenone, Silvia; Musumeci, Francesca; Brullo, Chiara; Sanita, Patrizia; DelleMonache, Simona; Angelucci, Adriano; Kissova, Miroslava; Crespan, Emmanuele; Maga, Giovanni; Botta, Maurizio; ChemMedChem; vol. 8; nb. 3; (2013); p. 484 - 496, View in Reaxys
52
Patent; Rigel Pharmaceuticals, Inc.; Goff, Dane; Payan, Donald G.; Braselmann, Sylvia; US2013/237524; (2013); (A1) English, View in Reaxys
Sl-1
Vallakati, Ravikrishna; Smuts, Jonathan P.; Armstrong, Daniel W.; May, Jeremy A.; Tetrahedron Letters; vol. 54; nb. 44; (2013); p. 5892 - 5894, View in Reaxys
44
Dethe, Dattatraya H.; Erande, Rohan D.; Ranjan, Alok; Journal of Organic Chemistry; vol. 78; nb. 20; (2013); p. 10106 - 10120, View in Reaxys
4
Gnecco, Dino; Juarez, Jorge; Galindo, Alberto; Marazano, Christian; Enriquez, Raul G.; Synthetic Communications; vol. 29; nb. 2; (1999); p. 281 - 287, View in Reaxys; McKay, Matthew J.; Carroll, Anthony R.; Quinn, Ronald J.; Hooper, John N. A.; Journal of Natural Products; vol. 65; nb. 4; (2002); p. 595 - 597, View in Reaxys; Pouilhes, Annie; Langlois, Yves; Chiaroni, Angele; Synlett; nb. 10; (2003); p. 1488 1490, View in Reaxys; Fisyuk; Mukanov; Chemistry of Heterocyclic Compounds; vol. 39; nb. 2; (2003); p. 277 - 279, View in Reaxys; Liu, Yanqin; Luo, Shengjun; Fu, Xingnian; Fang, Fang; Zhuang, Zeyang; Xiong, Wanting; Jia, Xueshun; Zhai, Hongbin; Organic Letters; vol. 8; nb. 1; (2006); p. 115 - 118, View in Reaxys; Tulyaganov; Chemistry of Natural Compounds; vol. 42; nb. 4; (2006); p. 459 - 461, View in Reaxys; Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys; Marzorati, Mattia; Hult, Karl; Riva, Sergio; Danieli, Bruno; Advanced Synthesis and Catalysis; vol. 349; nb. 11-12; (2007); p. 1963 - 1968, View in Reaxys; Bremner, John B.; Sengpracha, Waya; Skelton, Brian W.; Synthetic Communications; vol. 38; nb. 12; (2008); p. 1931 -
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1939, View in Reaxys; Patent; THE UNIVERSITY OF BRITISH COLUMBIA; WO2008/52352; (2008); (A1) English, View in Reaxys; Carr, Gavin; Chung, Marco K. W.; Mauk, A. Grant; Andersen, Raymond J.; Journal of Medicinal Chemistry; vol. 51; nb. 9; (2008); p. 2634 - 2637, View in Reaxys; Patent; XUE, LIANG; Chan, William K.; Linnet, Stan W.; Linnet, Timothy N.; US2012/322816; (2012); (A1) English, View in Reaxys H-1
Patent; Gruenenthal GmbH; US2010/48554; (2010); (A1) English, View in Reaxys; Patent; Gruenenthal GmbH; US2012/29006; (2012); (A1) English, View in Reaxys
2a'
Concepcion Lozada; Soria-Arteche, Olivia; Teresa Ramirez Apan, Ma.; Nieto-Camacho, Antonio; Enriquez, Raul G.; Izquierdo, Teresa; Jimenez-Corona, Arturo; Bioorganic and Medicinal Chemistry; vol. 20; nb. 17; (2012); p. 5077 - 5084, View in Reaxys
4b
Yang, Yi; Jiang, Xueliang; Qing, Feng-Ling; Journal of Organic Chemistry; vol. 77; nb. 17; (2012); p. 7538 - 7547, View in Reaxys
2g
Kavala, Veerababurao; Janreddy, Donala; Raihan, Mustafa J.; Kuo, Chun-Wei; Ramesh, Chintakunta; Yao, Ching-Fa; Advanced Synthesis and Catalysis; vol. 354; nb. 11-12; (2012); p. 2229 - 2240, View in Reaxys
1k
Arifuddin, M.; Lakshmikant, N.; Rajasekar, N.; Shinde, D. B.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 51; nb. 8; (2012); p. 1168 - 1172,5, View in Reaxys
6{3}
Khoury, Kareem; Sinha, Mantosh K.; Nagashima, Tadamichi; Doemling, Alexander; Herdtweck, Eberhardt; Angewandte Chemie, International Edition; vol. 51; nb. 41; (2012); p. 10280 - 10283,4; Angewandte Chemie; vol. 124; nb. 41; (2012); p. 10426 - 10429, View in Reaxys; Khoury, Kareem; Sinha, Mantosh K.; Nagashima, Tadamichi; Herdtweck, Eberhardt; Doemling, Alexander; Angewandte Chemie - International Edition; vol. 51; nb. 41; (2012); p. 10280 - 10283; Angewandte Chemie; vol. 124; nb. 41; (2012); p. 10426 - 10429, View in Reaxys
Ind-1
Patent; GRUNENTHAL GmbH; US2010/9986; (2010); (A1) English, View in Reaxys
27
Patent; Universita Degli Studi Di Siena; US2009/238761; (2009); (A1) English, View in Reaxys
25; Compound 25 Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys; Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys TRY
Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys
42
Ling, Ke-Qing; Li, Wen-Shan; Sayre, Lawrence M.; Journal of the American Chemical Society; vol. 130; nb. 3; (2008); p. 933 - 944, View in Reaxys
Table1,entry5,product
Bailey, Patrick D.; Beard, Mark A.; Dang, Hoa P.T.; Phillips, Theresa R.; Price, Richard A.; Whittaker, James H.; Tetrahedron Letters; vol. 49; nb. 13; (2008); p. 2150 - 2153, View in Reaxys
25a
Simila, Suvi T.M.; Martin, Stephen F.; Tetrahedron Letters; vol. 49; nb. 29-30; (2008); p. 4501 - 4504, View in Reaxys
2(5)
Werner; Turner; Chambers; Brummond; Tetrahedron; vol. 64; nb. 29; (2008); p. 6997 - 7007, View in Reaxys
2A
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 3865, View in Reaxys
amine
Alonso, Fernando; Acebedo, Sofia L.; Bruttomesso, Andrea C.; Ramirez, Javier A.; Steroids; vol. 73; nb. 12; (2008); p. 1270 - 1276, View in Reaxys
amine, d,m
Das, Biswanath; Kanth, Boddu Shashi; Majhi, Anjoy; Reddy, Kongara Ravinder; Heteroatom Chemistry; vol. 19; nb. 6; (2008); p. 630 - 633, View in Reaxys
22
Choy, Jason; Jaime-Figueroa, Saul; Jiang, Laurence; Wagner, Paul; Synthetic Communications; vol. 38; nb. 21; (2008); p. 3840 - 3853, View in Reaxys
amine/11
Chinni Mahesh; Narasimhulu; Srikanth Reddy; Suryakiran; Venkateswarlu; Tetrahedron Letters; vol. 48; nb. 1; (2007); p. 55 - 59, View in Reaxys
39
Rose, Mickea D.; Cassidy, Michael P.; Rashatasakhon, Paitoon; Padwa, Albert; Journal of Organic Chemistry; vol. 72; nb. 2; (2007); p. 538 - 549, View in Reaxys
3e
Sarang, Prajakta S.; Yadav, Arun A.; Patil, Prashant S.; Krishna, Urlam Murali; Trivedi, Girish K.; Salunkhe, Manikrao M.; Synthesis; nb. 7; (2007); p. 1091 - 1095, View in Reaxys
4j
Androsov, Dmitry A.; Neckers, Douglas C.; Journal of Organic Chemistry; vol. 72; nb. 14; (2007); p. 5368 5373, View in Reaxys
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TRA
Carney, Joel R.; Zwier, Timothy S.; Chemical Physics Letters; vol. 341; nb. 1-2; (2001); p. 77 - 85, View in Reaxys; Carney; Dian; Florio; Zwier; Journal of the American Chemical Society; vol. 123; nb. 23; (2001); p. 5596 - 5597, View in Reaxys; Caminati, Walther; Physical Chemistry Chemical Physics; vol. 6; nb. 10; (2004); p. 2806 - 2809, View in Reaxys; Clarkson, Jasper R.; Dian, Brian C.; Moriggi, Loick; Defusco, Albert; McCarthy, Valerie; Jordan, Kenneth D.; Zwier, Timothy S.; Journal of Chemical Physics; vol. 122; nb. 21; (2005); Art.No: 214311, View in Reaxys; LeGreve, Tracy A.; Baquero, Esteban E.; Zwier, Timothy S.; Journal of the American Chemical Society; vol. 129; nb. 13; (2007); p. 4028 - 4038, View in Reaxys; Nguyen, Tri V.; Pratt, David W.; Journal of Chemical Physics; vol. 124; nb. 5; (2006); Art.No: 054317, View in Reaxys
educt to 3j
Willand, Nicolas; Folleas, Benoit; Boutillon, Christophe; Verbraeken, Liesbeth; Gesquiere, JeanClaude; Tartar, Andre; Deprez, Benoit; Tetrahedron Letters; vol. 48; nb. 29; (2007); p. 5007 - 5011, View in Reaxys
NH2CH2CH2Ind
Kamoune, Laila; De Borggraeve, Wim M.; Gielens, Constant; Voet, Arnout; Robeyns, Koen; De Maeyer, Marc; Van Meervelt, Luc; Compernolle, Frans; Hoornaert, Georges; European Journal of Organic Chemistry; nb. 18; (2007); p. 2977 - 2986, View in Reaxys
6g
Shinkre, Bidhan A.; Raisch, Kevin P.; Fan, Liming; Velu, Sadanandan E.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 10; (2007); p. 2890 - 2893, View in Reaxys
educt to 2f
Pereira, Maria de Fatima; Thiery, Valerie; Besson, Thierry; Tetrahedron Letters; vol. 48; nb. 43; (2007); p. 7657 - 7659, View in Reaxys
IIa
Shestakov; Sidorenko; Shikhaliev; Pavlenko; Russian Journal of General Chemistry; vol. 77; nb. 10; (2007); p. 1749 - 1760, View in Reaxys
Table 4, entry 9, amine
Hollmann, Dirk; Baehn, Sebastian; Tillack, Annegret; Beller, Matthias; Angewandte Chemie - International Edition; vol. 46; nb. 43; (2007); p. 8291 - 8294, View in Reaxys
I-4a
Ates-Alagoz, Zeynep; Coban, Tulay; Buyukbingol, Erdem; Archiv der Pharmazie; vol. 339; nb. 4; (2006); p. 193 - 200, View in Reaxys
29d
Zhu, Guangyu; Yang, Fanglong; Balachandran, Raghavan; Hoeoek, Peter; Vallee, Richard B.; Curran, Dennis P.; Day, Billy W.; Journal of Medicinal Chemistry; vol. 49; nb. 6; (2006); p. 2063 - 2076, View in Reaxys
24, R4=3-indolyl(CH2)2
Doncaster, Jeremy R.; Etchells, Laura L.; Kershaw, Neil M.; Nakamura, Ryoichi; Ryan, Hazel; Takeuchi, Ryo; Sakaguchi, Kengo; Sardarian, Ali; Whitehead, Roger C.; Bioorganic and Medicinal Chemistry Letters; vol. 16; nb. 11; (2006); p. 2877 - 2881, View in Reaxys
VIIa
Fisyuk; Mukanov; Russian Journal of Organic Chemistry; vol. 42; nb. 9; (2006); p. 1269 - 1274, View in Reaxys
Am5
Chung, Yun Mi; Raman, Balamurali; Ahn, Kyo Han; Tetrahedron; vol. 62; nb. 50; (2006); p. 11645 - 11651, View in Reaxys
R2-C
Habashita, Hiromu; Kokubo, Masaya; Hamano, Shin-Ichi; Hamanaka, Nobuyuki; Toda, Masaaki; Shibayama, Shiro; Tada, Hideaki; Sagawa, Kenji; Fukushima, Daikichi; Maeda, Kenji; Mitsuya, Hiroaki; Journal of Medicinal Chemistry; vol. 49; nb. 14; (2006); p. 4140 - 4152, View in Reaxys; Habashita, Hiromu; Kokubo, Masaya; Hamano, Shin-ichi; Hamanaka, Nobuyuki; Toda, Masaaki; Shibayama, Shiro; Tada, Hideaki; Sagawa, Kenji; Fukushima, Daikichi; Maeda, Kenji; Mitsuya, Hiroaki; J. Med. Chem.; vol. 49; nb. 14; (2006); p. 4145 - 4152, View in Reaxys
1o
Das, Biswanath; Venkateswarlu, Katta; Krishnaiah, Maddeboina; Holla, Harish; Tetrahedron Letters; vol. 47; nb. 43; (2006); p. 7551 - 7556, View in Reaxys
6j
Haak, Edgar; Synlett; nb. 12; (2006); p. 1847 - 1848, View in Reaxys
a
McCoy, Elizabeth; O'Connor, Sarah E.; Journal of the American Chemical Society; vol. 128; nb. 44; (2006); p. 14276 - 14277, View in Reaxys
tam
Wigley, Lucy J.; Mantle, Peter G.; Perry, David A.; Phytochemistry; vol. 67; nb. 6; (2006); p. 561 - 569, View in Reaxys
I
Burkoth, Timothy S.; Fafarman, Aaron T.; Charych, Deborah H.; Connolly, Michael D.; Zuckermann, Ronald N.; Journal of the American Chemical Society; vol. 125; nb. 29; (2003); p. 8841 - 8845, View in Reaxys; Shen, Ya-Ching; Chen, Ching-Yeu; Hsieh, Pei-Wen; Duh, Chang-Yih; Lin, Yat-Min; Ko, Chin-Lien; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 1; (2005); p. 32 - 36, View in Reaxys
6d
Pradhan, Prasun K.; Dey, Sumit; Jaisankar, Parasuraman; Giri, Venkatachalam S.; Synthetic Communications; vol. 35; nb. 7; (2005); p. 913 - 922, View in Reaxys
III-4a
Gurkan, A. Selen; Karabay, Arzu; Buyukbingol, Zeliha; Adejare, Adeboye; Buyukbingol, Erdem; Archiv der Pharmazie; vol. 338; nb. 2-3; (2005); p. 67 - 73, View in Reaxys
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amine f
Kuhnert, Nikolai; Le-Gresley, Adam; Tetrahedron Letters; vol. 46; nb. 12; (2005); p. 2059 - 2062, View in Reaxys
3d
Rosamilia, Anthony E.; Scott, Janet L.; Strauss, Christopher R.; Organic Letters; vol. 7; nb. 8; (2005); p. 1525 - 1528, View in Reaxys
61
Feldman, Ken S.; Vidulova, Daniela Boneva; Karatjas, Andrew G.; Journal of Organic Chemistry; vol. 70; nb. 16; (2005); p. 6429 - 6440, View in Reaxys
amine, T.1, e.4
Yan, Ri-Bai; Yang, Fan; Wu, Yanfen; Zhang, Li-He; Ye, Xin-Shan; Tetrahedron Letters; vol. 46; nb. 52; (2005); p. 8993 - 8995, View in Reaxys
substrate to 6
Ho, Tse-Lok; Chen, Chun-Kuei; Helvetica Chimica Acta; vol. 88; nb. 10; (2005); p. 2764 - 2770, View in Reaxys
8<12>
Wipf, Peter; Werner, Stefan; Woo, Grace H.C.; Stephenson, Corey R.J.; Walczak, Maciej A.A.; Coleman, Claire M.; Twining, Leslie A.; Tetrahedron; vol. 61; nb. 48; (2005); p. 11488 - 11500, View in Reaxys
educt to 7-11
Li, Donghong; Zhang, Yongbin; Guo, Wei; Xia, Chizhong; Heterocycles; vol. 65; nb. 5; (2005); p. 1063 1069, View in Reaxys
8c
Karpov, Alexei S.; Rominger, Frank; Mueller, Thomas J. J.; Organic and Biomolecular Chemistry; vol. 3; nb. 24; (2005); p. 4382 - 4391, View in Reaxys
25
Feldman, Ken S.; Vidulova, Daniela Boneva; Organic Letters; vol. 6; nb. 11; (2004); p. 1869 - 1871, View in Reaxys; Patent; SEQUELLA, INC.; WO2005/34857; (2005); (A2) English, View in Reaxys
start to 5,6
Voskressensky, Leonid G.; Borisova, Tatiana N.; Kulikova, Larisa N.; Varlamov, Alexej V.; Catto, Marco; Altomare, Cosimo; Carotti, Angelo; European Journal of Organic Chemistry; nb. 14; (2004); p. 3128 3135, View in Reaxys
2s
Mortoni, Annalisa; Martinelli, Marisa; Piarulli, Umberto; Regalia, Nickolas; Gagliardi, Stefania; Tetrahedron Letters; vol. 45; nb. 35; (2004); p. 6623 - 6627, View in Reaxys
7c
Sawa, Masaaki; Tateishi, Hirotaka; Mizuno, Kazuhiro; Harada, Hiroshi; Oue, Mayumi; Tsujiuchi, Hiroshi; Furutani, Yasuji; Kato, Shiro; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 24; (2004); p. 5963 - 5966, View in Reaxys
Tab. 1, entry 1, amine
Andrade, Carlos Kleber Z.; Takada, Sayuri Cristina S.; Magalhaes Alves, Luana; Petrocchi Rodrigues, Juliana; Suarez, Paulo Anselmo Z.; Brandao, Rodrigo Fleury; Soares, Valerio Cassiano D.; Synlett; nb. 12; (2004); p. 2135 - 2138, View in Reaxys
IIId
Mironov; Tokareva; Ivantsova; Mokrushin; Russian Journal of Organic Chemistry; vol. 40; nb. 6; (2004); p. 847 - 853, View in Reaxys
amine 5
Bashford, Katherine E.; Burton, Matthew B.; Cameron, Stuart; Cooper, Anthony L.; Hogg, Rebecca D.; Kane, Peter D.; MacManus, David A.; Matrunola, Christopher A.; Moody, Christopher J.; Robertson, Avril A. B.; Warne, Mark R.; Tetrahedron Letters; vol. 44; nb. 8; (2003); p. 1627 - 1629, View in Reaxys
sch1, amine/d
Zhu, Xiaoxiang; Yu, Qian-sheng; Greig, Nigel H.; Flippen-Anderson, Judith L.; Brossi, Arnold; Heterocycles; vol. 59; nb. 1; (2003); p. 115 - 128, View in Reaxys
6(n-5)
Giacomelli, Giampaolo; Porcheddu, Andrea; Salaris, Margherita; Taddei, Maurizio; European Journal of Organic Chemistry; nb. 3; (2003); p. 537 - 541, View in Reaxys
amine run 9-12
Zhang, Wei; Chen, Christine Hiu-Tung; Nagashima, Tadamichi; Tetrahedron Letters; vol. 44; nb. 10; (2003); p. 2065 - 2068, View in Reaxys
22 (tab3 run3)
Nagle, Advait S.; Salvatore, Ralph N.; Cross, Richard M.; Kapxhiu, Elona A.; Sahab, Suma; Yoon, Cheol Hwan; Jung, Kyung Woon; Tetrahedron Letters; vol. 44; nb. 30; (2003); p. 5695 - 5698, View in Reaxys
5<3>
Chen, Christine Hiu-Tung; Zhang, Wei; Organic Letters; vol. 5; nb. 7; (2003); p. 1015 - 1017, View in Reaxys
Educt, Tab.1, run 7
Gaj, Xinjie; Grigg, Ronald; Khamnaen, Tossapol; Rajviroongit, Shuleewan; Sridharan, Visuvanathar; Zhang, Lixin; Collard, Simon; Keep, Ann; Tetrahedron Letters; vol. 44; nb. 40; (2003); p. 7441 - 7444, View in Reaxys
to 5 n=1,2 Table 1 Abelman, Matthew M.; Curtis, Jeffrey K.; James, Donald R.; Tetrahedron Letters; vol. 44; nb. 34; (2003); p. 6527 - 6531, View in Reaxys 4f
Karpov, Alexei S.; Mueller, Thomas J. J.; Synthesis; nb. 18; (2003); p. 2815 - 2826, View in Reaxys
Indole-3CH2CH2-NH2
Henkel, Bernd; Westner, Benedikt; Doemling, Alexander; Synlett; nb. 15; (2003); p. 2410 - 2412, View in Reaxys
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5, R = H
Jiang, Weiqin; Zhang, Xuqing; Sui, Zhihua; Organic letters; vol. 5; nb. 1; (2003); p. 43 - 46, View in Reaxys
80
Box, Karl; Bevan, Christopher; Comer, John; Hill, Alan; Allen, Ruth; Reynolds, Derek; Analytical Chemistry; vol. 75; nb. 4; (2003); p. 883 - 892, View in Reaxys
scheme 6
Marchetti; Botteghi; Paganelli; Taddei; Advanced Synthesis and Catalysis; vol. 345; nb. 11; (2003); p. 1229 - 1236, View in Reaxys
educt to 6a
Brown, Richard T.; Dauda, Bukar E.N.; Pratt, Simon B.; Richards, Paul; Heterocycles; vol. 56; nb. 1-2; (2002); p. 51 - 58, View in Reaxys
8b
Mutulis, Felikss; Mutule, Ilze; Lapins, Maris; Wikberg, Jarl E.S.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 7; (2002); p. 1035 - 1038, View in Reaxys
educt to III.263
Fernandez; Garcia-Ochoa; Huss; Mallo; Bueno; Micheli; Paio; Piga; Zarantonello; Tetrahedron Letters; vol. 43; nb. 27; (2002); p. 4741 - 4745, View in Reaxys
Substr., Tab.1, run 1-4
Connors, Richard V.; Zhang, Alex J.; Shuttleworth, Stephen J.; Tetrahedron Letters; vol. 43; nb. 37; (2002); p. 6661 - 6663, View in Reaxys
26
Nicewonger, Robert B; Ditto, Lori; Kerr, Doug; Varady, Laszlo; Bioorganic and medicinal chemistry letters; vol. 12; nb. 14; (2002); p. 1799 - 1802, View in Reaxys
educt to 8
Wasserman, Harry H.; Long, Yun Oliver; Zhang, Rui; Parr, Jonathan; Heterocycles; vol. 58; (2002); p. 393 - 403, View in Reaxys
triptamin-NH2
Chang, Meng-Yang; Chen, Shui-Tein; Chang, Nein-Chen; Heterocycles; vol. 57; nb. 12; (2002); p. 2321 2334, View in Reaxys
tryptyl-NH2
Rodenko, Boris; Wanner, Martin J.; Koomen, Gerrit-Jan; Journal of the Chemical Society. Perkin Transactions 1; nb. 10; (2002); p. 1247 - 1252, View in Reaxys
Tryp
Wee; Yu; Journal of Organic Chemistry; vol. 66; nb. 26; (2001); p. 8935 - 8943, View in Reaxys; Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys
R1R2NH (entry m)
Marcotte, Felix-Antoine; Lubell, William D.; Organic Letters; vol. 4; nb. 15; (2002); p. 2601 - 2603, View in Reaxys
educt, Tab. 1, run 7
Eguchi, Masakatsu; Lee, Min S.; Stasiak, Marcin; Kahn, Michael; Tetrahedron Letters; vol. 42; nb. 7; (2001); p. 1237 - 1239, View in Reaxys
3-Indolyl(CH2)2NH2
McLay, Iain M.; Halley, Frank; Souness, John E.; McKenna, Jeffrey; Benning, Veronique; Birrell, Mark; Burton, Brenda; Belvisi, Maria; Collis, Alan; Constan, Alex; Foster, Martyn; Hele, David; Jayyosi, Zaid; Kelley, Mike; Maslen, Chris; Miller, Glen; Ouldelhkim, Marie-Claude; Page, Kenneth; Phipps, Simon; Pollock, Kenneth; Porter, Barry; Ratcliffe, Andrew J.; Redford, Elisabeth J.; Webber, Stephen; Slater, Bryan; Thybaud, Veronique; Wilsher, Nicola; Bioorganic and Medicinal Chemistry; vol. 9; nb. 2; (2001); p. 537 - 554, View in Reaxys
24
Chu, Lin; Hutchins, Jennifer E.; Weber, Ann E.; Lo, Jane-Ling; Yang, Yi-Tien; Cheng, Kang; Smith, Roy G.; Fisher, Michael H.; Wyvratt, Matthew J.; Goulet, Mark T.; Bioorganic and Medicinal Chemistry Letters; vol. 11; nb. 4; (2001); p. 509 - 513, View in Reaxys
3b
Stefane, Bogdan; Ernigoj, Urh; Kocevar, Marijan; Polanc, Slovenko; Tetrahedron Letters; vol. 42; nb. 38; (2001); p. 6659 - 6662, View in Reaxys
6c
Somei; Yamada; Kurauchi; Nagahama; Hasegawa; Teranishi; Sato; Kaneko; Chemical and Pharmaceutical Bulletin; vol. 49; nb. 1; (2001); p. 87 - 96, View in Reaxys
educt to 11
Magnus, Philip; Gazzard, Lewis; Hobson, Lindsay; Payne, Andrew H.; Lynch, Vince; Tetrahedron Letters; vol. 40; nb. 28; (1999); p. 5135 - 5138, View in Reaxys; Zhang, Jing-Xin; Wang, Guang-Xing; Xie, Ping; Chen, Shu-Feng; Liang, Xiao-Tian; Tetrahedron Letters; vol. 41; nb. 13; (2000); p. 2211 - 2213, View in Reaxys
Merck 9927
Van Hooft, Johannes A.; Vijverberg, Henk P.M.; British Journal of Pharmacology; vol. 117; nb. 5; (1996); p. 839 - 846, View in Reaxys; Miyafuji, Akio; Ito, Katsuji; Katsuki, Tsutomu; Heterocycles; vol. 52; nb. 1; (2000); p. 261 - 272, View in Reaxys
educt to 10
Wee, Andrew G.H.; Yu, Qing; Tetrahedron Letters; vol. 41; nb. 5; (2000); p. 587 - 590, View in Reaxys
NH2-β-(3-indolyl)ethyl
Heaney, Harry; Taha, Mutasem O.; Tetrahedron Letters; vol. 41; nb. 12; (2000); p. 1993 - 1996, View in Reaxys
6A
Barrett, Anthony G. M.; Cramp, Susan M.; Roberts, Richard S.; Zecri, Frederic J.; Organic Letters; vol. 2; nb. 3; (2000); p. 261 - 264, View in Reaxys
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12/155
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educt to 6
Bagley; Hind; Moody; Tetrahedron Letters; vol. 41; nb. 35; (2000); p. 6897 - 6900, View in Reaxys
1e
Bubnov, Yury N.; Zhun', Ilya V.; Klimkina, Elena V.; Ignatenko, Anatoly V.; Starikova, Zoya A.; European Journal of Organic Chemistry; nb. 19; (2000); p. 3323 - 3327, View in Reaxys
2f
Spychala, Jaroslaw; Tetrahedron; vol. 56; nb. 40; (2000); p. 7981 - 7986, View in Reaxys
Tab.4., run 8, amine
Chung, In Hwa; Cha, Ki Suk; Seo, Jae Hong; Kim, Joong Hyup; Chung, Bong Young; Kim, Choong Sup; Heterocycles; vol. 53; nb. 3; (2000); p. 529 - 533, View in Reaxys
educt to 13
Karoyan, Philippe; Triolo, Antonio; Nannicini, Rossano; Giannotti, Danilo; Altamura, Maria; Chassaing, Gerard; Perrotta, Enzo; Tetrahedron Letters; vol. 40; nb. 1; (1999); p. 71 - 74, View in Reaxys
precursor of 10 and 11
Koike, Kazuo; Yoshino, Hiroshi; Nikaido, Tamotsu; Heterocycles; vol. 51; nb. 2; (1999); p. 315 - 323, View in Reaxys
Amine, Tab. 1/2,run3/4-5
Bussolari; Rehborn; Combs; Tetrahedron Letters; vol. 40; nb. 7; (1999); p. 1241 - 1244, View in Reaxys
educt to 23a
Mehta, Goverdhan; Reddy, D. Srinivasa; Tetrahedron Letters; vol. 40; nb. 5; (1999); p. 991 - 994, View in Reaxys
RNH2, R=2-(3-indolyl)Et
Filigheddu, Silvia N.; Masala, Simonetta; Taddei, Maurizio; Tetrahedron Letters; vol. 40; nb. 35; (1999); p. 6503 - 6506, View in Reaxys
educt to 2
Boumendjel, Ahcene; Nuzillard, Jean-Marc; Massiot, Georges; Tetrahedron Letters; vol. 40; nb. 51; (1999); p. 9033 - 9036, View in Reaxys
2. educt to 4
Ducrot, Pierre; Thal, Claude; Tetrahedron Letters; vol. 40; nb. 51; (1999); p. 9037 - 9040, View in Reaxys
1, TA
Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414, View in Reaxys
5i
Spadoni, Gilberto; Balsamini, Cesarino; Bedini, Annalida; Carey, Aedin; Diamantini, Giuseppe; Di Giacomo, Barbara; Tontini, Andrea; Tarzia, Giorgio; Nonno, Romolo; Lucini, Valeria; Pannacci, Marilou; Michaylov Stankov, Bojidar; Fraschini, Franco; Medicinal Chemistry Research; vol. 8; nb. 9; (1998); p. 487 - 498, View in Reaxys
T
Guardado, Pilar; Balon, Manuel; Carmona, Carmen; Munoz, Maria A.; Domene, Carmen; Journal of Pharmaceutical Sciences; vol. 86; nb. 1; (1997); p. 106 - 109, View in Reaxys
peak P18
Williamson, Brian L.; Benson, Linda M.; Tomlinson, Andy J.; Mayeno, Arthur N.; Gleich, Gerald J.; Naylor, Stephen; Toxicology Letters; vol. 92; nb. 2; (1997); p. 139 - 148, View in Reaxys
Patent-Specific Data (18) Prophetic ComLocation in Patent References pound Page/Page column
Patent; INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF MEDICAL SCIENCES; Shi, Jiangong; Zhang, Jianjun; Yue, Zhenggang; Li, Min; Zhu, Chenggen; Zhang, Ying; Zi, Jiachen; Wang, Yafang; Fan, Xiaona; Xu, Ruiming; Lin, Sheng; Li, Yan; Yang, Yongchun; Sheng, Li; US2013/45942; (2013); (A1) English, View in Reaxys; Patent; Papa, Patrick; Cathers, Brian Edwin; CALABRESE, Andrew Antony; WHITEFIELD, Brandon Wade; BENNETT, Brydon; CASHION, Daniel; MORTENSEN, Deborah; HUANG, Dehua; TORRES, Eduardo; PARNES, Jason; SAPIENZA, John; HANSEN, Joshua; LEFTHERIS, Katerina; CORREA, Matthew; DELGADO, Maria Mercedes; RAHEJA, Neil; BAHMANYAR, Sami; HEGDE, Sayee; NORRIS, Stephen; PLANTEVIN-KRENITSKY, Veronique; US2015/175557; (2015); (A1) English, View in Reaxys Patent; NEUROPORE THERAPIES, INC.; STOCKING, Emily, M.; WRASIDLO, Wolfgang; WO2015/116663; (2015); (A1) English, View in Reaxys Patent; Nippon Zoki Pharmaceutical Co., Ltd.; OOKUBO, Tomohiro; NAKAMURA, Ko; NAKAZAWA, Yoshitaka; NANBA, Hiroyoshi; YOSHIDA, Hiroyuki; EP2940003; (2015); (A1) English, View in Reaxys Patent; CHEMILIA AB; HOeGBERG, Marita; DAHLSTEDT, Emma; SMITT, Olof; JOHANSSON, Tommy; WO2012/127032; (2012); (A1) English, View in Reaxys Patent; GRUNENTHAL GmbH; US2010/9986; (2010); (A1) English, View in Reaxys Patent; ACURE PHARMA AB; US2010/98629; (2010); (A1) English, View in Reaxys
prophetic product
Claim
Patent; Saurat, Jean Hilaire; US2010/324109; (2010); (A1) English, View in Reaxys Patent; Gruenenthal GmbH; US2009/111842; (2009); (A1) English, View in Reaxys
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Patent; Banner, David; Hilpert, Hans; Kuhn, Bernd; Mauser, Harald; US2007/129421; (2007); (A1) English, View in Reaxys Patent; Fourtillan, Jean-Bernard; Fourtillan, Marianne; Karam, Omar; Zunino, Fabien; Jacquesy, Jean-Claude; Tafani, Jean-Pierre; US2006/89372; (2006); (A1) English, View in Reaxys Patent; WYETH; WO2006/124875; (2006); (A2) English, View in Reaxys Patent; GRUeNENTHAL GMBH; WO2005/66183; (2005); (A1) German, View in Reaxys Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/63186; (2004); (A1) English, View in Reaxys Patent; GRUeNENTHAL GMBH; WO2004/43967; (2004); (A1) German, View in Reaxys prophetic product
Patent; Schmitz, Robert A.; US6299892; (2001); (B1) English, View in Reaxys; Patent; ISIS Pharmaceuticals, Inc.; US6828427; (2004); (B1) English, View in Reaxys Patent; GRUeNENTHAL GMBH; WO2004/43899; (2004); (A1) German, View in Reaxys Patent; Pfizer Inc.; US2004/192698; (2004); (A1) English, View in Reaxys Patent; Aventis Pharma Limited; US6352977; (2002); (B1) English, View in Reaxys
Related Structure (3) Related Structure References The author inves- Philips, Laura A.; Levy, Donald H.; Journal of Physical Chemistry; vol. 90; nb. 21; (1986); p. 4921 - 4923, tigated the config- View in Reaxys uration In der frueher (s. E I 22 636) unter dieser Konstitution beschriebenen Verbindung (F: 145-146grad) hat wahrscheinlich <2-Indol-3-ylaethyl>-isopropyliden-amin vorgelegen.
Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys
Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys Derivative (49) Comment (Derivative)
Derivative
By formation of salt/complex with TFA; Additional data: 1H NMR, shifts, D2O, 400 MHz, 15 deg C; 13C NMR, shifts, D2O, 126 MHz, 15 deg C
References Maresh, Justin J.; Giddings, Lesley-Ann; Friedrich, Anne; Loris, Elke A.; Panjikar, Santosh; Trout, Bernhardt L.; Stoeckigt, Joachim; Peters, Baron; O'Connor, Sarah E.; Journal of the American Chemical Society; vol. 130; nb. 2; (2008); p. 710 - 723, View in Reaxys
tryptamine hydochloride
Biswas, Kshetra M.; Jackson, Anthony H.; Kobaisy, Mozaina M.; Shannon, Patrick V. R.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1992); p. 461 - 468, View in Reaxys; Tulyaganov, T. S.; Chemistry of Natural Compounds; vol. 29; nb. 1; (1993); p. 31 - 34; Khimiya Prirodnykh Soedinenii; nb. 1; (1993); p. 39 - 43, View in Reaxys
TMS-Der.: MS
Raeisaenen; Kaerkkaeinen; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 33; (1979); p. 11, View in Reaxys
Protoniertes Kation = HTam+: ODMR-Frequenzen (S.7142); Rk. m. CH3HgOH: Gleichgew.-konst. (S.7140)
Svejda et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 7138, View in Reaxys
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Hydrochlorid: F: 248-249grad
Kametani et al.; Synthesis; (1972); p. 475, View in Reaxys; Patent; Nikhon kemifa h.h; JP5230513; (1977); Ref. Zh., Khim.; vol. 15; nb. O150P; (1978), View in Reaxys
Hydrochlorid: F: 240grad; IR
Patent; Buzas; Lavielle; FR2338259; (1977); Chem.Abstr.; vol. 88; nb. 120984, View in Reaxys
Hydrochlorid: FDMS (Tab. III)
Wood et al.; Analytical Chemistry; vol. 48; (1976); p. 981, View in Reaxys
Hydrochlorid
Okubo et al.; Journal of Physical Chemistry; vol. 79; (1975); p. 2108,2109, View in Reaxys
Komplex m. NATH: Ass.Konst. (Tab. I)
Okubo et al.; Journal of Physical Chemistry; vol. 79; (1975); p. 2108,2109, View in Reaxys
Hydrochlorid: F: 248-250grad
Suvorov et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 10; (1974); p. 1316,1320; Khimiya Geterotsiklicheskikh Soedinenii; vol. 10; (1974); p. 1496, View in Reaxys
Pikrat: F: 247-248grad
Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys
Tartrat: F: 182-183grad
Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys
Hydrochlorid: Konform.; Atomabstaende, Bindungswinkel; Kristallstruktur; F: 256-257grad; D=1.261
Wakahara et al.; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 2481,2482-2486, View in Reaxys
Hydrochlorid: Diff.-Sp. in W.
Andrews; Forster; Biochemistry; vol. 11; nb. 10; (1972); p. 1875 - 1879, View in Reaxys
3,5-Dinitro-benzoyl-Derivat: Rk. m. Na-ethylat, NaOH, Acn.: Abs.-Sp. d. Reaktionsprodukts
Obtemperanskaya; Likhosherstova; J. Anal. Chem. USSR (Engl. Transl.); vol. 26; (1971); p. 158,140, View in Reaxys
(2,4-Dinitro-benzoyl)-Acn.-Komplex: Abs.
Obtemperanskaya et al.; J. Anal. Chem. USSR (Engl. Transl.); vol. 25; (1970); p. 2033,1744, View in Reaxys
Hydrochlorid C10H12N2*HCl: F: 244.5-245.5grad
Avramenko et al.; Pharmaceutical Chemistry Journal; nb. 12; (1970); p. 671; KhimikoFarmatsevticheskii Zhurnal; nb. 12; (1970); p. 10, View in Reaxys
Hydrochlorid: Loeschung d. Riboflavin-Phosphat-Fluoreszenz, Kinetik
Bowd et al.; Photochemistry and Photobiology; vol. 11; (1970); p. 445,447, View in Reaxys
Hydrochlorid: F: 256-257grad; ρ=1.261 g/cm3; Roentgenstruktur; H-Bruecken; Molekuelpackung
Wakahara; Fujiwara; Tomita; Tetrahedron letters; vol. 57; (1970); p. 4999 - 5002, View in Reaxys
<C10H13N2> +<C25H23Br2O5 S>-: Prep.: Ionenpaarextraktion m. CH2Cl2 (Bromthymolblau); logE(HAHY), -
Borg et al.; Journal of Pharmacy and Pharmacology; vol. 22; (1970); p. 507,508,509, View in Reaxys
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logk(d(A))*k'(HAT) ; Produktverteilung logD(HAHY) Hydrochlorid: ε(630)
Kitaoka; Nakano; Journal of Biochemistry (Tokyo, Japan); vol. 66; (1969); p. 87,91, View in Reaxys
Hydrochlorid: Rk. m. Secologanin (Phosphatpuffer, pH 4.5) fuehrt zu Vincosid- u. Isovincosid-hydrochlorid
Battersby,A.R. et al.; Journal of the Chemical Society [Section] C: Organic; (1969); p. 1193 - 1200, View in Reaxys
Hydrochlorid v. <1'-14C>-Tryptamin: Rk. m. 1.) Tosylchlorid, 2.) <14C>-Methyliodid, 3.) Na, fl. NH3 fuehrt zu <N(ω)-14C>Methyl-<1'-14C>tryptamin
Gross et al.; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 9; nb. 2; (1969); p. 64, View in Reaxys
Hydrochlorid: Rk. m. Secologanin (Phosphatpuffer, pH 6.2) fuehrt zu 2-(2-cis-β-D-Glucopyranosyloxy-3-vinyl-5-methoxycarbonyl-3ref,4-cis-Dihydro-2H-pyranyl-4methyl)-spiro(pyrrolidin-....
Battersby,A.R. et al.; Journal of the Chemical Society [Section] C: Organic; (1969); p. 1193 - 1200, View in Reaxys
Hydrochlorid: F: 256grad
Bridges; Williams; Biochemical Journal; vol. 107; (1968); p. 225,228, View in Reaxys
Charge-TransferBanden m. Trinitrobenzol (S.210)
Millie et al.; Journal of Medicinal Chemistry; vol. 11; nb. 2; (1968); p. 207,209,210, View in Reaxys
Charge-TransferBanden m. Tetracyanethylen (S. 210)
Millie et al.; Journal of Medicinal Chemistry; vol. 11; nb. 2; (1968); p. 207,209,210, View in Reaxys
Pikrat: F: 240242grad (Zers.)
Grandberg et al.; Doklady Chemistry; vol. 176; (1967); p. 828; Doklady Akademii Nauk SSSR; vol. 176; (1967); p. 583, View in Reaxys
Hydrochlorid: F: 251-253grad
Pfeil,E.; Harder,U.; Angewandte Chemie; vol. 79; (1967); p. 188, View in Reaxys
Hydrochlorid: Rk. m. Pivaloylchlorid fuehrt zu N(β)Pivaloyltryptamin; Rk. m. Diphenylacetylchlorid fuehrt zu N(β)-Diphenylacetyltryptamin
Eichele; Mutschler; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 300; nb. 12; (1967); p. 1038, View in Reaxys
Flavinmononucleotid-Komplex: ΔF; ΔH; ΔS; Abs.Sp. (Tab. 1); Assoziationskonst.
Wilson; Biochemistry; vol. 5; (1966); p. 1351,1355, View in Reaxys
Hydrochlorid: F: 252.5-254.5grad
Brubacher,L.J.; Bender,M.L.; Journal of the American Chemical Society; vol. 88; (1966); p. 5871 - 5880, View in Reaxys
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(Zers.); pK(a); Rk. m. trans-Cinnamoyl-Papain (Kinetik): Geschw.konst. Pikrat C10H12N2*C6H3 N3O7: F: 243grad (Zers.)
Tacconi; Farmaco, Edizione Scientifica; vol. 20; (1965); p. 891,895,899, View in Reaxys
Hydrochlorid: Inhibitions-Konstante f. Acetylcholinesterase
Krupka; Biochemistry; vol. 4; (1965); p. 429,431, View in Reaxys
Hydrochlorid 2d: Prep.: N-Isopropyliden-tryptamin, HCl; F: 248grad (A.-E.)
Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys
Pikrat 2e: Prep.: N-Isopropylidentryptamin, Pikrinsaeure; F: 244grad (?) (A.), (242grad); rot
Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys
Sulfat: Rk. m. Vanillin in verd. wss. H2SO4 fuehrt zu 1-(4-Hydroxy-3methoxy-phenyl)-1,2,3,4-tetrahydro-β-carbolin; Rk. m. Benzaldehyd in verd. wss. H2SO4 fuehrt zu 1-Phenyl-1,2,3,4tetrahydro-β-carbolin (S.179)
Freter,K. et al.; Justus Liebigs Annalen der Chemie; vol. 684; (1965); p. 159 - 187, View in Reaxys
Hydrobromid: Rk. m. N-Brom-succinimid in wss. tertButylalkohol (MolVerh. 1:1) fuehrt zu 3-(2-Aminoethyl)-oxindol*HBr
Hinman; Bauman; Journal of Organic Chemistry; vol. 29; (1964); p. 1206, View in Reaxys
Nω-Benzamid: Rk. m. N-Bromsuccinimid in wss. tert-Butylalkohol (Mol-Verh. 1:1) fuehrt zu 3-(2Benzamino-ethyl)-oxindol
Hinman; Bauman; Journal of Organic Chemistry; vol. 29; (1964); p. 1206, View in Reaxys
Hydrochlorid: Rk. m. 3,4-Dimethoxy-phenyl-acetaldehyd/A.+W. in A.+2N H2SO4 (Raumtemp., 24 h) fuehrt zu 1(3,4-Dimethoxybenzyl)-1,2,3,4tetrahydro-β-carbolin-HCl
Taborsky; McIsaac; Journal of Medicinal Chemistry; vol. 7; (1964); p. 135,140, View in Reaxys
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Acetat: F: 134.5-135.5grad
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Hydrochlorid: Rk. m. (3,4-Dihydroxyphenyl)-brenztraubensaeure, W. (2 Wochen, 20grad) -> 1-(3,4Dihydroxybenzyl)-1,2,3,4-tetrahydro-β-carbolin-1-carbonsaeure; bei 12 h kochen (N2) -> 1(3,4-Dihydroxybenzyl)-1,2,3,4tetrahydro-β-carbolin (I R=H)
Harley-Mason; Waterfield; Tetrahedron; vol. 19; (1963); p. 65,71, View in Reaxys
Pikrat C10H12N2*C6H3 N3O7: F: 246grad (korr.); F: 247-248grad (A., korr.); rot
Piozzi; Merlini; Gazzetta Chimica Italiana; vol. 92; (1962); p. 1105,1107-1116, View in Reaxys
Hydrochlorid: F: 116grad
Bocourt; Vignau; Bulletin de la Societe Chimique de France; (1961); p. 1190, View in Reaxys
Chlorhydrat: F: 246-247grad
Matkovics et al.; Acta Physica et Chemica; vol. 7; (1961); p. 51, View in Reaxys
Hydrochlorid C10H12N2*HCl: IR-Sp. (6-11 μ) d. wss. Lsg.
Kirschenbaum; Parker; Spectrochimica Acta; vol. 17; (1961); p. 785,789; Chem.Abstr.; nb. 16254; (1960), View in Reaxys
2,4-DinitrophenylDerivat: F: 217grad
Asatoor; Journal of Chromatography; vol. 4; (1960); p. 144,145-152; Chem.Abstr.; vol. 56; nb. 9393; (1962), View in Reaxys
Hydrochlorid C10H12N2*HCl: F: 248-252grad (A., Kofler)
Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys
o-tolyl acetate (mp: 170 degree ); Further Data see Handbook
Julian et al.; Journal of the American Chemical Society; vol. 70; (1948); p. 180,182, View in Reaxys
Melting Point (30) 1 of 30
Melting Point [°C]
110 - 112
Guo, Xiaoke; Yang, Qian; Xu, Jing; Zhang, Li; Chu, Hongxi; Yu, Peng; Zhu, Yingying; Wei, Jinglian; Chen, Weilin; Zhang, Yaozhong; Zhang, Xiaojin; Sun, Haopeng; Tang, Yiqun; You, Qidong; Bioorganic and Medicinal Chemistry; vol. 21; nb. 21; (2013); p. 6466 - 6476, View in Reaxys 2 of 30
Melting Point [°C]
111 - 112
Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys; Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys 3 of 30
Melting Point [°C]
111 - 112
Choy, Jason; Jaime-Figueroa, Saul; Jiang, Laurence; Wagner, Paul; Synthetic Communications; vol. 38; nb. 21; (2008); p. 3840 - 3853, View in Reaxys 4 of 30
Melting Point [°C]
112 - 113
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys
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5 of 30
Melting Point [°C]
119
Mortoni, Annalisa; Martinelli, Marisa; Piarulli, Umberto; Regalia, Nickolas; Gagliardi, Stefania; Tetrahedron Letters; vol. 45; nb. 35; (2004); p. 6623 - 6627, View in Reaxys 6 of 30
Melting Point [°C]
116 - 117
Solvent (Melting Point)
acetone
Tulyaganov, T. S.; Chemistry of Natural Compounds; vol. 29; nb. 1; (1993); p. 31 - 34; Khimiya Prirodnykh Soedinenii; nb. 1; (1993); p. 39 - 43, View in Reaxys 7 of 30
Melting Point [°C]
114 - 119
Wang, Alan P. L.; Li, Liang; Analytical Chemistry; vol. 64; nb. 7; (1992); p. 769 - 775, View in Reaxys 8 of 30
Melting Point [°C]
114 - 115
Barton et al.; Journal of the Chemical Society; (1965); p. 3990,3993, View in Reaxys; Ibragimov, A. A.; Yunusov, S. Yu.; Chemistry of Natural Compounds; vol. 21; nb. 4; (1985); p. 502 - 509; Khimiya Prirodnykh Soedinenii; vol. 21; nb. 4; (1985); p. 536 - 544, View in Reaxys 9 of 30
Melting Point [°C]
116 - 117
Solvent (Melting Point)
benzene
Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys; Deetz, J. S.; Behrman, E. J.; Journal of Organic Chemistry; vol. 45; nb. 1; (1980); p. 135 - 140, View in Reaxys 10 of 30
Melting Point [°C]
115
Fleming,I.; Woolias,M.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1979); p. 829 - 837, View in Reaxys 11 of 30
Melting Point [°C]
116 - 117.5
Takano et al.; Heterocycles; vol. 6; (1977); p. 1167,1168, 1169, 1170, View in Reaxys 12 of 30
Melting Point [°C]
118 - 120
Buzas et al.; Synthesis; (1977); p. 129, View in Reaxys; Patent; Richter Gedeon Vegyeszeti Gyar R.T.; FR2261271; (1973); DE2344919; Chem.Abstr.; vol. 80; nb. 146016, View in Reaxys; Szantay et al.; Synthesis; (1974); p. 354, View in Reaxys 13 of 30
Melting Point [°C]
110 - 112
Patent; Grandberg; Bobrowa; SU451696; (1976); Ref. Zh., Khim.; vol. 8; nb. O143P; (1976), View in Reaxys 14 of 30
Melting Point [°C]
112
Konda; Suzuki; Omura; Onda; Chemical and Pharmaceutical Bulletin; vol. 24; nb. 1; (1976); p. 92 - 96, View in Reaxys 15 of 30
Melting Point [°C]
240 - 242
Suvorov et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 45; (1975); p. 1600,1565,1568, View in Reaxys 16 of 30
Melting Point [°C]
114 - 116
Suvorov et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 10; (1974); p. 1316,1320; Khimiya Geterotsiklicheskikh Soedinenii; vol. 10; (1974); p. 1496, View in Reaxys 17 of 30
Melting Point [°C]
113 - 114
Grandberg et al.; Doklady Chemistry; vol. 176; (1967); p. 828; Doklady Akademii Nauk SSSR; vol. 176; (1967); p. 583, View in Reaxys; Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys 18 of 30
Melting Point [°C]
117 - 118
Bergman,J. et al.; Tetrahedron; vol. 29; (1973); p. 971 - 976, View in Reaxys 19 of 30
Melting Point [°C]
112 - 113
Solvent (Melting Point)
petroleum ether; benzene
Grandberg et al.; Sintezy Geterotsiklicheskikh Soedinenii; vol. 9; (1972); p. 18; Chem.Abstr.; vol. 79; nb. 146321, View in Reaxys 20 of 30
Melting Point [°C]
115 - 117
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Johns et al.; Australian Journal of Chemistry; vol. 19; (1966); p. 893, View in Reaxys 21 of 30
Melting Point [°C]
118
Solvent (Melting Point)
petroleum ether
Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys 22 of 30
Melting Point [°C]
114
Solvent (Melting Point)
diethyl ether
Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys 23 of 30
Melting Point [°C]
118
Manske; Canadian Journal of Research; vol. 5; (1931); p. 599; Chem. Zentralbl.; vol. 103; nb. I; (1932); p. 2475, View in Reaxys; Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys 24 of 30
Melting Point [°C]
114
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys; Julia et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 251; (1960); p. 394, View in Reaxys 25 of 30
Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys
26 of 30
Melting Point [°C]
102 - 103
Solvent (Melting Point)
hexane
Piozzi; Merlini; Gazzetta Chimica Italiana; vol. 92; (1962); p. 1105,1107-1116, View in Reaxys 27 of 30
Melting Point [°C]
116
Matkovics et al.; Acta Physica et Chemica; vol. 7; (1961); p. 51, View in Reaxys; Patent; Lab.francais de chimiotherapie; US2920080; (1960); Chem.Abstr.; vol. 54; nb. 13018hi; (1960), View in Reaxys 28 of 30
Melting Point [°C]
242 - 244
Mndzhoyan; Papayan; Izvestiya Akademii Nauk Armyanskoi SSR, Khimicheskie Nauki; vol. 14; (1961); p. 603; Chem.Abstr.; vol. 58; nb. 4497c; (1963), View in Reaxys 29 of 30
Melting Point [°C]
116 - 118
Ahmad et al.; Canadian Journal of Chemistry; vol. 38; (1960); p. 2523, View in Reaxys 30 of 30
Melting Point [°C]
120
Asahina; Acta Phytochimica; vol. 1; (1922); p. 81; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 248, View in Reaxys Boiling Point (6) Boiling Point [°C]
Pressure (Boiling Point) [Torr]
Location
References
137
0.15
supporting information
Pablos, Jess L.; Vallejos, Sal; Muoz, Asuncin; Rojo, Mara J.; Serna, Felipe; Garca, Flix C.; Garca, Jos M.; Chemistry - A European Journal; vol. 21; nb. 24; (2015); p. 8733 - 8736, View in Reaxys
140 - 155
0.3
Takano et al.; Heterocycles; vol. 6; (1977); p. 1167,1168, 1169, 1170, View in Reaxys
185 - 187
0.5
Patent; Grandberg; Bobrowa; SU451696; (1976); Ref. Zh., Khim.; vol. 8; nb. O143P; (1976), View in Reaxys; Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys; Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 10; (1974); p. 943; Khimiya Geterotsiklicheskikh Soedinenii; vol. 10; (1974); p. 1085, View in Reaxys
185 - 188
0.5
Grandberg et al.; Doklady Chemistry; vol. 176; (1967); p. 828; Doklady Akademii Nauk SSSR; vol. 176; (1967); p. 583, View in Reaxys
143 - 146
0.8
Pfeil,E.; Harder,U.; Angewandte Chemie; vol. 79; (1967); p. 188, View in Reaxys
121
0.01 - 0.02
de Groot,S.; Strating,J.; Recueil des Travaux Chimiques des PaysBas; vol. 80; (1961); p. 121 - 133, View in Reaxys
Association (MCS) (33)
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1 of 33
Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))
acetonitrile
Temperature (Association (MCS)) [°C]
25
Partner (Association (MCS))
2',4',6'-trimethyl-3',5'-bis(4-phenyl-4,5-dihydrooxazol-2-ylmethyl)biphenyl-2-ol
Chung, Yun Mi; Raman, Balamurali; Ahn, Kyo Han; Tetrahedron; vol. 62; nb. 50; (2006); p. 11645 - 11651, View in Reaxys 2 of 33
Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))
aq. phosphate buffer
Temperature (Association (MCS)) [°C]
27
Partner (Association (MCS))
cucurbit[8]uril; paraquat dichloride
Bush, Meghan E.; Bouley, Nicole D.; Urbach, Adam R.; Journal of the American Chemical Society; vol. 127; nb. 41; (2005); p. 14511 - 14517, View in Reaxys 3 of 33
Description (Association Enthalpy of association (MCS)) Solvent (Association (MCS))
aq. phosphate buffer
Temperature (Association (MCS)) [°C]
27
Partner (Association (MCS))
cucurbit[8]uril; paraquat dichloride
Bush, Meghan E.; Bouley, Nicole D.; Urbach, Adam R.; Journal of the American Chemical Society; vol. 127; nb. 41; (2005); p. 14511 - 14517, View in Reaxys 4 of 33
Description (Association NMR spectrum of the complex (MCS)) Solvent (Association (MCS))
D2O
Temperature (Association (MCS)) [°C]
25
Partner (Association (MCS))
cucurbit[8]uril; paraquat dichloride
Bush, Meghan E.; Bouley, Nicole D.; Urbach, Adam R.; Journal of the American Chemical Society; vol. 127; nb. 41; (2005); p. 14511 - 14517, View in Reaxys 5 of 33
Description (Association IR spectrum of the complex (MCS)) Partner (Association (MCS))
H2O
Carney; Dian; Florio; Zwier; Journal of the American Chemical Society; vol. 123; nb. 23; (2001); p. 5596 - 5597, View in Reaxys 6 of 33
Description (Association Further physical properties of the complex (MCS)) Solvent (Association (MCS))
D2O; various solvent(s)
Temperature (Association (MCS)) [°C]
29.9
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Partner (Association (MCS))
calf thymus DNA sodium salt
Sartorius, Joachim; Schneider, Hans-Joerg; Journal of the Chemical Society. Perkin Transactions 2; nb. 11; (1997); p. 2319 - 2327, View in Reaxys 7 of 33
Description (Association Dipole moment of the complex (MCS)) Solvent (Association (MCS))
1,2-dichloro-ethane
Partner (Association (MCS))
I2
Abu-Eittah; Abdou; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 93; nb. 11-12; (1996); p. 1958 - 1973, View in Reaxys 8 of 33
Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))
H2O; various solvent(s)
Temperature (Association (MCS)) [°C]
25
Partner (Association (MCS))
bovine serum albumin (BSA)
Okabe; Adachi; Chemical and Pharmaceutical Bulletin; vol. 40; nb. 2; (1992); p. 499 - 500, View in Reaxys 9 of 33
Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))
D2O
Temperature (Association (MCS)) [°C]
50
Partner (Association (MCS))
C50H60N8O12
Kikuchi, Jun-ichi; Egami, Kazuko; Suehiro, Kazuaki; Murakami, Yukito; Chemistry Letters; nb. 9; (1992); p. 1685 - 1688, View in Reaxys 10 of 33
Description (Association Further physical properties of the complex (MCS)) Solvent (Association (MCS))
D2O
Temperature (Association (MCS)) [°C]
50
Partner (Association (MCS))
C50H60N8O12
Kikuchi, Jun-ichi; Egami, Kazuko; Suehiro, Kazuaki; Murakami, Yukito; Chemistry Letters; nb. 9; (1992); p. 1685 - 1688, View in Reaxys 11 of 33
Description (Association NMR spectrum of the complex (MCS)) Solvent (Association (MCS))
CDCl3
Partner (Association (MCS))
Rebek's cleft
Rebek, J.; Askew, B.; Ballester, P.; Costero, A.; Journal of the American Chemical Society; vol. 110; nb. 3; (1988); p. 923 - 927, View in Reaxys 12 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
2-Methylcyclohexanol
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Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 13 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
benzene
Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 14 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
acetone
Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 15 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
dichloromethane
Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 16 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
H2O
Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 17 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
methanol
Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 18 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
ethanol
Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 19 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
propan-1-ol
Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 20 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
isopropyl alcohol
Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 21 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
2-methyl-propan-1-ol
Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 22 of 33
Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))
tert-Amyl alcohol
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Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys 23 of 33
Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))
H2O
Partner (Association (MCS))
thymidine 5'-phosphate
Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 24 of 33
Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))
H2O
Partner (Association (MCS))
thymidine 5'-phosphate; sodium cacodylate
Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 25 of 33
Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))
H2O
Partner (Association (MCS))
disodium uridine-5'-monophosphate
Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 26 of 33
Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))
H2O
Partner (Association (MCS))
disodium uridine-5'-monophosphate; sodium cacodylate
Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 27 of 33
Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))
H2O
Partner (Association (MCS))
adenosine 5'-monophosphate
Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 28 of 33
Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))
H2O
Partner (Association (MCS))
adenosine 5'-monophosphate; sodium cacodylate
Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 29 of 33
Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))
H2O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Partner (Association (MCS))
guanosine-5'-monophosphoric acid disodium salt
Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 30 of 33
Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))
H2O
Partner (Association (MCS))
guanosine-5'-monophosphoric acid disodium salt; sodium cacodylate
Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 31 of 33
Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))
H2O
Partner (Association (MCS))
cytidine monophosphate
Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 32 of 33
Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))
H2O
Partner (Association (MCS))
cytidine monophosphate; sodium cacodylate
Toulme, Francine; Helene, Claude; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 77; nb. 9; (1980); p. 855 - 860, View in Reaxys 33 of 33
Description (Association Association with compound (MCS)) Helene et al.; Biochemistry; vol. 10; (1971); p. 3802,3806, View in Reaxys; McMenamy; Journal of Biological Chemistry; vol. 240; (1965); p. 4235,4236 - 4238, View in Reaxys
Chromatographic Data (4) Chromatographic Location data HPLC (High performance liquid chromatography) HPLC (High performance liquid chromatography)
References Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Cautela, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 60; nb. 37; (2012); p. 9512 - 9518, View in Reaxys; Kalb, Daniel; Gressler, Julia; Hoffmeister, Dirk; ChemBioChem; vol. 17; nb. 2; (2016); p. 132 - 136, View in Reaxys
supporting information
Ren, Adeline; Martinez, Jean; Cavelier, Florine; European Journal of Organic Chemistry; vol. 2014; nb. 36; (2014); p. 8142 - 8147, View in Reaxys
LC (Liquid chromatography)
Bracchitta, Giuseppina; Catalfo, Alfio; De Guidi, Guido; Photochemical and Photobiological Sciences; vol. 12; nb. 6; (2013); p. 967 - 973, View in Reaxys
UPLC (Ultra performance liquid chromatography)
Rangiah, Kannan; Palakodeti, Dasaradhi; Rapid Communications in Mass Spectrometry; vol. 27; nb. 21; (2013); p. 2439 - 2452, View in Reaxys
Conformation (3) Object of Investi- References gation Conformation
Culvenor,C.C.J.; Ham,N.S.; Australian Journal of Chemistry; vol. 27; (1974); p. 2191 - 2198, View in Reaxys; Kumbar; Sankar; Journal of the American Chemical Society; vol. 97; (1975); p. 7411,7412-7416, View in Reaxys; Philips, Laura A.; Levy, Donald H.; Journal of Physical Chemistry; vol. 90; nb. 21; (1986); p. 4921 - 4923, View in Reaxys; Feng, Ke; Kleinermanns, Karl; Chemical Physics Letters; vol. 473; nb. 4-6; (2009); p. 220 - 222, View in Reaxys
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The author investigated the; Conformation
Carney, Joel R.; Zwier, Timothy S.; Chemical Physics Letters; vol. 341; nb. 1-2; (2001); p. 77 - 85, View in Reaxys; Schmitt, Michael; Boehm, Marcel; Ratzer, Christian; Vu, Chau; Kalkman, Ivo; Meerts, W. Leo; Journal of the American Chemical Society; vol. 127; nb. 29; (2005); p. 10356 - 10364, View in Reaxys; Clarkson, Jasper R.; Dian, Brian C.; Moriggi, Loick; Defusco, Albert; McCarthy, Valerie; Jordan, Kenneth D.; Zwier, Timothy S.; Journal of Chemical Physics; vol. 122; nb. 21; (2005); Art.No: 214311, View in Reaxys
Conformer equilibrium
Philips, Laura A.; Levy, Donald H.; Journal of Chemical Physics; vol. 89; nb. 1; (1988); p. 85 - 90, View in Reaxys
Crystal Phase (1) Description (Crys- References tal Phase) Crystal structure determination
Nowell, Harriott; Attfield, J. Paul; Cole, Jason C.; Acta Crystallographica Section B: Structural Science; vol. 58; nb. 5; (2002); p. 835 - 840, View in Reaxys
Crystal Property Description (6) Colour & Other Location Properties red
Paragraph 0045
References Patent; Kyushu University, National University Corporation; OHSHIMA Takashi; MORIMOTO Hiroyuki; SHIMIZU Yuhei; EP2821389; (2015); (A1) English, View in Reaxys
white
Jin, Huijuan; Zhang, Puyong; Bijian, Krikor; Ren, Sumei; Wan, Shengbiao; AlaouiJamali, Moulay A.; Jiang, Tao; Marine Drugs; vol. 11; nb. 5; (2013); p. 1427 - 1439, View in Reaxys
brown
Baron, Marc; Metay, Estelle; Lemaire, Marc; Popowycz, Florence; Green Chemistry; vol. 15; nb. 4; (2013); p. 1006 - 1015, View in Reaxys
yellow
Guo, Xiaoke; Yang, Qian; Xu, Jing; Zhang, Li; Chu, Hongxi; Yu, Peng; Zhu, Yingying; Wei, Jinglian; Chen, Weilin; Zhang, Yaozhong; Zhang, Xiaojin; Sun, Haopeng; Tang, Yiqun; You, Qidong; Bioorganic and Medicinal Chemistry; vol. 21; nb. 21; (2013); p. 6466 - 6476, View in Reaxys
red
supporting information
Shimizu, Yuhei; Morimoto, Hiroyuki; Zhang, Ming; Ohshima, Takashi; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8564 - 8567, View in Reaxys
white
supporting information
Nicolaou; Krasovskiy, Arkady; Trepanier, Vincent E.; Chen, David Y.-K.; Angewandte Chemie - International Edition; vol. 47; nb. 22; (2008); p. 4217 - 4220, View in Reaxys; Nicolaou, K. C.; Krasovskiy, Arkady; Majumder, Utpal; Trepanier, Vincent E.; Chen, David Y.-K.; Journal of the American Chemical Society; vol. 131; (2009); p. 3690 - 3699, View in Reaxys
Crystal System (1) Crystal System References rhombic
Nowell, Harriott; Attfield, J. Paul; Cole, Jason C.; Acta Crystallographica Section B: Structural Science; vol. 58; nb. 5; (2002); p. 835 - 840, View in Reaxys
Dielectric Constant (1) References Kumbar; Sankar; Journal of the American Chemical Society; vol. 97; (1975); p. 7411,7412-7416, View in Reaxys Dissociation Exponent (14) 1 of 14
Dissociation Exponent (pK)
10.2
Solvent (Dissociation Exponent)
water
Type (Dissociation Exponent)
b1/apparent
Comment (Dissociation Exponent)
DE
Samoylenko, Volodymyr; Ashfaq, Mohammad K.; Jacob, Melissa R.; Tekwani, Babu L.; Khan, Shabana I.; Manly, Susan P.; Joshi, Vaishali C.; Walker, Larry A.; Muhammad, Ilias; Journal of Natural Products; vol. 72; nb. 1; (2009); p. 92 - 98, View in Reaxys 2 of 14
Dissociation Exponent (pK)
4.2
Dissociation Group
H
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Method (Dissociation Exponent)
spectrophotometric
Type (Dissociation Exponent)
a1/apparent
Hela; Anipindi; Priyadarsini; O'Neill; Journal of Physical Chemistry B; vol. 103; nb. 40; (1999); p. 8606 - 8611, View in Reaxys 3 of 14
Dissociation Exponent (pK)
10.18
Temperature (Dissociation Exponent) [°C]
20
Type (Dissociation Exponent)
a1/apparent
Eftink, Maurice R.; Jia, Yiwei; Hu, Dana; Ghiron, Camillo, A.; Journal of Physical Chemistry; vol. 99; (1995); p. 5713 - 5723, View in Reaxys 4 of 14
Dissociation Exponent (pK)
10.35
Temperature (Dissociation Exponent) [°C]
20
Type (Dissociation Exponent)
a1/apparent
Eftink, Maurice R.; Jia, Yiwei; Hu, Dana; Ghiron, Camillo, A.; Journal of Physical Chemistry; vol. 99; (1995); p. 5713 - 5723, View in Reaxys 5 of 14
Comment (Dissociation Exponent)
(pk')pK(a) (S.7140) nach D.D.Perrin 'Dissociation Constants of Organic Bases in Aqueous Solution', Butterworths, London, 1965, p.239
Svejda et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 7138, View in Reaxys 6 of 14
Comment (Dissociation Exponent)
(pk')pK(2)
Nowotarska; Podkowinska; Roczniki Chemii; vol. 50; (1976); p. 789,790, 791, 793, View in Reaxys 7 of 14
Comment (Dissociation Exponent)
(pk')pK (Tab. I)
Chen; Hoffmann; Journal of Physical Chemistry; vol. 78; (1974); p. 2099, View in Reaxys 8 of 14
Comment (Dissociation Exponent)
(pk')pK(b)
Julia; Lallemand; Bulletin de la Societe Chimique de France; (1973); p. 2058,2059, 2061, View in Reaxys 9 of 14
Comment (Dissociation Exponent)
(pk')pK(a)
Marziano et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1973); p. 1915,1917, View in Reaxys 10 of 14
Comment (Dissociation Exponent)
(pk')pK (S.2099)
Weber; Simeon; Journal of Inorganic and Nuclear Chemistry; vol. 33; (1971); p. 2097,2099, View in Reaxys 11 of 14
Comment (Dissociation Exponent)
(pk')Mess. d. pK-Werte (S.2858)
Yagil; Tetrahedron; vol. 23; nb. 6; (1967); p. 2855 - 2861, View in Reaxys 12 of 14
Comment (Dissociation Exponent)
(pk')pK(a) (50percent-ig. wss. A.): 8.69
Grandberg et al.; Doklady Chemistry; vol. 176; (1967); p. 828; Doklady Akademii Nauk SSSR; vol. 176; (1967); p. 583, View in Reaxys 13 of 14
Comment (Dissociation Exponent)
(pk')pK(a) (H+) (25grad, photom.): -6.31 (Thermodyn. .... wegen grosser Verd.)
Hinman; Lang; Journal of the American Chemical Society; vol. 86; (1964); p. 3796,3797,3804, View in Reaxys
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14 of 14
Dissociation Exponent (pK)
10.2
Solvent (Dissociation Exponent)
H2O
Method (Dissociation Exponent)
potentiometric
Type (Dissociation Exponent)
a/apparent
Vane; British Journal of Pharmacology and Chemotherapy; vol. 14; (1959); p. 87,91, View in Reaxys Electrical Moment (3) 1 of 3
Description (Electrical Moment)
Dipole moment
Moment (Electrical Moment) [D]
1.6 - 2.7
Method (Electrical Moment)
Stark effect
Solvent (Electrical Moment)
vapour
Comment (Electrical Moment)
various conformers. Object(s) of Study: ground state
Nguyen, Tri V.; Pratt, David W.; Journal of Chemical Physics; vol. 124; nb. 5; (2006); Art.No: 054317, View in Reaxys 2 of 3
Description (Electrical Moment)
Dipole moment
Moment (Electrical Moment) [D]
1.4 - 2.5
Method (Electrical Moment)
Stark effect
Solvent (Electrical Moment)
vapour
Comment (Electrical Moment)
various conformers. Object(s) of Study: excited singlet state
Nguyen, Tri V.; Pratt, David W.; Journal of Chemical Physics; vol. 124; nb. 5; (2006); Art.No: 054317, View in Reaxys 3 of 3
Description (Electrical Moment)
Dipole moment
Kumbar; Sankar; Journal of the American Chemical Society; vol. 97; (1975); p. 7411,7412-7416, View in Reaxys Electrochemical Behaviour (2) Description (Elec- References trochemical Behaviour) Protonation
Box, Karl; Bevan, Christopher; Comer, John; Hill, Alan; Allen, Ruth; Reynolds, Derek; Analytical Chemistry; vol. 75; nb. 4; (2003); p. 883 - 892, View in Reaxys
Electrolytic dissociation / protonation equilibrium
Balon, Manuel; Hidalgo, Jose; Guardado, Pilar; Munoz, Maria A.; Carmona, Carmen; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 1; (1993); p. 91 - 97, View in Reaxys
Electrochemical Characteristics (2) 1 of 2
Description (Electrochemical Characteristics)
Electrochemical characteristics given
Estevao, Monica S.; Carvalho, Luisa C.; Ferreira, Luisa M.; Fernandes, Eduarda; Marques, M. Manuel B.; Tetrahedron Letters; vol. 52; nb. 1; (2011); p. 101 - 106, View in Reaxys
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2 of 2
Description (Electrochemical Characteristics)
polarographic half-wave potential
Solvent (Electrochemical Characteristics)
aq. phosphate buffer; dimethylformamide
Levina; Chechekin; Arzamastsev; Gaevskii; Degterev; Grigor'ev; Pharmaceutical Chemistry Journal; vol. 32; nb. 10; (1998); p. 557 - 558, View in Reaxys Further Information (32) Description (Fur- References ther Information) Further information
Wood et al.; Analytical Chemistry; vol. 48; (1976); p. 981, View in Reaxys
Further information
Wakahara et al.; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 2481,2482-2486, View in Reaxys
Further information
Andrews; Forster; Biochemistry; vol. 11; nb. 10; (1972); p. 1875 - 1879, View in Reaxys
Further information
Persson; Acta Pharmaceutica Suecica; vol. 8; (1971); p. 193,198, View in Reaxys
Further information
Obtemperanskaya; Likhosherstova; J. Anal. Chem. USSR (Engl. Transl.); vol. 26; (1971); p. 158,140, View in Reaxys
Further information
Vinnik et al.; Russian Journal of Physical Chemistry; vol. 44; (1970); p. 1621,1624, View in Reaxys
Further information
Bowd et al.; Photochemistry and Photobiology; vol. 11; (1970); p. 445,447, View in Reaxys
Further information
Jamieson; Hutzinger; Phytochemistry (Elsevier); vol. 9; (1970); p. 2029,2033, View in Reaxys
Further information
Wakahara; Fujiwara; Tomita; Tetrahedron letters; vol. 57; (1970); p. 4999 - 5002, View in Reaxys
Further information
Obtemperanskaya et al.; J. Anal. Chem. USSR (Engl. Transl.); vol. 25; (1970); p. 2033,1744, View in Reaxys
Further information
Borg et al.; Journal of Pharmacy and Pharmacology; vol. 22; (1970); p. 507,508,509, View in Reaxys
Further information
Kitaoka; Nakano; Journal of Biochemistry (Tokyo, Japan); vol. 66; (1969); p. 87,91, View in Reaxys
Further information
Keglevic et al.; Croatica Chemica Acta; vol. 40; (1968); p. 7,10, View in Reaxys
Further information
Millie et al.; Journal of Medicinal Chemistry; vol. 11; nb. 2; (1968); p. 207,209,210, View in Reaxys
Further information
Smaller et al.; Journal of Chemical Physics; vol. 46; (1967); p. 3976,3979, View in Reaxys
Further information
Eichele; Mutschler; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 300; nb. 12; (1967); p. 1038, View in Reaxys
Further information
Sugiyama et al.; Bulletin of the Chemical Society of Japan; vol. 40; (1967); p. 348,349, View in Reaxys
Further information
Wilson; Biochemistry; vol. 5; (1966); p. 1351,1355, View in Reaxys
Further information
Brubacher,L.J.; Bender,M.L.; Journal of the American Chemical Society; vol. 88; (1966); p. 5871 - 5880, View in Reaxys
Further information
Fleming et al.; Analytical Chemistry; vol. 37; (1965); p. 692,693, View in Reaxys
Further information
Krupka; Biochemistry; vol. 4; (1965); p. 429,431, View in Reaxys
Further information
Freter,K. et al.; Justus Liebigs Annalen der Chemie; vol. 684; (1965); p. 159 - 187, View in Reaxys
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Further information
Hinman; Bauman; Journal of Organic Chemistry; vol. 29; (1964); p. 1206, View in Reaxys
Further information
Taborsky; McIsaac; Journal of Medicinal Chemistry; vol. 7; (1964); p. 135,140, View in Reaxys
Further information
Harley-Mason; Waterfield; Tetrahedron; vol. 19; (1963); p. 65,71, View in Reaxys
Further information
Trojanek et al.; Tetrahedron Letters; (1961); p. 702,706, View in Reaxys
Further information
Kirschenbaum; Parker; Spectrochimica Acta; vol. 17; (1961); p. 785,789; Chem.Abstr.; nb. 16254; (1960), View in Reaxys
Further information
Cohen et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 2184, View in Reaxys
Further information
Kanaoka et al.; Chemical and Pharmaceutical Bulletin; vol. 8; (1960); p. 294,296, View in Reaxys
Further information
Knowlton et al.; Analytical Chemistry; vol. 32; (1960); p. 666, View in Reaxys
Further information
Harley-Mason; Waterfield; Chemistry and Industry (London, United Kingdom); (1960); p. 1478, View in Reaxys
Further information
Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys
Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles
Method of determination: powder X-ray diffraction
Liquid Phase (1) Description (Liquid Phase)
References
Self-association in solution
Nowell, Harriott; Attfield, J. Paul; Cole, Jason C.; Acta Crystallographica Section B: Structural Science; vol. 58; nb. 5; (2002); p. 835 - 840, View in Reaxys
Helene; Dimicoli; Journal of the American Chemical Society; vol. 95; (1973); p. 1036, View in Reaxys
Liquid/Liquid Systems (MCS) (4) 1 of 4
Description (Liquid/ Liquid Systems (MCS))
Distribution between solvent 1 + 2
Solvent (Liquid/Liquid Systems (MCS))
H2O
Partner (Liquid/Liquid Systems (MCS))
toluene
Zissimos, Andreas M.; Abraham, Michael H.; Barker, Matthew C.; Box, Karl J.; Tam, Kin Y.; Journal of the Chemical Society. Perkin Transactions 2; nb. 3; (2002); p. 470 - 477, View in Reaxys 2 of 4
Description (Liquid/ Liquid Systems (MCS))
Distribution between solvent 1 + 2
Solvent (Liquid/Liquid Systems (MCS))
H2O
Partner (Liquid/Liquid Systems (MCS))
cyclohexane
Zissimos, Andreas M.; Abraham, Michael H.; Barker, Matthew C.; Box, Karl J.; Tam, Kin Y.; Journal of the Chemical Society. Perkin Transactions 2; nb. 3; (2002); p. 470 - 477, View in Reaxys 3 of 4
Description (Liquid/ Liquid Systems (MCS))
Distribution between solvent 1 + 2
Solvent (Liquid/Liquid Systems (MCS))
H2O
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Partner (Liquid/Liquid Systems (MCS))
chloroform
Zissimos, Andreas M.; Abraham, Michael H.; Barker, Matthew C.; Box, Karl J.; Tam, Kin Y.; Journal of the Chemical Society. Perkin Transactions 2; nb. 3; (2002); p. 470 - 477, View in Reaxys 4 of 4
Description (Liquid/ Liquid Systems (MCS))
Distribution between solvent 1 + 2
Kang; Green; Nature (London, United Kingdom); vol. 222; (1969); p. 794, View in Reaxys Molecular Deformation (2) Description (MoComment (Molec- References lecular Deforma- ular Deformation) tion) Rotational constants Rotational constants
Schmitt, Michael; Boehm, Marcel; Ratzer, Christian; Vu, Chau; Kalkman, Ivo; Meerts, W. Leo; Journal of the American Chemical Society; vol. 127; nb. 29; (2005); p. 10356 - 10364, View in Reaxys two conformers
Caminati, Walther; Physical Chemistry Chemical Physics; vol. 6; nb. 10; (2004); p. 2806 - 2809, View in Reaxys
Partition octan-1-ol/water (MCS) (2) 1 of 2
log POW
2.147
Zissimos, Andreas M.; Abraham, Michael H.; Barker, Matthew C.; Box, Karl J.; Tam, Kin Y.; Journal of the Chemical Society. Perkin Transactions 2; nb. 3; (2002); p. 470 - 477, View in Reaxys 2 of 2
log POW
1.35
Temperature (Partition octan-1-ol/water (MCS)) [°C]
24.85
Guardado, Pilar; Balon, Manuel; Carmona, Carmen; Munoz, Maria A.; Domene, Carmen; Journal of Pharmaceutical Sciences; vol. 86; nb. 1; (1997); p. 106 - 109, View in Reaxys Solubility (MCS) (1) 1 of 1
Comment (Solubility (MCS))
insoluble in buffer
Singudas, Rohith; Adusumalli, Srinivasa Rao; Joshi, Pralhad Namdev; Rai, Vishal; Chemical Communications; vol. 51; nb. 3; (2015); p. 473 - 476, View in Reaxys Space Group (1) Space Group 19
References Nowell, Harriott; Attfield, J. Paul; Cole, Jason C.; Acta Crystallographica Section B: Structural Science; vol. 58; nb. 5; (2002); p. 835 - 840, View in Reaxys
Transport Phenomena (MCS) (1) 1 of 1
Description (Transport Phenomena (MCS))
Diffusion
Temperature (Transport 25 Phenomena (MCS)) [°C] Partner (Transport Phenomena (MCS))
aq. sodium phosphate buffer
Robinson, David; Anderson, James E.; Lin, Jeong-long; Journal of Physical Chemistry; vol. 94; nb. 2; (1990); p. 1003 - 1005, View in Reaxys NMR Spectroscopy (32) 1 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
400
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Original Text (NMR Spectroscopy)
1H
Location
Paragraph 0045
NMR (400 MHz, DMSO-d6) δ 10.8 (br, 1H), 7.65 (brd, J = 7.6 Hz, 1H), 7.32 (brd, J = 8.0 Hz, 1H), 6.62-6.50 (d, J = 2.4 Hz, 1H), 7.05 (dd, J = 1.2, 8.0 Hz, 1H), 6.95 (dd, J = 1.2, 7.6 Hz, 1H), 2.82-2.71 (m, 4H), 2.52 (br, 2H)
Patent; Kyushu University, National University Corporation; OHSHIMA Takashi; MORIMOTO Hiroyuki; SHIMIZU Yuhei; EP2821389; (2015); (A1) English, View in Reaxys 2 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Original Text (NMR Spectroscopy)
13C NMR (100 MHz, CDCl ) δ 136.31, 127.38, 122.63, 120.86, 118.38, 118.26, 112.60, 3 111.37, 42.73, 29.48
Location
Paragraph 0045
Patent; Kyushu University, National University Corporation; OHSHIMA Takashi; MORIMOTO Hiroyuki; SHIMIZU Yuhei; EP2821389; (2015); (A1) English, View in Reaxys 3 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
250.1
Carvalho, Marcos A.; Arruda, Eduardo G.R.; Profirio, Daniel M.; Gomes, Alexandre F.; Gozzo, Fbio C.; Formiga, Andr L.B.; Corbi, Pedro P.; Journal of Molecular Structure; vol. 1100; (2015); p. 6 - 13; Art.No: 21675, View in Reaxys 4 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
62.9
Carvalho, Marcos A.; Arruda, Eduardo G.R.; Profirio, Daniel M.; Gomes, Alexandre F.; Gozzo, Fbio C.; Formiga, Andr L.B.; Corbi, Pedro P.; Journal of Molecular Structure; vol. 1100; (2015); p. 6 - 13; Art.No: 21675, View in Reaxys 5 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
15N
Carvalho, Marcos A.; Arruda, Eduardo G.R.; Profirio, Daniel M.; Gomes, Alexandre F.; Gozzo, Fbio C.; Formiga, Andr L.B.; Corbi, Pedro P.; Journal of Molecular Structure; vol. 1100; (2015); p. 6 - 13; Art.No: 21675, View in Reaxys 6 of 32
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Szostak, Michal; Sautier, Brice; Spain, Malcolm; Procter, David J.; Organic Letters; vol. 16; nb. 4; (2014); p. 1092 - 1095, View in Reaxys 7 of 32
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Szostak, Michal; Sautier, Brice; Spain, Malcolm; Procter, David J.; Organic Letters; vol. 16; nb. 4; (2014); p. 1092 - 1095, View in Reaxys 8 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Huan, Uozhen; Klin, Beata; Darras, Fouad H.; Heilmann, Joer; Decker, Michael; European Journal of Medicinal Chemistry; vol. 81; (2014); p. 15 - 21, View in Reaxys 9 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Jin, Huijuan; Zhang, Puyong; Bijian, Krikor; Ren, Sumei; Wan, Shengbiao; Alaoui-Jamali, Moulay A.; Jiang, Tao; Marine Drugs; vol. 11; nb. 5; (2013); p. 1427 - 1439, View in Reaxys 10 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
151
Jin, Huijuan; Zhang, Puyong; Bijian, Krikor; Ren, Sumei; Wan, Shengbiao; Alaoui-Jamali, Moulay A.; Jiang, Tao; Marine Drugs; vol. 11; nb. 5; (2013); p. 1427 - 1439, View in Reaxys 11 of 32
Description (NMR Spec- Chemical shifts; Spectrum troscopy)
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Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Baron, Marc; Metay, Estelle; Lemaire, Marc; Popowycz, Florence; Green Chemistry; vol. 15; nb. 4; (2013); p. 1006 - 1015, View in Reaxys 12 of 32
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Location
supporting information
Baron, Marc; Metay, Estelle; Lemaire, Marc; Popowycz, Florence; Green Chemistry; vol. 15; nb. 4; (2013); p. 1006 - 1015, View in Reaxys 13 of 32
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Zhu, Yan-Ping; Liu, Mei-Cai; Cai, Qun; Jia, Feng-Cheng; Wu, An-Xin; Chemistry - A European Journal; vol. 19; nb. 31; (2013); p. 10132 - 10137, View in Reaxys 14 of 32
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
29
Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Shimizu, Yuhei; Morimoto, Hiroyuki; Zhang, Ming; Ohshima, Takashi; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8564 - 8567, View in Reaxys 15 of 32
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)
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Temperature (NMR Spectroscopy) [°C]
29
Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Shimizu, Yuhei; Morimoto, Hiroyuki; Zhang, Ming; Ohshima, Takashi; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8564 - 8567, View in Reaxys 16 of 32
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Ankner, Tobias; Hilmersson, Goeran; Organic Letters; vol. 11; nb. 3; (2009); p. 503 - 506, View in Reaxys 17 of 32
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)
1H
Comment (NMR Spectroscopy)
Signals given
NMR (CDCl3), δ 8.35 (broad s, 1H), 7.64 (d, J=7.91 Hz, 1H), 7.44-7.32 (m, 1H), 7.26-7.18 (m, 1H), 7.18-7.09 (m, 1H), 7.04 (d, J=2.26 Hz, 1H), 1.36 (broad s, 2H), 3.11-3.01 (m, 2H), 2.99-2.86 (m, 2H)
Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys 18 of 32
Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)
13C NMR (CDCl ) δ 136.44, 127.49, 122.06, 121.96, 119.21, 118.87, 113.69, 111.16, 3 42.34, 29.49
Comment (NMR Spectroscopy)
Signals given
Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys 19 of 32
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300.13
Original Text (NMR Spectroscopy)
1H
Comment (NMR Spectroscopy)
Signals given
NMR (CDCl3), 8.35 (broad s, 1H), 7.64 (d, J=7.91 Hz, 1H), 7.44 - 7.32 (m, 1H), 7.26 7.18 (m, 1H), 7.18 - 7.09 (m, 1H), 7.04 (d, J=2.26 Hz, 1H), 1.36 (broad s, 2H), 3.11 - 3.01 (m,2H), 2.99 - 2.86 (m, 2H)
Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys 20 of 32
Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy)
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Frequency (NMR Spectroscopy) [MHz]
75.43
Original Text (NMR Spectroscopy)
13C NMR (CDCl ) 136.44, 127.49, 122.06, 121.96, 119.21, 118.87, 113.69, 111.16, 42.34, 3 29.49
Comment (NMR Spectroscopy)
Signals given
Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys 21 of 32
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
15
Frequency (NMR Spectroscopy) [MHz]
600.468
Maresh, Justin J.; Giddings, Lesley-Ann; Friedrich, Anne; Loris, Elke A.; Panjikar, Santosh; Trout, Bernhardt L.; Stoeckigt, Joachim; Peters, Baron; O'Connor, Sarah E.; Journal of the American Chemical Society; vol. 130; nb. 2; (2008); p. 710 - 723, View in Reaxys 22 of 32
Description (NMR Spec- 2D-NMR troscopy) Nucleus (NMR Spectroscopy)
13C; 1H
Maresh, Justin J.; Giddings, Lesley-Ann; Friedrich, Anne; Loris, Elke A.; Panjikar, Santosh; Trout, Bernhardt L.; Stoeckigt, Joachim; Peters, Baron; O'Connor, Sarah E.; Journal of the American Chemical Society; vol. 130; nb. 2; (2008); p. 710 - 723, View in Reaxys 23 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
300.13
Choy, Jason; Jaime-Figueroa, Saul; Jiang, Laurence; Wagner, Paul; Synthetic Communications; vol. 38; nb. 21; (2008); p. 3840 - 3853, View in Reaxys 24 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
75.43
Choy, Jason; Jaime-Figueroa, Saul; Jiang, Laurence; Wagner, Paul; Synthetic Communications; vol. 38; nb. 21; (2008); p. 3840 - 3853, View in Reaxys 25 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy)
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Frequency (NMR Spectroscopy) [MHz]
300
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys 26 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Diallo. A. O.; Mehri, H.; Iouzalen, L.; Plat, M.; Phytochemistry (Elsevier); vol. 40; nb. 3; (1995); p. 975 - 978, View in Reaxys; Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414, View in Reaxys 27 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
90
Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414, View in Reaxys 28 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Sato, Hiroji; Kawagishi, Hirokazu; Nishimura, Tsutomu; Yoneyama, Syozou; Yoshimoto, Yuko; et al.; Agricultural and Biological Chemistry; vol. 49; nb. 10; (1985); p. 2969 - 2974, View in Reaxys 29 of 32
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
35
Ernst, Ludger; Kang, Sungzong; Journal of Chemical Research, Miniprint; nb. 9; (1981); p. 3019 - 3038, View in Reaxys 30 of 32
Description (NMR Spec- NMR troscopy) Konda; Suzuki; Omura; Onda; Chemical and Pharmaceutical Bulletin; vol. 24; nb. 1; (1976); p. 92 - 96, View in Reaxys; Helene; Dimicoli; Journal of the American Chemical Society; vol. 95; (1973); p. 1036, View in Reaxys; Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys
31 of 32
Description (NMR Spec- Spin-spin coupling constants troscopy) Culvenor,C.C.J.; Ham,N.S.; Australian Journal of Chemistry; vol. 27; (1974); p. 2191 - 2198, View in Reaxys
32 of 32
Description (NMR Spec- Spectrum troscopy) Cohen et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 2184, View in Reaxys
IR Spectroscopy (3)
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1 of 3
Description (IR Spectroscopy)
Bands
Kanaoka et al.; Chemical and Pharmaceutical Bulletin; vol. 8; (1960); p. 294,296, View in Reaxys; Carvalho, Marcos A.; Arruda, Eduardo G.R.; Profirio, Daniel M.; Gomes, Alexandre F.; Gozzo, Fbio C.; Formiga, Andr L.B.; Corbi, Pedro P.; Journal of Molecular Structure; vol. 1100; (2015); p. 6 - 13; Art.No: 21675, View in Reaxys 2 of 3
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
film
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys 3 of 3
Description (IR Spectroscopy)
IR
Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys; De Antoni et al.; Gazzetta Chimica Italiana; vol. 100; (1970); p. 1039,1042, 1044, View in Reaxys Mass Spectrometry (18) Description (Mass Location Spectrometry)
Comment (Mass Spectrometry)
References
liquid chromatography mass spectrometry (LCMS); high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum
Kalb, Daniel; Gressler, Julia; Hoffmeister, Dirk; ChemBioChem; vol. 17; nb. 2; (2016); p. 132 - 136, View in Reaxys
liquid chromatog- Page/Page colraphy mass spec- umn 85 trometry (LCMS); spectrum
Patent; UCL BUSINESS PLC; MARSON, Charles Michael; FERRETTI, Patrizia; WO2014/188193; (2014); (A1) English, View in Reaxys
high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum
Baron, Marc; Metay, Estelle; Lemaire, Marc; Popowycz, Florence; Green Chemistry; vol. 15; nb. 4; (2013); p. 1006 - 1015, View in Reaxys
tandem mass spectrometry; CID (collision-induced dissociation); electrospray ionisation (ESI); liquid chromatography mass spectrometry (LCMS); spectrum
Rangiah, Kannan; Palakodeti, Dasaradhi; Rapid Communications in Mass Spectrometry; vol. 27; nb. 21; (2013); p. 2439 - 2452, View in Reaxys
liquid chromatography mass spectrometry (LCMS); electrospray ionisation (ESI); tandem mass spectrometry; spectrum
Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Casale, Rosario; Cautela, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 61; nb. 21; (2013); p. 5156 5162, View in Reaxys
spectrum
Elam, Jeffrey W.; Levy, Donald H.; Journal of Physical Chemistry B; vol. 102; nb. 41; (1998); p. 8113 - 8120, View in Reaxys; Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Cautela, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 60; nb. 37; (2012); p. 9512 - 9518,7, View in Reaxys; Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Cautela,
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Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 60; nb. 37; (2012); p. 9512 - 9518, View in Reaxys LCMS (Liquid chromatography mass spectrometry); Spectrum
Urayama, Shiro; Zou, Wei; Brooks, Kindra; Tolstikov, Vladimir; Rapid Communications in Mass Spectrometry; vol. 24; nb. 5; (2010); p. 613 - 620, View in Reaxys
ESI (Electrospray ionisation)
Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys
ESI (Electrospray ionisation); HRMS (High resolution mass spectrometry)
Patent; Roch Palo Alto LLC; US2009/203910; (2009); (A1) English, View in Reaxys
ESI (Electrospray ionisation)
Molecular peak
Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys
ESI (Electrospray ionisation); HRMS (High resolution mass spectrometry)
Molecular peak
Patent; F. Hoffmann-La Roche AG; EP2070899; (2009); (A1) English, View in Reaxys
spectrum; tandem mass spectrometry
Williamson, Brian L.; Benson, Linda M.; Tomlinson, Andy J.; Mayeno, Arthur N.; Gleich, Gerald J.; Naylor, Stephen; Toxicology Letters; vol. 92; nb. 2; (1997); p. 139 - 148, View in Reaxys
fragmentation pattern
MIKE (mass ion kinetic energy)
Bertazzo, Antonella; Catinella, Silvia; Traldi, Pietro; Journal of Mass Spectrometry; vol. 31; nb. 7; (1996); p. 735 - 740, View in Reaxys
spectrum; electron impact (EI)
FAB (fast atom bombardment)
Bertazzo, Antonella; Catinella, Silvia; Traldi, Pietro; Journal of Mass Spectrometry; vol. 31; nb. 7; (1996); p. 735 - 740, View in Reaxys
spectrum
laser desorption
Hrubowchak; Ervin; Wood; Winograd, Nicholas; Analytical Chemistry; vol. 63; nb. 18; (1991); p. 1947 - 1953, View in Reaxys; Tembreull; Lubman; Analytical chemistry; vol. 59; nb. 8; (1987); p. 1082 - 1088, View in Reaxys; Li, Liang; Lubman, David M.; Analytical Chemistry; vol. 61; nb. 17; (1989); p. 1911 - 1915, View in Reaxys; Wang, Alan P. L.; Guo, Xijian; Li, Liang; Analytical Chemistry; vol. 66; nb. 21; (1994); p. 3664 - 3675, View in Reaxys
spectrum; electron impact (EI)
Gynther, Jukka; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 42; nb. 7; (1988); p. 433 - 441, View in Reaxys
spectrum; chemical ionization (CI)
Gynther, Jukka; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 42; nb. 7; (1988); p. 433 - 441, View in Reaxys Reisch et al.; Journal of Pharmacy and Pharmacology; vol. 20; (1968); p. 81,85, View in Reaxys; Jamieson; Hutzinger; Phytochemistry (Elsevier); vol. 9; (1970); p. 2029,2033, View in Reaxys; Milne et al.; Analytical Chemistry; vol. 45; (1973); p. 1952,1953, View in Reaxys; Chmel'nickij et al.; Zhurnal Organicheskoi Khimii; vol. 5; (1969); p. 417,406, View in Reaxys; Agurell et al.; Acta Chemica Scandinavica (1947-1973); vol. 23; (1969); p. 903, View in Reaxys; Ghosal; Srivastava; Phytochemistry (Elsevier); vol. 12; (1973); p. 193,196, View in Reaxys
UV/VIS Spectroscopy (18) 1 of 18
Description (UV/VIS Spectroscopy)
Spectrum
LeGreve, Tracy A.; Baquero, Esteban E.; Zwier, Timothy S.; Journal of the American Chemical Society; vol. 129; nb. 13; (2007); p. 4028 - 4038, View in Reaxys; Kalb, Daniel; Gressler, Julia; Hoffmeister, Dirk; ChemBioChem; vol. 17; nb. 2; (2016); p. 132 - 136, View in Reaxys 2 of 18
Description (UV/VIS Spectroscopy)
Spectrum
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Solvent (UV/VIS Spectroscopy)
water
Lynch, Daniel E.; Cox, Martin J.; King, Patrick M.; Smith, Graham; Journal of Photochemistry and Photobiology A: Chemistry; vol. 324; (2016); p. 87 - 95, View in Reaxys 3 of 18
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
water; dimethyl sulfoxide
Lynch, Daniel E.; Cox, Martin; Smith, Graham; Dyes and Pigments; vol. 121; (2015); p. 385 - 393, View in Reaxys 4 of 18
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
acetonitrile; H2O
Comment (UV/VIS Spectroscopy)
Ratio of solvents: 70:30 v/v
Ling, Ke-Qing; Li, Wen-Shan; Sayre, Lawrence M.; Journal of the American Chemical Society; vol. 130; nb. 3; (2008); p. 933 - 944, View in Reaxys 5 of 18
Solvent (UV/VIS Spectroscopy)
various solvent(s)
Comment (UV/VIS Spectroscopy)
Remark: in liquid helium
Absorption Maxima (UV/ 286.044 VIS) [nm] Lindinger, Albrecht; Lugovoj, Eugene; Peter Toennies; Vilesov, Andrei F.; Zeitschrift fur Physikalische Chemie; vol. 215; nb. 3; (2001); p. 401 - 416, View in Reaxys 6 of 18
Description (UV/VIS Spectroscopy)
UV two-photon absorption
Comment (UV/VIS Spectroscopy)
gas
Carney, Joel R.; Zwier, Timothy S.; Chemical Physics Letters; vol. 341; nb. 1-2; (2001); p. 77 - 85, View in Reaxys 7 of 18
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
1,2-dichloro-ethane
Comment (UV/VIS Spectroscopy)
200 - 610 nm
Abu-Eittah; Abdou; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 93; nb. 11-12; (1996); p. 1958 - 1973, View in Reaxys 8 of 18
Description (UV/VIS Spectroscopy)
Absorption maxima
Solvent (UV/VIS Spectroscopy)
aq. KOH; methanol
Absorption Maxima (UV/ 220; 278; 286 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
36308; 5888; 4266
Balon, Manuel; Hidalgo, Jose; Guardado, Pilar; Munoz, Maria A.; Carmona, Carmen; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 1; (1993); p. 91 - 97, View in Reaxys 9 of 18
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
gaseous matrix
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Comment (UV/VIS Spectroscopy)
285.5 - 287.5 nm
Pang, Ho Ming; Lubman, David M.; Analytical Chemistry; vol. 61; nb. 7; (1989); p. 777 - 779, View in Reaxys 10 of 18
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
gaseous matrix
Comment (UV/VIS Spectroscopy)
284.5 - 287.5 nm
Li, Liang; Lubman, David M.; Analytical Chemistry; vol. 60; nb. 23; (1988); p. 2591 - 2598, View in Reaxys 11 of 18
Description (UV/VIS Spectroscopy)
Absorption maxima
Solvent (UV/VIS Spectroscopy)
ethanol
Absorption Maxima (UV/ 292; 282; 276; 228 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
4467; 5370; 5129; 33884
Groen, C.; Christophersen, C.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 38; nb. 8; (1984); p. 709 - 712, View in Reaxys 12 of 18
Description (UV/VIS Spectroscopy)
Absorption maxima
Solvent (UV/VIS Spectroscopy)
ethanol
Absorption Maxima (UV/ 292; 284; 276; 228 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
4467; 5370; 5129; 33884
Groen, C.; Christophersen, C.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 38; nb. 8; (1984); p. 709 - 712, View in Reaxys 13 of 18
Description (UV/VIS Spectroscopy)
Absorption maxima
Solvent (UV/VIS Spectroscopy)
H2O
Absorption Maxima (UV/ 450 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
200
Deetz, J. S.; Behrman, E. J.; Journal of Organic Chemistry; vol. 45; nb. 1; (1980); p. 135 - 140, View in Reaxys 14 of 18
Description (UV/VIS Spectroscopy)
Absorption maxima
Jackson; Smith; Journal of the Chemical Society; (1965); p. 3498, View in Reaxys; Ramachandran; Witkop; Biochemistry; vol. 3; (1964); p. 1603,1606, View in Reaxys; Jackson; Smith; Journal of the Chemical Society; (1964); p. 5510,5511, View in Reaxys; Gasco; Farmaco, Edizione Scientifica; vol. 30; (1975); p. 512,513, View in Reaxys; Hinman; Lang; Journal of the American Chemical Society; vol. 86; (1964); p. 3796,3797,3804, View in Reaxys 15 of 18
Description (UV/VIS Spectroscopy)
Triplet-triplet band
Bazin et al.; Chemical Physics Letters; vol. 36; (1975); p. 505,506, 507, View in Reaxys 16 of 18
Description (UV/VIS Spectroscopy)
UV/VIS
Mollan et al.; Phytochemistry (Elsevier); vol. 12; (1973); p. 447,448, View in Reaxys; Yagil; Tetrahedron; vol. 23; nb. 6; (1967); p. 2855 - 2861, View in Reaxys; Grandberg; Bobrova; Chemistry of Heterocyclic Compounds (New
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York, NY, United States); vol. 9; (1973); p. 196,199; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 213, View in Reaxys; Ghosal; Srivastava; Phytochemistry (Elsevier); vol. 12; (1973); p. 193,196, View in Reaxys 17 of 18
Description (UV/VIS Spectroscopy)
Spectrum
Comment (UV/VIS Spectroscopy)
230 - 390 nm
Hoshino; Tamura; Justus Liebigs Annalen der Chemie; vol. 500; (1933); p. 42,45, View in Reaxys; Claudatus et al.; Archives of Biochemistry; vol. 72; (1957); p. 316,319, View in Reaxys 18 of 18
Description (UV/VIS Spectroscopy)
Absorption maxima
Absorption Maxima (UV/ 222; 276; 282; 291 VIS) [nm] Noland; Hartman; Journal of the American Chemical Society; vol. 76; (1954); p. 3227, View in Reaxys ESR Spectroscopy (1) 1 of 1
Description (ESR Spectroscopy)
Spectrum
Grady et al.; Journal of the American Chemical Society; vol. 90; (1968); p. 2949, View in Reaxys Rotational Spectroscopy (2) Description (Rota- Comment (Rota- References tional Spectrosco- tional Spectroscopy) py) Rotational spectrum
vibrational analysis
Schmitt, Michael; Boehm, Marcel; Ratzer, Christian; Vu, Chau; Kalkman, Ivo; Meerts, W. Leo; Journal of the American Chemical Society; vol. 127; nb. 29; (2005); p. 10356 - 10364, View in Reaxys
Rotational spectrum
two conformers
Caminati, Walther; Physical Chemistry Chemical Physics; vol. 6; nb. 10; (2004); p. 2806 - 2809, View in Reaxys
Luminescence Spectroscopy (5) Description (LuComment (Lumiminescence nescence SpecSpectroscopy) troscopy)
References
Luminescence quantum yield
Lasser; Feitelson; Journal of Physical Chemistry; vol. 77; (1973); p. 1011,1015, View in Reaxys; Ricci; Photochemistry and Photobiology; vol. 12; (1970); p. 67,70, View in Reaxys; Szabo, A. G.; Rayner, D. M.; Journal of the American Chemical Society; vol. 102; nb. 2; (1980); p. 554 - 563, View in Reaxys; Shetty, Ashok S.; Majumdar, Nirmalya; Aruna, R. V.; Singh, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 2; (1993); p. 208 - 210, View in Reaxys; Arnold, Steven; Tong, Ling; Sulkes, Mark; Journal of Physical Chemistry; vol. 98; nb. 9; (1994); p. 2325 - 2327, View in Reaxys; Eftink, Maurice R.; Jia, Yiwei; Hu, Dana; Ghiron, Camillo, A.; Journal of Physical Chemistry; vol. 99; (1995); p. 5713 - 5723, View in Reaxys
Luminescence lifetime
Lasser; Feitelson; Journal of Physical Chemistry; vol. 77; (1973); p. 1011,1015, View in Reaxys; Szabo, A. G.; Rayner, D. M.; Journal of the American Chemical Society; vol. 102; nb. 2; (1980); p. 554 - 563, View in Reaxys; Arnold, Steven; Tong, Ling; Sulkes, Mark; Journal of Physical Chemistry; vol. 98; nb. 9; (1994); p. 2325 - 2327, View in Reaxys; Eftink, Maurice R.; Jia, Yiwei; Hu, Dana; Ghiron, Camillo, A.; Journal of Physical Chemistry; vol. 99; (1995); p. 5713 - 5723, View in Reaxys
Electroluminescence
Sipior, Jeffrey; Sulkes, Mark; Journal of Chemical Physics; vol. 88; nb. 10; (1988); p. 6146 - 6156, View in Reaxys
Luminescence quenching
Froehlich; Nelson; Journal of Physical Chemistry; vol. 82; (1978); p. 2401, View in Reaxys; Lasser; Feitelson; Journal of Physical Chemistry; vol. 77; (1973); p. 1011,1015, View in Reaxys; Davidson; Trethewey; Journal of the American Chemical Society; vol. 98; (1976); p. 4008, View in Reaxys; Eftink; Ghiron; Journal of Physical Chemistry; vol. 800; (1976); p. 486,489, View in Reaxys
Luminescence quantum yield
Quantenausbeute White; Biochemical Journal; vol. 71; (1959); p. 217,219, View in Reaxys der Fluorescenz von wss. Loesungen vom pH 7-12.
Fluorescence Spectroscopy (18)
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Description (Fluo- Solvent (Fluoresrescence Speccence Spectrotroscopy) scopy)
Comment (Fluorescence Spectroscopy)
References
Maxima; Spectrum
Meng, Xue; Guo, Wenjuan; Qin, Xiaoli; Liu, Yiming; Zhu, Xiangwei; Pei, Meishan; Wang, Luyan; RSC Advances; vol. 4; nb. 73; (2014); p. 38649 - 38654, View in Reaxys
Fluorescence
Bowman et al.; Science (Washington, DC, United States); vol. 122; (1955); p. 32, View in Reaxys; Kirby; Steiner; Journal of Physical Chemistry; vol. 74; (1970); p. 4480, View in Reaxys; Bridges; Williams; Biochemical Journal; vol. 107; (1968); p. 225,228, View in Reaxys; Roshchupkin et al.; Photochemistry and Photobiology; vol. 30; (1979); p. 635,637, View in Reaxys; Lawaczeck; Berichte der Bunsen-Gesellschaft; vol. 82; (1978); p. 930, View in Reaxys; Abdallah et al.; European Journal of Biochemistry; vol. 89; (1978); p. 397,401, View in Reaxys; Feng, Ke; Kleinermanns, Karl; Chemical Physics Letters; vol. 473; nb. 4-6; (2009); p. 220 - 222, View in Reaxys
Fluorescence excitation spectrum
influence of an electric field. Object(s) of Study: vapour
Nguyen, Tri V.; Pratt, David W.; Journal of Chemical Physics; vol. 124; nb. 5; (2006); Art.No: 054317, View in Reaxys
Fluorescence excitation spectrum
vapour
Clarkson, Jasper R.; Dian, Brian C.; Moriggi, Loick; Defusco, Albert; McCarthy, Valerie; Jordan, Kenneth D.; Zwier, Timothy S.; Journal of Chemical Physics; vol. 122; nb. 21; (2005); Art.No: 214311, View in Reaxys
Maxima
vapour
Fluorescence quantum yield
Clarkson, Jasper R.; Dian, Brian C.; Moriggi, Loick; Defusco, Albert; McCarthy, Valerie; Jordan, Kenneth D.; Zwier, Timothy S.; Journal of Chemical Physics; vol. 122; nb. 21; (2005); Art.No: 214311, View in Reaxys pH dependence
Guzow, Katarzyna; Szabelski, Mariusz; Rzeska, Alicja; Karolczak, Jerzy; Sulowska, Hanna; Wiczk, Wieslaw; Chemical Physics Letters; vol. 362; nb. 5-6; (2002); p. 519 - 526, View in Reaxys
Spectrum
various solvent(s)
low temperature. Object(s) of Study: various conformers
Lindinger, Albrecht; Lugovoj, Eugene; Peter Toennies; Vilesov, Andrei F.; Zeitschrift fur Physikalische Chemie; vol. 215; nb. 3; (2001); p. 401 - 416, View in Reaxys
Maxima
various solvent(s)
low temperature. Object(s) of Study: various conformers
Lindinger, Albrecht; Lugovoj, Eugene; Peter Toennies; Vilesov, Andrei F.; Zeitschrift fur Physikalische Chemie; vol. 215; nb. 3; (2001); p. 401 - 416, View in Reaxys
Fluorescence excitation spectrum; Spectrum
Piuzzi, Francois; Dimicoli, Iliana; Mons, Michel; Tardivel, Benjamin; Zhao, Qingchun; Chemical Physics Letters; vol. 320; nb. 3-4; (2000); p. 282 - 288, View in Reaxys
Maxima
H2O
363 nm
Eftink, Maurice R.; Jia, Yiwei; Hu, Dana; Ghiron, Camillo, A.; Journal of Physical Chemistry; vol. 99; (1995); p. 5713 - 5723, View in Reaxys
Spectrum
methanol
300 - 450 nm
Shetty, Ashok S.; Majumdar, Nirmalya; Aruna, R. V.; Singh, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 2; (1993); p. 208 - 210, View in Reaxys
Spectrum
various solvent(s)
300 - 450 nm
Shetty, Ashok S.; Majumdar, Nirmalya; Aruna, R. V.; Singh, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 2; (1993); p. 208 - 210, View in Reaxys
Maxima
aq. KOH; methanol
361 nm
Balon, Manuel; Hidalgo, Jose; Guardado, Pilar; Munoz, Maria A.; Carmona, Carmen; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 1; (1993); p. 91 - 97, View in Reaxys
Maxima
various solvent(s)
346 nm
Shetty, Ashok S.; Majumdar, Nirmalya; Aruna, R. V.; Singh, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Includ-
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ing Medicinal Chemistry; vol. 32; nb. 2; (1993); p. 208 - 210, View in Reaxys Maxima
methanol
352 nm
Shetty, Ashok S.; Majumdar, Nirmalya; Aruna, R. V.; Singh, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 2; (1993); p. 208 - 210, View in Reaxys
Spectrum
CHCl3
294.12 - 285.71 nm
Peteanu, Linda A.; Levy, Donald H.; Journal of Physical Chemistry; vol. 92; nb. 23; (1988); p. 6554 - 6561, View in Reaxys
Spectrum
287.36 - 278.55 nm
Park, Young D.; Rizzo, Thomas R.; Peteanu, Linda A.; Levy, Donald H.; Journal of Chemical Physics; vol. 84; nb. 12; (1986); p. 6539 - 6549, View in Reaxys
Maxima
Intensitaet der Fluorescenz von wss. Loesungen vom pH 1-7.
White; Biochemical Journal; vol. 71; (1959); p. 217,219, View in Reaxys
Phosphorescence Spectroscopy (1) Description References (Phosphorescence Spectroscopy) Phosphorescence Svejda et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 7138, View in Reaxys Other Spectroscopic Methods (1) Description (Oth- References er Spectroscopic Methods) Photoelectron spectrum
Domelsmith et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 4311,4315, View in Reaxys
Pharmacological Data (193) 1 of 193
Comment (Pharmacological Data)
Bioactivities present
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D.; Organic Letters; vol. 18; nb. 5; (2016); p. 1198 - 1201, View in Reaxys; Li, Jun; Li, Jianzu; Xu, Yuan; Wang, Yunjie; Zhang, Luyong; Ding, Li; Xuan, Yining; Pang, Tao; Lin, Hansen; Natural Product Research; vol. 30; nb. 7; (2016); p. 800 - 805, View in Reaxys; Bertamino, Alessia; Ostacolo, Carmine; Ambrosino, Paolo; Musella, Simona; Di Sarno, Veronica; Ciaglia, Tania; Soldovieri, Maria Virginia; Iraci, Nunzio; Fernandez Carvajal, Asia; De La Torre-Martinez, Roberto; Ferrer-Montiel, Antonio; Gonzalez Muniz, Rosario; Novellino, Ettore; Taglialatela, Maurizio; Campiglia, Pietro; Gomez-Monterrey, Isabel; Journal of Medicinal Chemistry; vol. 59; nb. 5; (2016); p. 2179 2191, View in Reaxys; Suja, Thachapully D.; Divya; Naik, Lakshma V.; Ravi Kumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 8; (2016); p. 2072 - 2076, View in Reaxys; Lai, Bingbing; Huang, Zhipeng; Jia, Zhifang; Bai, Rongxian; Gu, Yanlong; Catalysis Science and Technology; vol. 6; nb. 6; (2016); p. 1810 - 1820, View in Reaxys; Lynch, Daniel E.; Cox, Martin J.; King, Patrick M.; Smith, Graham; Journal of Photochemistry and Photobiology A: Chemistry; vol. 324; (2016); p. 87 - 95, View in Reaxys; Muscia, Gisela C.; De Mara, Leonardo O.; Buldain, Graciela Y.; Ass, Silvia E.; Journal of Heterocyclic Chemistry; vol. 53; nb. 2; (2016); p. 647 - 650, View in Reaxys; Singh, Thokchom Prasanta; Singh, Okram Mukherjee; Journal of Chemical Sciences; vol. 128; nb. 4; (2016); p. 565 - 572, View in Reaxys; Okada, Masashi; Mei, Zhen-Wu; Imran Hossain, Md.; Wang, Li; Tominaga, Taihei; Takebayashi, Takeshi; Murakami, Masaharu; Yasuda, Mizuki; Shigehiro, Tsukasa; Kasai, Tomonari; Mizutani, Akifumi; Murakami, Hiroshi; El Sayed, Ibrahim El Tantawy; Dan, Shingo; Yamori, Takao; Seno, Masaharu; Inokuchi, Tsutomu; Medicinal Chemistry Research; vol. 25; nb. 5; (2016); p. 879 892, View in Reaxys; brnyi-Balogh, Pter; Földesi, Tams; Grün, Alajos; Volk, Balzs; Keglevich, György; Milen, Mtys; Tetrahedron Letters; vol. 57; nb. 18; (2016); p. 1953 - 1957, View in Reaxys; Deldaele, Christopher; Evano, Gwilherm; ChemCatChem; vol. 8; nb. 7; (2016); p. 1319 - 1328, View in Reaxys; Filipponi, Paolo; Baxendale, Ian
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R.; European Journal of Organic Chemistry; vol. 2016; nb. 11; (2016); p. 2000 - 2012, View in Reaxys; Wehle, Sarah; Espargar, Alba; Sabat, Raimon; Decker, Michael; Tetrahedron; vol. 72; nb. 20; (2016); p. 2535 - 2543, View in Reaxys; Dine, Tharwat Mohy El; Evans, David; Rouden, Jacques; Blanchet, Jrme; Chemistry - A European Journal; vol. 22; nb. 17; (2016); p. 5894 - 5898, View in Reaxys; Patent; UNIVERSITÄT REGENSBURG; FRIEDRICH-SCHILLER-UNIVERSITÄT JENA; UNIVERSITÄTSKLINIKUM JENA; MAHBOOBI, Siavosh; SELLMER, Andreas; PONGRATZ, Herwig; LEONHARDT, Michel; KRÄMER, Oliver; BÖHMER, Frank-Dietmar; KELTER, Gerhard; (257 pag.); WO2016/20369; (2016); (A1) English, View in Reaxys; Knouse, Kyle W.; Wuest, William M.; Journal of Antibiotics; vol. 69; nb. 4; (2016); p. 337 - 339, View in Reaxys; Zheng, Nan; Chang, YuanYuan; Zhang, Li-Jie; Gong, Jian-Xian; Yang, Zhen; Chemistry - An Asian Journal; vol. 11; nb. 3; (2016); p. 371 375, View in Reaxys; Devaraj; Sollert; Juds; Gates; Pilarski; Chemical Communications; vol. 52; nb. 34; (2016); p. 5868 - 5871, View in Reaxys; Subba Reddy; Reddy; Siriwardena; Organic and Biomolecular Chemistry; vol. 14; nb. 18; (2016); p. 4276 - 4282, View in Reaxys; Abhishek A. Kulkarni; Amol M. Pachpinde; Devanand B. Shinde; Firoz A. Kalam Khan; Jaiprakash N. Sangshetti; Kishan S. Lohar; Rajendra H. Patil; Bioorganic & medicinal chemistry letters; vol. 26; (2016); p. 829 - 835, View in Reaxys 2 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Hosaka, Shinya; Murayama, Norie; Satsukawa, Masahiro; Shimizu, Makiko; Uehara, Shotaro; Fujino, Hideki; Iwasaki, Kazuhide; Iwano, Shunsuke; Uno, Yasuhiro; Yamazaki, Hiroshi; Drug Metabolism and Disposition; vol. 43; nb. 1; (2015); p. 27 - 33, View in Reaxys 3 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Henrottin, Jean; Zervosen, Astrid; Lemaire, Christian; Sapunaric, Frdric; Laurent, Sophie; Van Den Eynde, Benoit; Goldman, Serge; Plenevaux, Alain; Luxen, Andr; ACS Medicinal Chemistry Letters; vol. 6; nb. 3; (2015); p. 260 - 265, View in Reaxys 4 of 193
Location
Paragraph
Comment (Pharmacological Data)
physiological behaviour discussed
Patent; THE BOARD OF REGENTS OF THE NEVADA SYSTEM OF HIGHER EDUCATION ON BEHALF OF THE UNIVERSITY; Abel-Santos, Ernesto; US2015/173357; (2015); (A1) English, View in Reaxys 5 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Shaala, Lamiaa A.; Youssef, Diaa T. A.; Marine Drugs; vol. 13; nb. 4; (2015); p. 1698 - 1709, View in Reaxys 6 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Eleftheriadis, Nikolaos; Neochoritis, Constantinos G.; Leus, Niek G. J.; Van Der Wouden, Petra E.; Dömling, Alexander; Dekker, Frank J.; Journal of Medicinal Chemistry; vol. 58; nb. 19; (2015); p. 7850 - 7862, View in Reaxys 7 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Chapy, Hlne; Goracci, Laura; Vayer, Philippe; Parmentier, Yannick; Carrupt, Pierre-Alain; Declves, Xavier; Scherrmann, Jean-Michel; Cisternino, Salvatore; Cruciani, Gabriele; British Journal of Pharmacology; vol. 172; nb. 20; (2015); p. 4888 - 4904, View in Reaxys 8 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Cheng, Yating; Jin, Un-Ho; Allred, Clint D.; Jayaraman, Arul; Chapkin, Robert S.; Safe, Stephen; Drug Metabolism and Disposition; vol. 43; nb. 10; (2015); p. 1536 - 1543, View in Reaxys 9 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Liu, Changlu; Bonaventure, Pascal; Lee, Grace; Nepomuceno, Diane; Kuei, Chester; Wu, Jiejun; Li, Qingqin; Joseph, Victory; Sutton, Steven W.; Eckert, William; Yao, Xiang; Yieh, Lynn; Dvorak, Curt; Carruthers, Nicholas; Coate, Heather; Yun, Sujin; Dugovic, Christine; Harrington, Anthony; Lovenberg, Timothy W.; Molecular Pharmacology; vol. 88; nb. 5; (2015); p. 911 - 925, View in Reaxys 10 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Herington, Jennifer L.; Swale, Daniel R.; Brown, Naoko; Shelton, Elaine L.; Choi, Hyehun; Williams, Charles H.; Hong, Charles C.; Paria, Bibhash C.; Denton, Jerod S.; Reese, Jeff; PLoS ONE; vol. 10; nb. 11; (2015); Art.No: E0143243, View in Reaxys
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Comment (Pharmacological Data)
physiological behaviour discussed
Jin, Un-Ho; Lee, Syng-Ook; Sridharan, Gautham; Lee, Kyongbum; Davidson, Laurie A.; Jayaraman, Arul; Chapkin, Robert S.; Alaniz, Robert; Safe, Stephen; Molecular Pharmacology; vol. 85; nb. 5; (2014); p. 777 - 788, View in Reaxys 12 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Oliveira, Rafael R.B.; Brito, Thaysnara B.; Nepel, Angelita; Costa, Emmanoel V.; Barison, Andersson; Nunes, Rogeria S.; Santos, Roseli L.C.; Cavalcanti, Socrates C.H.; Medicinal Chemistry; vol. 10; nb. 6; (2014); p. 580 587, View in Reaxys 13 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys 14 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Toy, Nurten; Özogul, Fatih; Özogul, Yesim; Food Chemistry; vol. 173; (2014); p. 45 - 53, View in Reaxys 15 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Luetje, Charles W.; Chen, Sisi; F1000Research; vol. 3; (2014), View in Reaxys 16 of 193
Effect (Pharmacological Data)
receptor; activation of
Species or Test-System (Pharmacological Data)
HEK293TGα16gust44 cells of human; genetically modified/infected with: human taste 2 receptor 39
Concentration (Pharmacological Data)
<= 0.03 mmol/l
Method (Pharmacological Data)
name of assay/method: spectrofluorometric assay using calcium-sensitive dye Fluo-4-AM
Further Details (Pharmacological Data)
HEK293TGα16gust44: HEK293T embryonic kidney cells stably expressing the chimeric G-protein α-subunit Gα16-Gust44;
Results
no effect (related to human taste 2 receptor 39)
Kohl, Susann; Behrens, Maik; Dunkel, Andreas; Hofmann, Thomas; Meyerhof, Wolfgang; Journal of Agricultural and Food Chemistry; vol. 61; nb. 1; (2013); p. 53 - 60, View in Reaxys 17 of 193
Effect (Pharmacological Data)
receptor; activation of
Species or Test-System (Pharmacological Data)
HEK293TGα16gust44 cells of human; genetically modified/infected with: human taste 2 receptor 4
Concentration (Pharmacological Data)
<= 0.03 mmol/l
Method (Pharmacological Data)
name of assay/method: spectrofluorometric assay using calcium-sensitive dye Fluo-4-AM
Further Details (Pharmacological Data)
HEK293TGα16gust44: HEK293T embryonic kidney cells stably expressing the chimeric G-protein α-subunit Gα16-Gust44;
Results
no effect (related to human taste 2 receptor 4)
Kohl, Susann; Behrens, Maik; Dunkel, Andreas; Hofmann, Thomas; Meyerhof, Wolfgang; Journal of Agricultural and Food Chemistry; vol. 61; nb. 1; (2013); p. 53 - 60, View in Reaxys 18 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
Broadley, Kenneth J.; Fehler, Martina; Ford, William R.; Kidd, Emma J.; European Journal of Pharmacology; vol. 715; nb. 1-3; (2013); p. 370 - 380, View in Reaxys 19 of 193
Comment (Pharmacological Data)
physiological behaviour discussed
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Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Casale, Rosario; Cautela, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 61; nb. 21; (2013); p. 5156 - 5162, View in Reaxys 20 of 193
Effect (Pharmacological Data)
butyl-induced enzyme activity; effect on
Species or Test-System (Pharmacological Data)
Rhodococcus opacus DSM 43250
Results
molecular target: amino oxidase
Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 21 of 193
Effect (Pharmacological Data)
butyl-induced enzyme activity; effect on
Species or Test-System (Pharmacological Data)
Rhodococcus opacus DSM 43250
Type (Pharmacological Data)
activity rate
Value of Type (Pharmacological Data)
18 percent
Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 22 of 193
Effect (Pharmacological Data)
methylamine-induced enzyme activity; effect on
Species or Test-System (Pharmacological Data)
Rhodococcus opacus DSM 43250
Results
molecular target: amino oxidase
Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 23 of 193
Effect (Pharmacological Data)
methylamine-induced enzyme activity; effect on
Species or Test-System (Pharmacological Data)
Rhodococcus opacus DSM 43250
Type (Pharmacological Data)
activity rate
Value of Type (Pharmacological Data)
29 percent
Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 24 of 193
Effect (Pharmacological Data)
phenylethylamine-induced enzyme activity; effect on
Species or Test-System (Pharmacological Data)
Rhodococcus opacus DSM 43250
Results
molecular target: amino oxidase
Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 25 of 193
Effect (Pharmacological Data)
phenylethylamine-induced enzyme activity; effect on
Species or Test-System (Pharmacological Data)
Rhodococcus opacus DSM 43250
Type (Pharmacological Data)
activity rate
Value of Type (Pharmacological Data)
85 percent
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Foster, Alexander; Barnes, Nicole; Speight, Robert; Keane, Mark A.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 73 - 82, View in Reaxys 26 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
brain membranes of Wistar rat
Sex
male
Further Details (Pharmacological Data)
in presence of 30 μmol/l spermine; radioligand binding assay ; radioligand: [3H]MK-801
Results
molecular target: NMDA receptor
Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 27 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
brain membranes of Wistar rat
Sex
male
Further Details (Pharmacological Data)
in presence of 30 μmol/l spermine; radioligand binding assay ; radioligand: [3H]MK-801; IC50 related to: NMDA receptor
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
484 μmol/l
Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 28 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
brain membranes of Wistar rat
Sex
male
Further Details (Pharmacological Data)
radioligand binding assay; radioligand: [3H]MK-801
Results
molecular target: NMDA receptor
Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 29 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
brain membranes of Wistar rat
Sex
male
Further Details (Pharmacological Data)
radioligand binding assay; radioligand: [3H]MK-801; IC50 related to: NMDA receptor
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
85 μmol/l
Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 30 of 193
Effect (Pharmacological Data)
receptor binding affinity
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Species or Test-System (Pharmacological Data)
hippocampal CA1 + dentate gyrus membranes of Wistar rat
Sex
male
Further Details (Pharmacological Data)
radioligand binding assay; radioligand: [3H]-OH-DPAT
Results
molecular target: 5-HT1A receptor
Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 31 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
hippocampal CA1 + dentate gyrus membranes of Wistar rat
Sex
male
Further Details (Pharmacological Data)
radioligand binding assay; radioligand: [3H]-OH-DPAT; IC50 related to: 5-HT1A receptor
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.33 μmol/l
Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 32 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
prefrontal cortex membranes of Wistar rat
Sex
male
Further Details (Pharmacological Data)
radioligand binding assay; radioligand: [3H]ketanserin
Results
molecular target: 5-HT2A receptor
Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 33 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
prefrontal cortex membranes of Wistar rat
Sex
male
Further Details (Pharmacological Data)
radioligand binding assay; radioligand: [3H]ketanserin; IC50 related to: 5-HT2A receptor
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
16.3 μmol/l
Berger; Palangsuntikul; Rebernik; Wolschann; Berner; Current Medicinal Chemistry; vol. 19; nb. 18; (2012); p. 3044 - 3057, View in Reaxys 34 of 193
Effect (Pharmacological Data)
antifungal
Species or Test-System (Pharmacological Data)
Leptosphaeria maculans
Concentration (Pharmacological Data)
0.1 - 0.5 mmol/l
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Kind of Dosing (Pharmacological Data)
title comp. dissolved in CH3CN
Further Details (Pharmacological Data)
mycelial radial growth bioassay
Type (Pharmacological Data)
inhibition rate
Value of Type (Pharmacological Data)
12 - 28 percent
Pedras, M. Soledade C.; Sarma-Mamillapalle, Vijay K.; Journal of Agricultural and Food Chemistry; vol. 60; nb. 32; (2012); p. 7792 - 7798, View in Reaxys 35 of 193
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
recombinant CYP2A13 of human
Further Details (Pharmacological Data)
substrate: p-nitrophenol; CYP2A13: cytochrome P450-2A13
Results
molecular target: CYP2A13; species of target: human
Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 36 of 193
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
recombinant CYP2A13 of human
Further Details (Pharmacological Data)
substrate: p-nitrophenol; CYP2A13: cytochrome P450-2A13; inhibition constant (ki)
Type (Pharmacological Data)
ki
Value of Type (Pharmacological Data)
16 μmol/l
Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 37 of 193
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
recombinant CYP2A6 of human
Further Details (Pharmacological Data)
substrate: p-nitrophenol; CYP2A6: cytochrome P450-2A6
Results
molecular target: CYP2A6; species of target: human
Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 38 of 193
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
recombinant CYP2A6 of human
Further Details (Pharmacological Data)
substrate: p-nitrophenol; CYP2A6: cytochrome P450-2A6; inhibition constant (ki)
Type (Pharmacological Data)
ki
Value of Type (Pharmacological Data)
1.7 μmol/l
Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys
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39 of 193
Effect (Pharmacological Data)
protein binding affinity
Species or Test-System (Pharmacological Data)
recombinant CYP2A13 of human
Method (Pharmacological Data)
name of assay/method: spectrophotometry
Further Details (Pharmacological Data)
CYP2A13: cytochrome P450-2A13
Results
molecular target: CYP2A13; species of target: human
Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 40 of 193
Effect (Pharmacological Data)
protein binding affinity
Species or Test-System (Pharmacological Data)
recombinant CYP2A13 of human
Method (Pharmacological Data)
name of assay/method: spectrophotometry
Further Details (Pharmacological Data)
CYP2A13: cytochrome P450-2A13; equilibrium dissociation constant (kd)
Type (Pharmacological Data)
kd
Value of Type (Pharmacological Data)
5.2 μmol/l
Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 41 of 193
Effect (Pharmacological Data)
protein binding affinity
Species or Test-System (Pharmacological Data)
recombinant CYP2A6 of human
Method (Pharmacological Data)
name of assay/method: spectrophotometry
Further Details (Pharmacological Data)
CYP2A6: cytochrome P450-2A6
Results
molecular target: CYP2A6; species of target: human
Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 42 of 193
Effect (Pharmacological Data)
protein binding affinity
Species or Test-System (Pharmacological Data)
recombinant CYP2A6 of human
Method (Pharmacological Data)
name of assay/method: spectrophotometry
Further Details (Pharmacological Data)
CYP2A6: cytochrome P450-2A6; equilibrium dissociation constant (kd)
Type (Pharmacological Data)
kd
Value of Type (Pharmacological Data)
2.3 μmol/l
Stephens, Eva S.; Walsh, Agnes A.; Scott, Emily E.; Drug Metabolism and Disposition; vol. 40; nb. 9; (2012); p. 1797 - 1802, View in Reaxys 43 of 193
Effect (Pharmacological Data)
protein binding
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Species or Test-System (Pharmacological Data)
AANAT2 of sea bream
Further Details (Pharmacological Data)
AANAT: arylalkylamine N-acetyltransferase
Results
molecular target: AANAT2
Zilberman-Peled, Bina; Bransburg-Zabary, Sharron; Klein, David C.; Gothilf, Yoav; Marine Drugs; vol. 9; nb. 5; (2011); p. 906 - 921, View in Reaxys 44 of 193
Effect (Pharmacological Data)
L-Proline uptake; inhibition of
Species or Test-System (Pharmacological Data)
oocyte of Xenopus laevis, frog; genetically modified/infected with: rat PAT2
Concentration (Pharmacological Data)
10 mmol/l
Further Details (Pharmacological Data)
PAT2 (SLC36A2): H+-coupled amino acid transporter; radiolabel (L-[3H]Proline) flux assay
Results
no effect
Edwards, Noel; Anderson, Catriona M.H.; Gatfield, Kelly M.; Jevons, Mark P.; Ganapathy, Vadivel; Thwaites, David T.; Biochimica et Biophysica Acta - Biomembranes; vol. 1808; nb. 1; (2011); p. 260 - 270, View in Reaxys 45 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
HEK-293 cell membranes; genetically modified/infected with: human 5-HT2C-S3.36A receptor DNA mixed with 33 μL lipofectamine 2000 reagent
Further Details (Pharmacological Data)
competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM
Results
molecular target: human 5-HT2C-S3.36A receptor
Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 46 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
HEK-293 cell membranes; genetically modified/infected with: human 5-HT2C-S3.36A receptor DNA mixed with 33 μL lipofectamine 2000 reagent
Further Details (Pharmacological Data)
competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM; Ki related to: human 5-HT2C-S3.36A receptor
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
1513 nmol/l
Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 47 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
HEK-293 cell membranes; genetically modified/infected with: human 5-HT2C-Y7.43A receptor DNA mixed with 33 μL lipofectamine 2000 reagent
Further Details (Pharmacological Data)
competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM
Results
molecular target: human 5-HT2C-Y7.43A receptor
Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 48 of 193
Effect (Pharmacological Data)
receptor binding affinity
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Species or Test-System (Pharmacological Data)
HEK-293 cell membranes; genetically modified/infected with: human 5-HT2C-Y7.43A receptor DNA mixed with 33 μL lipofectamine 2000 reagent
Further Details (Pharmacological Data)
competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM; Ki related to: human 5-HT2C-Y7.43A receptor
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
298.5 nmol/l
Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 49 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
HEK-293 cells membranes; genetically modified/infected with: human 5-HT2C receptor DNA mixed with 33 μL lipofectamine 2000 reagent
Further Details (Pharmacological Data)
competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM
Results
molecular target: human 5-HT2C receptor
Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 50 of 193
Effect (Pharmacological Data)
receptor binding affinity
Species or Test-System (Pharmacological Data)
HEK-293 cells membranes; genetically modified/infected with: human 5-HT2C receptor DNA mixed with 33 μL lipofectamine 2000 reagent
Further Details (Pharmacological Data)
competitive displacement binding assay; radioligand: [3H]-mesulergine at 1-2 nM; Ki related to: human 5-HT2C receptor
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
57.1 nmol/l
Canal, Clinton E.; Cordova-Sintjago, Tania C.; Villa, Nancy Y.; Fang, Li-Juan; Booth, Raymond G.; European Journal of Pharmacology; vol. 673; nb. 1-3; (2011); p. 1 - 12, View in Reaxys 51 of 193
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
bovine pancreatic trypsin
Kind of Dosing (Pharmacological Data)
title comp. in DMSO
Further Details (Pharmacological Data)
fluorescence-based inhibition assay
Results
molecular target: bovine pancreatic trypsin
Yamane, Junji; Yao, Min; Zhou, Yong; Hiramatsu, Yasuyuki; Fujiwara, Kenichiro; Yamaguchi, Tohru; Yamaguchi, Hiroto; Togame, Hiroko; Tsujishita, Hideki; Takemoto, Hiroshi; Tanaka, Isao; Journal of Applied Crystallography; vol. 44; nb. 4; (2011); p. 798 - 804, View in Reaxys 52 of 193
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
bovine pancreatic trypsin
Kind of Dosing (Pharmacological Data)
title comp. in DMSO
Further Details (Pharmacological Data)
fluorescence-based inhibition assay; inhibitory concentration (IC)
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Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
873 μmol/l
Yamane, Junji; Yao, Min; Zhou, Yong; Hiramatsu, Yasuyuki; Fujiwara, Kenichiro; Yamaguchi, Tohru; Yamaguchi, Hiroto; Togame, Hiroko; Tsujishita, Hideki; Takemoto, Hiroshi; Tanaka, Isao; Journal of Applied Crystallography; vol. 44; nb. 4; (2011); p. 798 - 804, View in Reaxys 53 of 193
Effect (Pharmacological Data)
sigma-1 receptor; binding to
Species or Test-System (Pharmacological Data)
liver membrane homogenate
Method (Pharmacological Data)
Competition assays against the sigma-1 receptor specific ligand, (+)- [3H] -pentazocine (10 nM) determined that the non-methylated trace amines tryptamine, phenethylamine, and tyramine bound the sigma-1 receptor poorly (Table 4), with Kd values of 431.55 μM, 97.4 μM, and >30000 μM, respectively. By contrast, the iV-methylated and iV,./V-dimethylated derivatives of these compounds bound sigma-1 receptors more tightly, with a clear increase in affinity as the ligands approached the sigma-1 receptor ligand pharmacophore (Figures 5a and 5b). With the exception of the iV-methylated tyramines, this trend did not apply to the sigma-2 receptor, which differs pharmacologically and functionally from the sigma-1 receptor (Table 4).Tryptamine, phenethylamine, and iV-methyltyramine, had the highest sigma-2 receptor affinities with Kd values of 4.91 μM, 7.31 μM, and 6.61 μM, respectively. In contrast to sigma-1 receptors, iV-methylation and ΛζiV-dimethylation of tryptamine and phenethylamine decreased sigma- 2 receptor affinity (Table 4).; Preparation of rat, guinea pig, and mouse liver membrane homogenates was performed as previously described (18, 31) with the exception that mouse livers were obtained from age-matched adult 129/SvEvBrd x C57BL6/J sigma- 1 receptor knock out (27) and wild- type mice.; Sigma Receptor Binding Assays. Competitive binding assays were performed as previously described (18) with the exception of testing new ligands shown in Table 4.
Type (Pharmacological Data)
KD
Value of Type (Pharmacological Data)
431.55 μmol/l
Location
Page/Page column 29-30; 34-35
Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English, View in Reaxys 54 of 193
Effect (Pharmacological Data)
sigma-2 receptor; binding to
Species or Test-System (Pharmacological Data)
liver membrane homogenate
Method (Pharmacological Data)
Competition assays against the sigma-1 receptor specific ligand, (+)- [3H] -pentazocine (10 nM) determined that the non-methylated trace amines tryptamine, phenethylamine, and tyramine bound the sigma-1 receptor poorly (Table 4), with Kd values of 431.55 μM, 97.4 μM, and >30000 μM, respectively. By contrast, the iV-methylated and iV,./V-dimethylated derivatives of these compounds bound sigma-1 receptors more tightly, with a clear increase in affinity as the ligands approached the sigma-1 receptor ligand pharmacophore (Figures 5a and 5b). With the exception of the iV-methylated tyramines, this trend did not apply to the sigma-2 receptor, which differs pharmacologically and functionally from the sigma-1 receptor (Table 4).Tryptamine, phenethylamine, and iV-methyltyramine, had the highest sigma-2 receptor affinities with Kd values of 4.91 μM, 7.31 μM, and 6.61 μM, respectively. In contrast to sigma-1 receptors, iV-methylation and ΛζiV-dimethylation of tryptamine and phenethylamine decreased sigma- 2 receptor affinity (Table 4).; Preparation of rat, guinea pig, and mouse liver membrane homogenates was performed as previously described (18, 31) with the exception that mouse livers were obtained from age-matched adult 129/SvEvBrd x C57BL6/J sigma- 1 receptor knock out (27) and wild- type mice.; Sigma Receptor Binding Assays. Competitive binding assays were performed as previously described (18) with the exception of testing new ligands shown in Table 4.
Type (Pharmacological Data)
KD
Value of Type (Pharmacological Data)
4.91 μmol/l
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Location
Page/Page column 29-30; 34-35
Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English, View in Reaxys 55 of 193
Effect (Pharmacological Data)
sigma-1 receptor photolabeling; inhibition of
Species or Test-System (Pharmacological Data)
liver membranes photolabelled with 3-[125I]iodo-4-azidococaine of rat
Method (Pharmacological Data)
The ability of tryptamine, iV-methyltryptamine, and DMT to block sigma receptor photolabeling in rat liver homogenates were tested by two radioactive photoaffinity labels, the sigma-1 receptor specific cocaine derivative 3-[125I]iodo-4-azidococaine ([125I]-IACoC) (17) (Figure 6a), and the sigma-1 and sigma-2 receptor fenpropimorph derivative l-N-(2',6'-dimethyl- morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) (18) (Figure 6b). Both of these compounds have been used to identify the drug binding region of the sigma-1 receptor (18, 19). [125I]-IACoC (sigma-1 Kd = 0.126 nM(l 7)) photolabeling of the 26 kDa sigma-1 receptor (Figure 6a) was protected best by DMT, with 61percent protection by 50 μM DMT and almost 100percent protection by 100 μM DMT. On the other hand, tryptamine and iV-methyltryptamine protected minimally against sigma-1 receptor [125I]-IACoC photolabeling, even at these high concentrations (Figure 6a). Similarly, [125I]IAF photolabeling of the sigma-1 (Kd = 194 nM (18)) receptor showed that DMT was the most potent protector. Ten μM DMT protected 31percent, while 50 μM and 100 μM DMT protected 43percent and 69percent, respectively (Figure 6b). With the exception of iV-methyltryptamine, protection of [125I]IAF sigma-2 (Kd = 2780 nM(iS)) receptor photolabeling paralleled the sigma-2 binding data. Tryptamine afforded the greatest protection of sigma-2 receptor photolabeling, with values of 47percent, 78percent, and 79percent for 10, 50, and 100 μM, respectively (Figure 6b).; Radiochemistry. Radiosynthesis of 3-[125I]iodo-4-azidococaine ([125I]-IACoC) (17) and 1-N- (2',6'dimethyl-morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) (18) was performed as described. Preparation of Rat/Guinea Pig/Mouse Liver membranes. Preparation of rat, guinea pig, and mouse liver membrane homogenates was performed as previously described (18, 31) with the exception that mouse livers were obtained from age-matched adult 129/SvEvBrd x C57BL6/J sigma- 1 receptor knock out (27) and wild- type mice.; Photoaffinity Labeling. Sigma- 1 and sigma-2 receptors were photolabeled with 3-[125I]iodo- 4-azidococaine ([125I]-IACoC) and l-N-(2',6'-dimethyl-morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) as described (18) with the exception of the protecting ligands, tryptamine, N- methyltryptamine, and iV,./V-dimethyltryptamine (DMT).
Results
band intensity sigma-1 (percent) = 111, 74 and 81 at a concentration of 10, 50 and 100 μmol/l, respectively
Location
Page/Page column 30; 34-35; 7/12
Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English, View in Reaxys 56 of 193
Effect (Pharmacological Data)
sigma-1 receptor photolabeling; inhibition of
Species or Test-System (Pharmacological Data)
liver membranes photolabelled with 1-N-(2',6'-dimethyl-morpholino)-3-(4-azido-3-[125I]iodophenyl)propane of rat
Method (Pharmacological Data)
The ability of tryptamine, iV-methyltryptamine, and DMT to block sigma receptor photolabeling in rat liver homogenates were tested by two radioactive photoaffinity labels, the sigma-1 receptor specific cocaine derivative 3-[125I]iodo-4-azidococaine ([125I]-IACoC) (17) (Figure 6a), and the sigma-1 and sigma-2 receptor fenpropimorph derivative l-N-(2',6'-dimethyl- morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) (18) (Figure 6b). Both of these compounds have been used to identify the drug binding region of the sigma-1 receptor (18, 19). [125I]-IACoC (sigma-1 Kd = 0.126 nM(l 7)) photolabeling of the 26 kDa sigma-1 receptor (Figure 6a) was protected best by DMT, with 61percent protection by 50 μM DMT and almost 100percent protection by 100 μM DMT. On the other hand, tryptamine and iV-methyltryptamine protected minimally against sigma-1 receptor [125I]-IACoC photolabeling, even at these high concentrations (Figure 6a). Similarly, [125I]IAF photolabeling of the sigma-1 (Kd = 194 nM (18)) receptor showed that DMT was the most potent protector. Ten μM DMT protected 31percent, while 50 μM and 100 μM DMT protected 43percent and 69percent, respectively (Figure 6b). With the exception of iV-methyltryptamine, protection of [125I]IAF sigma-2 (Kd = 2780 nM(iS)) receptor photolabeling paralleled the sigma-2 binding data. Tryptamine afforded the greatest protection of sigma-2 receptor photolabeling, with values of 47percent, 78percent, and 79percent for 10, 50, and 100 μM,
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respectively (Figure 6b).; Radiochemistry. Radiosynthesis of 3-[125I]iodo-4-azidococaine ([125I]-IACoC) (17) and 1-N- (2',6'dimethyl-morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) (18) was performed as described. Preparation of Rat/Guinea Pig/Mouse Liver membranes. Preparation of rat, guinea pig, and mouse liver membrane homogenates was performed as previously described (18, 31) with the exception that mouse livers were obtained from age-matched adult 129/SvEvBrd x C57BL6/J sigma- 1 receptor knock out (27) and wild- type mice.; Photoaffinity Labeling. Sigma- 1 and sigma-2 receptors were photolabeled with 3-[125I]iodo- 4-azidococaine ([125I]-IACoC) and l-N-(2',6'-dimethyl-morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) as described (18) with the exception of the protecting ligands, tryptamine, N- methyltryptamine, and iV,./V-dimethyltryptamine (DMT). Results
band intensity sigma-1 (percent) = 100, 81 and 65 at a concentration of 10, 50 and 100 μmol/l, respectively
Location
Page/Page column 30; 34-35; 7/12
Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English, View in Reaxys 57 of 193
Effect (Pharmacological Data)
sigma-2 receptor photolabeling; inhibition of
Species or Test-System (Pharmacological Data)
liver membranes photolabelled with 1-N-(2',6'-dimethyl-morpholino)-3-(4-azido-3-[125I]iodophenyl)propane of rat
Method (Pharmacological Data)
The ability of tryptamine, iV-methyltryptamine, and DMT to block sigma receptor photolabeling in rat liver homogenates were tested by two radioactive photoaffinity labels, the sigma-1 receptor specific cocaine derivative 3-[125I]iodo-4-azidococaine ([125I]-IACoC) (17) (Figure 6a), and the sigma-1 and sigma-2 receptor fenpropimorph derivative l-N-(2',6'-dimethyl- morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) (18) (Figure 6b). Both of these compounds have been used to identify the drug binding region of the sigma-1 receptor (18, 19). [125I]-IACoC (sigma-1 Kd = 0.126 nM(l 7)) photolabeling of the 26 kDa sigma-1 receptor (Figure 6a) was protected best by DMT, with 61percent protection by 50 μM DMT and almost 100percent protection by 100 μM DMT. On the other hand, tryptamine and iV-methyltryptamine protected minimally against sigma-1 receptor [125I]-IACoC photolabeling, even at these high concentrations (Figure 6a). Similarly, [125I]IAF photolabeling of the sigma-1 (Kd = 194 nM (18)) receptor showed that DMT was the most potent protector. Ten μM DMT protected 31percent, while 50 μM and 100 μM DMT protected 43percent and 69percent, respectively (Figure 6b). With the exception of iV-methyltryptamine, protection of [125I]IAF sigma-2 (Kd = 2780 nM(iS)) receptor photolabeling paralleled the sigma-2 binding data. Tryptamine afforded the greatest protection of sigma-2 receptor photolabeling, with values of 47percent, 78percent, and 79percent for 10, 50, and 100 μM, respectively (Figure 6b).; Radiochemistry. Radiosynthesis of 3-[125I]iodo-4-azidococaine ([125I]-IACoC) (17) and 1-N- (2',6'dimethyl-morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) (18) was performed as described. Preparation of Rat/Guinea Pig/Mouse Liver membranes. Preparation of rat, guinea pig, and mouse liver membrane homogenates was performed as previously described (18, 31) with the exception that mouse livers were obtained from age-matched adult 129/SvEvBrd x C57BL6/J sigma- 1 receptor knock out (27) and wild- type mice.; Photoaffinity Labeling. Sigma- 1 and sigma-2 receptors were photolabeled with 3-[125I]iodo- 4-azidococaine ([125I]-IACoC) and l-N-(2',6'-dimethyl-morpholino)-3-(4-azido-3-[125I]iodo-phenyl) propane ([125I]IAF) as described (18) with the exception of the protecting ligands, tryptamine, N- methyltryptamine, and iV,./V-dimethyltryptamine (DMT).
Results
band intensity sigma-2 (percent) = 53, 22 and 21 at a concentration of 10, 50 and 100 μmol/l, respectively
Location
Page/Page column 30; 34-35; 7/12
Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English, View in Reaxys 58 of 193
Effect (Pharmacological Data)
buds/plant thinning
Species or Test-System (Pharmacological Data)
chrysanthemum, cv Herby Mixed
Method (Pharmacological Data)
EXAMPLE 2 - CHRYSANTHEMUM - cv Herby MixedA. To demonstrate the benefits to flower bud thinning of applying an auxin/auxin precursor or auxin/auxin precursor plus acetaminophen.Cultural Details: plants were sown in a commercial seed compost and then "pricked out" into a professional grade all-purpose compost in 9cm pots set out in a
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randomized block design. Normal daylight plus supplementary lighting to provide a minimum of 10 hours per day. Heating was given to a minimum of 60 degrees Fahrenheit during the day and 40 degrees F at night.Sowing Date: 5 October 2009, in plugs. Application Date: 2 December 2009 (first bud). Measurement Date: 12 January 2010 (flowering). Measurement: Number of buds per plant.A number of auxins or auxin precursors were applied, each at 10"2 Molar solutions. Addition of acetaminophen (AC) was at 3g per hectare equivalent in each test.Application of an auxin or auxin precursor resulted in a reduced mean number of buds per plant, as expected from an effective thinning agent. Application of AC in addition to an auxin or auxin precursor resulted in further reduction in mean number of buds per plant. Results
improvement over control (percent) = +0.0
Location
Page/Page column 25-26
Comment (Pharmacological Data)
potential area of application: agro
Metabolite XRN (Pharmacological Data)
143358; 121586; 125488; 474217; 1528281; 20752795
Metabolite (Pharmacological Data)
indole-3-acetic acid; indole-3-acetaldehyde; indole-3-acetonitrile; N-Hydroxytryptamine; (Z/E)-3-Indolylacetaldoxime; C10H10N2O2
Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard; DECKERS, Tom; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116256; (2010); (A2) English, View in Reaxys 59 of 193
Effect (Pharmacological Data)
buds/plant thinning
Species or Test-System (Pharmacological Data)
chrysanthemum, cv Herby Mixed
Method (Pharmacological Data)
EXAMPLE 2 - CHRYSANTHEMUM - cv Herby MixedA. To demonstrate the benefits to flower bud thinning of applying an auxin/auxin precursor or auxin/auxin precursor plus acetaminophen.Cultural Details: plants were sown in a commercial seed compost and then "pricked out" into a professional grade all-purpose compost in 9cm pots set out in a randomized block design. Normal daylight plus supplementary lighting to provide a minimum of 10 hours per day. Heating was given to a minimum of 60 degrees Fahrenheit during the day and 40 degrees F at night.Sowing Date: 5 October 2009, in plugs. Application Date: 2 December 2009 (first bud). Measurement Date: 12 January 2010 (flowering). Measurement: Number of buds per plant.A number of auxins or auxin precursors were applied, each at 10"2 Molar solutions. Addition of acetaminophen (AC) was at 3g per hectare equivalent in each test.Application of an auxin or auxin precursor resulted in a reduced mean number of buds per plant, as expected from an effective thinning agent. Application of AC in addition to an auxin or auxin precursor resulted in further reduction in mean number of buds per plant.
Results
mean number of buds/plant = 2.7
Location
Page/Page column 25-26
Comment (Pharmacological Data)
potential area of application: agro
Metabolite XRN (Pharmacological Data)
143358; 121586; 125488; 474217; 1528281; 20752795
Metabolite (Pharmacological Data)
indole-3-acetic acid; indole-3-acetaldehyde; indole-3-acetonitrile; N-Hydroxytryptamine; (Z/E)-3-Indolylacetaldoxime; C10H10N2O2
Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard; DECKERS, Tom; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116256; (2010); (A2) English, View in Reaxys 60 of 193
Effect (Pharmacological Data)
Petal abscission; delaying of
Species or Test-System (Pharmacological Data)
Papaver nudicale Iceland Poppy
Method (Pharmacological Data)
1. PAPAVER Nudicaule (Iceland Poppy)Cultural Details: plants were sown in a commercial seed compost and then "pricked out" into a professional grade all-purpose compost in 9cm pots set out in a randomized block design. Normal daylight plus supplementary lighting to provide a minimum of 10 hours per day. Heating was given to a minimum of 60 degrees Fahrenheit during the day and 40 degrees at night.Sowing Date: 18 November 2009, in plugs. Application Date: 5 January 2010. Measurement Date: 12 January 2010 at daily intervals.A number of auxins or auxin precursors were applied, each at 10"2 Molar
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solutions. Addition of acetaminophen (AC) was at 3g per hectare equivalent in each test. Measurement: Delay of first petal fall for each treatment (in days).Petal abscission is delayed by the application of an auxin/auxin precursor. Petal abscission is further delayed by the application of an auxin/auxin precursor plus acetaminophen. Thus, flower longevity is benefited. Results
Improvement (percent) = 19.4 at a dose 0.01 mol/l
Location
Page/Page column 35-36
Comment (Pharmacological Data)
potential area of application: agro
Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard, Henry; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116263; (2010); (A2) English, View in Reaxys 61 of 193
Effect (Pharmacological Data)
shelf-life; improvement of
Species or Test-System (Pharmacological Data)
radish - cv F1 Apache
Method (Pharmacological Data)
RADISH - cv F 1 ApacheTo demonstrate the benefits to post-harvest shelf-life from adding an auxin/auxin precursor or auxin/auxin precursor plus acetaminophen.Cultural Details: plants were sown in a commercial seed compost and then "pricked out" into a professional grade all-purpose compost in 9cm pots set out in a randomized block design. Normal daylight plus supplementary lighting to provide a minimum of 10 hours per day. Heating was given to a minimum of 60 degrees Fahrenheit during the day and 40 degrees at night.Sowing Date: 3 November 2009, in plugs. Application Dates: 28 December 2009 fb 4 January 2010. Harvest Date: 11 January 2010.Measurement: Shelf-Life (days after harvest) at ambient temperature. A number of auxins or auxin precursors were compared, each at 10"2 Molar solutions. Addition of acetaminophen (AC) was at 3g per hectare equivalent in each test.
Results
Shelf-life improvement (percent) = 11.1 at a dose 0.01 mol/l
Location
Page/Page column 38-39
Comment (Pharmacological Data)
potential area of application: agro
Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard, Henry; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116263; (2010); (A2) English, View in Reaxys 62 of 193
Effect (Pharmacological Data)
HOCl-induced oxidation; inhibition of
Species or Test-System (Pharmacological Data)
dihydrorhodamine 123
Further Details (Pharmacological Data)
inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
6 μmol/l
Estevao, Monica S.; Carvalho, Luisa C.; Ribeiro, Daniela; Couto, Diana; Freitas, Marisa; Gomes, Ana; Ferreira; Fernandes, Eduarda; Marques, M. Manuel B.; European Journal of Medicinal Chemistry; vol. 45; nb. 11; (2010); p. 4869 - 4878, View in Reaxys 63 of 193
Effect (Pharmacological Data)
peroxyl-induced oxidation; inhibition of
Species or Test-System (Pharmacological Data)
fluorescein
Further Details (Pharmacological Data)
inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
1.86 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
102/155
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Estevao, Monica S.; Carvalho, Luisa C.; Ribeiro, Daniela; Couto, Diana; Freitas, Marisa; Gomes, Ana; Ferreira; Fernandes, Eduarda; Marques, M. Manuel B.; European Journal of Medicinal Chemistry; vol. 45; nb. 11; (2010); p. 4869 - 4878, View in Reaxys 64 of 193
Effect (Pharmacological Data)
NO radical-induced oxidation; inhibition of
Species or Test-System (Pharmacological Data)
4,5-diaminofluorescein
Further Details (Pharmacological Data)
inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
672 μmol/l
Estevao, Monica S.; Carvalho, Luisa C.; Ribeiro, Daniela; Couto, Diana; Freitas, Marisa; Gomes, Ana; Ferreira; Fernandes, Eduarda; Marques, M. Manuel B.; European Journal of Medicinal Chemistry; vol. 45; nb. 11; (2010); p. 4869 - 4878, View in Reaxys 65 of 193
Effect (Pharmacological Data)
ONOO--induced oxidation; inhibition of
Species or Test-System (Pharmacological Data)
dihydrorhodamine 123
Further Details (Pharmacological Data)
PDP value is dependent on the presence of NaHCO3; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
10.4 - 31.8 μmol/l
Estevao, Monica S.; Carvalho, Luisa C.; Ribeiro, Daniela; Couto, Diana; Freitas, Marisa; Gomes, Ana; Ferreira; Fernandes, Eduarda; Marques, M. Manuel B.; European Journal of Medicinal Chemistry; vol. 45; nb. 11; (2010); p. 4869 - 4878, View in Reaxys 66 of 193
Effect (Pharmacological Data)
1O
Species or Test-System (Pharmacological Data)
dihydrorhodamine 123
Further Details (Pharmacological Data)
inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
682 μmol/l
2-induced
oxidation; inhibition of
Estevao, Monica S.; Carvalho, Luisa C.; Ribeiro, Daniela; Couto, Diana; Freitas, Marisa; Gomes, Ana; Ferreira; Fernandes, Eduarda; Marques, M. Manuel B.; European Journal of Medicinal Chemistry; vol. 45; nb. 11; (2010); p. 4869 - 4878, View in Reaxys 67 of 193
Effect (Pharmacological Data)
nitric oxide formation; inhibition of
Species or Test-System (Pharmacological Data)
cerebellum of Sprague-Dawley rat
Sex
male
Concentration (Pharmacological Data)
1E-05 - 0.01 mol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in potassium phosphate buffer (pH 7.4)
Further Details (Pharmacological Data)
supernatant of cerebellum homogenate used; mass of species: 120 - 150 g; inhibitory concentration (IC)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
1.641E-4 mol/l
Wilkes, Dennis K.; De Vries, Armand; Oliver, Douglas W.; Malan, Sarel F.; Archiv der Pharmazie; vol. 342; nb. 2; (2009); p. 73 - 79, View in Reaxys 68 of 193
Effect (Pharmacological Data)
nitric oxide formation; inhibition of
Species or Test-System (Pharmacological Data)
cerebellum of Sprague-Dawley rat
Sex
male
Concentration (Pharmacological Data)
1E-05 - 0.01 mol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in potassium phosphate buffer (pH 7.4)
Further Details (Pharmacological Data)
supernatant of cerebellum homogenate used; mass of species: 120 - 150 g; inhibitory concentration (IC)
Type (Pharmacological Data)
log IC50
Value of Type (Pharmacological Data)
-3.785
Wilkes, Dennis K.; De Vries, Armand; Oliver, Douglas W.; Malan, Sarel F.; Archiv der Pharmazie; vol. 342; nb. 2; (2009); p. 73 - 79, View in Reaxys 69 of 193
Effect (Pharmacological Data)
nitric oxide formation; inhibition of
Species or Test-System (Pharmacological Data)
cerebellum of Sprague-Dawley rat
Sex
male
Concentration (Pharmacological Data)
1E-05 - 0.01 mol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in potassium phosphate buffer (pH 7.4)
Further Details (Pharmacological Data)
supernatant of cerebellum homogenate used; mass of species: 120 - 150 g
Type (Pharmacological Data)
maximum inhibition
Value of Type (Pharmacological Data)
23 percent
Wilkes, Dennis K.; De Vries, Armand; Oliver, Douglas W.; Malan, Sarel F.; Archiv der Pharmazie; vol. 342; nb. 2; (2009); p. 73 - 79, View in Reaxys 70 of 193
Effect (Pharmacological Data)
nitric oxide formation; inhibition of
Species or Test-System (Pharmacological Data)
cerebellum of Sprague-Dawley rat
Sex
male
Concentration (Pharmacological Data)
1E-05 - 0.01 mol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in potassium phosphate buffer (pH 7.4)
Further Details (Pharmacological Data)
supernatant of cerebellum homogenate used; mass of species: 120 - 150 g
Results
molecular target: nitric oxide synthase
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Wilkes, Dennis K.; De Vries, Armand; Oliver, Douglas W.; Malan, Sarel F.; Archiv der Pharmazie; vol. 342; nb. 2; (2009); p. 73 - 79, View in Reaxys 71 of 193
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
HEK293 cells expressing rhesus monkey D2s
Concentration (Pharmacological Data)
1E-09 - 0.0001 mol/l
Method (Pharmacological Data)
cells incub. with title comp. in presence of <3H>dopamine at 25 deg C for 1 h; filtered; counted on scintillation spectrophotometer; <3H>dopamine binding determined
Further Details (Pharmacological Data)
ref.: <3H>dopamine; nonspecific binding was determined in presence of 10 μM raclopride; D2s: dopamine D2 receptor short isoform; HEK: human embryonic kidney
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 10 μmol/l
Results
title comp. had poor binding affinity for D2s relative to dopamine; fig.
Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 72 of 193
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
HEK293 cells expressing human α2A
Concentration (Pharmacological Data)
1E-10 - 1E-05 mol/l
Method (Pharmacological Data)
cells incub. with title comp. in presence of <3H>norepinephrine at 25 deg C for 1 h; filtered; counted on scintillation spectrophotometer; <3H>norepinephrine binding determined
Further Details (Pharmacological Data)
ref.: <3H>norepinephrine; nonspecific binding was determined in presence of 10 μM SKF86466; HEK: human embryonic kidney; α2A: subtype A of α-adrenal receptor 2
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 10 μmol/l
Results
title comp. had poor binding affinity for α2A relative to norepinephrine; fig.
Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 73 of 193
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
HEK293 cells expressing human α2B
Concentration (Pharmacological Data)
1E-10 - 1E-05 mol/l
Method (Pharmacological Data)
cells incub. with title comp. in presence of <3H>norepinephrine at 25 deg C for 1 h; filtered; counted on scintillation spectrophotometer; <3H>norepinephrine binding determined
Further Details (Pharmacological Data)
ref.: <3H>norepinephrine; nonspecific binding was determined in presence of 10 μM SKF86466; HEK: human embryonic kidney; α2B: subtype B of α-adrenal receptor 2
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 10 μmol/l
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Results
title comp. had poor binding affinity for α2B relative to norepinephrine; fig.
Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 74 of 193
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
HEK293 cells expressing 5HT1A
Concentration (Pharmacological Data)
1E-10 - 1E-05 mol/l
Method (Pharmacological Data)
cells incub. with title comp. in presence of <3H>serotonin at 25 deg C for 1 h; filtered; counted on scintillation spectrophotometer; <3H>serotonin binding determined
Further Details (Pharmacological Data)
ref.: <3H>serotonin; nonspecific binding was determined in presence of 10 μM methiothepin; HEK: human embryonic kidney; 5HT1A: subtype A of serotonin receptor 1
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 10 μmol/l
Results
title comp. had poor binding affinity for 5HT1A relative to serotonin; fig.
Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 75 of 193
Effect (Pharmacological Data)
receptor; activation of
Species or Test-System (Pharmacological Data)
embryonic kidney 293 cells of human
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
cells transfected with rhesus monkey TAAR1 (trace amine-associated receptor) along with CRE-Luc (cAMP-response element-driven luciferase receptor); treated with title comp. for 18 h; CRE-Luc expressed detd. as measure of cAMP accumulation in cells
Further Details (Pharmacological Data)
control: vehicle; further study done in cells expressing rhesus monkey TAAR1 along with autoreceptors D2s (dopamine D2 receptor short isoform), α2A, α2B, 5HT1A or 5HT1B
Results
title comp. activated TAAR1; TAAR1 signaling in response to title comp. was not affected by any of the monoamine autoreceptors tests; fig.
Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 76 of 193
Effect (Pharmacological Data)
receptor; activation of
Species or Test-System (Pharmacological Data)
embryonic kidney 293 cells of human
Concentration (Pharmacological Data)
1E-08 - 0.0001 mol/l
Method (Pharmacological Data)
cells transfected with rhesus monkey TAAR1 along with CRE-Luc and PGL4.73; treated with title comp. for 18 h; lysed; CRE-Luc expression was determined as measure of cAMP accumulation in cells
Further Details (Pharmacological Data)
TAAR1: trace amine-associated receptor 1; CRE-Luc: cAMP-response element-driven luciferase reporter; controls: cells transfected with CRE-Luc and PGL4.73
Results
title comp. increased CRE-Luc expression in a TAAR1-dependent manner; fig.
Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 77 of 193
Effect (Pharmacological Data)
receptor; binding activity
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Species or Test-System (Pharmacological Data)
HEK293 cells expressing 5HT1B
Concentration (Pharmacological Data)
1E-10 - 1E-05 mol/l
Method (Pharmacological Data)
cells incub. with title comp. in presence of <3H>serotonin at 25 deg C for 1 h; filtered; counted on scintillation spectrophotometer; <3H>serotonin binding determined
Further Details (Pharmacological Data)
ref.: <3H>serotonin; nonspecific binding was determined in presence of 10 μM methiothepin; HEK: human embryonic kidney; 5HT1B: subtype B of serotonin receptor 1
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 10 μmol/l
Results
title comp. had poor binding affinity for 5HT1B relative to serotonin; fig.
Xie, Zhihua; Miller, Gregory M.; Journal of Pharmacology and Experimental Therapeutics; vol. 325; nb. 2; (2008); p. 617 - 628, View in Reaxys 78 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
2.4 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 79 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Ala173Cys mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
1.05 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 80 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Ala173Thr mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
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Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
2.0 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 81 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Ala169Ile mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
7.6 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 82 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Thr439Ser mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
0.83 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 83 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Thr439Ala mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
1.41 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 84 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Tyr176Phe mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
4.8 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 85 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Tyr175Phe mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
0.84 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 86 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Asp98Glu mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
0.37 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 87 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Ala173Leu mutant
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
4.6 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 88 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Ala173Met mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
1.94 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 89 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Ala173Asp mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
0.95 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 90 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Thr439Val mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Value of Type (Pharmacological Data)
2.0 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 91 of 193
Effect (Pharmacological Data)
5-HT uptake; inhibition of
Species or Test-System (Pharmacological Data)
HEK-293 MSR cells transfected with hSERT, Ala173Ser mutant
Method (Pharmacological Data)
inhibition of <3H>-5-HT uptake assayed; cells preincubated with title comp. for 30 min in PBSCM pH 7.4; uptake initiated by addition of <3H>-5-HT (50-100 nM) and continued for 10 min; cells lysed, radiolabeled 5-HT quantified by scintillation counting
Further Details (Pharmacological Data)
hSERT: human serotonin transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
1.26 μmol/l
Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865, View in Reaxys 92 of 193
Effect (Pharmacological Data)
cardiac output; effect on
Species or Test-System (Pharmacological Data)
heart of Wistar rat
Sex
male
Concentration (Pharmacological Data)
100 μmol/l
Method (Pharmacological Data)
isolated rat hearts perfused for 50 min with standard buffer in presence of title comp.; 36.8 - 37 deg C, pH 7.4; aortic flow (AF) measured after perfusion
Further Details (Pharmacological Data)
further invest. in presence of tyrosine kinase inhibitor genistein (37 μM); control: standard buffer
Results
title comp. alone had no effect but reduced AF in presence of genistein; table
Frascarelli, Sabina; Ghelardoni, Sandra; Chiellini, Grazia; Vargiu, Romina; Ronca-Testoni, Simonetta; Scanlan, Thomas S.; Grandy, David K.; Zucchi, Riccardo; European Journal of Pharmacology; vol. 587; nb. 1-3; (2008); p. 231 - 236, View in Reaxys 93 of 193
Effect (Pharmacological Data)
coronary flow; decrease of
Species or Test-System (Pharmacological Data)
heart of Wistar rat
Sex
male
Concentration (Pharmacological Data)
100 μmol/l
Method (Pharmacological Data)
isolated rat hearts perfused for 50 min with standard buffer in presence of title comp.; 36.8 - 37 deg C, pH 7.4; coronary flow measured after perfusion
Further Details (Pharmacological Data)
further invest. in presence of tyrosine kinase inhibitor genistein; control: standard buffer
Comment (Pharmacological Data)
No effect
Frascarelli, Sabina; Ghelardoni, Sandra; Chiellini, Grazia; Vargiu, Romina; Ronca-Testoni, Simonetta; Scanlan, Thomas S.; Grandy, David K.; Zucchi, Riccardo; European Journal of Pharmacology; vol. 587; nb. 1-3; (2008); p. 231 - 236, View in Reaxys
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94 of 193
Effect (Pharmacological Data)
inotropic neg.
Species or Test-System (Pharmacological Data)
heart of Wistar rat
Sex
male
Concentration (Pharmacological Data)
Ca. 1E-06 - 0.0003 mol/l
Method (Pharmacological Data)
isolated rat hearts perfused for 50 min with standard buffer in presence of title comp.; 36.8 - 37 deg C, pH 7.4; cardiac output (CO) at all doses tested and peak systolic aortic pressure (PAP) measured after perfusion
Further Details (Pharmacological Data)
further invest. of 100 μM title comp. for time course during perfusion, and in presence of tyrosine kinase inhibitor genistein; control: standard buffer; reference comp.: thyronamine, 3-iodothyronamine
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 242 μmol/l
Results
title comp. dose-dependently reduced CO at conc. >1E-4 M, with maximum by ca. 38percent at highest dose; further reduction of CO in presence of genistein; title comp. also decreased PAP; table, figures
Frascarelli, Sabina; Ghelardoni, Sandra; Chiellini, Grazia; Vargiu, Romina; Ronca-Testoni, Simonetta; Scanlan, Thomas S.; Grandy, David K.; Zucchi, Riccardo; European Journal of Pharmacology; vol. 587; nb. 1-3; (2008); p. 231 - 236, View in Reaxys 95 of 193
Effect (Pharmacological Data)
chronotropic pos.
Species or Test-System (Pharmacological Data)
heart of Wistar rat
Sex
male
Concentration (Pharmacological Data)
100 μmol/l
Method (Pharmacological Data)
isolated rat hearts perfused for 50 min with standard buffer in presence of title comp.; 36.8 - 37 deg C, pH 7.4; heart rate (HR) monitored during perfusion
Further Details (Pharmacological Data)
further invest. in presence tyrosine kinase inhibitor genistein or β-adrenergic blocker propranolol; control: standard buffer; reference comp.: thyronamine, 3-iodothyronamine
Results
title comp. increased HR by ca. 20-35percent vs. baseline; effect was blunted in presence of genistein and abolished by propranolol; table, figure
Frascarelli, Sabina; Ghelardoni, Sandra; Chiellini, Grazia; Vargiu, Romina; Ronca-Testoni, Simonetta; Scanlan, Thomas S.; Grandy, David K.; Zucchi, Riccardo; European Journal of Pharmacology; vol. 587; nb. 1-3; (2008); p. 231 - 236, View in Reaxys 96 of 193
Effect (Pharmacological Data)
DNA; examination of
Species or Test-System (Pharmacological Data)
leukemic U937 cells of human
Concentration (Pharmacological Data)
0.5 - 5 mmol/l
Method (Pharmacological Data)
cells treated with various conc. of title comp. for 24 h; DNA extracted and separated by agarose gel electrophoresis; gel stained with ethidium bromide and imaged with FluorImager
Results
title comp. induced DNA fragmentation at conc. >= 3 mM; fig.
Inagaki, Shyuichiro; Morimura, Shigeru; Gondo, Kazunobu; Tang, Yueqin; Akutagawa, Hiroshi; Kida, Kenji; Bioscience, Biotechnology and Biochemistry; vol. 71; nb. 2; (2007); p. 371 - 379, View in Reaxys 97 of 193
Effect (Pharmacological Data)
drug interaction
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Species or Test-System (Pharmacological Data)
Caco-2 cells
Concentration (Pharmacological Data)
<= 30 mmol/l
Method (Pharmacological Data)
uptake of <3H>clonidine (3 nmol/l) by cell monolayer measured at pH 7.5 for 2 min or pH 8.5 in the absence or presence of title comp.; liquid scintillation counting
Further Details (Pharmacological Data)
inhibition of <3H>clonidine transport by title comp. investigated; control: <3H>clonidine uptake without title comp. = 100 percent
Results
<3H>clonidine uptake at pH 7.5 in the presence of 2 mmol/l title comp. was 68 percent (table); Ki = 2.5 mmol/l and 1.0 mmol/l for pH 7.5 and 8.5, respectively (table, diagram)
Fischer, Wiebke; Metzner, Linda; Hoffmann, Kathrin; Neubert, Reinhard H. H.; Brandsch, Matthias; Pharmaceutical Research; vol. 23; nb. 1; (2006); p. 131 - 137, View in Reaxys 98 of 193
Effect (Pharmacological Data)
cytotoxicity
Species or Test-System (Pharmacological Data)
colon cancer CaCo2 cells
Kind of Dosing (Pharmacological Data)
title comp. dissolved in DMSO or H2O and further diluted with fresh complete medium
Method (Pharmacological Data)
standard tetrazolium MTT assay; test cells incubated with title comp.; MTT reagent added; after 4 h incubation at 37 deg C medium removed, DMSO added; formed MTT product dissolved in DMSO; absorbance at 560 nm recorded
Further Details (Pharmacological Data)
before addition of title comp. exponentially growing cells plated into 96-well plates and incubated for 72 h at 37 deg C
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
198.0 μmol/l
Shoeb, Mohammad; MacManus, Stephen M.; Jaspars, Marcel; Trevidu, Jioji; Nahar, Lutfun; Kong-Thoo-Lin, Paul; Sarker, Satyajit D.; Tetrahedron; vol. 62; nb. 48; (2006); p. 11172 - 11177, View in Reaxys 99 of 193
Effect (Pharmacological Data)
membrane currents; inhibition of
Species or Test-System (Pharmacological Data)
Xenopus laevis oocyte
Method (Pharmacological Data)
oocytes expressing rat NMDA receptor subunits NR1a+2B; Ca(2+)- and Mg(2+)-free solution at 18 deg C; two-electrode voltage clamp at -70 mV; bath application of title comp.; inhibition of currents induced by 100 μmol/l glutamate and 10 μmol/l glycine
Further Details (Pharmacological Data)
NMDA: N-methyl-D-aspartate
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
138 μmol/l
Kloda, Anna; Adams, David J.; British Journal of Pharmacology; vol. 144; nb. 3; (2005); p. 323 - 330, View in Reaxys 100 of 193 Effect (Pharmacological Data)
membrane currents; inhibition of
Species or Test-System (Pharmacological Data)
Xenopus laevis oocyte
Method (Pharmacological Data)
oocytes expressing rat NMDA receptor subunits NR1a+2B; Ca(2+)- and Mg(2+)-free solution at 18 deg C; two-electrode voltage clamp at -120 mV; bath application of title comp.; inhibition of currents induced by 100 μmol/l glutamate and 10 μmol/l glycine
Further Details (Pharmacological Data)
NMDA: N-methyl-D-aspartate
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Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
32 μmol/l
Kloda, Anna; Adams, David J.; British Journal of Pharmacology; vol. 144; nb. 3; (2005); p. 323 - 330, View in Reaxys 101 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
Wistar rat kidney P2 membranes
Sex
male
Method (Pharmacological Data)
affinity at α2-adrenergic receptor evaluated by radioligand (<3H>RX821002) competition binding assay
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
19000 nmol/l
Glennon, Richard A.; Grella, Brian; Tyacke, Robin J.; Lau, Alice; Westaway, Julie; Hudson, Alan L.; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 4; (2004); p. 999 - 1002, View in Reaxys 102 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
Wistar rat whole brain P2 membranes
Sex
male
Method (Pharmacological Data)
affinity at imidazoline I2 receptor evaluated by radioligand (<3H>2-BFI) competition binding assay
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
5400 nmol/l
Glennon, Richard A.; Grella, Brian; Tyacke, Robin J.; Lau, Alice; Westaway, Julie; Hudson, Alan L.; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 4; (2004); p. 999 - 1002, View in Reaxys 103 of 193 Effect (Pharmacological Data)
transport; inhibition of
Species or Test-System (Pharmacological Data)
human choriocarcinoma JEG-3 cell monolayers
Concentration (Pharmacological Data)
1 mmol/l
Method (Pharmacological Data)
uptake of <3H>clonidine (3 nmol/l, pH 7.5, 1 min, room temperature) measured in presence of title comp.; cells solubilized and prepared for scintillation counting
Further Details (Pharmacological Data)
control: <3H>clonidine uptake in absence of title comp.: 100 percent
Results
<3H>clonidine uptake decreased to 87 percent in presence of title comp.
Mueller, Johanna; Neubert, Reinhard; Brandsch, Matthias; Pharmaceutical Research; vol. 21; nb. 4; (2004); p. 692 - 694, View in Reaxys 104 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
HEK-293 cell membranes expressing human 5-HT2A receptor
Concentration (Pharmacological Data)
1E-11 - 1E-06 mol/l
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Method (Pharmacological Data)
competition binding assay; 0.1 nmol/l <125I>-DOI used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer supplemented with 5 mmol/l CaCl2; radioactivity quantified by Packard Topcount plate reader
Further Details (Pharmacological Data)
nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); DOI: 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane; title comp. binding affinity to recombinant 5-HT2A receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate
Type (Pharmacological Data)
pKi
Value of Type (Pharmacological Data)
6.66 dimensionless
Knight, Antony R.; Misra, Anil; Quirk, Kathleen; Benwell, Karen; Revell, Dean; Kennett, Guy; Bickerdike, Mike; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 370; nb. 2; (2004); p. 114 - 123, View in Reaxys 105 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
CHO-K1 cell membranes expressing human 5-HT2B receptor
Concentration (Pharmacological Data)
1E-11 - 1E-06 mol/l
Method (Pharmacological Data)
competition binding assay; 5 nmol/l <3H>-5-HT used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer supplemented with 4 mmol/l CaCl2; radioactivity quantified by Packard Topcount plate reader
Further Details (Pharmacological Data)
nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); title comp. binding affinity to recombinant 5-HT2B receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate
Type (Pharmacological Data)
pKi
Value of Type (Pharmacological Data)
6.99 dimensionless
Knight, Antony R.; Misra, Anil; Quirk, Kathleen; Benwell, Karen; Revell, Dean; Kennett, Guy; Bickerdike, Mike; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 370; nb. 2; (2004); p. 114 - 123, View in Reaxys 106 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
HEK-293 cell membranes expressing human 5-HT2C receptor
Concentration (Pharmacological Data)
1E-11 - 1E-06 mol/l
Method (Pharmacological Data)
competition binding assay; 1 nmol/l <3H>-5-HT used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer; radioactivity quantified by Packard Topcount plate reader
Further Details (Pharmacological Data)
nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); title comp. binding affinity to recombinant 5-HT2C receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate
Type (Pharmacological Data)
pKi
Value of Type (Pharmacological Data)
5.63 dimensionless
Knight, Antony R.; Misra, Anil; Quirk, Kathleen; Benwell, Karen; Revell, Dean; Kennett, Guy; Bickerdike, Mike; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 370; nb. 2; (2004); p. 114 - 123, View in Reaxys 107 of 193 Effect (Pharmacological Data)
agonist
Endpoint of Effect (Pharmacological Data)
arachidonic acid (AA) release
Species or Test-System (Pharmacological Data)
NIH3T3 fibroblasts stably expressing 5-HT2A receptors
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Concentration (Pharmacological Data)
0.0001 - 10 μmol/l
Method (Pharmacological Data)
cells labeled with <3H>AA for 4 h; washed three times with DMEM and incubated with title comp. for 30 min at 37 deg C; <3H>AA in medium counted
Further Details (Pharmacological Data)
5-HT = 5-hydroxytryptamine; DMEM = Dulbecco's modified Eagle's medium; control: without title comp.
Type (Pharmacological Data)
EC50
Value of Type (Pharmacological Data)
1200 nmol/l
Results
title comp. stimulated the <3H>AA accumulation conc.-dependently (table)
Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 1; (2003); p. 229 - 237, View in Reaxys 108 of 193 Effect (Pharmacological Data)
agonist
Endpoint of Effect (Pharmacological Data)
IPs accumulation
Species or Test-System (Pharmacological Data)
NIH3T3 fibroblasts stably expressing 5-HT2A receptors
Concentration (Pharmacological Data)
0.001 - 10 μmol/l
Method (Pharmacological Data)
cells loaded with myo-<2-3H(N)>inositol and pretreated with 10 μmol/l pargyline and 10 mmol/l LiCl for 15 min at 37 deg C in CMRL-1066 media; then title comp. added for 30 min; <3H>IPs of cell lysate separated by ion-exchange chromatography and counted
Further Details (Pharmacological Data)
5-HT = 5-hydroxytryptamine; IPs = a mixture of inositol mono- bis-, and triphosphate; control: without title comp.
Type (Pharmacological Data)
EC50
Value of Type (Pharmacological Data)
1100 nmol/l
Results
title comp. stimulated the <3H>IPs accumulation conc.-dependently (table)
Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 1; (2003); p. 229 - 237, View in Reaxys 109 of 193 Effect (Pharmacological Data)
receptor; binding activity
Endpoint of Effect (Pharmacological Data)
<125I>2,5-dimethoxy-4-iodoamphetamine (DOI) binding
Species or Test-System (Pharmacological Data)
NIH3T3 fibroblasts stably expressing 5-HT2A receptors
Concentration (Pharmacological Data)
1E-05 - 10 μmol/l
Method (Pharmacological Data)
competition binding study; cells incubated with 2E-1 nmol/l <125I>DOI in the presence title comp. for 60 min at 25 deg C in Tris-EDTA buffer, pH 7.4; nonspecific binding determ. with 10 μmol/l cinanserin; filter-bound radioactivity counted
Further Details (Pharmacological Data)
5-HT = 5-hydroxytryptamine; control: without title comp.
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
49 nmol/l
Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 1; (2003); p. 229 - 237, View in Reaxys
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110 of 193
Effect (Pharmacological Data)
mutagenic
Species or Test-System (Pharmacological Data)
calf thymus DNA
Concentration (Pharmacological Data)
1 - 10 mmol/l
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
DNA exposed to title comp. with/without S9 (conc. 1.5 percent); incubated at 37 deg C for 3 h; during the last 1 h and after purified RNAses added; analyzed for DNA adducts by 32P-postlabeling analysis
Further Details (Pharmacological Data)
S9 prepared from phenobarbital/β-naphthoflavone induced male Sprague-Dawley rats; RNAses: ribonucleases; solvent (K2HPO4, pH 7.0, containing isocitrate and NADP(+)) as control
Results
title comp. no significantly produced DNA adducts in the presence of S9 (table)
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 111 of 193
Effect (Pharmacological Data)
mutagenic
Species or Test-System (Pharmacological Data)
Escherichia coli WP2 uvrA pKM101
Concentration (Pharmacological Data)
4000 - 12000 μg/plate
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
log-phase culture added to molten agar (5E7 cells/ml) and buffer/co-factor mix with/without S9 and with title comp.; then placed on solid agar; incub. at 37 deg C for 48 h; colonies number counted and analyzed DNA adducts by 32P-postlabeling analysis
Further Details (Pharmacological Data)
S9 prepared from phenobarbital/β-naphthoflavone induced male Sprague-Dawley rats; solid agar with/without histidine or tryptophan; benzo(a)pyrene and 2-aminoanthracene as positive control (induced mutations)
Results
title comp. showed induced mutations and DNA adducts in a dose-dependent manner (diagrams)
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 112 of 193
Effect (Pharmacological Data)
mutagenic
Species or Test-System (Pharmacological Data)
Salmonella typhimurium TA1535
Concentration (Pharmacological Data)
4000 - 12000 μg/plate
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
log-phase culture added to molten agar (5E7 cells/ml) and buffer/co-factor mix with/without S9 and with title comp.; then placed on solid agar; incub. at 37 deg C for 48 h; colonies number counted and analyzed DNA adducts by 32P-postlabeling analysis
Further Details (Pharmacological Data)
S9 prepared from phenobarbital/β-naphthoflavone induced male Sprague-Dawley rats; solid agar with/without histidine or tryptophan; benzo(a)pyrene and 2-aminoanthracene as positive control (induced mutations)
Comment (Pharmacological Data)
No effect
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Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 113 of 193
Effect (Pharmacological Data)
mutagenic
Species or Test-System (Pharmacological Data)
Salmonella typhimurium TA100
Concentration (Pharmacological Data)
4000 - 12000 μg/plate
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
log-phase culture added to molten agar (5E7 cells/ml) and buffer/co-factor mix with/without S9 and with title comp.; then placed on solid agar; incub. at 37 deg C for 48 h; colonies number counted and analyzed DNA adducts by 32P-postlabeling analysis
Further Details (Pharmacological Data)
S9 prepared from phenobarbital/β-naphthoflavone induced male Sprague-Dawley rats; solid agar with/without histidine or tryptophan; benzo(a)pyrene and 2-aminoanthracene as positive control (induced mutations)
Results
title comp. showed induced mutations and DNA adducts in a dose-dependent manner (diagrams)
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 114 of 193
Effect (Pharmacological Data)
mutagenic
Species or Test-System (Pharmacological Data)
Salmonella typhimurium TA98
Concentration (Pharmacological Data)
4000 - 12000 μg/plate
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
log-phase culture added to molten agar (5E7 cells/ml) and buffer/co-factor mix with/without S9 and with title comp.; then placed on solid agar; incub. at 37 deg C for 48 h; colonies number counted and analyzed DNA adducts by 32P-postlabeling analysis
Further Details (Pharmacological Data)
S9 prepared from phenobarbital/β-naphthoflavone induced male Sprague-Dawley rats; solid agar with/without histidine or tryptophan; benzo(a)pyrene and 2-aminoanthracene as positive control (induced mutations)
Comment (Pharmacological Data)
No effect
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 115 of 193
Effect (Pharmacological Data)
mutagenic
Species or Test-System (Pharmacological Data)
Salmonella typhimurium TA97a
Concentration (Pharmacological Data)
4000 - 12000 μg/plate
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
log-phase culture added to molten agar (5E7 cells/ml) and buffer/co-factor mix with/without S9 and with title comp.; then placed on solid agar; incub. at 37 deg C for 48 h; colonies number counted and analyzed DNA adducts by 32P-postlabeling analysis
Further Details (Pharmacological Data)
S9 prepared from phenobarbital/β-naphthoflavone induced male Sprague-Dawley rats; solid agar with/without histidine or tryptophan; benzo(a)pyrene and 2-aminoanthracene as positive control (induced mutations)
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Results
title comp. showed induced mutations and DNA adducts in a dose-dependent manner (diagrams)
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 116 of 193
Effect (Pharmacological Data)
genotoxic
Species or Test-System (Pharmacological Data)
rat hepatocytes
Concentration (Pharmacological Data)
1 - 10 mmol/l
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
cells from induced (PB/β-NF) or uninduced rats treated for 3 h at 37 deg C; alkaline elution assay; DNA single-strand breaks and adduct formation determined by 32P-postlabeling analysis
Further Details (Pharmacological Data)
PB/β-NF: phenobarbital/β-naphthoflavone; aflatoxin B1 (AFB1), γ-radiation and benzo(a)pyrene as positive controls: γ-radiation produced DNA strand breaks, AFB1 produced strand breaks in uninduced hypatocytes; two replicates
Results
title comp. showed negative effect for the induction of DNA single-strand breaks in cultured primary hepatocytes isolated from uninduced or induced rats with PB/β-NF; intensity of DNA adduct formation in a dose-dependent manner (table)
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 117 of 193
Effect (Pharmacological Data)
cytotoxicity
Species or Test-System (Pharmacological Data)
CHO cells
Concentration (Pharmacological Data)
1 - 4 mmol/l
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
culture (2-3E6 cells) incubated with title comp. for 3 h; at the end for the last 30 min of incubation added BrdUrd for staining; reduction in total cell DNA (PI) number analyzed using flow cytometer
Further Details (Pharmacological Data)
BrdUrd: 5-bromodeoxyuridine; PI: propidium iodide
Results
title comp. increased in a dose-dependent manner both with/without S9 (diagrams)
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 118 of 193
Effect (Pharmacological Data)
DNA synthesis; inhibition of
Species or Test-System (Pharmacological Data)
CHO cells
Concentration (Pharmacological Data)
1 - 4 mmol/l
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
culture (2-3E6 cells) incubated with title comp. for 3 h; at the end for the last 30 min of incubation added BrdUrd and FITC labeled secondary antibody to mouse anti-BrdUrd; inhibition of DNA synthesis measured as suppression of BrdUrd uptake/S phase
Further Details (Pharmacological Data)
BrdUrd: 5-bromodeoxyuridine; two replicates
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Results
title comp. induced strong (dose-dependent) inhibition of DNA synthesis with/without S9 (diagrams)
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 119 of 193
Effect (Pharmacological Data)
genotoxic
Species or Test-System (Pharmacological Data)
CHO cells
Concentration (Pharmacological Data)
1 - 4 mmol/l
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
culture (2-3E6 cells) incubated with title comp. for 3 h; at the end for the last 30 min of incubation added BrdUrd and FITC labeled secondary antibody to mouse anti-BrdUrd; DNA adducts measured
Further Details (Pharmacological Data)
BrdUrd: 5-bromodeoxyuridine; two replicates
Comment (Pharmacological Data)
No effect
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 120 of 193 Effect (Pharmacological Data)
genotoxic
Species or Test-System (Pharmacological Data)
CHO cells
Concentration (Pharmacological Data)
1 - 4 mmol/l
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
culture (2-3E6 cells) incubated with title comp. with/without S9 for 3 h; then once more incubated for an additional 17 h title comp.; percent of cells (in methaphase) with chromosomal aberration (Abs) in treated culture evaluated
Further Details (Pharmacological Data)
S9 prepared from phenobarbital/β-naphthoflavone induced male Sprague-Dawley rats; cyclophosphamide and mitomycin C as positive controls (induced Abs as expected)
Results
title comp. produced no significant increases in Abs over the controls with/without S9 (diagrams)
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 121 of 193 Effect (Pharmacological Data)
cytotoxicity
Species or Test-System (Pharmacological Data)
rat hepotocytes
Concentration (Pharmacological Data)
1 - 10 mmol/l
Kind of Dosing (Pharmacological Data)
title comp. stock solution prepared in DMSO
Method (Pharmacological Data)
cells from induced (PB/β-NF) or uninduced rats treated for 3 h at 37 deg C; Trypan blue dye exclusion viability assay; cell viability after treated or 3 h and intracellular ATP determined
Further Details (Pharmacological Data)
PB/β-NF: phenobarbital/β-naphthoflavone; aflatoxin B1, γ-radiation and benzo(a)pyrene as positive controls
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Results
title comp. showed decreased number of cell viability and cellular ATP content of controls in a dose-dependent manner (table)
Reddy, M. Vijayaraj; Storer, Richard D.; Laws, George M.; Armstrong, Michael J.; Barnum, John E.; Gara, Jennifer P.; McKnight, Crystal G.; Skopek, Thomas R.; Sina, Joseph F.; DeLuca, John G.; Galloway, Sheila M.; Environmental and Molecular Mutagenesis; vol. 40; nb. 1; (2002); p. 1 - 17, View in Reaxys 122 of 193 Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
cathepsin K
Concentration (Pharmacological Data)
100 mg/l
Kind of Dosing (Pharmacological Data)
in DMSO
Method (Pharmacological Data)
in the presence of 160 ng/mL cathepsin K and 20 μmol/l ZFR-AMC (phenylalanine-arginine-aminomethylcoumarin)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
15 μmol/l
Patil, Ashok D.; Freyer, Alan J.; Carte, Brad; Taylor, Paul B.; Johnson, Randall K.; Faulkner, D. John; Journal of Natural Products; vol. 65; nb. 4; (2002); p. 628 - 629, View in Reaxys 123 of 193 Effect (Pharmacological Data)
enzyme; examination of
Species or Test-System (Pharmacological Data)
coclaurine N-methyltransferase
Method (Pharmacological Data)
0.1 mM norreticuline, 100 mM potassium phosphate buffer, 1 mM (methyl-3H)-S-adenosyl-L-methionine, 20 μl of enzyme soln., 30 deg C, 60 min; 1 mM (S)-coclaurine
Results
relative activity (vs (S)-coclaurine when activity = 100) is 0 (no methylation)
Choi, Kum-Boo; Morishige, Takashi; Sato, Fumihiko; Phytochemistry; vol. 56; nb. 7; (2001); p. 649 - 655, View in Reaxys 124 of 193 Effect (Pharmacological Data)
transmitter releasing
Species or Test-System (Pharmacological Data)
rat brain stem
Kind of Dosing (Pharmacological Data)
decreasing concentrations: 5.0; 2.5; 1.0; 0.5; 0.25; 0.1; 0.05; 0.01; 0.005 mg/L
Method (Pharmacological Data)
as in Knoll, J. et al. Life Sci. 1996, 58, 2101; LT incorp. into transmitter stores of brain stem slices by preincubation; counting of released LT amount before and after brain stem stimulation with/without title comp.; each concn. for two brain stems
Further Details (Pharmacological Data)
LT: labeled transmitter (5-hydroxy-<G-3H>-tryptamine creatinine sulphate (10-20 Ci/ mmol)); stimulation by rectang. pulses 3 Hz, 1 ms, 60 V, 3 min; start with 3 3-min resting periods before first stimulation, then 7 resting periods between stimulations
Results
title comp. concn. which increases on both stems at least 25 percent of <3H>-serotonin amount released after stimulation is 0.25 mg/L compared with 5.0 mg/L for fluoxetine and > 5 mg/L for bromocryptine, pergolide, clorgyline, lazabemide and amantadine
Yoneda, Fumio; Moto, Toshiaki; Sakae, Masatoshi; Ohde, Hironori; Knoll, Berta; Miklya, Ildiko; Knoll, Joseph; Bioorganic and Medicinal Chemistry; vol. 9; nb. 5; (2001); p. 1197 - 1212, View in Reaxys 125 of 193 Effect (Pharmacological Data)
transmitter releasing
Species or Test-System (Pharmacological Data)
rat brain stem
Kind of Dosing (Pharmacological Data)
decreasing concentrations: 5.0; 2.5; 1.0; 0.5; 0.25; 0.1; 0.05; 0.01; 0.005 mg/L
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Method (Pharmacological Data)
as in Knoll, J. et al. Life Sci. 1996, 58, 2101; LT incorp. into transmitter stores of brain stem slices by preincubation; counting of released LT amount before and after brain stem stimulation with/without title comp.; each concn. for two brain stems
Further Details (Pharmacological Data)
LT: labeled transmitter (<2,5,6-3H>-dopamine (5-15 Ci/mmol)); stimulation by rectangular pulses 3 Hz, 1 ms, 60 V, 3 min; start with 3 consecutive 3-min resting periods before first stimulation, then 7 resting periods between stimulations
Results
title comp. concn. which increases on both stems at least 25 percent of LT amount released after stimulation is 2.5 mg/L compared with 0.25 mg/L for bromocryptine, 0.5 mg/L for pergolide and > 5 mg/L for fluoxetine, clorgyline, lazabemide and amantadine
Yoneda, Fumio; Moto, Toshiaki; Sakae, Masatoshi; Ohde, Hironori; Knoll, Berta; Miklya, Ildiko; Knoll, Joseph; Bioorganic and Medicinal Chemistry; vol. 9; nb. 5; (2001); p. 1197 - 1212, View in Reaxys 126 of 193 Effect (Pharmacological Data)
transmitter releasing
Species or Test-System (Pharmacological Data)
rat brain stem
Kind of Dosing (Pharmacological Data)
decreasing concentrations: 5.0; 2.5; 1.0; 0.5; 0.25; 0.1; 0.05; 0.01; 0.005 mg/L
Method (Pharmacological Data)
as in Knoll, J. et al. Life Sci. 1996, 58, 2101; LT incorp. into transmitter stores of brain stem slices by preincubation; counting of released LT amount before and after brain stem stimulation with/without title comp.; each concn. for two brain stems
Further Details (Pharmacological Data)
LT: labeled transmitter (1-<7,8-3H>-noradrenaline (30-50 Ci/mmol)); stimulation by rectangular pulses 3 Hz, 1 ms, 60 V, 3 min; start with 3 consecutive 3-min resting periods before first stimulation, then 7 resting periods between stimulations
Results
title comp. concn. which increases on both stems at least 25 percent of LT amount released after stimulation is 2.5 mg/L compared with 2.5 mg/L for bromocryptine and > 5 mg/L for pergolide, fluoxetine, clorgyline, lazabemide and amantadine
Yoneda, Fumio; Moto, Toshiaki; Sakae, Masatoshi; Ohde, Hironori; Knoll, Berta; Miklya, Ildiko; Knoll, Joseph; Bioorganic and Medicinal Chemistry; vol. 9; nb. 5; (2001); p. 1197 - 1212, View in Reaxys 127 of 193 Effect (Pharmacological Data)
tumor cell migration; inhibition of
Species or Test-System (Pharmacological Data)
murine colon 26-L5 adenocarcinoma cell line
Concentration (Pharmacological Data)
100 mg/l
Kind of Dosing (Pharmacological Data)
title comp. added in dimethyl sulfoxide
Method (Pharmacological Data)
2E5 cells incub. with var. conc. of title comp. in RPMI-1640 medium with 0.1 percent bovine serum albumin for 30 min on ice, then added to upper compartment of Transwell chamber, incub. 3 h at 37 deg C; cells stained, migrated cells extracted, absorbance det.
Further Details (Pharmacological Data)
vehicle control; cells stained with 0.5 percent crystal violet for 30 min
Results
title comp. inhibited tumor cell migration (30 - 40 percent inhibition of control)
Ogasawara, Masaru; Matsubara, Toshiyuki; Suzuki, Hideyo; Biological and Pharmaceutical Bulletin; vol. 24; nb. 6; (2001); p. 720 - 723, View in Reaxys 128 of 193 Effect (Pharmacological Data) Species or Test-System (Pharmacological Data)
enzyme; inhib. of phenylalanine ammonia-lyase
Kim, Seong Hwan; Kronstad, James W.; Ellis, Brian E.; Phytochemistry; vol. 58; nb. 6; (2001); p. 849 - 857, View in Reaxys 129 of 193 Effect (Pharmacological Data) Species or Test-System (Pharmacological Data)
agonist HEK293 cells expressing rTAR1
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Concentration (Pharmacological Data)
Ca. 1E-09 - 1E-05 mol/l
Method (Pharmacological Data)
cells incubated in KRH with 100 μmol/l 3-isobutyl-1-methylxanthine and title comp. for 1 h at 37 deg C; cAMP content measured using competitive binding of <3H>cAMP to a cAMPbinding protein
Further Details (Pharmacological Data)
HEK: human embryonic kidney; rTAR1: rat trace amine receptor 1; reference comp.: forskolin; KRH: Krebs-Ringer-HEPES buffer
Type (Pharmacological Data)
EC50
Value of Type (Pharmacological Data)
310 nmol/l
Results
title comp. induced cAMP production acting as agonist (diagram)
Bunzow; Sonders; Arttamangkul; Harrison; Zhang; Quigley; Darland; Suchland; Pasumamula; Kennedy; Olson; Magenis; Amara; Grandy; Molecular Pharmacology; vol. 60; nb. 6; (2001); p. 1181 - 1188, View in Reaxys 130 of 193 Effect (Pharmacological Data)
biotransformation
Species or Test-System (Pharmacological Data)
Phoma lingam virulent isolate BJ 125
Concentration (Pharmacological Data)
0.0002 mol/l
Method (Pharmacological Data)
in vitro; inoculated with fungal spores (2E9 per flask); minimal medium; incubation 14 days; metabolites isolated by preparative TLC
Metabolite XRN (Pharmacological Data)
170780; 143358
Metabolite (Pharmacological Data)
N-Acetyltryptamine; indole-3-acetic acid
Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys 131 of 193 Effect (Pharmacological Data)
biotransformation
Species or Test-System (Pharmacological Data)
Phoma lingam avirulent isolate Unity
Concentration (Pharmacological Data)
0.0002 mol/l
Method (Pharmacological Data)
in vitro; inoculated with fungal spores (2E9 per flask); minimal medium; incubation 5 days; metabolites isolated by preparative TLC
Metabolite XRN (Pharmacological Data)
125553; 129435
Metabolite (Pharmacological Data)
2-(3-indole)-ethanol; 1H-indole-3-carboxylic acid
Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys 132 of 193 Effect (Pharmacological Data)
fungistatic
Species or Test-System (Pharmacological Data)
Phoma lingam virulent isolate
Concentration (Pharmacological Data)
0.0001 - 0.0005 mol/l
Method (Pharmacological Data)
in vitro; mycelial radial growth bioassay; incubation time 72 h
Results
percent inhibition/dose (M): 0/1E-4, and 1/5E-4
Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys
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133 of 193 Effect (Pharmacological Data)
fungistatic
Species or Test-System (Pharmacological Data)
Phoma lingam avirulent isolate Unity
Concentration (Pharmacological Data)
0.0001 - 0.0005 mol/l
Method (Pharmacological Data)
in vitro; mycelial radial growth bioassay; incubation time 72 h
Results
percent inhibition/dose (M): 0/1E-4, and 1/5E-4
Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys 134 of 193 Effect (Pharmacological Data)
fungistatic
Species or Test-System (Pharmacological Data)
Alternaria brassica
Concentration (Pharmacological Data)
0.0001 - 0.0005 mol/l
Method (Pharmacological Data)
in vitro; mycelial radial growth bioassay; incubation time 72 h
Comment (Pharmacological Data)
No effect
Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys 135 of 193 Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
deacetylipecoside synthase
Concentration (Pharmacological Data)
0.1 - 1.0 mM
Comment (Pharmacological Data)
No effect
De-Eknamkul, Wanchai; Suttipanta, Nitima; Kutchan, Toni M; Phytochemistry; vol. 55; nb. 2; (2000); p. 177 181, View in Reaxys 136 of 193 Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human liver microsomes
Concentration (Pharmacological Data)
0.1 - 500 μmol/l
Method (Pharmacological Data)
human liver samples were obtained from unrelated white Spanish patients (no liver disease); microsomal fractions were prepared; CYP3A enzyme activity was measured using the enzyme-specific substrate midazolam (0.5-20 μmol/l), incubated with title comp.
Further Details (Pharmacological Data)
midazolam and its main metabolites, 1'-hydroxymidazolam and 4-hydroxymidazolam analysed by HPLC
Comment (Pharmacological Data)
No effect
Martinez; Gervasini; Agundez; Carrillo; Ramos; Garcia-Gamito; Gallardo; Benitez; European Journal of Clinical Pharmacology; vol. 56; nb. 2; (2000); p. 145 - 151, View in Reaxys 137 of 193 Comment (Pharmacological Data)
weak inhibitory activity on NADPH-dependent lipid peroxidation in rat liver microsomes (IC50 260 μM)
Takahashi, Satoshi; Matsunaga, Takayuki; Hasegawa, Chika; Saito, Haruo; Fujita, Daisuke; Kiuchi, Fumiyuki; Tsuda, Yoshisuke; Chemical and Pharmaceutical Bulletin; vol. 46; nb. 10; (1998); p. 1527 - 1529, View in Reaxys
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138 of 193 Effect (Pharmacological Data)
inhibition of forskolin-induced cAMP production
Species or Test-System (Pharmacological Data)
HA7 cell line
Exposure Period (Pharmacological Data)
10 min
Method (Pharmacological Data)
cell preincubation; forskolin (100 μM) and title compd. addn., incubation (10 min, room temp.), cellular extract anal.
Type (Pharmacological Data)
pEC50
Value of Type (Pharmacological Data)
5.36 -log(M)
Koek; Patoiseau; Assie; Cosi; Kleven; Dupont-Passelaigue; Carilla-Durand; Palmier; Valentin; John; Pauwels; Tarayre; Colpaert; Journal of Pharmacology and Experimental Therapeutics; vol. 287; nb. 1; (1998); p. 266 283, View in Reaxys 139 of 193 Effect (Pharmacological Data)
intracellular cAMP stimulation
Species or Test-System (Pharmacological Data)
murine fibroblasts (LMtk-) cell line
Exposure Period (Pharmacological Data)
10 min
Method (Pharmacological Data)
cell line membrane preincubated (HEPES-buffered saline, pH 7.4, 37 deg C, 30 min), then incubated in presence of title compd.
Type (Pharmacological Data)
EC50
Value of Type (Pharmacological Data)
13342 nmol/l
Results
affinity const. Ki = 57 nM
Adham, Nika; Zgombick, John M.; Bard, Jonathan; Journal of Pharmacology and Experimental Therapeutics; vol. 287; nb. 2; (1998); p. 508 - 514, View in Reaxys 140 of 193 Effect (Pharmacological Data)
agonist
Species or Test-System (Pharmacological Data)
Chinese hamster ovary FA4 cells
Concentration (Pharmacological Data)
20 μmol/l
Method (Pharmacological Data)
ability of title comp. to activate PLC-mediated IP accumulation studied; cells labeled with 1 μCi/ml myo-<3H>inositol (24 h, 37 deg C) incubated with title comp. for 10 min; mono-, di-, triphosphates of inositol separated by ion exchange chromatography
Further Details (Pharmacological Data)
radioactivity counted by liquid scintillation; cells expressing human 5-HT2A receptors; 5HT: 5-hydroxytryptamine; PLC: phospholipase C; IP: inositol phosphates; 5-HT used as reference comp.; Emax: maximal response
Results
Emax title comp./Emax 5-HT ca. 0.60 (figure)
Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.; Molecular Pharmacology; vol. 54; nb. 1; (1998); p. 94 - 104, View in Reaxys 141 of 193 Effect (Pharmacological Data)
agonist
Species or Test-System (Pharmacological Data)
Chinese hamster ovary FA4 cells
Concentration (Pharmacological Data)
20 μmol/l
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Method (Pharmacological Data)
ability of title comp. to activate PLA2-mediated arachidonic acid release studied; cells labeled with 0.1 μCi/ml <14C>arachidonic acid (4 h, 37 deg C) incubated with title comp. for 10 min; radioactivity measured by liquid scintillation counting
Further Details (Pharmacological Data)
cells expressing human 5-HT2A receptors; 5-HT: 5-hydroxytryptamine; PLA2: phospholipase A2; 5-HT used as reference comp.; Emax: maximal response
Results
Emax title comp./Emax 5-HT ca.1.4 (figure)
Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.; Molecular Pharmacology; vol. 54; nb. 1; (1998); p. 94 - 104, View in Reaxys 142 of 193 Effect (Pharmacological Data)
agonist
Species or Test-System (Pharmacological Data)
Chinese hamster ovary FA4 cells
Concentration (Pharmacological Data)
20 μmol/l
Method (Pharmacological Data)
ability of title comp. to increase Ca(2+) conc. studied; cells loaded with Fura-2; intracellular Ca(2+) conc. determined by measuring fluorescence (340/380 nm)
Further Details (Pharmacological Data)
cells expressing human 5-HT2A receptors; 5-HT: 5-hydroxytryptamine; 5-HT used as reference comp.; Emax: maximal response
Results
Emax title comp./Emax 5-HT ca. 0.45 (figure)
Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.; Molecular Pharmacology; vol. 54; nb. 1; (1998); p. 94 - 104, View in Reaxys 143 of 193 Comment (Pharmacological Data)
inhibition of 2-<125I>-iodomelatonin binding in membrane preparations of rat testes, IC50=31000 nmol/L
Vera; Tijmes; Valladares; Steroids; vol. 62; nb. 2; (1997); p. 226 - 229, View in Reaxys 144 of 193 Comment (Pharmacological Data)
substrate specificity for phenylethylamine oxidase of Arthrobacter globiformis IFO 12137 (ATCC 8010), Km = 0.017 mM, Vmax = 7.63 μmol/min/mg, Vmax/Km = 449; relative reaction rate 16percent of that observed with 2-phenylethylamine at 1.0 mM
Shimizu, Eiichi; Ohta, Keiichi; Takayama, Shigeo; Kitagaki, Yuzuru; Tanizawa, Katsuyuki; Yorifuji, Takamitsu; Bioscience, Biotechnology and Biochemistry; vol. 61; nb. 3; (1997); p. 501 - 505, View in Reaxys 145 of 193 Effect (Pharmacological Data)
transport
Species or Test-System (Pharmacological Data)
Caco-2 cells
Concentration (Pharmacological Data)
50 μmol/l
Exposure Period (Pharmacological Data)
5 - 60 min
Method (Pharmacological Data)
cells seeded on microporous membrane filters inside Transwell cell culture chambers; incubation medium; pH 7.5 (apical side); 37 deg C or ambient temp.; also in the presence of imipramine; samples from basal side withdrawn; HPLC
Results
imipramine reduced drug uptake at pH 7.5
Iseki, Ken; Kaido, Koh-Ichi; Kobayashi, Michiya; Sugawara, Mitsuru; Miyazaki, Katsumi; Biological and Pharmaceutical Bulletin; vol. 20; nb. 7; (1997); p. 794 - 799, View in Reaxys 146 of 193 Effect (Pharmacological Data)
transport
Species or Test-System (Pharmacological Data)
rat intestinal brush-border membrane vesicles
Concentration (Pharmacological Data)
1 mmol/l
Exposure Period (Pharmacological Data)
0.5 - 30 min
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Method (Pharmacological Data)
vesicles from small intestine of rats (Wistar, male, 175-240 g); pH 7.5; rapid filtration technique; drug trapped on filter measured by HPLC; also in the presence of imipramine
Results
imipramine reduced drug uptake at pH 7.5
Iseki, Ken; Kaido, Koh-Ichi; Kobayashi, Michiya; Sugawara, Mitsuru; Miyazaki, Katsumi; Biological and Pharmaceutical Bulletin; vol. 20; nb. 7; (1997); p. 794 - 799, View in Reaxys 147 of 193 Effect (Pharmacological Data)
muscle contractive
Species or Test-System (Pharmacological Data)
Beagle dog colon longitudinal muscle
Sex
male and female
Concentration (Pharmacological Data)
Ca. 1E-06 - 0.0001 mol/l
Method (Pharmacological Data)
dogs (7-14kg) decerebrated, a piece of midcolon ca. 5 cm dissected, luminal contents removed; mucosa, submucosa and mesenterium dissected, strips of longitudinal muscle prepared
Further Details (Pharmacological Data)
concentration-response curve in the presence of 10 nM SB 204070
Results
concentration-dependent contraction: title compound concentration (logM), ca. contraction percent: -6, 0; -5, 15
Prins, Nicolaas H.; Briejer, Michel R.; Schuurkes, Jan A.J.; British Journal of Pharmacology; vol. 120; nb. 4; (1997); p. 714 - 720, View in Reaxys 148 of 193 Effect (Pharmacological Data)
protein binding
Species or Test-System (Pharmacological Data)
Wistar rat brain cortical membranes
Sex
male
Method (Pharmacological Data)
membranes (0.5-0.6 mg protein/ml) were incubated with 1.3-1.5 nmol/l <3H>citalopram for 60 min at 22 deg C in presence of title comp.; inhibition of <3H>citalopram binding to 5-HT transporter was assayed by liquid scintillation spectrometry
Further Details (Pharmacological Data)
incubation buffer (mmol/l): 50 Tris-HCl, 120 NaCl, 5 KCl, pH 7.4; Ki=IC50/(1+C/Kd); Hill coefficient (nH) was determined from Hill plots of saturation experiments; 5-HT: 5-hydroxytryptamine
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
3600 nmol/l
Results
nH = 0.87 (table)
Paehkla, Rein; Raego, Lembit; Callaway, James J.; Airaksinen, Mauno M.; Pharmacology and Toxicology; vol. 80; nb. 3; (1997); p. 122 - 126, View in Reaxys 149 of 193 Effect (Pharmacological Data)
enzyme; induction of
Species or Test-System (Pharmacological Data)
HL-60 cell membranes
Concentration (Pharmacological Data)
1 - 3000 μmol/l
Method (Pharmacological Data)
effect of title compound on GTPase activity studied; dibutyryl-cAMP differentiated HL-60 cells; purified by repeated centrifugation and resuspension; disintegrated by 25 bar N2 cavitation at 4 deg C; EDTA and mercaptoethanol added; centrifuged
Further Details (Pharmacological Data)
incubation in pH 7.4 medium containing membranes, adenosine 5'-(βγ-imido)triphosphate, (γ-32P)GTP, and bovine serum albumin at 25 deg C, for 15-25 min
Comment (Pharmacological Data)
No effect
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Klinker, Jan F.; Seifert, Roland; Damm, Henning; Rommelspacher, Hans; Biochemical Pharmacology; vol. 53; nb. 11; (1997); p. 1621 - 1626, View in Reaxys 150 of 193 Effect (Pharmacological Data)
enzyme; induction of
Species or Test-System (Pharmacological Data)
bovine retinal G-protein transducin
Concentration (Pharmacological Data)
1 - 3000 μmol/l
Method (Pharmacological Data)
effect of title compound on GTPase activity studied; transducin prepared from bovine rod outer segment disk membranes
Further Details (Pharmacological Data)
incubation in pH 7.4 medium containing transducin, ATP, adenosine 5'-(βγ-imido)triphosphate, (γ-32P)GTP and bovine serum albumin at 25 deg C, 15-25 min
Type (Pharmacological Data)
EC50
Value of Type (Pharmacological Data)
350 μmol/l
Results
effect in 1 mmol/l concentration of title compound: 13 percent above basal
Klinker, Jan F.; Seifert, Roland; Damm, Henning; Rommelspacher, Hans; Biochemical Pharmacology; vol. 53; nb. 11; (1997); p. 1621 - 1626, View in Reaxys 151 of 193 Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
recombinant human IDO
Concentration (Pharmacological Data)
1 mmol/l
Method (Pharmacological Data)
recombinant human indoleamine 2,3-dioxygenase (IDO) from E. coli YA21; activity assayed by measuring the kynurenine; yellow-coloured complex measured by spectrophotometer
Further Details (Pharmacological Data)
activity of IDO in the presence of 1 mM of title comp.; relative to the activity with 200 μM Ltryptophan
Results
percentage of in vitro activity 32 percent and inhibition 28 percent
Southan, Michael D.; Truscott, Roger J. W.; Jamie, Joanne F.; Pelosi, Luciana; Walker, Mark J.; Maeda, Hiroyasu; Iwamoto, Yoshiki; Tone, Shigenobu; Medicinal Chemistry Research; vol. 6; nb. 5; (1996); p. 343 - 352, View in Reaxys 152 of 193 Effect (Pharmacological Data)
agonist
Species or Test-System (Pharmacological Data)
neuroblastoma cells of N1E-115 mouse
Method (Pharmacological Data)
5-HT3 receptor-mediated ion currents evoked by title comp. in cells investigated in wholecell voltage clamp experiments at 20-24 deg C
Further Details (Pharmacological Data)
potency for desensitization (IC50); Student's t test
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
17 μmol/l
Results
desensitizes completely 5-HT3 receptor-mediated inward current; conc.-effect curve; recovery from desensitization is single exponential
Van Hooft, Johannes A.; Vijverberg, Henk P.M.; British Journal of Pharmacology; vol. 117; nb. 5; (1996); p. 839 846, View in Reaxys 153 of 193 Effect (Pharmacological Data)
agonist
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Species or Test-System (Pharmacological Data)
neuroblastoma cells of N1E-115 mouse
Method (Pharmacological Data)
5-HT3 receptor-mediated ion currents evoked by title comp. in cells investigated in wholecell voltage clamp experiments at 20-24 deg C
Further Details (Pharmacological Data)
potency for activation (EC50); Student's t test
Type (Pharmacological Data)
EC50
Value of Type (Pharmacological Data)
44 μmol/l
Results
partial agonism on 5-HT3 receptors; Emax=33.0 percent; time constant of inward current decay 22.7 s (n=6) for 100 μM of title comp.
Van Hooft, Johannes A.; Vijverberg, Henk P.M.; British Journal of Pharmacology; vol. 117; nb. 5; (1996); p. 839 846, View in Reaxys 154 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
mutant A5.46S 5-HT2C receptors expressed in COS-1 cells
Method (Pharmacological Data)
incubation at 37 deg C for 1 h in Tris*HCl buffer solution
Further Details (Pharmacological Data)
Ki: binding affinity
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
174 nmol/l
Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 155 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
wild-type 5-HT2C receptors expressed in COS-1 cells
Method (Pharmacological Data)
incubation at 37 deg C for 1 h in Tris*HCl buffer solution
Further Details (Pharmacological Data)
Ki: binding affinity
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
284 nmol/l
Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 156 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
mutant S5.46A 5-HT2A receptors expressed in COS-1 cells
Method (Pharmacological Data)
incubation at 37 deg C for 1 h in Tris*HCl buffer solution
Further Details (Pharmacological Data)
Ki: binding affinity
Type (Pharmacological Data)
Ki
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Value of Type (Pharmacological Data)
3493 nmol/l
Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 157 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
wild-type 5-HT2A receptors expressed in COS-1 cells
Method (Pharmacological Data)
incubation at 37 deg C for 1 h in Tris*HCl buffer solution
Further Details (Pharmacological Data)
Ki: binding affinity
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
929 nmol/l
Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 158 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
h5-HT1Dβ L929sA cells
Method (Pharmacological Data)
radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>5-alniditan (2 nM)
Further Details (Pharmacological Data)
Ki = apparent equilibrium inhibition constant
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
150 nmol/l
Leysen; Gommeren; Heylen; Luyten; Van De Weyer; Vanhoenacker; Haegeman; Schotte; Van Gompel; Wouters; Lesage; Molecular Pharmacology; vol. 50; nb. 6; (1996); p. 1567 - 1580, View in Reaxys 159 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
h5-HT1Dβ L929sA cells
Method (Pharmacological Data)
radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>5-HT (4 nM)
Further Details (Pharmacological Data)
Ki = apparent equilibrium inhibition constant
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
58 nmol/l
Leysen; Gommeren; Heylen; Luyten; Van De Weyer; Vanhoenacker; Haegeman; Schotte; Van Gompel; Wouters; Lesage; Molecular Pharmacology; vol. 50; nb. 6; (1996); p. 1567 - 1580, View in Reaxys 160 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
h5-HT1Dα C6 glioma cells
Method (Pharmacological Data)
radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>5-HT (4 nM)
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Further Details (Pharmacological Data)
Ki = apparent equilibrium inhibition constant
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
42 nmol/l
Leysen; Gommeren; Heylen; Luyten; Van De Weyer; Vanhoenacker; Haegeman; Schotte; Van Gompel; Wouters; Lesage; Molecular Pharmacology; vol. 50; nb. 6; (1996); p. 1567 - 1580, View in Reaxys 161 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
h5-HT1Dα C6 glioma cells
Method (Pharmacological Data)
radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>alniditan (2 nM)
Further Details (Pharmacological Data)
Ki = apparent equilibrium inhibition constant
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
141 nmol/l
Leysen; Gommeren; Heylen; Luyten; Van De Weyer; Vanhoenacker; Haegeman; Schotte; Van Gompel; Wouters; Lesage; Molecular Pharmacology; vol. 50; nb. 6; (1996); p. 1567 - 1580, View in Reaxys 162 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
5-HT1D calf substantia nigra
Method (Pharmacological Data)
radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>alniditan (2 nM)
Further Details (Pharmacological Data)
Ki = apparent equilibrium inhibition constant
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
91 nmol/l
Leysen; Gommeren; Heylen; Luyten; Van De Weyer; Vanhoenacker; Haegeman; Schotte; Van Gompel; Wouters; Lesage; Molecular Pharmacology; vol. 50; nb. 6; (1996); p. 1567 - 1580, View in Reaxys 163 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
5-HT1D calf substantia nigra
Method (Pharmacological Data)
radioligand assay; incubation at 37 deg C, for 30 min; radioactivity measured by scintillation; in presence of <3H>5-HT (4 nM)
Further Details (Pharmacological Data)
Ki = apparent equilibrium inhibition constant
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
34 nmol/l
Leysen; Gommeren; Heylen; Luyten; Van De Weyer; Vanhoenacker; Haegeman; Schotte; Van Gompel; Wouters; Lesage; Molecular Pharmacology; vol. 50; nb. 6; (1996); p. 1567 - 1580, View in Reaxys 164 of 193 Effect (Pharmacological Data)
inhibition of binding to receptor
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Species or Test-System (Pharmacological Data)
human 5-HT1B receptor
Method (Pharmacological Data)
C6-glial cells (CCL 107, rat), ATCC, stably transfected with pcDNA3/5-HT1B plasmid; cellular membranes prepared; radioligand binding with 0.5 nM <3H>-5-carboxamidotryptamine in presence of title comp., 25 deg C, 30 min
Further Details (Pharmacological Data)
5-HT=serotonin
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
6.42 nmol/l
Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 165 of 193 Effect (Pharmacological Data)
inhibition of nucleotide formation
Species or Test-System (Pharmacological Data)
human 5-HT1B receptor
Method (Pharmacological Data)
C6-glial cells (CCL 107, rat), ATCC, stably transfected with pcDNA3/5-HT1B plasmid; incub. with 100 μM forskolin plus title comp., 37 deg C, 5 min; cellular cAMP content by radioimunoassay
Further Details (Pharmacological Data)
EC50: conc. of title comp. yielding 50 percent of the inhibition by 1 μM serotonin (5-HT)
Type (Pharmacological Data)
EC50
Value of Type (Pharmacological Data)
100.00 nmol/l
Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 166 of 193 Effect (Pharmacological Data)
inhibition of nucleotide formation
Species or Test-System (Pharmacological Data)
human 5-HT1D receptor
Method (Pharmacological Data)
C6-glial cells (CCL 107, rat), ATCC, stably transfected with pRcRSV/5-HT1D plasmid; incub. with 100 μM forskolin plus title comp., 37 deg C, 5 min; cellular cAMP content by radioimunoassay
Further Details (Pharmacological Data)
EC50: conc. of title comp. yielding 50 percent of the inhibition by 1 μM serotonin (5-HT)
Type (Pharmacological Data)
EC50
Value of Type (Pharmacological Data)
24.70 nmol/l
Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 167 of 193 Effect (Pharmacological Data)
inhibition of nucleotide formation
Species or Test-System (Pharmacological Data)
human 5-HT1D receptor
Method (Pharmacological Data)
C6-glial cells (CCL 107, rat), ATCC, stably transfected with pcDNA3/5-HT1D plasmid; incub. with 100 μM forskolin plus title comp., 37 deg C, 5 min; cellular cAMP content by radioimunoassay
Further Details (Pharmacological Data)
EC50: conc. of title comp. yielding 50 percent of the inhibition by 1 μM serotonin (5-HT)
Type (Pharmacological Data)
EC50
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Value of Type (Pharmacological Data)
53.30 nmol/l
Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 168 of 193 Effect (Pharmacological Data)
inhibition of binding to receptor
Species or Test-System (Pharmacological Data)
human 5-HT1D receptor
Method (Pharmacological Data)
C6-glial cells (CCL 107, rat), ATCC, stably transfected with pcDNA3/5-HT1D plasmid; cellular membranes prepared; radioligand binding with 3 nM <3H>-sumatriptan in presence of title comp., 25 deg C, 30 min
Further Details (Pharmacological Data)
5-HT=serotonin
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
27.23 nmol/l
Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 169 of 193 Effect (Pharmacological Data)
inhibition of binding to receptor
Species or Test-System (Pharmacological Data)
human 5-HT1D receptor
Method (Pharmacological Data)
C6-glial cells (CCL 107, rat), ATCC, stably transfected with pcDNA3/5-HT1D plasmid; cellular membranes prepared; radioligand binding with 0.5 nM <3H>-5-carboxamidotryptamine (5-CT) in presence of title comp., 25 deg C, 30 min
Further Details (Pharmacological Data)
5-HT=serotonin
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
18.69 nmol/l
Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 170 of 193 Effect (Pharmacological Data)
inhibition of binding to receptor
Species or Test-System (Pharmacological Data)
human 5-HT1D receptor
Method (Pharmacological Data)
C6-glial cells (CCL 107, rat), ATCC, stably transfected with pRcRSV/5-HT1D plasmid; cellular membranes prepared; radioligand binding with <3H>-5-carboxamidotryptamine in presence of title comp., 25 deg C, 30 min
Further Details (Pharmacological Data)
5-HT=serotonin
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
14.59 nmol/l
Pauwels; Palmier; Wurch; Colpaert; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 2; (1996); p. 144 - 156, View in Reaxys 171 of 193 Comment (Pharmacological Data)
affinity and intrinsic efficacy at 5-HT1D receptor in rabbit saphenous vein and affinity at 5HT2A receptor in rabbit aorta
Glen, Robert C.; Martin, Graeme R.; Hill, Alan P.; Hyde, Richard M.; Woollard, Patrick M.; et al.; Journal of Medicinal Chemistry; vol. 38; nb. 18; (1995); p. 3566 - 3580, View in Reaxys
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172 of 193 Effect (Pharmacological Data)
muscle relaxant
Species or Test-System (Pharmacological Data)
Dunkin-Hartley guinea-pig ileum
Sex
male
Method (Pharmacological Data)
250-350 g pigs killed, ileal segments suspended in Krebs solution + (μM) cocaine 10, corticosterone 10, pargyline 5, indomethacin 1, atropine 1 at 37 deg C, pH 7.4; H: without/ with desensitization by 60 min equilibr. with 3 μM 5-carboxamidotryptamine
Further Details (Pharmacological Data)
contractions induced by 1 μM histamine (H) or 30 nM substance P (SP) for 30 s, 5 min dose-cycle; when stable contractions, title comp. added 3 min before spasmogen; change in isometric tension recorded
Comment (Pharmacological Data)
No effect
Carter; Champney; Hwang; Eglen; European Journal of Pharmacology; vol. 280; nb. 3; (1995); p. 243 - 250, View in Reaxys 173 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
mouse 1C11 cells
Exposure Period (Pharmacological Data)
30 min
Method (Pharmacological Data)
in vitro; cells cultured for 2 d in the presence of 1 mM dibutyryl-cAMP and 0.05 percent cyclohexane carboxylic acid; 5HT2B receptors; competitive binding with <125I>-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane
Further Details (Pharmacological Data)
inhibition of <125I>-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane binding; diagram
Type (Pharmacological Data)
pKi
Value of Type (Pharmacological Data)
6.83 dimensionless
Loric, Sylvain; Maroteaux, Luc; Kellermann, Odile; Launay, Jean-Marie; Molecular Pharmacology; vol. 47; nb. 3; (1995); p. 458 - 466, View in Reaxys 174 of 193 Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
mouse LMTK- fibroplast cells
Exposure Period (Pharmacological Data)
30 min
Method (Pharmacological Data)
in vitro; cells stably transfected with NP75 cDNA; 5-HT2B receptors; competitive binding with <125I>-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane
Further Details (Pharmacological Data)
inhibition of <125I>-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane binding; diagram
Type (Pharmacological Data)
pKi
Value of Type (Pharmacological Data)
6.87 dimensionless
Loric, Sylvain; Maroteaux, Luc; Kellermann, Odile; Launay, Jean-Marie; Molecular Pharmacology; vol. 47; nb. 3; (1995); p. 458 - 466, View in Reaxys 175 of 193 Effect (Pharmacological Data)
metabolic
Species or Test-System (Pharmacological Data)
human saliva
Sex
male
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Concentration (Pharmacological Data)
1 - 10 mg/l
Method (Pharmacological Data)
in vitro; TBC and MTBC formation assayed; intact or heated saliva obtained from smokers (while smoking or without); 37 deg C; incubated for 0.5-15 min; TBC and MTBC formation determined by HPLC
Further Details (Pharmacological Data)
TBC: 1,2,3,4-tetrahydro-β-carboline; MTBC: 1-methyl-1,2,3,4-tetrahydro-β-carboline
Results
in intact and heated saliva obtained while smoking fromation of TBC and MTBC increased with increasing time of incubation and conc. of title comp.; in saliva obtained from smokers without smoking neither TBC nor MTBC was found
Tsuchiya; Ohtani; Yamada; Tajima; Sato; Biochemical Pharmacology; vol. 50; nb. 12; (1995); p. 2109 - 2112, View in Reaxys 176 of 193 Effect (Pharmacological Data)
metabolic
Species or Test-System (Pharmacological Data)
human saliva
Sex
male
Concentration (Pharmacological Data)
2.5 mg/l
Method (Pharmacological Data)
in vitro; TBC and MTBC formation assayed; smoke of single cigarette bubbled through 5 ml of saliva; 37 deg C; incubated for 10 min; TBC and MTBC formation determined by HPLC
Further Details (Pharmacological Data)
TBC: 1,2,3,4-tetrahydro-β-carboline; MTBC: 1-methyl-1,2,3,4-tetrahydro-β-carboline
Results
graphical representation; TBC and MTBC in saliva increased; level of TBC was higher than MTBC; TBC and MTBC conc. were dependent on volume of added smoke saliva
Tsuchiya; Ohtani; Yamada; Tajima; Sato; Biochemical Pharmacology; vol. 50; nb. 12; (1995); p. 2109 - 2112, View in Reaxys 177 of 193 Effect (Pharmacological Data)
agonist
Species or Test-System (Pharmacological Data)
rat C6-glial cells expressing human 5-HT1Dβ receptor
Concentration (Pharmacological Data)
1E-10 - 1E-05 mol/l
Method (Pharmacological Data)
in vitro; inhibition of forskolin-stimulated cAMP formation evaluated; 100 μmol/l forskolin; 1 mmol/l isobutylmethylxanthine; controlled salt solution, pH 7.4; humidified 95 percent air/5 percent CO2; 37 deg C; incubated for 5 min
Further Details (Pharmacological Data)
cellular cAMP content assayed using RIA; EC50: conc. yielding 50 percent of inhibition of forskolin-induced cAMP formation produced by 1 μmol/l 5-HT; Emax: max. percent inhibition of forskolin-induced cAMP formation vs. that obtained with 1 μmol/l 5-HT
Type (Pharmacological Data)
EC50
Value of Type (Pharmacological Data)
100 nmol/l
Results
Emax: 96 percent (conc.-response curve)
Pauwels, Petrus J.; Colpaert, Francis C.; Biochemical Pharmacology; vol. 50; nb. 10; (1995); p. 1651 - 1658, View in Reaxys 178 of 193 Comment (Pharmacological Data)
activity against Mycobacterium tuberculosis H 37 Ra, MIC: 256 μg/ml
Mahboobi; Grothus; Meindl; Archiv der Pharmazie; vol. 327; nb. 2; (1994); p. 105 - 114, View in Reaxys 179 of 193 Comment (Pharmacological Data)
antifouling activity
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Kon-Ya, Kazumi; Shimidzu, Nobuyoshi; Miki, Wataru; Endo, Mamoru; Bioscience, Biotechnology, and Biochemistry; vol. 58; nb. 12; (1994); p. 2178 - 2181, View in Reaxys 180 of 193 Effect (Pharmacological Data)
antimutagenic
Species or Test-System (Pharmacological Data)
Salmonella typhimurium TA 100
Concentration (Pharmacological Data)
0.33 - 10 μmol/plate
Exposure Period (Pharmacological Data)
48 h
Method (Pharmacological Data)
4-nitroquinoline (4-NQO) as mutagenic agent; standard plate incorporation assay; 37 deg C
Further Details (Pharmacological Data)
inhibition of direct-acting mutagenicity of 4-NQO
Comment (Pharmacological Data)
No effect
De Flora; Rosenkranz; Klopman; Mutagenesis; vol. 9; nb. 1; (1994); p. 39 - 45, View in Reaxys 181 of 193 Comment (Pharmacological Data)
receptor binding affinities (pKl) for 6 subtypes of serotonin/tryptamin receptors: 5-HT1A: 7.35; 5-HT1B: 7.32; 5-HT1C: 7.78; 5-HT1D: 7.24; 5-HT2: 5.41; 5-HT3: <5.14; tryptamine: 8.21.
Dijkstra, Gerard D. H.; Tulp, Martin Th. M.; Hermkens, Pedro H. H.; Maarseveen, Jan H. van; Scheeren, Hans W.; Kruse, Chris G.; Recueil des Travaux Chimiques des Pays-Bas; vol. 112; nb. 2; (1993); p. 131 - 136, View in Reaxys 182 of 193 Comment (Pharmacological Data)
competitive inhibitor of L-tryptophan 2',3'-oxidase from Chromobacterium violaceum
Genet, R; Denoyelle, C; Menez, A; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 31; nb. 12; (1992); p. 848 - 850, View in Reaxys 183 of 193 Comment (Pharmacological Data)
LD 50: 276; dose (mg/kg): 92 on male Swiss albino mice
Cingolani; Claudi; Venturi; European Journal of Medicinal Chemistry; vol. 23; nb. 3; (1988); p. 291 - 294, View in Reaxys 184 of 193 Comment (Pharmacological Data)
inhibition of the metabolism by clorgyline or semicarbazide in human umbilical artery
Precious; Lyles; Journal of Pharmacy and Pharmacology; vol. 40; nb. 9; (1988); p. 627 - 633, View in Reaxys 185 of 193 Comment (Pharmacological Data)
in vitro anti-acetylcholine activity ID 50: 46 μg/ml; anti-histamine activity ID 50: 16.3 μg/ml on guinea pig ileum
Cingolani; Claudi; Venturi; European Journal of Medicinal Chemistry; vol. 23; nb. 3; (1988); p. 291 - 294, View in Reaxys 186 of 193 Comment (Pharmacological Data)
toxicity (at 160 mg/kg s.c.) in combination with deltamethrin (1.5 g/kg p.o.) or iproniazid (250 mg/kg p.o.) in white mice (Swiss strain) of either sex
Pham Huu Chanh; Navarro Delmasure Ch.; et al.; Arzneimittel-Forschung/Drug Research; vol. 34; nb. 2; (1984); p. 175 - 181, View in Reaxys 187 of 193 Comment (Pharmacological Data)
effects on syntheses of tyramine oxidase and β-galactosidase in strains with tyn :: lac or ats :: lac fusions (Escherichia coli)
Yamashita, Mitsuo; Murooka, Yoshikatsu; Agricultural and Biological Chemistry; vol. 48; nb. 6; (1984); p. 1459 1470, View in Reaxys 188 of 193 Comment (Pharmacological Data)
no effect on the production of polyamine oxidase by Penicillium sp. No. PO-1
Kobayashi, Yoshinori; Horikoshi, Koki; Agricultural and Biological Chemistry; vol. 45; nb. 12; (1981); p. 2943 2946, View in Reaxys 189 of 193 Comment (Pharmacological Data)
effect on oxidations of putrescine by putrescine oxidase from Micrococcus rubens and spermine by the Penicillium enzyme
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Isobe, Kimiyasu; Tani, Yoshiki; Yamada, Hideaki; Agricultural and Biological Chemistry; vol. 45; nb. 3; (1981); p. 727 - 734, View in Reaxys 190 of 193 Comment (Pharmacological Data)
increases the cyclic GMP content in human blood platelets
Laubscher; Pletscher; Journal of Pharmacy and Pharmacology; vol. 32; nb. 8; (1980); p. 601 - 602, View in Reaxys 191 of 193 Comment (Pharmacological Data)
effect on spermine and spermidine oxidation by polyamine oxidase from Penicillium chrysogenum and by polyamine oxidase from Aspergillus terreus
Isobe, Kimiyasu; Tani, Yoshiki; Yamada, Hideaki; Agricultural and Biological Chemistry; vol. 44; nb. 12; (1980); p. 2955 - 2960, View in Reaxys 192 of 193 Comment (Pharmacological Data)
Uebersicht ueber d. pharmakologische Wirkung
Daly; Witkop; Angewandte Chemie; vol. 75; (1963); p. 552,558-560, View in Reaxys 193 of 193 Comment (Pharmacological Data)
Zum Metabolismus beim malabsorption syndrom
Haverback et al.; New England Journal of Medicine; vol. 262; (1960); p. 754; Chem.Abstr.; nb. 14429; (1960), View in Reaxys Ecotoxicology (4) 1 of 4
Effect (Ecotoxicology)
toxicity to invertebrates
Species or Test-System (Ecotoxicology)
brine shrimp
Kind of Dosing (Ecotoxi- title comp. dissolved in 20 percent aq. DMSO to 1 mg/ml concentration, formed solution cology) serially diluted two times to seven different concentrations Method (Ecotoxicology)
brine shrimp lethality assay carried out with nauplii; 1 ml title comp. solution of different concentrations transferred into vials and 9 ml aerated seawater added; about 10 nauplii transferred into each vial; number of alive nauplii after 24 h noted
Further Details (Ecotoxi- podophyllotoxin as control with LD50 2.79 mg/l; shrimp eggs hatched in flask with artificial cology) seawater, flask aerated and kept at 29-30 deg C, light source left on, nauplii hatched within 48 h Type (Ecotoxicology)
LD50
Value of Type (Ecotoxicology)
83 mg/l
Shoeb, Mohammad; MacManus, Stephen M.; Jaspars, Marcel; Trevidu, Jioji; Nahar, Lutfun; Kong-Thoo-Lin, Paul; Sarker, Satyajit D.; Tetrahedron; vol. 62; nb. 48; (2006); p. 11172 - 11177, View in Reaxys 2 of 4
Effect (Ecotoxicology)
biotransformation
Species or Test-System (Ecotoxicology)
hairy roots of Catharanthus roseus
Concentration (Ecotoxicology)
1 mmol/l
Kind of Dosing (Ecotoxi- on day 7 in DMSO cology) Method (Ecotoxicology)
culture grown at 26 deg C and pH 5.7; extraction and LC-MS on day 21
Comment (Ecotoxicology)
Further metabolite(s)
Metabolite (Ecotoxicology)
serpentine; ajmalicine; Yohimbine
McCoy, Elizabeth; O'Connor, Sarah E.; Journal of the American Chemical Society; vol. 128; nb. 44; (2006); p. 14276 - 14277, View in Reaxys 3 of 4
Effect (Ecotoxicology)
biotransformation
Species or Test-System (Ecotoxicology)
Penicillum sp. isolate N934-53
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Kind of Dosing (Ecotoxi- 14C-labeled title comp. (0.14 μCi) dissolved in water and delivered in 4 equal sub-doses cology) at 48, 64, 68 and 72 h Method (Ecotoxicology)
title comp. delivered to test species; culture harvested at 80 h; metabolites isolated by extraction; scintillation counting
Results
title comp. incorporated into communesin alkaloids during biosynthesis; table
Metabolite (Ecotoxicology)
communesin A; communesin B
Wigley, Lucy J.; Mantle, Peter G.; Perry, David A.; Phytochemistry; vol. 67; nb. 6; (2006); p. 561 - 569, View in Reaxys 4 of 4
Effect (Ecotoxicology)
biotransformation
Species or Test-System (Ecotoxicology)
Alangium lamarckii Thw.
Kind of Dosing (Ecotoxi- soln. in H2O-DMSO cology) Method (Ecotoxicology)
<14-C>-label. title comp. fed to young plants by wick feeding technique; H2O added after uptake was complete; plants kept alive for 7-8 d; macerated in EtOH; chromatography
Results
0.16 percent and 0.175 percent radioactivity incorporation into deoxytubulosine and alangimarckine, resp.; biosynthesis sequence: tyrosine -> dopamine -> N-deacetylisoipecoside (-> ahkorine) -> deoxytubulosine -> alangimarckine
Metabolite (Ecotoxicology)
deoxytubulosine; (-)-alangimarckine
Jain, Sudha; Sinha, Archana; Bhakuni, Dewan S.; Phytochemistry; vol. 60; nb. 8; (2002); p. 853 - 859, View in Reaxys Use (21) Laboratory Use and Handling
Use Pattern
Location
References
Pharmaceuticals
Page/Page column 22-30
Patent; JANSSEN PHARMACEUTICA NV; DVORAK, Curt A.; LIU, Changlu; KUEI, Chester; WO2014/152917; (2014); (A2) English, View in Reaxys
activating GPR139
Page/Page column 22-30
Patent; JANSSEN PHARMACEUTICA NV; DVORAK, Curt A.; LIU, Changlu; KUEI, Chester; WO2014/152917; (2014); (A2) English, View in Reaxys
for detecting GPR139 activation
Page/Page column 22-30
Patent; JANSSEN PHARMACEUTICA NV; DVORAK, Curt A.; LIU, Changlu; KUEI, Chester; WO2014/152917; (2014); (A2) English, View in Reaxys
modulating Phenylketonuria (PKU)
Page/Page column 22-30
Patent; JANSSEN PHARMACEUTICA NV; DVORAK, Curt A.; LIU, Changlu; KUEI, Chester; WO2014/152917; (2014); (A2) English, View in Reaxys
modulating a neu- Page/Page colrological function umn 22-30
Patent; JANSSEN PHARMACEUTICA NV; DVORAK, Curt A.; LIU, Changlu; KUEI, Chester; WO2014/152917; (2014); (A2) English, View in Reaxys
A part of composition suitable for improving seed quality in a plant
Page/Page column 38
Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116260; (2010); (A2) English, View in Reaxys
thinning agent
Page/Page column Title page; 29
Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard; DECKERS, Tom; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116256; (2010); (A2) English, View in Reaxys
A part of composition used as a plant safener
Page/Page column 136
Patent; TAMINCO, NAAMLOZE VENNOOTSCHAP; WILLIAMS, Richard; ROOSE, Peter; DE SAEGHER, Johan Josef; WO2010/116264; (2010); (A2) English, View in Reaxys
insect attractant
Page/Page column 23
Patent; ACTIVETRAD (PROPRIETARY) LIMITED; WO2008/110984; (2008); (A1) English, View in Reaxys
pest control composition
Page/Page column 23
Patent; ACTIVETRAD (PROPRIETARY) LIMITED; WO2008/110984; (2008); (A1) English, View in Reaxys
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aryl hydrocarbon receptor binding ligand
Patent; G.I.M.-GESELLSCHAFT FUeR INNOVATIVE MEDIZIN GMBH NFG OHG; EP1842541; (2007); (A1) English, View in Reaxys
endometriosis
Patent; G.I.M.-GESELLSCHAFT FUeR INNOVATIVE MEDIZIN GMBH NFG OHG; EP1842541; (2007); (A1) English, View in Reaxys
antidyslipidemic formulation comprising vanadium (IV)/(V) compounds
Patent; GENMEDICA THERAPEUTICS SL; WO2006/64061; (2006); (A1) English, View in Reaxys
semicarbazidesensitive amine oxidase (SSAO) substrates
Page/Page column 10; 30; 32
Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys
diabetes
Page/Page column 10; 30; 32
Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys
diabetes type 1
Page/Page column 10; 30; 32
Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys
diabetes type 2
Page/Page column 10; 30; 32
Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys
diabetes mellitus
Page/Page column 10; 30; 32
Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys
obesity
Page/Page column 10; 30; 32
Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English, View in Reaxys
Comparative compound for investigation of inhibition of lipid peroxidation used as inhibitor in reaction of peroxidation of 1stearoyl 2-linoleoyl sn-glycerol 3phosphocholine induced by FeCl2*4H2O
Patent; Board of Trustees of Michigan State University; US2005/59727; (2005); (A1) English, View in Reaxys
Jayaprakasam, Bolleddula; Strasburg, Gale A.; Nair, Muraleedharan G.; Tetrahedron; vol. 60; nb. 13; (2004); p. 3109 - 3121, View in Reaxys
Isolation from Natural Product (24) Isolation from References Natural Product Penicillium sp. CYE-87; isolated from Didemnum sp., marine tunicate; collected from Suez Canal, Egypt, around a man-made support at a depth of 1–2 m in July 2010
Shaala, Lamiaa A.; Youssef, Diaa T. A.; Marine Drugs; vol. 13; nb. 4; (2015); p. 1698 - 1709, View in Reaxys
South China Sea Qi, Shu-Hua; Miao, Li; Gao, Cheng-Hai; Xu, Ying; Zhang, Si; Qian, Pei-Yuan; Helvetica Chimica Acta; gorgonian coral vol. 93; nb. 3; (2010); p. 511 - 516, View in Reaxys Isis minorbrachyblasta collected in Sanya, Hainan Province, China, in May 2007 leaves, flowers, stems and aerial parts of Prosopis
Samoylenko, Volodymyr; Ashfaq, Mohammad K.; Jacob, Melissa R.; Tekwani, Babu L.; Khan, Shabana I.; Manly, Susan P.; Joshi, Vaishali C.; Walker, Larry A.; Muhammad, Ilias; Journal of Natural Products; vol. 72; nb. 1; (2009); p. 92 - 98, View in Reaxys
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glandulosa Torrey var. glandulosa (Leguminosae); collected from Nevada Chimonanthus Kitajima, Mariko; Mori, Ikue; Arai, Kazumichi; Kogure, Noriyuki; Takayama, Hiromitsu; Tetrahedron Letpraecox f. concol- ters; vol. 47; nb. 19; (2006); p. 3199 - 3202, View in Reaxys or Makino (Calycanthaceae); seeds and rinds seeds of Centaur- Shoeb, Mohammad; MacManus, Stephen M.; Jaspars, Marcel; Trevidu, Jioji; Nahar, Lutfun; Kongea montana Thoo-Lin, Paul; Sarker, Satyajit D.; Tetrahedron; vol. 62; nb. 48; (2006); p. 11172 - 11177, View in Reaxys Didemnum sp. Segraves, Nathaniel L.; Robinson, Sarah J.; Garcia, Daniel; Said, Sadri A.; Fu, Xiong; Schmitz, Francis Monniot and Mon- J.; Pietraszkiewicz, Halina; Valeriote, Frederick A.; Crews, Phillip; Journal of Natural Products; vol. 67; niot 1997, tuninb. 5; (2004); p. 783 - 792, View in Reaxys cate, collected in Northern Sulawesi, Indonesia marine sponge Smenospongia sp. (Thorectidae)
McKay, Matthew J.; Carroll, Anthony R.; Quinn, Ronald J.; Hooper, John N. A.; Journal of Natural Products; vol. 65; nb. 4; (2002); p. 595 - 597, View in Reaxys
sponge (PAL93-055)
Patil, Ashok D.; Freyer, Alan J.; Carte, Brad; Taylor, Paul B.; Johnson, Randall K.; Faulkner, D. John; Journal of Natural Products; vol. 65; nb. 4; (2002); p. 628 - 629, View in Reaxys
culture of Rauvol- Sheludko; Gerasimenko; Platonova; Planta Medica; vol. 66; nb. 7; (2000); p. 656 - 659, View in Reaxys fia serpentina Benth. ex Kurz * Rhazya stricta Decaisne (Apocynaceae), RxR17K callus strain stimulated with 100 μM methyl jasmonate aerial part of Nitraria schoberi L.
Tulyaganov; Nazarov; Chemistry of Natural Compounds; vol. 36; nb. 4; (2000); p. 393 - 395, View in Reaxys
Villagorgia rubra
Espada, Alfonso; Tetrahedron Letters; vol. 34; nb. 48; (1993); p. 7773 - 7776, View in Reaxys
epigeal part of Ni- Tulyaganov, T. S.; Chemistry of Natural Compounds; vol. 29; nb. 1; (1993); p. 31 - 34; Khimiya Prirodnykh traria komarovii Soedinenii; nb. 1; (1993); p. 39 - 43, View in Reaxys leaves of Tecoma stans
Kunapuli, Satya P.; Vaidyanathan, C. S.; Phytochemistry (Elsevier); vol. 23; nb. 8; (1984); p. 1826 - 1827, View in Reaxys
aus Desmodium tiliaefolium
Ghosal; Srivastava; Phytochemistry (Elsevier); vol. 12; (1973); p. 193,196, View in Reaxys
Vork. u. Isol. aus Acacia caesia
Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys
Vork. u. Isol. aus Acacia leucophloea
Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys
Vork. u. Isol. aus Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys Acacia farnesiana Vork. u. Isol. aus Desmodium triflorum
Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys
aus Petalostylis Labicheoides
Johns et al.; Australian Journal of Chemistry; vol. 19; (1966); p. 893, View in Reaxys
Abtrennung v. Indol-Derivaten aus Urin mittels Sephadex G25
Schlossberger et al.; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 333; (1963); p. 152, View in Reaxys
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Ausscheidung im Urin nach Eingabe v. versch. Drogen
Svoerdsma et al.; Proceedings of the Society for Experimental Biology and Medicine; vol. 103; (1960); p. 485; Chem.Abstr.; vol. 54; nb. 13415; (1960), View in Reaxys
aus Acacia podalyriifolia
White; New Zealand J. Sci. Technol. <B>; vol. 33; (1951); p. 54,60, View in Reaxys
aus Acacia floriWhite; New Zealand J. Sci. Technol. <B>; vol. 25; (1944); p. 137,158, View in Reaxys bunda und Acacia pruinosa bei der VergaerGrimmer; Wiemann; Forschg. Milchwirtsch. Molkereiw.; vol. 1; p. 2; Chem. Zentralbl.; vol. 92; nb. I; (1921); ung von Casein p. 775, View in Reaxys durch Bac. mesentericus vulgatus
Reaxys ID 3568419 View in Reaxys
Cl
2/2 CAS Registry Number: 343-94-2 Chemical Name: tryptamine hydochloride; 3-(2-aminoethyl)indole hydrochloride; Tryptamine hydrochloride; tryptamine hydrochloride; tryptamine monohydrochloride; triptamine hydrochloride; tryptamine hydrochloide Linear Structure Formula: C10H13N2 (1+)*Cl(1-) Molecular Formula: C10H13N2*Cl Molecular Weight: 196.68 Type of Substance: heterocyclic InChI Key: KDFBGNBTTMPNIG-UHFFFAOYSA-N Note:
H NH
NH 2
Substance Label (24) Label References 7
Arazny; Czarnocki; Wojtasiewicz; Maurin; Tetrahedron Asymmetry; vol. 11; nb. 13; (2000); p. 2793 - 2800, View in Reaxys; Gattuso, Giuseppe; Notti, Anna; Parisi, Melchiorre F.; Pisagatti, Ilenia; Marcos, Paula Maria; Ascenso, Jos Rosrio; Brancatelli, Giovanna; Geremia, Silvano; New Journal of Chemistry; vol. 39; nb. 2; (2015); p. 817 - 821, View in Reaxys
1*HCl
Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414, View in Reaxys; Mizoguchi, Haruki; Oikawa, Hideaki; Oguri, Hiroki; Nature Chemistry; vol. 6; nb. 1; (2014); p. 57 - 64, View in Reaxys
2
Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys; Takasu, Kiyosei; Shimogama, Tsubasa; Saiin, Chalerm; Kim, HyeSook; Wataya, Yusuke; Ihara, Masataka; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 7; (2004); p. 1689 - 1692, View in Reaxys; Takasu, Kiyosei; Shimogama, Tsubasa; Saiin, Chalerm; Kim, Hye-Sook; Wataya, Yusuke; Brun, Reto; Ihara, Masataka; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 6; (2005); p. 653 - 661, View in Reaxys; Reimer, Daniela; Nollmann, Friederike I.; Schultz, Katharina; Kaiser, Marcel; Bode, Helge B.; Journal of Natural Products; vol. 77; nb. 8; (2014); p. 1976 - 1980, View in Reaxys
1
Li, Yuexian; Prakash, Shimoga R.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 48; nb. 5; (2005); p. 323 - 330, View in Reaxys; Fischereder, Eva; Pressnitz, Desiree; Kroutil, Wolfgang; Lutz, Stefan; Bioorganic and Medicinal Chemistry; vol. 22; nb. 20; (2014); p. 5633 - 5637, View in Reaxys
8
Tian, Jingjing; Du, Qiuchen; Guo, Rui; Li, Yun; Cheng, Bin; Zhai, Hongbin; Organic Letters; vol. 16; nb. 12; (2014); p. 3173 - 3175, View in Reaxys
TRY
Sirocchi, Veronica; Caprioli, Giovanni; Ricciutelli, Massimo; Vittori, Sauro; Sagratini, Gianni; Journal of Mass Spectrometry; vol. 49; nb. 9; (2014); p. 819 - 825, View in Reaxys
12
Panosyan; Still; Canadian Journal of Chemistry; vol. 79; nb. 7; (2001); p. 1110 - 1114, View in Reaxys; Panarese, Joseph D.; Waters, Stephen P.; Organic and Biomolecular Chemistry; vol. 11; nb. 21; (2013); p. 3428 - 3431, View in Reaxys
6
Eschenbrenner-Lux, Vincent; Dueckert, Heiko; Khedkar, Vivek; Bruss, Hanna; Waldmann, Herbert; Kumar, Kamal; Chemistry - A European Journal; vol. 19; nb. 7; (2013); p. 2294 - 2304, View in Reaxys
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4a
Sanaboina, Chakrapani; Jana, Samaresh; Chidara, Sridhar; Patro, Balaram; Raolji, Gajendrasinh Balvantsinh; Eppakayala, Laxminarayana; Tetrahedron Letters; vol. 53; nb. 37; (2012); p. 5027 - 5029,3, View in Reaxys
4
Miyake, Fumiko Y.; Yakushijin, Kenichi; Horne, David A.; Organic Letters; vol. 6; nb. 5; (2004); p. 711 713, View in Reaxys; Nemet, Ina; Varga-Defterdarovic, Lidija; Bioorganic and Medicinal Chemistry; vol. 16; nb. 8; (2008); p. 4551 - 4562, View in Reaxys
5
Shen, Shuren; Bremont, Beatrice; Serraz, Isabelle; Andrieux, Jean; Poncet, Annie; Mathe-Allainmat, Monique; Chanut, Evelyne; Trouvin, Jean-Hugues; Langlois, Michel; European Journal of Pharmacology; vol. 307; nb. 2; (1996); p. 133 - 140, View in Reaxys; Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 10; (2004); p. 2545 - 2552, View in Reaxys; Molt, Oliver; Ruebeling, Daniel; Schaefer, Gerhard; Schrader, Thomas; Chemistry - A European Journal; vol. 10; nb. 17; (2004); p. 4225 - 4232, View in Reaxys; Fokas, Demosthenes; Wang, Zhimin; Synthetic Communications; vol. 38; nb. 21; (2008); p. 3816 - 3822, View in Reaxys
2b
Tonkikh; Strakovs; Petrova; Chemistry of Heterocyclic Compounds; vol. 41; nb. 8; (2005); p. 1053 - 1058, View in Reaxys; Tulyaganov; Kozimova; Allaberdiev; Chemistry of Natural Compounds; vol. 42; nb. 2; (2006); p. 198 - 200, View in Reaxys
2e*HCl
Pal, Bikash; Jaisankar, Parasuraman; Giri, Venkatachalam S.; Synthetic Communications; vol. 34; nb. 7; (2004); p. 1317 - 1323, View in Reaxys
2a; 4a; 5a
Patent; ELI LILLY AND COMPANY; EP942722; (2004); (B1) English, View in Reaxys
11
Itoh, Atsuko; Tanahashi, Takao; Nagakura, Naotaka; Nishi, Toyoyuki; Phytochemistry; vol. 62; nb. 3; (2003); p. 359 - 369, View in Reaxys
1a
Fokas, Demosthenes; Patterson, Jean E.; Slobodkin, Gregory; Baldino, Carmen M.; Tetrahedron Letters; vol. 44; nb. 27; (2003); p. 5137 - 5140, View in Reaxys
2f*HCl
Strakovs; Tonkikh; Petrova; Ryzhanova; Palitis; Chemistry of Heterocyclic Compounds; vol. 38; nb. 4; (2002); p. 449 - 455, View in Reaxys
1, R=R1=R2=H
Novak; Hanania; Kovacs; Kolonits; Szantay; Synthesis; nb. 1; (2001); p. 108 - 118, View in Reaxys
TA
Borsarelli, Claudio D.; Bertolotti, Sonia G.; Previtali, Carlos M.; Photochemistry and Photobiology; vol. 73; nb. 2; (2001); p. 97 - 104, View in Reaxys
3
Tulyaganov; Nazarov; Levkovich; Abdullaev; Chemistry of Natural Compounds; vol. 37; nb. 1; (2001); p. 61 - 64, View in Reaxys
7*HCl
Bringmann, Gerhard; Feineis, Doris; Brueckner, Ralph; Blank, Michael; Peters, Karl; Peters, Eva-Maria; Reichmann, Heinz; Janetzky, Bernd; Grote, Christoph; Clement, Hans-Willi; Wesemann, Wolfgang; Bioorganic and Medicinal Chemistry; vol. 8; nb. 6; (2000); p. 1467 - 1478, View in Reaxys
5g
Herr; Kuhler; Meckler; Opalka; Synthesis; nb. 11; (2000); p. 1569 - 1574, View in Reaxys
16
Tietze, Lutz F.; Zhou, Yifa; Toepken, Enno; European Journal of Organic Chemistry; nb. 12; (2000); p. 2247 - 2252, View in Reaxys
1a*HCl
Patthy-Lukats, Agnes; Kocsis, Akos; Szabo, Laszlo F.; Podanyi; Journal of Natural Products; vol. 62; nb. 11; (1999); p. 1492 - 1499, View in Reaxys
Patent-Specific Data (2) References Patent; NATREON, INC.; Ghosal, Shibnath; Veeraragavan, Muruganandam; Kalidindi, Sanyasi R.; US2013/115316; (2013); (A1) English, View in Reaxys Patent; Les Laboratoires Servier; US6350757; (2002); (B1) English, View in Reaxys Melting Point (10) 1 of 10
Melting Point [°C]
245 - 248
Solvent (Melting Point)
ethanol
Location
supporting information
Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 - 2700, View in Reaxys 2 of 10
Melting Point [°C]
247 - 248
Solvent (Melting Point)
aq. ethanol; ethyl acetate
Tulyaganov, T. S.; Chemistry of Natural Compounds; vol. 29; nb. 1; (1993); p. 31 - 34; Khimiya Prirodnykh Soedinenii; nb. 1; (1993); p. 39 - 43, View in Reaxys
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3 of 10
Melting Point [°C]
251 - 253
Solvent (Melting Point)
ethanol; ethyl acetate
Biswas, Kshetra M.; Jackson, Anthony H.; Kobaisy, Mozaina M.; Shannon, Patrick V. R.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1992); p. 461 - 468, View in Reaxys 4 of 10
Melting Point [°C]
256
Hashimoto, Mitsunori; Eda, Yutaka; Osanai, Yasutomo; Iwai, Toshiaki; Aoki, Seiichi; Chemistry Letters; (1986); p. 893 - 896, View in Reaxys 5 of 10
Melting Point [°C]
248 - 249
Solvent (Melting Point)
ethanol; ethyl acetate
Ibragimov, A. A.; Yunusov, S. Yu.; Chemistry of Natural Compounds; vol. 21; nb. 4; (1985); p. 502 - 509; Khimiya Prirodnykh Soedinenii; vol. 21; nb. 4; (1985); p. 536 - 544, View in Reaxys 6 of 10
Melting Point [°C]
248 - 249
Tulyaganov, T. S.; Ibragimov, A. A.; Yunusov, S. Yu.; Chemistry of Natural Compounds; vol. 17; (1981); p. 149 152; Khimiya Prirodnykh Soedinenii; vol. 17; nb. 2; (1981); p. 192 - 195, View in Reaxys 7 of 10
Melting Point [°C]
250 - 252
Solvent (Melting Point)
ethanol; diethyl ether
Brutcher; Vanderwerff; Journal of Organic Chemistry; vol. 23; (1958); p. 146, View in Reaxys 8 of 10
Melting Point [°C]
249 - 250
Solvent (Melting Point)
methanol; ethyl acetate
Comment (Melting Point)
Decomp.
Young; Journal of the Chemical Society; (1958); p. 3493,3494, View in Reaxys 9 of 10
Melting Point [°C]
248
Manske; Journal of the American Chemical Society; vol. 51; (1929); p. 1203; Canadian Journal of Research; vol. 4; (1931); p. 594; Chem. Zentralbl.; vol. 102; nb. II; (1931); p. 2738, View in Reaxys 10 of 10
Melting Point [°C]
251 - 253
Jackson; Journal of Biological Chemistry; vol. 84; (1929); p. 5, View in Reaxys Association (MCS) (5) 1 of 5
Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))
D2O
Temperature (Association (MCS)) [°C]
27
Comment (Association (MCS))
temperature dependence
Partner (Association (MCS))
2,19,28,45-tetraoxa-3,18,29,44-tetraoxo-10,36-diyne-22,25,48,51-tetrakis(dimethoxyphosphorylmethyl)-[3.2.3.2]paracyclophane tetralithium salt
Molt, Oliver; Ruebeling, Daniel; Schaefer, Gerhard; Schrader, Thomas; Chemistry - A European Journal; vol. 10; nb. 17; (2004); p. 4225 - 4232, View in Reaxys 2 of 5
Description (Association NMR spectrum of the complex (MCS)) Solvent (Association (MCS))
D2O
Comment (Association (MCS))
ambient temperature
Partner (Association (MCS))
2,19,28,45-tetraoxa-3,18,29,44-tetraoxo-10,36-diyne-22,25,48,51-tetrakis(dimethoxyphosphorylmethyl)-[3.2.3.2]paracyclophane tetralithium salt
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Molt, Oliver; Ruebeling, Daniel; Schaefer, Gerhard; Schrader, Thomas; Chemistry - A European Journal; vol. 10; nb. 17; (2004); p. 4225 - 4232, View in Reaxys 3 of 5
Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))
aq. phosphate buffer
Temperature (Association (MCS)) [°C]
25
Partner (Association (MCS))
5,10,15,20-tetrakis(4-methylpyridinium)porphyrin tetrahydrochloride
Rekharsky; Nakamura; Hembury; Inoue; Bulletin of the Chemical Society of Japan; vol. 74; nb. 3; (2001); p. 449 457, View in Reaxys 4 of 5
Description (Association Association with compound (MCS)) Solvent (Association (MCS))
methanol
Temperature (Association (MCS)) [°C]
30
Partner (Association (MCS))
3,10-dimethyl-1',4',7',10',13',16'-hexaoxacyclooctadec-2'-enolt;2',3'-igt;isoalloxazine; K(1+)
Shinkai, Sheiji; Ishikawa, Yuichi; Shinkai, Hiroko; Tsuno, Takaharu; Makishima, Hiroki; et al.; Journal of the American Chemical Society; vol. 106; nb. 6; (1984); p. 1801 - 1808, View in Reaxys 5 of 5
Description (Association Association with compound (MCS)) Solvent (Association (MCS))
methanol
Temperature (Association (MCS)) [°C]
30
Partner (Association (MCS))
3-methyllumiflavin; K(1+)
Shinkai, Sheiji; Ishikawa, Yuichi; Shinkai, Hiroko; Tsuno, Takaharu; Makishima, Hiroki; et al.; Journal of the American Chemical Society; vol. 106; nb. 6; (1984); p. 1801 - 1808, View in Reaxys Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)
Fischereder, Eva; Pressnitz, Desiree; Kroutil, Wolfgang; Lutz, Stefan; Bioorganic and Medicinal Chemistry; vol. 22; nb. 20; (2014); p. 5633 - 5637, View in Reaxys; Sirocchi, Veronica; Caprioli, Giovanni; Ricciutelli, Massimo; Vittori, Sauro; Sagratini, Gianni; Journal of Mass Spectrometry; vol. 49; nb. 9; (2014); p. 819 - 825, View in Reaxys
Crystal Property Description (1) Colour & Other Location Properties brown
supporting information
References Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 2700, View in Reaxys
NMR Spectroscopy (9) 1 of 9
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]
400
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Location
supporting information
Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 - 2700, View in Reaxys 2 of 9
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- water-d2 scopy) Location
supporting information
Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 - 2700, View in Reaxys 3 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
δH 2.97 2H t J=9, 3.13 2H t J=8, 7.01 1H t J=4, 7.07-7.12 2H m, 7.34 1H d J=4, 7.49 1H d J=4;
Location
Paragraph 0053
Patent; Morrison, Richard W.; Jackson, Douglas Michael; US2014/275569; (2014); (A1) English, View in Reaxys 4 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- water-d2 scopy) Original Text (NMR Spectroscopy)
δC 22.88, 40.03, 109.36, 112.30, 118.54, 119.68, 122.44, 124.53, 126.70, 136.69
Location
Paragraph 0053
Patent; Morrison, Richard W.; Jackson, Douglas Michael; US2014/275569; (2014); (A1) English, View in Reaxys 5 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Teuber, Hans-Joachim; Quintanilla-Licea, Ramiro; Journal fuer Praktische Chemie/Chemiker-Zeitung; vol. 336; nb. 5; (1994); p. 452 - 457, View in Reaxys 6 of 9
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)
1H-1H
Teuber, Hans-Joachim; Quintanilla-Licea, Ramiro; Journal fuer Praktische Chemie/Chemiker-Zeitung; vol. 336; nb. 5; (1994); p. 452 - 457, View in Reaxys
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7 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Saito; Muramatsu; Sugiyama; et al.; Tetrahedron Letters; vol. 26; nb. 48; (1985); p. 5891 - 5894, View in Reaxys 8 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
35
Ernst, Ludger; Kang, Sungzong; Journal of Chemical Research, Miniprint; nb. 9; (1981); p. 3019 - 3038, View in Reaxys 9 of 9
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6; trifluoroacetic acid scopy) Temperature (NMR Spectroscopy) [°C]
35
Ernst, Ludger; Kang, Sungzong; Journal of Chemical Research, Miniprint; nb. 9; (1981); p. 3019 - 3038, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Comment (IR Spectroscopy)
3333 - 1250 cm**(-1)
Nakanishi et al.; Bulletin of the Chemical Society of Japan; vol. 30; (1957); p. 403,405, View in Reaxys Mass Spectrometry (3) Description (Mass References Spectrometry) liquid chromatog- Sirocchi, Veronica; Caprioli, Giovanni; Ricciutelli, Massimo; Vittori, Sauro; Sagratini, Gianni; Journal of raphy mass spec- Mass Spectrometry; vol. 49; nb. 9; (2014); p. 819 - 825, View in Reaxys trometry (LCMS); electrospray ionisation (ESI); tandem mass spectrometry; spectrum liquid chromatog- Sirocchi, Veronica; Caprioli, Giovanni; Ricciutelli, Massimo; Vittori, Sauro; Sagratini, Gianni; Journal of raphy mass spec- Mass Spectrometry; vol. 49; nb. 9; (2014); p. 819 - 825, View in Reaxys trometry (LCMS); electrospray ionisation (ESI); tandem mass spectrometry; IT (ion trap); spectrum LCMS (Liquid chromatography mass spectrometry); Tandem mass spectrome-
Sagratini; Fernandez-Franzon; De Berardinis; Font; Vittori; Manes; Food Chemistry; vol. 132; nb. 1; (2012); p. 537 - 543, View in Reaxys
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try; ESI (Electrospray ionisation); Spectrum UV/VIS Spectroscopy (2) 1 of 2
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
methanol
Comment (UV/VIS Spectroscopy)
300 - 600 nm
Hayakawa, Kenji; Kido, Keiko; Kanematsu, Ken; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 511 - 520, View in Reaxys 2 of 2
Description (UV/VIS Spectroscopy)
Absorption maxima
Absorption Maxima (UV/ 221; 275; 281; 290 VIS) [nm] Noland; Hartman; Journal of the American Chemical Society; vol. 76; (1954); p. 3227, View in Reaxys Luminescence Spectroscopy (1) Description (LuReferences minescence Spectroscopy) Luminescence lifetime
Shizuka, Haruo; Serizawa, Manabu; Kobayashi, Hirokazu; Kameta, Kosei; Sugiyama, Hiroshi; et al.; Journal of the American Chemical Society; vol. 110; nb. 6; (1988); p. 1726 - 1732, View in Reaxys
Fluorescence Spectroscopy (5) Description (Fluo- Solvent (Fluoresrescence Speccence Spectrotroscopy) scopy)
Comment (Fluorescence Spectroscopy)
References
Fluorescence
Medici, Rosario; De Maria, Pablo Dominguez; Otten, Linda G.; Straathof, Adrie J. J.; Advanced Synthesis and Catalysis; vol. 353; nb. 13; (2011); p. 2369 - 2376, View in Reaxys
Maxima
benzene
Maxima
H2O
Fluorescence quantum yield Maxima
in the presence of Borsarelli, Claudio D.; Bertolotti, Sonia G.; Previtali, Carlos M.; organic comPhotochemistry and Photobiology; vol. 73; nb. 2; (2001); p. 97 - 104, pounds View in Reaxys Borsarelli, Claudio D.; Bertolotti, Sonia G.; Previtali, Carlos M.; Photochemistry and Photobiology; vol. 73; nb. 2; (2001); p. 97 - 104, View in Reaxys in the presence of Borsarelli, Claudio D.; Bertolotti, Sonia G.; Previtali, Carlos M.; organic comPhotochemistry and Photobiology; vol. 73; nb. 2; (2001); p. 97 - 104, pounds View in Reaxys
H2O
355 nm
Sprince et al.; Science (Washington, DC, United States); vol. 125; (1957); p. 442, View in Reaxys; Bertrand; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 1023,1025, View in Reaxys
Pharmacological Data (11) 1 of 11
Comment (Pharmacological Data)
Bioactivities present
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J.; Kwart, Lawrence D.; Magnusson, Goeran; Showalter, H. D. Hollis; Tetrahedron; vol. 37; nb. 23; (1981); p. 4017 - 4025, View in Reaxys; Afsah, El-Sayed M.; Jackson, Anthony H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 8; (1984); p. 1929 - 1932, View in Reaxys; Gribble; Switzer; Soll; Journal of Organic Chemistry; vol. 53; nb. 14; (1988); p. 3164 - 3170, View in Reaxys; Biswas, Kshetra M.; Jackson, Anthony H.; Kobaisy, Mozaina M.; Shannon, Patrick V. 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Chemical and Engineering Data; vol. 29; nb. 2; (1984); p. 229 - 231, View in Reaxys; Shizuka, Haruo; Serizawa, Manabu; Kobayashi, Hirokazu; Kameta, Kosei; Sugiyama, Hiroshi; et al.; Journal of the American Chemical Society; vol. 110; nb. 6; (1988); p. 1726 - 1732, View in Reaxys; Afsah, E.M.; Hammouda, M.; Hamama, W.S.; Monatshefte fuer Chemie; vol. 116; (1985); p. 851 - 856, View in Reaxys; Gribble, Gordon W.; Switzer, Frank L.; Synthetic Communications; vol. 17; nb. 4; (1987); p. 377 - 384, View in Reaxys; Kirkpatrick, Alan; Maclaren, John A.; Australian Journal of Chemistry; vol. 36; nb. 4; (1983); p. 833 - 838, View in Reaxys; Mueller, Johann; Pindur, Ulf; Archiv der Pharmazie (Weinheim, Germany); vol. 317; nb. 6; (1984); p. 555 - 561, View in Reaxys; Harrison, David M.; Sharma, Ram Bilas; Tetrahedron; vol. 49; nb. 15; (1993); p. 3165 - 3184, View in Reaxys; Shinkai, Sheiji; Ishikawa, Yuichi; Shinkai, Hiroko; Tsuno, Takaharu; Makishima, Hiroki; et al.; Journal of the American Chemical Society; vol. 106; nb. 6; (1984); p. 1801 - 1808, View in Reaxys; Mandal, Sukhendu B.; Pakrashi, Satyesh C.; Heterocycles; vol. 23; nb. 4; (1985); p. 931 - 934, View in Reaxys; Johansen, Jon E.; Christie, Bradley D.; Rapoport, Henry; Journal of Organic Chemistry; vol. 46; nb. 24; (1981); p. 4914 - 4920, View in Reaxys; Kutney; Choi; Honda; et al.; Helvetica Chimica Acta; vol. 65; nb. 7; (1982); p. 2088 - 2101, View in Reaxys; Laske; Schonenberger; Holler; Archiv der Pharmazie; vol. 322; nb. 12; (1989); p. 857 - 862, View in Reaxys; Agarwal, Alka; Agarwal, Shiv K.; Bhakuni, D. 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Rodolphe; Guillot, Regis; Kouklovsky, Cyrille; Vincent, Guillaume; Chemistry - A European Journal; vol. 20; nb. 24; (2014); p. 7492 - 7500, View in Reaxys; Gandy, Michael N.; Raston, Colin L.; Stubbs, Keith A.; Organic and Biomolecular Chemistry; vol. 12; nb. 26; (2014); p. 4594 - 4597, View in Reaxys; Liew, Lydia P.P.; Fleming, Jessica M.; Longeon, Arlette; Mouray, Elisabeth; Florent, Isabelle; Bourguet-Kondracki, Marie-Lise; Copp, Brent R.; Tetrahedron; vol. 70; nb. 33; (2014); p. 4910 - 4920, View in Reaxys; Tian, Jingjing; Du, Qiuchen; Guo, Rui; Li, Yun; Cheng, Bin; Zhai, Hongbin; Organic Letters; vol. 16; nb. 12; (2014); p. 3173 - 3175, View in Reaxys; Shimizu, Mai; Fukami, Tatsuki; Nakajima, Miki; Yokoi, Tsuyoshi; Drug Metabolism and Disposition; vol. 42; nb. 7; (2014); p. 1103 - 1109, View in Reaxys; Patent; Morrison, Richard W.; Jackson, Douglas Michael; US2014/275569; (2014); (A1) English, View in Reaxys; Reimer, Daniela; Nollmann, Friederike I.; Schultz, Katharina; Kaiser, Marcel; Bode, Helge B.; Journal of Natural Products; vol. 77; nb. 8; (2014); p. 1976 - 1980, View in Reaxys; Fischereder, Eva; Pressnitz, Desiree; Kroutil, Wolfgang; Lutz, Stefan; Bioorganic and Medicinal Chemistry; vol. 22; nb. 20; (2014); p. 5633 - 5637, View in Reaxys; Sirocchi, Veronica; Caprioli, Giovanni; Ricciutelli, Massimo; Vittori, Sauro; Sagratini, Gianni; Journal of Mass Spectrometry; vol. 49; nb. 9; (2014); p. 819 825, View in Reaxys; Baumann, Marcus; Baxendale, Ian R.; Organic Letters; vol. 16; nb. 23; (2014); p. 6076 6079, View in Reaxys; Gattuso, Giuseppe; Notti, Anna; Parisi, Melchiorre F.; Pisagatti, Ilenia; Marcos, Paula Maria; Ascenso, Jos Rosrio; Brancatelli, Giovanna; Geremia, Silvano; New Journal of Chemistry; vol. 39; nb. 2; (2015); p. 817 - 821, View in Reaxys; Majumder, Joydeb; Deb, Jolly; Husain, Ahmad; Jana, Siddhartha Sankar; Dastidar, Parthasarathi; Journal of Materials Chemistry B; vol. 3; nb. 32; (2015); p. 6634 - 6644, View in Reaxys; Oda, Shingo; Fujiwara, Ryoichi; Kutsuno, Yuki; Fukami, Tatsuki; Itoh, Tomoo; Yokoi, Tsuyoshi; Nakajima, Miki; Drug Metabolism and Disposition; vol. 43; nb. 6; (2015); p. 812 - 818, View in Reaxys; Patent; Jaswant S. Gidda; David L. Nelson; James E. Audia; Marlene Cohen; US5705519; (A); (1998), View in Reaxys; Patent; James E. Audia; Marlene L. Cohen; Jaswant S. Gidda; David L. G. Nelson; US5736544; (A); (1998), View in Reaxys; Patent; BAKER Stephen Richard; EZQUERRA-CARRERA Jesus; LAMAS-PETEIRA Carlos; AUDIA James Edmund; COHEN Marlene Lois; GIDDA Jaswant Singh; NELSON David Lloyd Garver; PEDREGAL-TERCERO Concepcion; WO1995/24200; (A1); (1995), View in Reaxys; Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 - 2700, View in Reaxys; Khalil, Iman M.; Barker, David; Copp, Brent R.; Journal of Organic Chemistry; vol. 81; nb. 1; (2016); p. 282 - 289, View in Reaxys 2 of 11
Comment (Pharmacological Data)
physiological behaviour discussed
Shimizu, Mai; Fukami, Tatsuki; Nakajima, Miki; Yokoi, Tsuyoshi; Drug Metabolism and Disposition; vol. 42; nb. 7; (2014); p. 1103 - 1109, View in Reaxys 3 of 11
Effect (Pharmacological Data)
agonist
Species or Test-System (Pharmacological Data)
HEK-293 cell membranes expressing rat 5-HT6 receptors
Concentration (Pharmacological Data)
Ca. 1E-10 - 1E-06 mol/l
Method (Pharmacological Data)
0.2 nmol/l <35S>GTPγS used as radioligand; 20 mmol/l HEPES buffer (pH 7.4), 1 h; Gα activation determined by SPA/antibody-immunocapture procedure; non-specific binding defined at 10 μmol/l GTPγS
Further Details (Pharmacological Data)
serotonin (5-HT) used for comparison (pEC50: 7.69; Emax at 1 μmol/l=100percent); SPA: scintillation proximity assay
Type (Pharmacological Data)
pEC50
Value of Type (Pharmacological Data)
6.13 dimensionless
Results
title comp. stimulated binding <35S>GTPγS to Gα proteins with Emax=109.8percent, thus acting as full agonist; fig.
Dupuis, Delphine S.; la Cour, Clotilde Mannoury; Chaput, Christine; Verriele, Laurence; Lavielle, Gilbert; Millan, Mark J.; European Journal of Pharmacology; vol. 588; nb. 2-3; (2008); p. 170 - 177, View in Reaxys 4 of 11
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
HEK-293 cell membranes expressing rat 5-HT6 receptors
Concentration (Pharmacological Data)
Ca. 1E-09 - 0.0001 mol/l
Method (Pharmacological Data)
radioligand binding assay; 0.1 nmol/l <125I>SB258,585 used as radioligand; 50 mmol/l Tris (pH 7.4) buffer, 37 deg C, 45 min; non-specific binding defined with 10 μmol/l methiothepin
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Further Details (Pharmacological Data)
5-HT: serotonin
Type (Pharmacological Data)
pKi
Value of Type (Pharmacological Data)
5.94 dimensionless
Results
title comp. showed high affinity for 5-HT6 receptors; fig.
Dupuis, Delphine S.; la Cour, Clotilde Mannoury; Chaput, Christine; Verriele, Laurence; Lavielle, Gilbert; Millan, Mark J.; European Journal of Pharmacology; vol. 588; nb. 2-3; (2008); p. 170 - 177, View in Reaxys 5 of 11
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
HEK cell membranes
Method (Pharmacological Data)
radioligand binding assay; in triplicate; assay tubes containing membranes, 2.5 nmol/l <3H>5-HT and varying concentrations of title comp. incubated for 20 min at 37 deg C; suspensions filtered and counted in liquid scintillation counter
Further Details (Pharmacological Data)
HEK cells stably expressing human 5-HT1E receptor; methiothepin (10 μmol/l) used to define nonspecific binding; 5-HT, serotonin
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
500 nmol/l
Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 10; (2004); p. 2545 - 2552, View in Reaxys 6 of 11
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
COS-7 cells
Method (Pharmacological Data)
h5-HT6 radioligand binding assay; 5-HT6-cDNA transfected by DEAE-dextran technique, harvested (centrifugated/washed) cells suspended in Tris-Cl/MgCl2/EDTA buffer (pH 7.40), room temp., 90 min, 1 nmol/l <3H>LSD, 10 μmol/l clozapine, title comp.
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
180 nmol/l
Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys 7 of 11
Effect (Pharmacological Data)
neuromuscular
Species or Test-System (Pharmacological Data)
Hartley guinea pig
Sex
male
Route of Application
inhalation
Concentration (Pharmacological Data)
0.001 - 0.01 percent
Kind of Dosing (Pharmacological Data)
through ultrasonic nebulizer
Method (Pharmacological Data)
350-820 g guinea pigs (12 h light:dark cycle) anesthetized; trachea transected; artificially ventilated through respirator; bronchial pressure measured as ventilation overflow (VO) through pneumotachograph
Further Details (Pharmacological Data)
tracheal pressure (TP) measured via pressure transducer; title comp. effect on VO, TP studied
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Results
VO increased; biphasic effect on TP: initial increase, then (3 min later) decrease (diagram)
Takahashia, Yoshinori; Ohno, Hiromitsu; Misawa, Miwa; European Journal of Pharmacology; vol. 302; nb. 1-3; (1996); p. 89 - 97, View in Reaxys 8 of 11
Effect (Pharmacological Data)
inhibition of 5-HT uptake
Species or Test-System (Pharmacological Data)
Wistar rats
Sex
male and female
Concentration (Pharmacological Data)
2900 - 5490 nmol/l
Exposure Period (Pharmacological Data)
22 min
Method (Pharmacological Data)
rats pretreated with pargyline (75 mg/kg i.p.) 18 and 2 h prior sacrifice; in anaesthesia thorax opened, heparin (2500 U/kg) injected intracardially; trachea, pulmonary artery, left atrium cannulated; perfusion via pulmonary artery
Further Details (Pharmacological Data)
lungs perfused with title compd. for 20 min and for 2 min with (3)H-5-HT (2 nmol/l) and (14)C-sorbitol (100 μmol/l); lungs homogenate supernatant and perfusion solution collected from pulmonary artery cannula; (3)H and (14)C content detd.
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
4080 nmol/l
Results
title compd. inhibited uptake of 5-HT in perfused lung
Paczkowski, Natalii J.; Vuocolo, Helen E.; Bryan-Lluka, Lesley J.; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 353; nb. 4; (1996); p. 423 - 430, View in Reaxys 9 of 11
Effect (Pharmacological Data)
binding to microsome; effect on
Species or Test-System (Pharmacological Data)
Sprague-Dawley rat liver microsomes
Sex
male
Concentration (Pharmacological Data)
0.01 - 50 μmol/l
Method (Pharmacological Data)
rats (2 - 3 months old), liver microsomes isolated; microsomal suspension treated with <3H>labelled stanozolol overnight at O deg C in the presence of increasing conc. of title comp.; DCC added, centrifuged; supernatant radioactivity counting
Further Details (Pharmacological Data)
DCC = Dextran T70-coated charcoal; protein conc. in microsomal susp. = 2 - 3 mg/ml; ability of the title comp. to compete with <3H>labelled stanozolol for its binding to liver microsomes tested
Comment (Pharmacological Data)
No effect
Boada, Luis D.; Fernandez, Leandro; Zumbado, Manuel; Luzardo, Octavio P.; Chirino, Ricardo; Diaz-Chico, Bonifacio N.; Journal of Pharmacology and Experimental Therapeutics; vol. 279; nb. 3; (1996); p. 1123 - 1129, View in Reaxys 10 of 11
Effect (Pharmacological Data)
agonist
Species or Test-System (Pharmacological Data)
Dunkin-Hartley guineapig proximal colon
Sex
male and female
Concentration (Pharmacological Data)
1E-06 - 0.001 mol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in distilled H2O
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Method (Pharmacological Data)
pig (400-600 g) killed; proximal colon removed; relaxation induced by title comp. in presence of ketanserin and tropisetron (to block contractions mediated by 5-HT2A,3,4 receptors) and strips precontracted with methacholine
Further Details (Pharmacological Data)
concentration-relaxation curve; relaxation expressed as percentage of relaxation induced by 10 μM 5-hydroxytryptamine
Results
title comp. active as partial agonist: induced relaxation with low potency and efficacy and pEC50 = 5.5
Briejer, Michel R.; Akkermans, Louis M. A.; Lefebvre, Romain A.; Schuurkes, Jan A. J.; European Journal of Pharmacology; vol. 279; nb. 2-3; (1995); p. 123 - 134, View in Reaxys 11 of 11
Comment (Pharmacological Data)
antiproliferative effect against the murine leukemic cell line P388D1; D 50: 58 μM
Laske; Schonenberger; Holler; Archiv der Pharmazie; vol. 322; nb. 12; (1989); p. 857 - 862, View in Reaxys Transport and Distribution (1) 1 of 1
Type (Transport and Distribution)
partition
Media (Transport and Distribution)
water-micellar interface
Results
partition constant K = 10-16
Method, Remarks (Transport and Distribution)
reverse micellar solution containing benzylhexadecyldimethylammonium chloride; title comp. dissolved in water; varying water/surfactant molar ratio; mixtures shaken of sonicated for a few min
Borsarelli, Claudio D.; Bertolotti, Sonia G.; Previtali, Carlos M.; Photochemistry and Photobiology; vol. 73; nb. 2; (2001); p. 97 - 104, View in Reaxys
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