2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine by Asch

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12 substances in Reaxys

2016-06-01 12h:59m:07s (EST)

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2016-06-01 13:02:51

Reaxys ID 138259 View in Reaxys

1/12 CAS Registry Number: 61-50-7 Chemical Name: N,N-dimethyltryptamine; N,N-Dimethyltryptamine; DMT; 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine; 2(1H-indol-3-yl)-N,N-dimethylethanamine; [2-(1H-indol-3-yl)-ethyl]-dimethylamine; 3-(2-dimethylaminoethyl)-1H-indole Linear Structure Formula: CH2C11H14N2 Molecular Formula: C12H16N2 Molecular Weight: 188.272 Type of Substance: heterocyclic InChI Key: DMULVCHRPCFFGV-UHFFFAOYSA-N Note:

Substance Label (23) Label References 8e

Olsen, Elisabeth K.; Hansen, Espen; Moodie, Lindon W. K.; Isaksson, Johan; Sepi, Kristina; Cergolj, Marija; Svenson, Johan; Andersen, Jeanette H.; Organic and Biomolecular Chemistry; vol. 14; nb. 5; (2016); p. 1629 - 1640, View in Reaxys

DMT

Riba, Jordi; Valle, Marta; Urbano, Gloria; Yritia, Mercedes; Morte, Adelaida; Barbanoj, Manel J.; Journal of Pharmacology and Experimental Therapeutics; vol. 306; nb. 1; (2003); p. 73 - 83, View in Reaxys; Chu, Uyen B.; Vorperian, Sevahn K.; Satyshur, Kenneth; Eickstaedt, Kelsey; Cozzi, Nicholas V.; Mavlyutov, Timur; Hajipour, Abdol R.; Ruoho, Arnold E.; Biochemistry; vol. 53; nb. 18; (2014); p. 2956 - 2965, View in Reaxys; Calvert, Matthew B.; Sperry, Jonathan; Chemical Communications; vol. 51; nb. 28; (2015); p. 6202 - 6205, View in Reaxys

Bartolucci, Silvia; Mari, Michele; Bedini, Annalida; Piersanti, Giovanni; Spadoni, Gilberto; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3217 - 3222, View in Reaxys

Tong, Shuo; Xu, Zhengren; Mamboury, Mathias; Wang, Qian; Zhu, Jieping; Angewandte Chemie - International Edition; vol. 54; nb. 40; (2015); p. 11809 - 11812; Angew. Chem.; vol. 127; nb. 40; (2015); p. 11975 11978,4, View in Reaxys

He, Yi; Li, Xiaolong; Li, Jue; Li, Xiaocen; Guo, Li; Hai, Li; Wu, Yong; Tetrahedron Letters; vol. 55; nb. 29; (2014); p. 3938 - 3941, View in Reaxys

Qu, Shi-Jin; Liu, Quan-Wen; Tan, Chang-Heng; Jiang, Shan-Hao; Zhu, Da-Yuan; Planta Medica; vol. 72; nb. 3; (2006); p. 264 - 266, View in Reaxys; Nyandege, Abner; Kolanos, Renata; Roth, Bryan L.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 6; (2007); p. 1691 - 1694, View in Reaxys; 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

KD38

Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; OZPOLAT, Bulent; LOPEZ-BERESTEIN, Gabriel; DALBY, Kevin N.; JOSE, Jiney; WO2013/63492; (2013); (A1) English, 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, Domenico; Castaldo, Domenico; Journal of Agricultural and Food Chemistry; vol. 60; nb. 37; (2012); p. 9512 - 9518, View in Reaxys

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

13; DMT

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.; Bioorganic and Medicinal Chemistry; vol. 16; nb. 8; (2008); p. 4661 - 4669, View in Reaxys

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

Buchanan, Malcolm S.; Carroll, Anthony R.; Pass, David; Quinn, Ronald J.; Magnetic Resonance in Chemistry; vol. 45; nb. 4; (2007); p. 359 - 361, View in Reaxys

Kolanos, Renata; Dukat, Malgorzata; Roth, Bryan L.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry Letters; vol. 16; nb. 22; (2006); p. 5832 - 5835, View in Reaxys

Schmidt, Axel M.; Eilbracht, Peter; Journal of Organic Chemistry; vol. 70; nb. 14; (2005); p. 5528 - 5535, 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

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11a

Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046, View in Reaxys

Somei; Yamada; Kurauchi; Nagahama; Hasegawa; Teranishi; Sato; Kaneko; Chemical and Pharmaceutical Bulletin; vol. 49; nb. 1; (2001); p. 87 - 96, View in Reaxys

N,N-DMT

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

Lee, Tzong-Huei; Chou, Chang-Hung; Journal of the Chinese Chemical Society; vol. 47; nb. 6; (2000); p. 1287 - 1290, View in Reaxys

1a, DMT

Blair, Joseph B.; Marona-Lewicka, Danuta; Kanthasamy, Arthi; Lucaites, Virginia L.; Nelson, David L.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 42; nb. 6; (1999); p. 1106 - 1111, View in Reaxys

4, DMT

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

Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys

Hong; Dukat; Teitler; Egan; Dupre; Herrick-Davis; Glennon; Medicinal Chemistry Research; vol. 9; nb. 6; (1999); p. 374 - 388, View in Reaxys

Patent-Specific Data (6) Prophetic ComLocation in Patent References pound Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; OZPOLAT, Bulent; LOPEZ-BERESTEIN, Gabriel; DALBY, Kevin N.; JOSE, Jiney; WO2013/63492; (2013); (A1) English, View in Reaxys Patent; Suven Pharmaceuticals Ltd.; WO2004/205; (2003); (A2) English, View in Reaxys Patent; SUVEN PHARMACEUTICALS LTD.; WO2004/845; (2003); (A1) English, View in Reaxys Claim

Patent; Strahilevitz; Meir; US4620977; (1986); (A1) English, View in Reaxys; Patent; Wilburn, Michael D.; US2003/78231; (2003); (A1) English, View in Reaxys; Patent; Psychiatric Genomics, Inc.; US2003/82802; (2003); (A1) English, View in Reaxys; Patent; Wilburn, Michael D.; US2003/7961; (2003); (A1) English, View in Reaxys Patent; SUVEN PHARMACEUTICALS LTD.; WO2004/849; (2003); (A2) English, View in Reaxys

prophetic product Derivative (23) Comment (Derivative)

Patent; Eli Lilly and Company; US5096908; (1992); (A1) English, View in Reaxys Derivative

References

N,N-Dimethyltryptamine oxalate

Sintas, Jose A.; Vitale, Arturo A.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 677 - 684, View in Reaxys

Pikrat: F: 167-168grad; MS

Ueno et al.; Chemical and Pharmaceutical Bulletin; vol. 26; (1978); p. 2411,2415, View in Reaxys

Pikrat: F: 168-170grad

Ghosal; Singh; Bhattacharya; Planta medica; vol. 19; nb. 3; (1971); p. 280 - 284, View in Reaxys; Wenkert; Kryger; Journal of the Indian Chemical Society; vol. 55; (1978); p. 1122, View in Reaxys; Marini-Bettolo et al.; Annali di Chimica (Rome, Italy); vol. 54; (1964); p. 1179,1185, View in Reaxys

Pikrat: Prep.: Tryptamin 4a, Pikrinsaeure; F: 168-170grad

Wenkert; Kryger; Journal of the Indian Chemical Society; vol. 55; (1978); p. 1122, View in Reaxys

Charge-TransferKomplex m. Hematoporphyrin: K(c) (Tab. 1)

Brucato et al.; Arzneimittel Forschung; vol. 27; (1977); p. 1015,1017, View in Reaxys

Pikrat: F: 166grad

Julia,M. et al.; Bulletin de la Societe Chimique de France; (1973); p. 1424 - 1426, View in Reaxys

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Pikrat: F: 168grad; gelb

Ghosal et al.; Planta Medica; vol. 21; (1972); p. 22,23, View in Reaxys

Hydrobromid: F: 114.5grad; Roentgenstrukturanalyse: Molekuel- u. Kristallstruktur

Falkenberg; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 28; (1972); p. 3075, View in Reaxys

Pikrat: F: 166-167grad; gelblich-orange

Ghosal et al.; Journal of Pharmaceutical Sciences; vol. 60; (1971); p. 1209,1211, View in Reaxys

Methoiodid: F: 216grad

Ghosal et al.; Journal of Pharmaceutical Sciences; vol. 60; (1971); p. 1209,1211, View in Reaxys

Pikrat: F: 160-168grad

Corothie; Nakano; Planta Medica; vol. 17; (1969); p. 184,186, View in Reaxys

Methoiodid: F: 197-198grad

Corothie; Nakano; Planta Medica; vol. 17; (1969); p. 184,186, View in Reaxys

Pikrat C12H16N2*C6H3 N3O7: F: 169grad; gelb

Rovelli; Vaughan; Australian Journal of Chemistry; vol. 20; (1967); p. 1299, View in Reaxys

Pikrat: F: 168-169grad

Dutta; Ghosal; Chemistry and Industry (London, United Kingdom); (1967); p. 2046, View in Reaxys

Oxalat C12H16N2*C2H2 O4: F: 147grad (Me., unkorr.)

Morimoto; Matsumoto; Justus Liebigs Annalen der Chemie; vol. 692; (1966); p. 194,197, View in Reaxys

Pikrat C12H16N2*C6H3 N3O7: F: 169grad (Me., unkorr.)

Morimoto; Matsumoto; Justus Liebigs Annalen der Chemie; vol. 692; (1966); p. 194,197, View in Reaxys

Iodmethalat C12H16N2*CH3I: F: 207grad (Acn., Me./Ae., unkorr.)

Morimoto; Matsumoto; Justus Liebigs Annalen der Chemie; vol. 692; (1966); p. 194,197, View in Reaxys

Pikrat C12H16N2*C6H3 N3O7: F: 171-171.5grad (A.) (rot); F: 170-171grad (A.) (gelb)

Fitzgerald; Sioumis; Australian Journal of Chemistry; vol. 18; (1965); p. 433,434, View in Reaxys

Pikrat C12H16N2*C6H3 N3O7: F: 166grad (Zers.)

Morimoto et al.; Justus Liebigs Annalen der Chemie; vol. 682; (1965); p. 212,218, View in Reaxys

Pikrat: F: 168grad

Ghosal; Mukherjee; Chemistry and Industry (London, United Kingdom); (1964); p. 1800, View in Reaxys

Pikrat C12H16N2*C6H3 N3O7: F: 169grad (A.); orange

Culvenor et al.; Australian Journal of Chemistry; vol. 17; (1964); p. 1301,1304, View in Reaxys

Methoiodid: Hofmannabbau -> 9percent monomeres, Rest polymeres 3-Vinyl-indol m. F: 160-175grad

Noland; Sundberg; Journal of Organic Chemistry; vol. 28; (1963); p. 884, View in Reaxys

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Pikrat: F: 170grad

Bodendorf; Walk; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 294; (1961); p. 484,487, View in Reaxys

Melting Point (27) 1 of 27

Melting Point [°C]

46 - 47

Solvent (Melting Point)

ethyl acetate; hexane

He, Yi; Li, Xiaolong; Li, Jue; Li, Xiaocen; Guo, Li; Hai, Li; Wu, Yong; Tetrahedron Letters; vol. 55; nb. 29; (2014); p. 3938 - 3941, View in Reaxys 2 of 27

Melting Point [°C]

45 - 47

Location

Page/Page column 33

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 3 of 27

Melting Point [°C]

Solvent (Melting Point)

hexane; ethyl acetate

Moura, Sidnei; Carvalho, Felipe Garcia; de Oliveira, Carolina Dizioli Rodrigues; Pinto, Ernani; Yonamine, Mauricio; Phytochemistry Letters; vol. 3; nb. 2; (2010); p. 79 - 83, View in Reaxys 4 of 27

Melting Point [°C]

38 - 40

Whitneys, Simon; Grigg, Ronald; Derrick, Andrew; Keep, Ann; Organic Letters; vol. 9; nb. 17; (2007); p. 3299 3302, View in Reaxys 5 of 27

Melting Point [°C]

45 - 47

Comment (Melting Point)

Method: distilled sample

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 6 of 27

Melting Point [°C]

44 - 45

Sintas, Jose A.; Vitale, Arturo A.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 677 - 684, View in Reaxys 7 of 27

Melting Point [°C]

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 8 of 27

Melting Point [°C]

48 - 49

Ueno et al.; Chemical and Pharmaceutical Bulletin; vol. 26; (1978); p. 2411,2415, View in Reaxys 9 of 27

Melting Point [°C]

45 - 47

Wenkert; Kryger; Journal of the Indian Chemical Society; vol. 55; (1978); p. 1122, View in Reaxys 10 of 27

Melting Point [°C]

Julia,M. et al.; Bulletin de la Societe Chimique de France; (1973); p. 1424 - 1426, View in Reaxys 11 of 27

Melting Point [°C]

65.5

Falkenberg; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 28; (1972); p. 3075, View in Reaxys 12 of 27

Melting Point [°C]

Poissan; Annales Pharmaceutiques Francaises; vol. 23; (1965); p. 241, View in Reaxys; Kan-Fan et al.; Phytochemistry (Elsevier); vol. 9; (1970); p. 1283,1289, View in Reaxys 13 of 27

Melting Point [°C]

58.2

Bergin et al.; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 24; (1968); p. 882, View in Reaxys 14 of 27

Melting Point [°C]

45 - 49

Hall; McCapra; Scott; Tetrahedron; vol. 23; nb. 10; (1967); p. 4131 - 4141, View in Reaxys 15 of 27

Melting Point [°C]

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Solvent (Melting Point)

petroleum ether

Rovelli; Vaughan; Australian Journal of Chemistry; vol. 20; (1967); p. 1299, View in Reaxys 16 of 27

Melting Point [°C]

53.5 - 57.5

Solvent (Melting Point)

hexane

Arthur et al.; Australian Journal of Chemistry; vol. 20; (1967); p. 811,812, View in Reaxys 17 of 27

Melting Point [°C]

Solvent (Melting Point)

petroleum ether

Morimoto et al.; Justus Liebigs Annalen der Chemie; vol. 682; (1965); p. 212,218, View in Reaxys; Morimoto; Matsumoto; Justus Liebigs Annalen der Chemie; vol. 692; (1966); p. 194,197, View in Reaxys 18 of 27

Melting Point [°C]

42 - 43

Noell,C.W.; Cheng,C.C.; Journal of Heterocyclic Chemistry; vol. 3; (1966); p. 5 - 8, View in Reaxys 19 of 27

Melting Point [°C]

57.5 - 58.5

Solvent (Melting Point)

hexane

Fitzgerald; Sioumis; Australian Journal of Chemistry; vol. 18; (1965); p. 433,434, View in Reaxys 20 of 27

Melting Point [°C]

46 - 47

Solvent (Melting Point)

hexane

Fitzgerald; Sioumis; Australian Journal of Chemistry; vol. 18; (1965); p. 433,434, View in Reaxys 21 of 27

Melting Point [°C]

Ghosal; Mukherjee; Chemistry and Industry (London, United Kingdom); (1964); p. 1800, View in Reaxys 22 of 27

Melting Point [°C]

46.5

Solvent (Melting Point)

petroleum ether

Culvenor et al.; Australian Journal of Chemistry; vol. 17; (1964); p. 1301,1304, View in Reaxys 23 of 27

Melting Point [°C]

47 - 48

Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 24 of 27

Melting Point [°C]

48 - 49

Solvent (Melting Point)

diethyl ether; petroleum ether

Bodendorf; Walk; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 294; (1961); p. 484,487, View in Reaxys 25 of 27

Melting Point [°C]

48 - 49

Solvent (Melting Point)

hexane; diethyl ether

Pachter et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 1285, View in Reaxys 26 of 27

Melting Point [°C]

73 - 74

Solvent (Melting Point)

hexane

Comment (Melting Point)

and :47 degreeC.-:49 degreeC.

Fish et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 3668,3670, View in Reaxys 27 of 27

Melting Point [°C]

49 - 50

Solvent (Melting Point)

diethyl ether; petroleum ether

Hoshino; Shimodaira; Justus Liebigs Annalen der Chemie; vol. 520; (1935); p. 19,26, View in Reaxys Boiling Point (2) Boiling Point [°C] 160

Pressure (Boiling Point) [Torr]

References

0.6

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

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80 - 135

0.03

Corothie; Nakano; Planta Medica; vol. 17; (1969); p. 184,186, View in Reaxys

Density (1) 1 of 1

Type (Density)

crystallographic

Bergin et al.; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 24; (1968); p. 882, View in Reaxys Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)

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

Conformation (1) 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

Crystal Phase (2) Description (Crys- Comment (Crystal References tal Phase) Phase) Crystal structure determination Crystal structure determination

Falkenberg; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 28; (1972); p. 3075, View in Reaxys .

Crystal Property Description (11) Colour & Other Location Properties

Bergin et al.; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 24; (1968); p. 882, View in Reaxys References

white

brown

Bartolucci, Silvia; Mari, Michele; Bedini, Annalida; Piersanti, Giovanni; Spadoni, Gilberto; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3217 - 3222, View in Reaxys

colourless

supporting information

brown

supporting information

He, Yi; Li, Xiaolong; Li, Jue; Li, Xiaocen; Guo, Li; Hai, Li; Wu, Yong; Tetrahedron Letters; vol. 55; nb. 29; (2014); p. 3938 - 3941, View in Reaxys

yellow

Paragraph 0509

Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; OZPOLAT, Bulent; LOPEZ-BERESTEIN, Gabriel; DALBY, Kevin N.; JOSE, Jiney; WO2013/63492; (2013); (A1) English, View in Reaxys

colourless

light-yellow

Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, Da-Yuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys Page/Page column 33

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

white

Moura, Sidnei; Carvalho, Felipe Garcia; de Oliveira, Carolina Dizioli Rodrigues; Pinto, Ernani; Yonamine, Mauricio; Phytochemistry Letters; vol. 3; nb. 2; (2010); p. 79 83, View in Reaxys

yellow

Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046, View in Reaxys Ghosal et al.; Planta Medica; vol. 21; (1972); p. 22,23, View in Reaxys; Ghosal et al.; Journal of Pharmaceutical Sciences; vol. 60; (1971); p. 1209,1211, View in Reaxys

dimorph

Fish et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 3668,3670, View in Reaxys

Crystal System (1) References

7/45

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Bergin et al.; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 24; (1968); p. 882, View in Reaxys Dissociation Exponent (1) 1 of 1

Comment (Dissociation Exponent)

(pk')pK(a)

Glennon; Gessner; Journal of Medicinal Chemistry; vol. 22; (1979); p. 428,430, View in Reaxys Further Information (7) Description (Fur- References ther Information) Further information

Brucato et al.; Arzneimittel Forschung; vol. 27; (1977); p. 1015,1017, View in Reaxys

Further information

Banerjee; Ghosal; Australian Journal of Chemistry; vol. 22; (1969); p. 275, View in Reaxys

Further information

Ghosal; Banerjee; Australian Journal of Chemistry; vol. 22; (1969); p. 2029, View in Reaxys

Further information

Morimoto; Matsumoto; Justus Liebigs Annalen der Chemie; vol. 692; (1966); p. 194,197, View in Reaxys

Further information

Noland; Sundberg; Journal of Organic Chemistry; vol. 28; (1963); p. 884, View in Reaxys

Further information

Pecher et al.; Tetrahedron Letters; (1961); p. 270,272, View in Reaxys

Further information

Cohen et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 2184, View in Reaxys

Ionization Potential (1) Ionization Poten- Comment (Ioniza- References tial [eV] tion Potential) 7.57

Type: vertical. Higher potentials: 8, 8.22, 9.54,

Kline; Benington; Morin; Beaton; Glennon; Domelsmith; Houk; Rozeboom; Journal of Medicinal Chemistry; vol. 25; nb. 11; (1982); p. 1381 - 1383, View in Reaxys

Other Thermochemical Data (1) Description (Oth- References er Thermochemical Data) Enthalpy

Gasco; Farmaco, Edizione Scientifica; vol. 30; (1975); p. 512,513, View in Reaxys

Solubility (MCS) (1) 1 of 1

Comment (Solubility (MCS))

In Ae. l.

Culvenor et al.; Australian Journal of Chemistry; vol. 17; (1964); p. 1301,1304, View in Reaxys Space Group (1) References Bergin et al.; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 24; (1968); p. 882, View in Reaxys NMR Spectroscopy (29) 1 of 29

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

600

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2 of 29

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

151

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

He, Yi; Li, Xiaolong; Li, Jue; Li, Xiaocen; Guo, Li; Hai, Li; Wu, Yong; Tetrahedron Letters; vol. 55; nb. 29; (2014); p. 3938 - 3941, View in Reaxys; Bartolucci, Silvia; Mari, Michele; Bedini, Annalida; Piersanti, Giovanni; Spadoni, Gilberto; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3217 - 3222, View in Reaxys 4 of 29

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400.1

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)

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Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

He, Yi; Li, Xiaolong; Li, Jue; Li, Xiaocen; Guo, Li; Hai, Li; Wu, Yong; Tetrahedron Letters; vol. 55; nb. 29; (2014); p. 3938 - 3941, View in Reaxys 7 of 29

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

XH (400 MHz CDC1 ) ? 8.47 (br, 1H), 7.52 (d, J= 7.7 Hz, 1H), 7.21 (d, J= 7.9 Hz, 1H), 3 7.08 (t, J= 7.2 Hz, 1H), 7.02 (t, J= 7.2 Hz, 1H), 6.84 (br, 1H), 2.87 (t, J= 7.8 Hz, 2H), 2.58 (t, J= 7.8 Hz, 2H), 2.27 (s, 6H)

Location

Paragraph 0558

Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; OZPOLAT, Bulent; LOPEZ-BERESTEIN, Gabriel; DALBY, Kevin N.; JOSE, Jiney; WO2013/63492; (2013); (A1) English, View in Reaxys 8 of 29

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

101

Original Text (NMR Spectroscopy)

13C (101 MHz CDC1 ) ? 136.36, 127.42, 121.83, 121.73, 1 19.09, 118.73, 113.90, 11 1.25, 3 60.49, 45.37, 23.60.

Location

Paragraph 0558

Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; OZPOLAT, Bulent; LOPEZ-BERESTEIN, Gabriel; DALBY, Kevin N.; JOSE, Jiney; WO2013/63492; (2013); (A1) English, View in Reaxys 9 of 29

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H NMR (400 MHz, CDC13): δ 8.68 (s, 1H), 7.63 (d, J = 7.7 Hz, 1H), 7.35 (d, J = 8.0 Hz, 1H), 7.21 (t, J = 1.1 Hz, 1H), 7.14 (t, J = 1.5 Hz, 1H), 6.97 (s, 1H), 3.00 (t, J = 1.5 Hz, 2H), 2.72 (t, J = 8.4 Hz, 2H), 2.40 (s, 6H).

Location

Page/Page column 54

Comment (NMR Spectroscopy)

Signals given

Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; KOZIKOWSKI, Alan; KALIN, Jay, Hans; BUTLER, Kyle, Vincent; BERGMAN, Joel; HANCOCK, Wayne, W.; WO2012/106343; (2012); (A2) English, View in Reaxys 10 of 29

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

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Solvents (NMR Spectro- [D3]acetonitrile; d(4)-methanol scopy) Seki, Takayuki; Fujiwara, Tomoya; Takeuchi, Yoshio; Journal of Fluorine Chemistry; vol. 132; nb. 3; (2011); p. 181 - 185, View in Reaxys 11 of 29

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, DaYuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys 12 of 29

Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

H NMR, δ: 10.43 (s, 1 H), 7.42-7.06 (m, 5 H), 2.68 (m, 4H), 2.26 (S, 6 H).

Location

Page/Page column 33

Comment (NMR Spectroscopy)

Signals given

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 14 of 29

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

13C

Location

Page/Page column 33

Comment (NMR Spectroscopy)

Signals given

NMR (CDCl3): δ 136.5, 124.3, 123.2, 121.2, 119.7, 117.6, 113.4, 111.1, 61.7, 41.2, 22.4.

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 15 of 29

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

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Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

300

Moura, Sidnei; Carvalho, Felipe Garcia; de Oliveira, Carolina Dizioli Rodrigues; Pinto, Ernani; Yonamine, Mauricio; Phytochemistry Letters; vol. 3; nb. 2; (2010); p. 79 - 83, View in Reaxys 16 of 29

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Grina, Jonas A.; Ratcliff, Matthew R.; Stermitz, Frank R.; Journal of Organic Chemistry; vol. 47; nb. 13; (1982); p. 2648 - 2651, View in Reaxys; Sintas, Jose A.; Vitale, Arturo A.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 677 - 684, View in Reaxys; 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 17 of 29

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Whitneys, Simon; Grigg, Ronald; Derrick, Andrew; Keep, Ann; Organic Letters; vol. 9; nb. 17; (2007); p. 3299 3302, View in Reaxys 19 of 29

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Whitneys, Simon; Grigg, Ronald; Derrick, Andrew; Keep, Ann; Organic Letters; vol. 9; nb. 17; (2007); p. 3299 3302, View in Reaxys 20 of 29

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

125

Buchanan, Malcolm S.; Carroll, Anthony R.; Pass, David; Quinn, Ronald J.; Magnetic Resonance in Chemistry; vol. 45; nb. 4; (2007); p. 359 - 361, View in Reaxys 21 of 29

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

500

Buchanan, Malcolm S.; Carroll, Anthony R.; Pass, David; Quinn, Ronald J.; Magnetic Resonance in Chemistry; vol. 45; nb. 4; (2007); p. 359 - 361, View in Reaxys 22 of 29

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046, View in Reaxys 23 of 29

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046, View in Reaxys 24 of 29

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

50.5

Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046, View in Reaxys 25 of 29

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13/45

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Grina, Jonas A.; Ratcliff, Matthew R.; Stermitz, Frank R.; Journal of Organic Chemistry; vol. 47; nb. 13; (1982); p. 2648 - 2651, View in Reaxys 27 of 29

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

28 of 29

Description (NMR Spec- NMR troscopy) Hall et al.; Tetrahedron; vol. 23; (1967); p. 4131, View in Reaxys; Corothie; Nakano; Planta Medica; vol. 17; (1969); p. 184,186, View in Reaxys

29 of 29

Description (NMR Spec- Spectrum troscopy) Cohen et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 2184, View in Reaxys

IR Spectroscopy (4) 1 of 4

Description (IR Spectroscopy)

Bands

Corothie; Nakano; Planta Medica; vol. 17; (1969); p. 184,186, View in Reaxys; Olsen, Elisabeth K.; Hansen, Espen; Moodie, Lindon W. K.; Isaksson, Johan; Sepi, Kristina; Cergolj, Marija; Svenson, Johan; Andersen, Jeanette H.; Organic and Biomolecular Chemistry; vol. 14; nb. 5; (2016); p. 1629 - 1640, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Whitneys, Simon; Grigg, Ronald; Derrick, Andrew; Keep, Ann; Organic Letters; vol. 9; nb. 17; (2007); p. 3299 3302, View in Reaxys 3 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3400 - 740 cm**(-1)

Grina, Jonas A.; Ratcliff, Matthew R.; Stermitz, Frank R.; Journal of Organic Chemistry; vol. 47; nb. 13; (1982); p. 2648 - 2651, View in Reaxys 4 of 4

Description (IR Spectroscopy)

Hall; McCapra; Scott; Tetrahedron; vol. 23; nb. 10; (1967); p. 4131 - 4141, View in Reaxys; Morimoto; Matsumoto; Justus Liebigs Annalen der Chemie; vol. 692; (1966); p. 194,197, View in Reaxys Mass Spectrometry (13) Description (Mass Location Spectrometry)

References

high resolution mass spectrometry (HRMS); elec-

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trospray ionisation (ESI); spectrum electrospray ionisation (ESI); spectrum

Bartolucci, Silvia; Mari, Michele; Bedini, Annalida; Piersanti, Giovanni; Spadoni, Gilberto; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3217 - 3222, View in Reaxys

electrospray ionisation (ESI); spectrum

supporting information

He, Yi; Li, Xiaolong; Li, Jue; Li, Xiaocen; Guo, Li; Hai, Li; Wu, Yong; Tetrahedron Letters; vol. 55; nb. 29; (2014); p. 3938 - 3941, View in Reaxys

electrospray ionisation (ESI); liquid chromatography mass spectrometry (LCMS); spectrum

Paragraph 0558

Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; OZPOLAT, Bulent; LOPEZ-BERESTEIN, Gabriel; DALBY, Kevin N.; JOSE, Jiney; WO2013/63492; (2013); (A1) English, View in Reaxys

high resolution Paragraph 0558 mass spectrometry (HRMS); spectrum

Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; OZPOLAT, Bulent; LOPEZ-BERESTEIN, Gabriel; DALBY, Kevin N.; JOSE, Jiney; WO2013/63492; (2013); (A1) English, 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

ESI (Electrospray ionisation); Spectrum

Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, Da-Yuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys

ESI (Electrospray ionisation); HRMS (High resolution mass spectrometry); Spectrum

Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, Da-Yuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys

LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation); Spectrum

Moura, Sidnei; Carvalho, Felipe Garcia; de Oliveira, Carolina Dizioli Rodrigues; Pinto, Ernani; Yonamine, Mauricio; Phytochemistry Letters; vol. 3; nb. 2; (2010); p. 79 83, View in Reaxys

spectrum; electron impact (EI)

Sintas, Jose A.; Vitale, Arturo A.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 677 - 684, View in Reaxys; Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046, View in Reaxys

electron impact (EI); spectrum

Grina, Jonas A.; Ratcliff, Matthew R.; Stermitz, Frank R.; Journal of Organic Chemistry; vol. 47; nb. 13; (1982); p. 2648 - 2651, View in Reaxys Hall; McCapra; Scott; Tetrahedron; vol. 23; nb. 10; (1967); p. 4131 - 4141, View in Reaxys; Poissan; Annales Pharmaceutiques Francaises; vol. 23; (1965); p. 241, View in Reaxys; Bellman; Journal - Association of Official Analytical Chemists; vol. 51; (1968); p. 164,169, View in Reaxys; Corothie; Nakano; Planta Medica; vol. 17; (1969); p. 184,186, View in Reaxys; Ueno et al.; Chemical and Pharmaceutical Bulletin; vol. 26; (1978); p. 2411,2415, View in Reaxys

UV/VIS Spectroscopy (6) 1 of 6

Description (UV/VIS Spectroscopy)

Spectrum

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Solvent (UV/VIS Spectroscopy)

gaseous matrix

Comment (UV/VIS Spectroscopy)

283.5 - 288 nm

Li, Liang; Lubman, David M.; Analytical Chemistry; vol. 60; nb. 23; (1988); p. 2591 - 2598, View in Reaxys 2 of 6

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 293; 284; 279; 226 VIS) [nm] Grina, Jonas A.; Ratcliff, Matthew R.; Stermitz, Frank R.; Journal of Organic Chemistry; vol. 47; nb. 13; (1982); p. 2648 - 2651, View in Reaxys 3 of 6

Description (UV/VIS Spectroscopy)

UV/VIS

Dutta; Ghosal; Chemistry and Industry (London, United Kingdom); (1967); p. 2046, View in Reaxys; Hall et al.; Tetrahedron; vol. 23; (1967); p. 4131, View in Reaxys; Wenkert; Kryger; Journal of the Indian Chemical Society; vol. 55; (1978); p. 1122, View in Reaxys; Ghosal et al.; Journal of Pharmaceutical Sciences; vol. 60; (1971); p. 1209,1211, View in Reaxys; Aaron et al.; Clinica Chimica Acta; vol. 45; (1973); p. 375,379, View in Reaxys; Corothie; Nakano; Planta Medica; vol. 17; (1969); p. 184,186, View in Reaxys; Ueno et al.; Chemical and Pharmaceutical Bulletin; vol. 26; (1978); p. 2411,2415, View in Reaxys 4 of 6

Description (UV/VIS Spectroscopy)

Absorption maxima

Ghosal et al.; Planta Medica; vol. 21; (1972); p. 22,23, View in Reaxys; Jackson; Smith; Journal of the Chemical Society; (1964); p. 5510,5511, View in Reaxys; Ghosal; Singh; Bhattacharya; Planta medica; vol. 19; nb. 3; (1971); p. 280 - 284, View in Reaxys; Poissan; Annales Pharmaceutiques Francaises; vol. 23; (1965); p. 241, View in Reaxys 5 of 6

Description (UV/VIS Spectroscopy)

Spectrum

Ghosal; Mukherjee; Chemistry and Industry (London, United Kingdom); (1964); p. 1800, View in Reaxys 6 of 6

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 274; 283; 291 VIS) [nm] Fish et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 5892,5895, View in Reaxys Luminescence Spectroscopy (1) Description (LuReferences minescence Spectroscopy) Luminescence quenching

Bowd et al.; Photochemistry and Photobiology; vol. 11; (1970); p. 445,447, View in Reaxys

Fluorescence Spectroscopy (2) Description (Fluo- Solvent (Fluoresrescence Speccence Spectrotroscopy) scopy)

Comment (Fluorescence Spectroscopy)

Fluorescence

Maxima

References

Bridges; Williams; Biochemical Journal; vol. 107; (1968); p. 225,228, View in Reaxys; Aaron et al.; Clinica Chimica Acta; vol. 45; (1973); p. 375,379, View in Reaxys ethanol

350 nm

Fish et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 5892,5895, View in Reaxys

Phosphorescence Spectroscopy (1) Description References (Phosphores-

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cence Spectroscopy) Phosphorescence Aaron et al.; Clinica Chimica Acta; vol. 45; (1973); p. 375,379, 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; Domelsmith; Munchausen; Houk; Journal of Medicinal Chemistry; vol. 20; nb. 10; (1977); p. 1346 - 1348, View in Reaxys

Pharmacological Data (50) 1 of 50

Comment (Pharmacological Data)

Bioactivities present

Culvenor,C.C.J.; Ham,N.S.; Australian Journal of Chemistry; vol. 27; (1974); p. 2191 - 2198, View in Reaxys; Patent; Strahilevitz; Meir; US4620977; (1986); (A1) English, View in Reaxys; Patent; Merck Sharp and Dohme Limited; US5298520; (1994); (A1) English, View in Reaxys; Glennon; Liebowitz; Mack; Journal of Medicinal Chemistry; vol. 21; nb. 8; (1978); p. 822 - 825, View in Reaxys; Hall; McCapra; Scott; Tetrahedron; vol. 23; nb. 10; (1967); p. 4131 - 4141, View in Reaxys; Patent; Sanofi; US4977274; (1990); (A1) English, View in Reaxys; Julia,M. et al.; Bulletin de la Societe Chimique de France; (1973); p. 1424 - 1426, View in Reaxys; 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; Patent; Eli Lilly and Company; US5096908; (1992); (A1) English, View in Reaxys; Noell,C.W.; Cheng,C.C.; Journal of Heterocyclic Chemistry; vol. 3; (1966); p. 5 - 8, View in Reaxys; Patent; Wilburn, Michael D.; US2003/78231; (2003); (A1) English, View in Reaxys; Patent; Psychiatric Genomics, Inc.; US2003/82802; (2003); (A1) English, View in Reaxys; Hochstein; Paradies; Journal of the American Chemical Society; vol. 79; (1957); p. 5735, View in Reaxys; Vitali; Mossini; Bollettino Scientifico della Facolta di Chimica Industriale di Bologna; vol. 17; (1959); p. 84,86, View in Reaxys; Manske; Canadian Journal of Research; vol. 5; (1931); p. 599; Chem. Zentralbl.; vol. 103; nb. I; (1932); p. 2475, View in Reaxys; Hoshino; Shimodaira; Justus Liebigs Annalen der Chemie; vol. 520; (1935); p. 19,26, View in Reaxys; Fish et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 3668,3670, View in Reaxys; Kondo et al.; Ann. Rep. ITSUU; Labor Nr. 10 <1959> 1, 8; engl. Ausg. S. 33, 42, View in Reaxys; Pachter et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 1285, View in Reaxys; Goto et al.; Yakugaku Zasshi; vol. 78; (1958); p. 464,466; Chem.Abstr.; (1958); p. 14082, View in Reaxys; Fish et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 5892,5895, View in Reaxys; Cohen et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 2184, View in Reaxys; Brucato et al.; Arzneimittel Forschung; vol. 27; (1977); p. 1015,1017, View in Reaxys; Noell et al.; Journal of Heterocyclic Chemistry; vol. 3; (1966); p. 5,9, View in Reaxys; Siehr; Journal of the American Chemical Society; vol. 83; (1961); p. 2401, View in Reaxys; Bowd et al.; Photochemistry and Photobiology; vol. 11; (1970); p. 445,447, View in Reaxys; Bridges; Williams; Biochemical Journal; vol. 107; (1968); p. 225,228, View in Reaxys; Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys; Ganellin et al.; Journal of the Chemical Society [Section] C: Organic; (1967); p. 2220, View in Reaxys; Noland; Sundberg; Journal of Organic Chemistry; vol. 28; (1963); p. 884, View in Reaxys; Morimoto et al.; Justus Liebigs Annalen der Chemie; vol. 682; (1965); p. 212,218, View in Reaxys; Dutta; Ghosal; Chemistry and Industry (London, United Kingdom); (1967); p. 2046, View in Reaxys; Ghosal et al.; Phytochemistry (Elsevier); vol. 10; (1971); p. 2852, View in Reaxys; Ghosal et al.; Planta Medica; vol. 21; (1972); p. 398,401, View in Reaxys; Ghosal et al.; Planta Medica; vol. 21; (1972); p. 22,23, View in Reaxys; Julia et al.; Bulletin de la Societe Chimique de France; (1973); p. 1424, View in Reaxys; Agurell et al.; Acta Chemica Scandinavica (1947-1973); vol. 23; (1969); p. 903, 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; Domelsmith et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 4311,4315, View in Reaxys; Hall et al.; Tetrahedron; vol. 23; (1967); p. 4131, View in Reaxys; Arthur et al.; Australian Journal of Chemistry; vol. 20; (1967); p. 811,812, View in Reaxys; Bodendorf; Walk; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 294; (1961); p. 484,487, View in Reaxys; Raeisaenen; Kaerkkaeinen; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 33; (1979); p. 11, View in Reaxys; Pecher et al.; Tetrahedron Letters; (1961); p. 270,272, View in Reaxys; Ghosal; Bhattacharya; Planta Medica; vol. 22; (1972); p. 434,437, View in Reaxys; Ghosal; Singh; Bhattacharya; Planta medica; vol. 19; nb. 3; (1971); p. 280 - 284, View in Reaxys; Wenkert; Kryger; Journal of the Indian Chemical Society; vol. 55; (1978); p. 1122, View in Reaxys; Glennon; Gessner; Journal of Medicinal Chemistry; vol. 22; (1979); p. 428,430, View in Reaxys; Morimoto; Matsumoto; Justus Liebigs Annalen der Chemie; vol. 692; (1966); p. 194,197, View in Reaxys; Bergin et al.; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 24; (1968); p. 882, View in Reaxys; Poissan; Annales Pharmaceutiques Francaises; vol. 23; (1965); p. 241, View in Reaxys; Ghosal; Dutta; Sanyal; Bhattacharya; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 480 - 483, View in Reaxys; Julia; Ricalens; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 269; (1969); p. 51, View in Reaxys; Fitzgerald; Sioumis; Australian Journal of Chemistry; vol. 18; (1965); p. 433,434, View in Reaxys; Rovelli; Vaughan; Australian Journal of Chemistry; vol. 20; (1967); p. 1299, View in Reaxys; Kan-Fan et al.; Phytochemistry (Elsevier); vol. 9; (1970); p. 1283,1289, View in Reaxys; Domelsmith; Munchausen; Houk; Journal of Medicinal Chemistry; vol. 20; nb. 10; (1977); p. 1346 - 1348, View in Reaxys; Ghosal; Mazumder; Phytochemistry (Elsevier); vol. 10; (1971); p. 2840, View in Reaxys; Ghosal et al.; Journal of Pharmaceutical Sciences; vol. 60; (1971); p. 1209,1211, View in Reaxys; Ghosal; Mukherjee; Chemistry and Industry (London, United Kingdom);

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Comment (Pharmacological Data)

physiological behaviour discussed

Comment (Pharmacological Data)

physiological behaviour discussed

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

HepG2.2.15 cells

Further Details (Pharmacological Data)

MTT assay; cytotoxic concentration (CC)

Type (Pharmacological Data)

CC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Effect (Pharmacological Data)

hepatitis B virus DNA replication; inhibition of

Species or Test-System (Pharmacological Data)

HepG2.2.15 cells

Further Details (Pharmacological Data)

inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

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Value of Type (Pharmacological Data)

> 100 μmol/l

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 wildtype 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)

Value of Type (Pharmacological Data)

14.75 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 7 of 50

Effect (Pharmacological Data)

sigma-2 receptor; binding to

Species or Test-System (Pharmacological Data)

liver membrane homogenate

Method (Pharmacological Data)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

21.71 μmol/l

Location

Page/Page column 29-30; 34-35

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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 8 of 50

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 wildtype 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) = 124, 39 and 0.02 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 9 of 50

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)

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pane ([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 wildtype 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) = 69, 57 and 31 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 10 of 50

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)

Results

band intensity sigma-2 (percent) = 58, 29 and 18 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 11 of 50

Effect (Pharmacological Data)

sodium channel; inhibition of

Species or Test-System (Pharmacological Data)

HEK293 cells expressing human cardiac Na+ channel hNav1.5

Method (Pharmacological Data)

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100 μM DMT inhibited INa by only 22 + 4percent (n = 3), but photolabeling has shown that these cells have much lower levels of endogenous sigma- 1 receptor compared to HEK293 cells (26) (Figure 7b).The difference between DMT inhibition of INa in HEK293 and COS-7 cells (Figure 7b, p Na inhibition on sigma- 1 receptors. Experiments in cardiac myocytes demonstrated the same DMT action in a native preparation (Figure 7c), and enabled further demonstration of sigma- 1 receptor dependence by using a sigma- 1 receptor knockout mouse (27). [%125I]IAF photolabeling of liver homogenates from wildtype (WT) and sigma- 1 receptor knockout (KO) mice indeed showed the absence of sigma- 1 receptor (26 kDa) in the KO samples (Figure 7a). In WT neonatal cardiac myocytes, 100 μM DMT reversibly inhibited INa by 29 +/- 3percent (n = 7), while INa was reduced by only 7 +/- 2percent (n = 7) in KO myocytes (Figure 7c, p 0C in 5percent CO&2/air atmosphere, and used for electrophysiological recordings within 3-5 days.Neonatal Myocyte Isolation and Culture. Neonatal mouse cardiac myocytes were enzymatically isolated and cultured on laminin-coated glass coverslips as previously described (33, 34) with minor changes (26).; Electrophysiology. lNa was recorded using whole-cell patch clamp at room temperature. All patch clamp solutions used as well as patch clamp methodology and instrumentation details are previously described (26) with the exception of testing lNa inhibition with 100 μM DMT.

Results

INa inhibition (percent) = 62 at a concentration of 100 μmol/l

Location

Page/Page column 31; 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 12 of 50

Effect (Pharmacological Data)

sodium channel; inhibition of

Species or Test-System (Pharmacological Data)

COS-7 cells expressing human cardiac Na+ channel hNav1.5

Method (Pharmacological Data)

photolabeling of liver homogenates from wildtype (WT) and sigma- 1 receptor knockout (KO) mice indeed showed the absence of sigma- 1 receptor (26 kDa) in the KO samples (Figure 7a). In WT neonatal cardiac myocytes, 100 μM DMT reversibly inhibited INa by 29 +/- 3percent (n = 7), while INa was reduced by only 7 +/- 2percent (n = 7) in KO myocytes (Figure 7c, p 0C in 5percent CO&2/air atmosphere, and used for electrophysiological recordings within 3-5 days.Neonatal Myocyte Isolation and Culture. Neonatal mouse cardiac myocytes were enzymatically isolated and cultured on laminin-coated glass coverslips as previously described (33, 34) with minor changes (26).; Electrophysiology. lNa was recorded using whole-cell patch clamp at room temperature. All patch clamp solutions used as well as patch clamp methodology and instrumentation details are previously described (26) with the exception of testing lNa inhibition with 100 μM DMT. Results

INa inhibition (percent) = 22 at a concentration of 100 μmol/l

Location

Page/Page column 31; 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 13 of 50

Effect (Pharmacological Data)

sodium channel; inhibition of

Species or Test-System (Pharmacological Data)

neonatal cardiac myocytes of mouse

Method (Pharmacological Data)

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-10 mV (Figure 7b). Application of 100 μM DMT inhibited INa by 62 +/- 3percent (n = 3), which reversed upon DMT removal. With hNavl.5 transiently transfected into COS-7 cells, 100 μM DMT inhibited INa by only 22 + 4percent (n = 3), but photolabeling has shown that these cells have much lower levels of endogenous sigma- 1 receptor compared to HEK293 cells (26) (Figure 7b).The difference between DMT inhibition of INa in HEK293 and COS-7 cells (Figure 7b, p Na inhibition on sigma- 1 receptors. Experiments in cardiac myocytes demonstrated the same DMT action in a native preparation (Figure 7c), and enabled further demonstration of sigma- 1 receptor dependence by using a sigma- 1 receptor knockout mouse (27). [%125I]IAF photolabeling of liver homogenates from wildtype (WT) and sigma- 1 receptor knockout (KO) mice indeed showed the absence of sigma- 1 receptor (26 kDa) in the KO samples (Figure 7a). In WT neonatal cardiac myocytes, 100 μM DMT reversibly inhibited INa by 29 +/- 3percent (n = 7), while INa was reduced by only 7 +/- 2percent (n = 7) in KO myocytes (Figure 7c, p 0C in 5percent CO&2/air atmosphere, and used for electrophysiological recordings within 3-5 days.Neonatal Myocyte Isolation and Culture. Neonatal mouse cardiac myocytes were enzymatically isolated and cultured on laminin-coated glass coverslips as previously described (33, 34) with minor changes (26).; Electrophysiology. lNa was recorded using whole-cell patch clamp at room temperature. All patch clamp solutions used as well as patch clamp methodology and instrumentation details are previously described (26) with the exception of testing lNa inhibition with 100 μM DMT.

Results

INa inhibition (percent) = 29 at a concentration of 100 μmol/l

Location

Page/Page column 31; 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 14 of 50

Effect (Pharmacological Data)

sodium channel; inhibition of

Species or Test-System (Pharmacological Data)

sigma-1 receptor knockout (KO) mouse neonatal cardiac myocytes

Method (Pharmacological Data)

To evaluate the capacity of DMT to induce physiological responses by binding to sigma receptors, the action of DMT on voltage-activated Na+ current was examined. Patch clamp recordings from HEK293 cells stably expressing the human cardiac Na+ channel hNavl.5 revealed voltage activated Na+ currents (INa) in response to voltage steps from -80 mV to -10 mV (Figure 7b). Application of 100 μM DMT inhibited INa by 62 +/- 3percent (n = 3), which reversed upon DMT removal. With hNavl.5 transiently transfected into COS-7 cells, 100 μM DMT inhibited INa by only 22 + 4percent (n = 3), but photolabeling has shown that these cells have much lower levels of endogenous sigma- 1 receptor compared to HEK293 cells (26) (Figure 7b).The difference between DMT inhibition of INa in HEK293 and COS-7 cells (Figure 7b, p Na inhibition on sigma- 1 receptors. Experiments in cardiac myocytes demonstrated the same DMT action in a native preparation (Figure 7c), and enabled further demonstration of sigma- 1 receptor dependence by using a sigma- 1 receptor knockout mouse (27). [%125I]IAF photolabeling of liver homogenates from wildtype (WT) and sigma- 1 receptor knockout (KO) mice indeed showed the absence of sigma- 1 receptor (26 kDa) in the KO samples (Figure 7a). In WT neonatal cardiac myocytes, 100 μM DMT reversibly inhibited INa by 29 +/- 3percent (n = 7), while INa was reduced by only 7 +/- 2percent (n = 7) in KO myocytes (Figure 7c, p 0C in 5percent CO&2/air atmosphere, and used for electrophysiological recordings within 3-5 days.Neonatal Myocyte Isolation and Culture. Neonatal mouse cardiac myocytes were enzymatically isolated and cultured on laminin-coated glass coverslips as previously described (33, 34) with minor changes (26).; Electrophysiology. lNa was recorded using whole-cell patch clamp at room temperature. All patch clamp solutions used as well as patch clamp methodology and instrumentation details are previously described (26) with the exception of testing lNa inhibition with 100 μM DMT.

Results

INa inhibition (percent) = 7 at a concentration of 100 μmol/l

Location

Page/Page column 31; 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 15 of 50

Effect (Pharmacological Data)

hypermobility induction

Species or Test-System (Pharmacological Data)

mouse

Route of Application

intraperitoneal

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Method (Pharmacological Data)

Mouse Behavior. All mice were maintained on a normal light/dark cycle and handled in accordance with Animal Care and Use Guidelines of the University of Wisconsin, Madison.Hypermobility effects induced by DMT in age-matched adult 129/SvEvBrd xC57BL6/J wild type (WT) and sigma- 1 receptor knockout (KO) mice were measured in an open-field assay. Mice were first acclimatized to the experimental room for one hour. WT and KO mice were injected with the monoamine oxidase inhibitor, pargyline (75 mg/kg, i.p.) two hours prior to DMT or vehicle injection(2S). The mice were observed in the open-field box for an hour and then injected with DMT (2 mg/kg, i.p.) (2S) or vehicle, and observed for 30 minutes. Each condition represents 8 to 14 mice (n = 8-14). For methamphetamine studies, WT and KO mice (n = 6) were placed in the open-field and observed for one hour prior to methamphetamine (3mg/kg, i.p.) injection (35) and observation (1 hour). A computer program was used to quantitate movement and after each experiment, 70percent ethanol was used to remove odors from the open-field.

Results

distance traveled over 30 min post-injection (cm) = ~7000 at a dose of 2 mg/kg

Location

Page/Page column 35; 9/12

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 16 of 50

Effect (Pharmacological Data)

hypermobility induction

Species or Test-System (Pharmacological Data)

sigma-1 receptor knockout (KO) mouse

Route of Application

intraperitoneal

Method (Pharmacological Data)

Results

distance traveled over 30 min post-injection (cm) = ~2000 at a dose of 2 mg/kg

Location

Page/Page column 35; 9/12

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 17 of 50

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

brain frontal cortex homogenate of Sprague-Dawley rat

Sex

male

Method (Pharmacological Data)

5-HT2A receptor binding assay; tissue homogenate, <3H>MDL 100,907 and title comp. incub. for 15 min at 37 deg C in a shaking water bath; vacuum filtration performed; radioactivity measured using liquid scintillation spectroscopy at 37percent efficiency

Further Details (Pharmacological Data)

non-specific binding was determined in the presence of cinanserin (10 μM); Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1636 nmol/l

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.; Bioorganic and Medicinal Chemistry; vol. 16; nb. 8; (2008); p. 4661 - 4669, View in Reaxys 18 of 50

Effect (Pharmacological Data)

functional activity

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Species or Test-System (Pharmacological Data)

rat

Method (Pharmacological Data)

drug discrimination assay using rats trained to distinguish the 5-HT2A receptor agonist LSD from saline; rat behavior observed

Results

title comp. indirectly determined to be an agonist of 5-HT2A receptor

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.; Bioorganic and Medicinal Chemistry; vol. 16; nb. 8; (2008); p. 4661 - 4669, View in Reaxys 19 of 50

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)

Value of Type (Pharmacological Data)

2.8 μmol/l

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)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.13 μmol/l

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)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.95 μmol/l

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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)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.63 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Ala173Leu mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.82 μmol/l

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)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.43 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Ala173Thr mutant

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Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.25 μmol/l

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)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.42 μmol/l

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)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

3.7 μmol/l

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)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

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Value of Type (Pharmacological Data)

1.74 μmol/l

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)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.74 μmol/l

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)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.81 μmol/l

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)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2.2 μmol/l

Effect (Pharmacological Data)

5-HT uptake; inhibition of

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Species or Test-System (Pharmacological Data)

HEK-293 MSR cells transfected with hSERT, Tyr175Phe mutant

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hSERT: human serotonin transporter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.47 μmol/l

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)

Value of Type (Pharmacological Data)

300 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 34 of 50

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

HEK293 cells expressing rTAR1

Concentration (Pharmacological Data)

1 μmol/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

Results

title comp. induced cAMP production acting as agonist (diagram)

Comment (Pharmacological Data)

in vivo receptor affinity measurements at the rat brain 5-HT1A receptor and the cloned human 5-HT2 receptor family

Comment (Pharmacological Data)

hallucinogen-like activity in the two-lever drug discrimination paradigm using LSD-trained rats (ED50 = 10.16 μmol/kg)

Effect (Pharmacological Data)

receptor; binding activity

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Species or Test-System (Pharmacological Data)

COS-7 cells

Kind of Dosing (Pharmacological Data)

as oxalate

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)

Value of Type (Pharmacological Data)

30 nmol/l

Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys 38 of 50

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

rat 5-HT2A receptors expressed in NIH-3T3 cells

Method (Pharmacological Data)

radioligand binding assay used 0.4 nM <3H>ketanserin; 10 μM mianserin used to define nonspecific binding

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

660 nmol/l

Hong; Dukat; Teitler; Egan; Dupre; Herrick-Davis; Glennon; Medicinal Chemistry Research; vol. 9; nb. 6; (1999); p. 374 - 388, View in Reaxys 39 of 50

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

rat 5-HT2C receptors expressed in A-9 cells

Method (Pharmacological Data)

radioligand binding assay used 1 nM <3H>mesulergine; 10 μM mesulergine used to define nonspecific binding

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1250 nmol/l

Hong; Dukat; Teitler; Egan; Dupre; Herrick-Davis; Glennon; Medicinal Chemistry Research; vol. 9; nb. 6; (1999); p. 374 - 388, View in Reaxys 40 of 50

Comment (Pharmacological Data)

binding affinity to 5-HT1A receptors

Yu; Ho; Liao; Chen; Journal of Natural Products; vol. 60; nb. 11; (1997); p. 1196 - 1198, View in Reaxys 41 of 50

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)

Value of Type (Pharmacological Data)

350 nmol/l

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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 42 of 50

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)

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 43 of 50

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)

Further Details (Pharmacological Data)

Ki = apparent equilibrium inhibition constant

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

53 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 44 of 50

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)

Value of Type (Pharmacological Data)

106 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 45 of 50

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

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Type (Pharmacological Data)

Value of Type (Pharmacological Data)

298 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 46 of 50

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)

Value of Type (Pharmacological Data)

80 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 47 of 50

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, 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

Results

concentration-dependent relaxation for contraction by H: pEC50: 6.0, relaxation: 106 percent; desens.: pEC: 5.9, relaxation: 93 percent; contraction by SP: no effect

Carter; Champney; Hwang; Eglen; European Journal of Pharmacology; vol. 280; nb. 3; (1995); p. 243 - 250, View in Reaxys 48 of 50

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 49 of 50

Comment (Pharmacological Data)

in vitro inhibition of <3H>diazepam binding to rat cerebral cortical membranes

Cain; Weber; Guzman; Cook; Barker; Rice; Crawley; Paul; Skolnick; Journal of Medicinal Chemistry; vol. 25; nb. 9; (1982); p. 1081 - 1091, View in Reaxys 50 of 50

Comment (Pharmacological Data)

hallucinogenic activity; ED 50: 15 μmol/kg (rats, intraperitoneally)

Adron Harris; Homfeld; Campaigne; Journal of Pharmacy and Pharmacology; vol. 33; nb. 5; (1981); p. 320 - 322, View in Reaxys Ecotoxicology (1) 1 of 1

Effect (Ecotoxicology)

phytotoxicity

Species or Test-System (Ecotoxicology)

Lactuca sativa, lettuce

Concentration (Ecotoxicology)

14 - 84 mmol/l

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Method (Ecotoxicology)

chromatographic bioassay method; 10 lettuce seeds planted on paper spotted with methanolic solution of title comp.; 26 deg C; incubation time 72 h; radicle growth of lettuce in mm was measured

Results

title comp. exerted significant phytotoxicity at conc. lower than 14 mmol/l; graphical representation

Lee, Tzong-Huei; Chou, Chang-Hung; Journal of the Chinese Chemical Society; vol. 47; nb. 6; (2000); p. 1287 1290, View in Reaxys Use (6) Use Pattern

Location

References

Parkinson's disease (PD)

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

Pharmaceuticals

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

inducing or facilitating micturition in combination with 5-HT1A receptor agonist, 5HT1A/7 receptor agonist, cholinesterase inhibitor, NMDA receptor agonist, noradrenaline/dopamine precursor

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

multiple sclerosis (MS)

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

spinal cord injury (SCI)

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

urinary retention

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

Isolation from Natural Product (41) Isolation from References Natural Product bark of Fissistigma latifolium (Dunal) Merr. (Annonaceae); collected from Dungun,Terengganu

Alias, Asmah; Hazni, Hazrina; Jaafar, Faridahanim Mohd; Awang, Khalijah; Ismail, Nor Hadiani; Molecules; vol. 15; nb. 7; (2010); p. 4583 - 4588, View in Reaxys

Acacia confusa

Buchanan, Malcolm S.; Carroll, Anthony R.; Pass, David; Quinn, Ronald J.; Magnetic Resonance in Chemistry; vol. 45; nb. 4; (2007); p. 359 - 361, View in Reaxys

Evodia fargesii Qu, Shi-Jin; Liu, Quan-Wen; Tan, Chang-Heng; Jiang, Shan-Hao; Zhu, Da-Yuan; Planta Medica; vol. 72; Dode (Rutaceae), nb. 3; (2006); p. 264 - 266, View in Reaxys roots and stems (Zhangshu, Jiangxi province, China) roots of Acacia confusa Merr. (Leguminosae), Nankang, Taipei, September 1999

Lee, Tzong-Huei; Chou, Chang-Hung; Journal of the Chinese Chemical Society; vol. 47; nb. 6; (2000); p. 1287 - 1290, View in Reaxys

the dried, unripe fruit of Evodia rutaecarpa

Yu; Ho; Liao; Chen; Journal of Natural Products; vol. 60; nb. 11; (1997); p. 1196 - 1198, View in Reaxys

Antirhea lucida (Sw.)

Weniger; Rafik; Bastida; Quirion; Anton; Planta Medica; vol. 61; nb. 6; (1995); p. 569 - 570, View in Reaxys

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bark of Virola sebifera Aublet

Kawanishi, K.; Uhara, Y.; Hashimoto, Y.; Phytochemistry (Elsevier); vol. 24; nb. 6; (1985); p. 1373 - 1376, View in Reaxys

Catharanthus roseus 953. cell line

Kutney; Aweryn; Choi; et al.; Tetrahedron; vol. 39; nb. 22; (1983); p. 3781 - 3795, View in Reaxys

leaves of ZanGrina, Jonas A.; Ratcliff, Matthew R.; Stermitz, Frank R.; Journal of Organic Chemistry; vol. 47; nb. 13; thoxylum arbores- (1982); p. 2648 - 2651, View in Reaxys cens batches of 953 line Catharanthus roseus cell cultures

Kurz; Chatson; Constabel; et al.; Helvetica Chimica Acta; vol. 63; nb. 7; (1980); p. 1891 - 1896, View in Reaxys

'943' cell line of Catharanthus roseus cell cultures

Kutney, James P.; Choi, Lewis S. L.; Kolodziejczyk, Pawel; Sleigh, Stephen K.; Stuart, Kenneth L.; et al.; Phytochemistry (Elsevier); vol. 19; (1980); p. 2589 - 2596, View in Reaxys

aus Wurzeln od. Stielen v. Desmodium candatum

Ueno et al.; Chemical and Pharmaceutical Bulletin; vol. 26; (1978); p. 2411,2415, View in Reaxys

Vork. u. Isol. aus Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys Banistereopsis argentea Vork. u. Isol. aus Phalaris arundinacea

Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys

Vork. u. Isol. aus Arundo donax

Ghosal et al.; Planta Medica; vol. 21; (1972); p. 22,23, View in Reaxys; Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys

Vork. u. Isol. aus Mucuna pruriens

Ghosal; Singh; Bhattacharya; Planta medica; vol. 19; nb. 3; (1971); p. 280 - 284, View in Reaxys; Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys

Vork. u. Isol. aus Desmodium gangeticum

Ghosal; Bhattacharya; Planta Medica; vol. 22; (1972); p. 434,437, View in Reaxys; Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys

Vork. u. Isol. aus Desmodium pulchellum

Ghosal et al.; Planta Medica; vol. 21; (1972); p. 398,401, View in Reaxys; Ghosal; Planta Medica; vol. 21; (1972); p. 200,203, View in Reaxys

aus Banistereopsis argentea

Ghosal; Mazumder; Phytochemistry (Elsevier); vol. 10; (1971); p. 2840, View in Reaxys; Ghosal et al.; Journal of Pharmaceutical Sciences; vol. 60; (1971); p. 1209,1211, View in Reaxys

aus Arundo donax

Ghosal et al.; Phytochemistry (Elsevier); vol. 10; (1971); p. 2852, View in Reaxys

aus Vepris ampody

Kan-Fan et al.; Phytochemistry (Elsevier); vol. 9; (1970); p. 1283,1289, View in Reaxys

Rinde von Virola sebifera

Corothie; Nakano; Planta Medica; vol. 17; (1969); p. 184,186, View in Reaxys

aus Anadenanthera peregrina

Agurell et al.; Acta Chemica Scandinavica (1947-1973); vol. 23; (1969); p. 903, View in Reaxys

aus 'Epena-Snuff'

Agurell et al.; Acta Chemica Scandinavica (1947-1973); vol. 23; (1969); p. 903, View in Reaxys

aus Virola Arten

Agurell et al.; Acta Chemica Scandinavica (1947-1973); vol. 23; (1969); p. 903, View in Reaxys

aus 'NyakwanaSnuff'

Agurell et al.; Acta Chemica Scandinavica (1947-1973); vol. 23; (1969); p. 903, View in Reaxys

aus Arundo donax L.

Dutta; Ghosal; Chemistry and Industry (London, United Kingdom); (1967); p. 2046, View in Reaxys; Ghosal; Dutta; Sanyal; Bhattacharya; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 480 - 483, View in Reaxys

aus Acacia phlebophylla

Rovelli; Vaughan; Australian Journal of Chemistry; vol. 20; (1967); p. 1299, View in Reaxys

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aus d. Stielen v. Acacia confusa Merr.

Arthur et al.; Australian Journal of Chemistry; vol. 20; (1967); p. 811,812, View in Reaxys

aus d. WurzelMorimoto; Matsumoto; Justus Liebigs Annalen der Chemie; vol. 692; (1966); p. 194,197, View in Reaxys rinde d. Extraktion m. Me. (Trennung d. Chromatographie) (S.198) aus d. Blaettern v. Morimoto; Matsumoto; Justus Liebigs Annalen der Chemie; vol. 692; (1966); p. 194,197, View in Reaxys Lespedeza bicolor var. japonica Nakai (Yamahagi) d. Extraktion m. Me. (Trennung d. Chromatographie) aus Acacia maidenii F. Muell.

Fitzgerald; Sioumis; Australian Journal of Chemistry; vol. 18; (1965); p. 433,434, View in Reaxys

aus d. Blaettern v. Poissan; Annales Pharmaceutiques Francaises; vol. 23; (1965); p. 241, View in Reaxys Natem- u. YageStraeuchern aus Desmodium Ghosal; Mukherjee; Chemistry and Industry (London, United Kingdom); (1964); p. 1800, View in Reaxys Pulchellum Benth. ex Baker aus Phalaris tuberosa

Culvenor et al.; Australian Journal of Chemistry; vol. 17; (1964); p. 1301,1304, View in Reaxys

Vork. u. Isol. aus Amanita citrina

Tyler; Groeger; Planta Medica; vol. 12; (1964); p. 397,399, View in Reaxys

Vork. u. Isol. aus Amanita porphyria

Tyler; Groeger; Planta Medica; vol. 12; (1964); p. 397,399, View in Reaxys

Vork. im 'Epena'Pulver (z.B. v. Mimosa acacioides od. Piptadeia peregrina)

Marini-Bettolo et al.; Annali di Chimica (Rome, Italy); vol. 54; (1964); p. 1179,1185, View in Reaxys

Isolierung aus den Wurzeln von Mimosa hostilis

Pachter et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 1285, View in Reaxys

Isolierung aus den Blaettern von Lespedeza bicolor var. japonica

Goto et al.; Yakugaku Zasshi; vol. 78; (1958); p. 464,466; Chem.Abstr.; (1958); p. 14082, View in Reaxys

Isolierung aus den Blaettern von Prestonia amazonicum

Hochstein; Paradies; Journal of the American Chemical Society; vol. 79; (1957); p. 5735, View in Reaxys

Reaxys ID 3785982 View in Reaxys

2/12 CAS Registry Number: 4382-50-7 Chemical Name: N,N-Dimethyltryptamine oxalate; (2-indol-3yl-ethyl)-dimethyl-amine; oxalate; (2-Indol-3-yl-aethyl)-dimethylamin; Oxalat Linear Structure Formula: C12H16N2*C2H2O4 Molecular Formula: C2H2O4*C12H16N2 Molecular Weight: 278.308 Type of Substance: heterocyclic InChI Key: LWHZUMHODQLJKN-UHFFFAOYSA-N

N HO O

O OH

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Note: Melting Point (2) 1 of 2

Melting Point [°C]

151

Sintas, Jose A.; Vitale, Arturo A.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 677 - 684, View in Reaxys 2 of 2

Melting Point [°C]

151 - 152

Solvent (Melting Point)

methanol

Kondo et al.; Ann. Rep. ITSUU; Labor Nr. 10 <1959> 1, 8; engl. Ausg. S. 33, 42, View in Reaxys Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Glennon; Liebowitz; Mack; Journal of Medicinal Chemistry; vol. 21; nb. 8; (1978); p. 822 - 825, View in Reaxys; Kondo et al.; Ann. Rep. ITSUU; Labor Nr. 10 <1959> 1, 8; engl. Ausg. S. 33, 42, View in Reaxys; Sintas, Jose A.; Vitale, Arturo A.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 677 - 684, View in Reaxys; Glennon, Richard A.; Dukat, Malgorzata; Grella, Brian; Hong, Seoung-Soo; Costantino, Luca; Teitler, Milt; Smith, Carol; Egan, Chris; Davis, Katherine; Mattson, Mariena V.; Drug and Alcohol Dependence; vol. 60; nb. 2; (2000); p. 121 - 132, View in Reaxys; Teitler, Milt; Scheick, Cynthia; Howard, Paul; Sullivan III, Joseph E.; Iwamura, Tatsunori; Glennon, Richard A.; Medicinal Chemistry Research; vol. 7; nb. 4; (1997); p. 207 - 218, View in Reaxys; Becker; Gettys; Middleton; Olsen; Albers; Lee -; Fanburg; Raymond; Molecular Pharmacology; vol. 42; nb. 5; (1992); p. 817 - 825, View in Reaxys; Lyon; Titeler; Seggel; Glennon; European Journal of Pharmacology; vol. 145; nb. 3; (1988); p. 291 - 297, View in Reaxys; Glennon; Young; Rosecrans; Kallman; Psychopharmacology; vol. 68; nb. 2; (1980); p. 155 - 158, View in Reaxys; Glennon; Gessner; Journal of Medicinal Chemistry; vol. 22; nb. 4; (1979); p. 428 - 432, View in Reaxys; Ross; Renyi; European journal of pharmacology; vol. 7; nb. 3; (1969); p. 270 - 277, View in Reaxys

Reaxys ID 3705170 View in Reaxys

3/12 CAS Registry Number: 2826-93-9 Chemical Name: N,N-dimethyltryptamine hydrochloride; (2-indol-3-yl-ethyl)-dimethyl-amine; hydrochloride; (2-Indol-3-yl-aethyl)-dimethyl-amin; Hydrochlorid Linear Structure Formula: C12H16N2*ClH Molecular Formula: C12H16N2*ClH Molecular Weight: 224.733 Type of Substance: heterocyclic InChI Key: FXCHKLOHTIIVJW-UHFFFAOYSA-N Note:

N Cl

Melting Point (1) 1 of 1

Melting Point [°C]

166 - 167.5

Solvent (Melting Point)

ethanol; diethyl ether

Vitali; Mossini; Bollettino Scientifico della Facolta di Chimica Industriale di Bologna; vol. 17; (1959); p. 84,86, View in Reaxys

Reaxys ID 3794124 View in Reaxys

4/12

CAS Registry Number: 68677-26-9 Chemical Name: N,N-dimethyltryptamine fumarate; (2-indol-3yl-ethyl)-dimethyl-amine; fumarate; (2-Indol-3-yl-aethyl)-dimethyl-amin; Fumarat Linear Structure Formula: C12H16N2*C4H4O4 Molecular Formula: C4H4O4*C12H16N2 Molecular Weight: 304.346 Type of Substance: heterocyclic InChI Key: OHMVTPSXVQQKPA-WLHGVMLRSA-N Note:

O HO

O NH

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Melting Point (1) 1 of 1

Melting Point [°C]

152 - 152.5

Solvent (Melting Point)

ethanol; butan-2-one; diethyl ether

Barlow; Khan; British Journal of Pharmacology and Chemotherapy; vol. 14; (1958); p. 99,100, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Barlow; Khan; British Journal of Pharmacology and Chemotherapy; vol. 14; (1958); p. 99,100, View in Reaxys; Eshleman, Amy J.; Forster, Michael J.; Wolfrum, Katherine M.; Johnson, Robert A.; Janowsky, Aaron; Gatch, Michael B.; Psychopharmacology; vol. 231; nb. 5; (2014); p. 875 - 888, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Eshleman, Amy J.; Forster, Michael J.; Wolfrum, Katherine M.; Johnson, Robert A.; Janowsky, Aaron; Gatch, Michael B.; Psychopharmacology; vol. 231; nb. 5; (2014); p. 875 - 888, View in Reaxys

Reaxys ID 3863056 View in Reaxys

5/12 CAS Registry Number: 1667-91-0 Chemical Name: (2-indol-3-yl-ethyl)-dimethyl-amine; picrate; (2-Indol-3-yl-aethyl)-dimethyl-amin; Picrat Linear Structure Formula: C12H16N2*C6H3N3O7 Molecular Formula: C6H3N3O7*C12H16N2 Molecular Weight: 417.378 Type of Substance: heterocyclic InChI Key: RWEYDVPLQNZXNK-UHFFFAOYSA-N Note:

O O

N O

Melting Point (2) 1 of 2

Melting Point [°C]

171 - 172

Solvent (Melting Point)

benzene

Pachter et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 1285, View in Reaxys 2 of 2

Melting Point [°C]

170 - 171

Solvent (Melting Point)

methanol

Hoshino; Shimodaira; Justus Liebigs Annalen der Chemie; vol. 520; (1935); p. 19,26, View in Reaxys Crystal Property Description (1) Colour & Other References Properties gelb

Pachter et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 1285, View in Reaxys

Reaxys ID 11196838 View in Reaxys

6/12 Chemical Name: N,N-dimethyl-[α,α,β,β-d4]-tryptamine; 3-(2-dimethylamino-[2H4]-ethyl)-1H-indole Linear Structure Formula: C12H12 (2)H4N2 Molecular Formula: C12H16N2 Molecular Weight: 192.241 InChI Key: DMULVCHRPCFFGV-OSEHSPPNSA-N Note:

N 2H

Substance Label (1) Label References 8

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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Melting Point (1) 1 of 1

Melting Point [°C]

43 - 44

Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300.1

Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100.6

Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys 4 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) 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 IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

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Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys Mass Spectrometry (2) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

ESI (Electrospray mol peak ionisation); HRMS (High resolution mass spectrometry)

spectrum; electron impact (EI)

Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys

Reaxys ID 398142 View in Reaxys

7/12 CAS Registry Number: 38112-90-2 Chemical Name: N,N-Dimethyl-<2-14C>-tryptamin; N,N-Dimethyl-[2-14C]-tryptamin Linear Structure Formula: C11 (14)CH16N2 Molecular Formula: C12H16N2 Molecular Weight: 190.261 Type of Substance: heterocyclic InChI Key: DMULVCHRPCFFGV-FOQJRBATSA-N Note:

14CH

Derivative (1) Comment (Derivative)

References

Pikrat: F: 172grad Baxter; Slaytor; Phytochemistry (Elsevier); vol. 11; (1972); p. 2767,2773, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

Baxter; Slaytor; Phytochemistry (Elsevier); vol. 11; (1972); p. 2767,2773, View in Reaxys

Reaxys ID 398143 View in Reaxys

8/12 CAS Registry Number: 41953-91-7 Chemical Name: <1-15N>-N,N-Dimethyl-tryptamin; [1-15N]N,N-Dimethyl-tryptamin Linear Structure Formula: C12H16N(15)N Molecular Formula: C12H16N2 Molecular Weight: 189.266 Type of Substance: heterocyclic InChI Key: DMULVCHRPCFFGV-KCKQSJSWSA-N Note:

Melting Point (1) 1 of 1

Melting Point [°C]

148 - 149

Dmitrevskaya et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 476; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 516, View in Reaxys

Reaxys ID 7092342 View in Reaxys

9/12

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Chemical Name: 3-<(dimethylamino)ethyl>indole-1-d; 3-[(dimethylamino)ethyl]indole-1-d Linear Structure Formula: C12H15DN2 Molecular Formula: C12H16N2 Molecular Weight: 189.264 Type of Substance: heterocyclic InChI Key: DMULVCHRPCFFGV-DYCDLGHISA-N Note:

N 2H

Substance Label (1) Label References XIV

Tupitsyn, I. F.; Komarov, V. I.; J. Gen. Chem. USSR (Engl. Transl.); vol. 57; nb. 8; (1987); p. 1826 1835,1632 - 1640, View in Reaxys

Reaxys ID 10240567 View in Reaxys

10/12 Chemical Name: ayahuasca Type of Substance: mixture (composition partially given) Composition: Comp. Name: Tetrahydroharmine; N,N-Dimethyltryptamine; Harmine; Harmaline Note:

No Structure

Pharmacological Data (7) 1 of 7

Comment (Pharmacological Data)

Bioactivities present

Effect (Pharmacological Data)

psychotonic

Species or Test-System (Pharmacological Data)

human

Sex

male and female

Route of Application

peroral

Concentration (Pharmacological Data)

0.125 - 0.5 g

Kind of Dosing (Pharmacological Data)

title substances (contained per kg of body wt: 0.6/0.85 mg DMT, 1.0/1.4 mg harmine, 0.07/0.09 mg harmaline, 0.82/1.16 mg THH for low and high doses, resp.) given as gelatin capsules

Method (Pharmacological Data)

title substances admin. to subjects (n = 18); pre and post 15, 30, 45, 60, 75 min and 1.5, 2, 2.5, 3, 3.5, 4, 6 and 8 h dosing, subjective effects measured by visual analog scales (VAS)

Further Details (Pharmacological Data)

control: placebo (0.75 g lactose); VAS: any effect, good effects, liking, drunken, stimulated, visions, high; DMT: N,N-dimethyltryptamine; THH: tetrahydroharmine

Results

title substances signif. increased VAS scorings between 90 and 120 min; table, diagram

Effect (Pharmacological Data)

psychotonic

Species or Test-System (Pharmacological Data)

human

Sex

male and female

Route of Application

peroral

Concentration (Pharmacological Data)

0.125 - 0.5 g

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Kind of Dosing (Pharmacological Data)

title substances (contained per kg of body wt: 0.6/0.85 mg DMT, 1.0/1.4 mg harmine, 0.07/0.09 mg harmaline, 0.82/1.16 mg THH for low and high doses, resp.) given as gelatin capsules

Method (Pharmacological Data)

title substances admin. to subjects (n = 18); after 4 h, subjective effects measured by Hallucinogen Rating Scale (HRS)

Further Details (Pharmacological Data)

control: placebo (0.75 g lactose); HRS measurements: affect, cognition, somaesthesia, perception, volition, intensity; DMT: N,N-dimethyltryptamine; THH: tetrahydroharmine

Results

title substances induced signif. increase in all HRS for low and high dose, except volition; tables, diagram

Effect (Pharmacological Data)

psychotonic

Species or Test-System (Pharmacological Data)

human

Sex

male and female

Route of Application

peroral

Concentration (Pharmacological Data)

0.125 - 0.5 g

Kind of Dosing (Pharmacological Data)

title substances (contained per kg of body wt: 0.6/0.85 mg DMT, 1.0/1.4 mg harmine, 0.07/0.09 mg harmaline, 0.82/1.16 mg THH for low and high doses, resp.) given as gelatin capsules

Method (Pharmacological Data)

title substances admin. to subjects (n = 18); after 4 h, subjective effects measured by Addiction Research Center Inventory (ARCI)

Further Details (Pharmacological Data)

control: placebo (0.75 g lactose); ARCI scales: morphine-benzedrine group (MBG), pentobarbital-chlorpromazine-alcohol group (PCAG), lysergic acid diethylamide (LSD), benzedrine group (BG) and A scale; DMT: N,N-dimethyltryptamine; THH: tetrahydroharmine

Results

title substances signif. dose-dependently increased stimulatory effects (A scale), euphoria (MBG scale) and somatic symptoms (LSD scale); tables, diagram

Effect (Pharmacological Data)

cardiovascular

Species or Test-System (Pharmacological Data)

human

Sex

male and female

Route of Application

peroral

Concentration (Pharmacological Data)

0.125 - 0.5 g

Kind of Dosing (Pharmacological Data)

title substances (contained per kg of body wt: 0.6/0.85 mg DMT, 1.0/1.4 mg harmine, 0.07/0.09 mg harmaline, 0.82/1.16 mg THH for low and high doses, resp.) given as gelatin capsules

Method (Pharmacological Data)

title substances admin. to subjects (n = 18); cardiovascular parameters measured before and 15, 30, 45, 60, 75, 90, 120, 150, 180, 210 and 240 min after administration using sphygmomanometer cuff

Further Details (Pharmacological Data)

control: placebo (0.75 g lactose); cardiovascular parameters: systolic blood pressure (SBP), diastolic blood pressure (DBP) and heart rate (HR); DMT: N,N-dimethyltryptamine; THH: tetrahydroharmine

Results

title substances signif. increased DBP at high dose (9 mm Hg at 75 min), SBP and HR increased moderately; diagram, table

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6 of 7

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human

Sex

male and female

Route of Application

peroral

Concentration (Pharmacological Data)

0.125 - 0.5 g

Kind of Dosing (Pharmacological Data)

title substances (contained per kg of body wt: 0.6/0.85 mg DMT, 1.0/1.4 mg harmine, 0.07/0.09 mg harmaline, 0.82/1.16 mg THH for low and high doses, resp.) given as gelatin capsules

Method (Pharmacological Data)

title substances admin. to subjects; urine collected in fractions of 0-8, 8-16 and 16-24 h; pH adjusted to 2-4 with 6N HCl; monoamine metabolites (VMA, HVA, 5-HIAA, metanephrine and normetanephrine) quantified by HPLC

Further Details (Pharmacological Data)

control: placebo (0.75 g lactose); VMA: vanillylmandelic acid; HVA: homavanillic acid; 5HIAA: 5-hydroxyindoleacetic acid; DMT: N,N-dimethyltryptamine; THH: tetrahydroharmine

Results

title substances increased the excretion of VMA, HVA and 5-HIAA; levels of metanephrine and normetanephrine increased with dose; table

Comment (Pharmacological Data)

Further metabolite(s)

Metabolite XRN (Pharmacological Data)

2213227; 2213447; 168797

Metabolite (Pharmacological Data)

2-(4'-Hydroxy-3'-methoxyphenyl)-2-hydroxyethanoic acid; 4-hydroxy 3-methoxy phenylacetic acid; 5-hydroxy-1H-indole-3-acetic acid

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

human

Sex

male and female

Route of Application

peroral

Concentration (Pharmacological Data)

0.125 - 0.5 g

Kind of Dosing (Pharmacological Data)

title substances (contained per kg of body wt: 0.6/0.85 mg DMT, 1.0/1.4 mg harmine, 0.07/0.09 mg harmaline, 0.82/1.16 mg THH for low and high doses, resp.) given as gelatin capsules

Method (Pharmacological Data)

title substances admin. to subjects; blood samples drawn before and at 30, 60, 90, 120, 150 min, 3, 4, 6, 8, 24 h after admin.; plasma conc. of DMT, β-carbolines (tetrahydroharmine (THH), harmine, harmaline) and pharmacokinetics (PK) parameters studied

Further Details (Pharmacological Data)

O-demethylated metabolites harmol, harmalol measured; DMT and β-carbolines measured by gas chromatography and HPLC, resp.; DMT: N,N-dimethyltryptamine; PK parameters: Cmax, Tmax, AUC from 0-8 h, clearance, terminal half-life, volume of distribution

Results

title substances increased Cmax, AUC, and Tmax; dose-dependently increased the level of harmol and harmalol; Cmax values for low and high doses were 12.14 ng/ml and 17.44 ng/ml, resp.; diagram, table

Metabolite XRN (Pharmacological Data)

173698; 201180

Metabolite (Pharmacological Data)

Harmol; Harmalol

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Reaxys ID 24205086 View in Reaxys

11/12 -1 HCl

Chemical Name: N,N-Dimethyltryptamine hydrochloride Linear Structure Formula: C12H16N2*(x)ClH Molecular Formula: C12H16N2*(x)ClH InChI Key: FXCHKLOHTIIVJW-UHFFFAOYSA-N Note:

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Whitaker; Seeman; Psychopharmacology; vol. 59; nb. 1; (1978); p. 1 - 5, View in Reaxys

Reaxys ID 25990097 View in Reaxys

12/12 Linear Structure Formula: C12H16N2*H(1+) Molecular Formula: C12H16N2*H Molecular Weight: 189.28 InChI Key: DMULVCHRPCFFGV-UHFFFAOYSA-O Note:

N H+

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Pratuangdejkul; Schneider; Jaudon; Rosilio; Baudoin; Loric; Conti; Launay; Manivet; Current Medicinal Chemistry; vol. 12; nb. 20; (2005); p. 2393 - 2410, View in Reaxys

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