1. Single Br– (C2–C6) by Asch

Query Query

Results

Date

43 substances in Reaxys

2016-06-12 06h:57m:28s (EST)

ALH

1. Query

* Br

HN ALH

Search as: As drawn, No mixtures, No charges, No radicals

1/53

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Reaxys ID 2802431 View in Reaxys

1/43 CAS Registry Number: 73918-56-6 Chemical Name: 4-Bromophenethylamine; 4-bromophenethylamin Linear Structure Formula: BrC6H4C2H4NH2 Molecular Formula: C8H10BrN Molecular Weight: 200.078 Type of Substance: isocyclic InChI Key: ZSZCXAOQVBEPME-UHFFFAOYSA-N Note:

NH 2

Substance Label (38) Label References 3

Strand, Joanna; Nordeman, Patrik; Honarvar, Hadis; Altai, Mohamed; Orlova, Anna; Larhed, Mats; Tolmachev, Vladimir; ChemistryOpen; vol. 4; nb. 2; (2015); p. 174 - 182, View in Reaxys

M43

He, Yantao; Guo, Xing; Yu, Zhi-Hong; Wu, Li; Gunawan, Andrea M.; Zhang, Yan; Dixon, Jack E.; Zhang, Zhong-Yin; Bioorganic and Medicinal Chemistry; vol. 23; nb. 12; (2015); p. 2798 - 2809, View in Reaxys; He, Rongjun; Yu, Zhi-Hong; Zhang, Ruo-Yu; Wu, Li; Gunawan, Andrea M.; Lane, Brandon S.; Shim, Joong S.; Zeng, Li-Fan; He, Yantao; Chen, Lan; Wells, Clark D.; Liu, Jun O.; Zhang, Zhong-Yin; ACS Medicinal Chemistry Letters; vol. 6; nb. 7; (2015); p. 782 - 786, View in Reaxys

572

Agrawalla, Bikram Keshari; Chandran, Yogeswari; Phue, Wut-Hmone; Lee, Sung-Chan; Jeong, YunMi; Wan, Si Yan Diana; Kang, Nam-Young; Chang, Young-Tae; Journal of the American Chemical Society; vol. 137; nb. 16; (2015); p. 5355 - 5362, View in Reaxys

13e

Ogiyama, Takashi; Yonezawa, Koichi; Inoue, Makoto; Katayama, Naoko; Watanabe, Toshihiro; Yoshimura, Seiji; Gotoh, Takayasu; Kiso, Tetsuo; Koakutsu, Akiko; Kakimoto, Shuichiro; Shishikura, JunIchi; Bioorganic and Medicinal Chemistry; vol. 23; nb. 15; (2015); p. 4638 - 4648, View in Reaxys

546

Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); (A1) English, View in Reaxys

Wang, Leming; Chen, Jiean; Huang, Yong; Angewandte Chemie - International Edition; vol. 54; nb. 51; (2015); p. 15414 - 15418; Angew. Chem.; vol. 127; nb. 51; (2015); p. 15634 - 15638,5, View in Reaxys

Saruta, Kunio; Ogiku, Tsuyoshi; Chemistry Letters; vol. 37; nb. 8; (2008); p. 820 - 821, View in Reaxys; Jacobsen, John R.; Aggen, James B.; Church, Timothy J.; Klein, Uwe; Pfeiffer, Juergen W.; PulidoRios, Teresa M.; Thomas, G. Roger; Yu, Cecile; Moran, Edmund J.; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 12; (2014); p. 2625 - 2630, View in Reaxys

I-3b

Patent; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; MOEBITZ, Henrik; SENGUPTA, Saumitra; WO2012/35078; (2012); (A1) English, View in Reaxys; Patent; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (2014); (A1) English, View in Reaxys

Szostak, Michal; Sautier, Brice; Spain, Malcolm; Procter, David J.; Organic Letters; vol. 16; nb. 4; (2014); p. 1092 - 1095, View in Reaxys

Lu, Zhiyao; Williams, Travis J.; Chemical Communications; vol. 50; nb. 40; (2014); p. 5391 - 5393, View in Reaxys

12c

Phillips, Dean P.; Gao, Wenqi; Yang, Yang; Zhang, Guobao; Lerario, Isabelle K.; Lau, Thomas L.; Jiang, Jiqing; Wang, Xia; Nguyen, Deborah G.; Bhat, B. Ganesh; Trotter, Carol; Sullivan, Heather; Welzel, Gustav; Landry, Jannine; Chen, Yali; Joseph, Sean B.; Li, Chun; Gordon, W. Perry; Richmond, Wendy; Johnson, Kevin; Bretz, Angela; Bursulaya, Badry; Pan, Shifeng; McNamara, Peter; Seidel, H. Martin; Journal of Medicinal Chemistry; vol. 57; nb. 8; (2014); p. 3263 - 3282, View in Reaxys

Gujarathi, Satheesh; Liu, Xingui; Song, Lin; Hendrickson, Howard; Zheng, Guangrong; Tetrahedron; vol. 70; nb. 34; (2014); p. 5267 - 5273, View in Reaxys; Gujarathi, Satheesh; Liu, Xingui; Song, Lin; Hendrickson, Howard; Zheng, Guangrong; Tetrahedron; vol. 70; nb. 34; (2014); p. 5267 - 5273, View in Reaxys

Heuson, Egon; Storgaard, Morten; Huynh, Tri H. V.; Charmantray, Franck; Gefflaut, Thierry; Bunch, Lennart; Organic and Biomolecular Chemistry; vol. 12; nb. 43; (2014); p. 8689 - 8695, View in Reaxys

Koike; Chemical and Pharmaceutical Bulletin; vol. 49; nb. 5; (2001); p. 558 - 562, View in Reaxys; Nguyen, Thanh Binh; Retailleau, Pascal; Al-Mourabit, Ali; Organic Letters; vol. 15; nb. 20; (2013); p. 5238 - 5241, View in Reaxys

Patent; SCHERING CORPORATION; WO2008/27466; (2008); (A1) English, View in Reaxys; Kabro, Anzhelika; Lachance, Hugo; Marcoux-Archambault, Iris; Perrier, Valerie; Dore, Vicky; Gros, Christina; Masson, Veronique; Gregoire, Jean-Marc; Ausseil, Frederic; Cheishvili, David; Laulan, Nathalie Bibens;

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St-Pierre, Yves; Szyf, Moshe; Arimondo, Paola B.; Gagnon, Alexandre; MedChemComm; vol. 4; nb. 12; (2013); p. 1562 - 1570, View in Reaxys 2

Fouchet, Marie-Helene; Donche, Frederic; Martin, Christelle; Bouillot, Anne; Junot, Christophe; Boullay, Anne-Benedicte; Potvain, Florent; Magny, Sylvie Demaria; Coste, Herve; Walker, Max; Issandou, Marc; Dodic, Nerina; Bioorganic and Medicinal Chemistry; vol. 16; nb. 11; (2008); p. 6218 - 6232, View in Reaxys; Murai, Yuta; Masuda, Katsuyoshi; Ogasawara, Yui; Wang, Lei; Hashidoko, Yasuyuki; Hatanaka, Yasumaru; Iwata, So; Kobayashi, Takuya; Hashimoto, Makoto; European Journal of Organic Chemistry; nb. 12; (2013); p. 2428 - 2433, View in Reaxys

Wang, Zhi-Xia; Chen, Jing-Lei; Qiao, Chunhua; Chemical Biology and Drug Design; vol. 82; nb. 2; (2013); p. 216 - 225, View in Reaxys

Dialer, Lukas O.; Selivanova, Svetlana V.; Mueller, Carmen J.; Mueller, Adrienne; Stellfeld, Timo; Graham, Keith; Dinkelborg, Ludger M.; Kraemer, Stefanie D.; Schibli, Roger; Reiher, Markus; Ametamey, Simon M.; Journal of Medicinal Chemistry; vol. 56; nb. 19; (2013); p. 7552 - 7563, View in Reaxys

Kumar, Vishal; Sharma, Upendra; Singh, Bikram; Kumar, Neeraj; Australian Journal of Chemistry; vol. 65; nb. 12; (2012); p. 1594 - 1598, View in Reaxys

Yoneyama, Hiroki; Shimoda, Ayako; Araki, Lisa; Hatano, Kouta; Sakamoto, Yasuhiko; Kurihara, Takushi; Yamatodani, Atsushi; Harusawa, Shinya; Journal of Organic Chemistry; vol. 73; nb. 6; (2008); p. 2096 - 2104, View in Reaxys

Imanishi, Masashi; Tomishima, Yasuyo; Itou, Shinji; Hamashima, Hitoshi; Nakajima, Yutaka; Washizuka, Kenichi; Sakurai, Minoru; Matsui, Shigeo; Imamura, Emiko; Ueshima, Koji; Yamamoto, Takao; Yamamoto, Nobuhiro; Ishikawa, Hirofumi; Nakano, Keiko; Unami, Naoko; Hamada, Kaori; Matsumura, Yasuhiro; Takamura, Fujiko; Hattori, Kouji; Journal of Medicinal Chemistry; vol. 51; nb. 6; (2008); p. 1925 - 1944, View in Reaxys

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Mendez-Andino, Jose L.; Colson, Anny-Odile; Meyers, Kenneth M.; Mitchell, Maria C.; Hodge, Karen; Howard, Jeremy M.; Kim, Nicholas; Ackley, David C.; Holbert, Jerry K.; Mittelstadt, Scott W.; Dowty, Martin E.; Obringer, Cindy M.; Suchanek, Paula; Reizes, Ofer; Eric Hu; Wos, John A.; Bioorganic and Medicinal Chemistry; vol. 15; nb. 5; (2007); p. 2092 - 2105, View in Reaxys

1, R1=p-Br-PhCH2CH2

Chen, Shaoqing; Chen, Li; Le, Nam T.; Zhao, Chunlin; Sidduri, Achyutharao; Lou, Jian Ping; Michoud, Christophe; Portland, Louis; Jackson, Nicole; Liu, Jin-Jun; Konzelmann, Fred; Chi, Feng; Tovar, Christian; Xiang, Qing; Chen, Yingsi; Wen, Yang; Vassilev, Lyubomir T.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 8; (2007); p. 2134 - 2138, View in Reaxys

tab. 1, entry 4, prod.

Ankner, Tobias; Hilmersson, Goeran; Tetrahedron Letters; vol. 48; nb. 32; (2007); p. 5707 - 5710, View in Reaxys

112

Patent; Hydra Biosciences; US2007/219222; (2007); (A1) English, View in Reaxys

c-2

Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/97534; (2006); (A1) English, View in Reaxys

R-NH2, a

Oikawa, Masato; Ikoma, Minoru; Sasaki, Makoto; Tetrahedron Letters; vol. 46; nb. 3; (2005); p. 415 - 418, View in Reaxys

Bruncko, Milan; McClellan, William J.; Wendt, Michael D.; Sauer, Daryl R.; Geyer, Andrew; Dalton, Christopher R.; Kaminski, Michele A.; Weitzberg, Moshe; Gong, Jane; Dellaria, Joseph F.; Mantei, Robert; Zhao, Xumiao; Nienaber, Vicki L.; Stewart, Kent; Klinghofer, Vered; Bouska, Jennifer; Rockway, Todd W.; Giranda, Vincent L.; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 1; (2005); p. 93 - 98, View in Reaxys

5, X=CH2CH2

Palani, Anandan; Shapiro, Sherry; McBriar, Mark D.; Clader, John W.; Greenlee, William J.; O'Neill, Kim; Hawes, Brian; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 23; (2005); p. 5234 - 5236, View in Reaxys

Muthas, Daniel; Noeteberg, Daniel; Sabnis, Yogesh A.; Hamelink, Elizabeth; Vrang, Lotta; Samuelsson, Bertil; Karlen, Anders; Hallberg, Anders; Bioorganic and Medicinal Chemistry; vol. 13; nb. 18; (2005); p. 5371 - 5390, View in Reaxys

Batra, Sanjay; Sabnis, Yogesh A.; Rosenthal, Philip J.; Avery, Mitchell A.; Bioorganic and Medicinal Chemistry; vol. 11; nb. 10; (2003); p. 2293 - 2299, View in Reaxys; Chern, Meei-Shiou; Li, Wen-Ren; Tetrahedron Letters; vol. 45; nb. 45; (2004); p. 8323 - 8326, View in Reaxys

Oikawa, Masato; Ikoma, Minoru; Sasaki, Makoto; Tetrahedron Letters; vol. 45; nb. 11; (2004); p. 2371 2375, View in Reaxys

Xiao, Ji-Chang; Chen, Qing-Yun; Journal of Fluorine Chemistry; vol. 123; nb. 2; (2003); p. 189 - 195, View in Reaxys

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tab. 2, entry 3, prod.

Mineno, Tomoko; Choi, Seoung-Ryoung; Avery, Mitchell A.; Synlett; nb. 6; (2002); p. 883 - 886, View in Reaxys

Locher; Synthetic Communications; vol. 31; nb. 19; (2001); p. 2895 - 2911, View in Reaxys

Mu; Coffing; Riese II; Geahlen; Verdier-Pinard; Hamel; Johnson; Cushman; Journal of Medicinal Chemistry; vol. 44; nb. 3; (2001); p. 441 - 452, View in Reaxys

Englert; Gerlach; Goegelein; Hartung; Heitsch; Mania; Scheidler; Journal of Medicinal Chemistry; vol. 44; nb. 7; (2001); p. 1085 - 1098, View in Reaxys

Patent-Specific Data (8) Prophetic ComLocation in Patent References pound Page/Page column

Patent; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (2014); (A1) English, View in Reaxys; Patent; DOW AGROSCIENCES LLC; Fischer, Lindsey G.; Baum, Erich W.; Crouse, Gary D.; DeAmicis, Carl; Lorsbach, Beth; Petkus, Jeff; Sparks, Thomas C.; Whiteker, Gregory T.; US2014/274688; (2014); (A1) English, View in Reaxys Patent; SANOFI-AVENTIS; US2011/124643; (2011); (A1) English, View in Reaxys Patent; Kang, Heonjoong; Ham, Jungyeob; US2008/269516; (2008); (A1) English, View in Reaxys Patent; ASTRAZENECA AB; WO2006/73366; (2006); (A1) English, View in Reaxys Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/97534; (2006); (A1) English, View in Reaxys Patent; Aventis Pharma Deutschland GmbH; US6337344; (2002); (B1) English, View in Reaxys

Claim

prophetic product Derivative (2) Comment (Derivative)

Patent; SmithKline Beecham Corporation; US5908960; (1999); (A1) English, View in Reaxys; Patent; Genzyme Corporation; US6008398; (1999); (A1) English, View in Reaxys Patent; A. H. Robins Company, Incorporated; US4857553; (1989); (A1) English, View in Reaxys

References

Verb. mit Picrinsaeure C8H10BrN*C6H3 N3O7. F: 200-201grad<Fis her-Johns; aus Propan-1-ol Hexan>

Shapiro et al.; Journal of Medicinal and Pharmaceutical Chemistry; vol. 5; (1962); p. 793,794, View in Reaxys

Hydrochlorid C8H10BrN*HCl. F: 242-243grad<Fis her-Johns; aus Propan-1-ol Hexan>

Shapiro et al.; Journal of Medicinal and Pharmaceutical Chemistry; vol. 5; (1962); p. 793,794, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties white

supporting information

References Lu, Zhiyao; Williams, Travis J.; Chemical Communications; vol. 50; nb. 40; (2014); p. 5391 - 5393, View in Reaxys

Dissociation Exponent (2) 1 of 2

Dissociation Exponent (pK)

9.65

Temperature (Dissociation Exponent) [°C]

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Solvent (Dissociation Exponent)

H2O

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a1/apparent

Deles,J. et al.; Polish Journal of Chemistry; vol. 53; (1979); p. 1025 - 1032, View in Reaxys 2 of 2

Comment (Dissociation Exponent)

(pk')pKa'<50percentig. wss. Me.; 25grad>: 9,20 (potentiometrisch)

Shapiro et al.; Journal of Medicinal and Pharmaceutical Chemistry; vol. 5; (1962); p. 793,794, View in Reaxys Further Information (1) Description (Fur- References ther Information) Further information

Shapiro et al.; Journal of Medicinal and Pharmaceutical Chemistry; vol. 5; (1962); p. 793,794, View in Reaxys

NMR Spectroscopy (6) 1 of 6

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

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

300

Original Text (NMR Spectroscopy)

Location

Paragraph 0196

Signals [ppm]

6.9 - 7.79; 2.58 - 3.15

Kind of signal

m, 4H; m, 4H

NMR (CDCl3, 300 MHz): δ 7.79-6.90 (m, 4H), 3.15-2.58 (m, 4H)

Patent; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (2014); (A1) English, View in Reaxys 2 of 6

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

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

400

Location

supporting information

Szostak, Michal; Sautier, Brice; Spain, Malcolm; Procter, David J.; Organic Letters; vol. 16; nb. 4; (2014); p. 1092 - 1095, View in Reaxys 3 of 6

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

13C

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

100

Location

supporting information

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Szostak, Michal; Sautier, Brice; Spain, Malcolm; Procter, David J.; Organic Letters; vol. 16; nb. 4; (2014); p. 1092 - 1095, View in Reaxys 4 of 6

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

Solvents (NMR Spectro- [D3]acetonitrile scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

600

Location

supporting information

Lu, Zhiyao; Williams, Travis J.; Chemical Communications; vol. 50; nb. 40; (2014); p. 5391 - 5393, View in Reaxys 5 of 6

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

13C

Solvents (NMR Spectro- [D3]acetonitrile scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

150

Location

supporting information

Lu, Zhiyao; Williams, Travis J.; Chemical Communications; vol. 50; nb. 40; (2014); p. 5391 - 5393, View in Reaxys 6 of 6

Nucleus (NMR Spectroscopy)

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

300

Original Text (NMR Spectroscopy)

NMR (CDCI3, 300 MHz): δ 7.79-6.90 (m, 4H), 3.15-2.58 (m, 4H).

Location

Page/Page column 38

Comment (NMR Spectroscopy)

Signals given

Patent; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; MOEBITZ, Henrik; SENGUPTA, Saumitra; WO2012/35078; (2012); (A1) English, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

Location

supporting information

Lu, Zhiyao; Williams, Travis J.; Chemical Communications; vol. 50; nb. 40; (2014); p. 5391 - 5393, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry) liquid chromatog- Paragraph 0197 raphy mass spec-

Peak

Intensity [%]

References

199.9 m/z

Patent; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra;

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trometry (LCMS); spectrum

US2014/45872; (2014); (A1) English, View in Reaxys

gas chromatogra- supporting inforphy mass specmation trometry (GCMS); spectrum

Lu, Zhiyao; Williams, Travis J.; Chemical Communications; vol. 50; nb. 40; (2014); p. 5391 5393, View in Reaxys

LCMS (Liquid chromatography mass spectrometry)

Patent; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; MOEBITZ, Henrik; SENGUPTA, Saumitra; WO2012/35078; (2012); (A1) English, View in Reaxys

Page/Page column 38

Pharmacological Data (6) 1 of 6

Comment (Pharmacological Data)

Bioactivities present

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Comment (Pharmacological Data)

physiological behaviour discussed

Wang, Kevin H.; Penmatsa, Aravind; Gouaux, Eric; Nature; vol. 521; nb. 7552; (2015); p. 322 - 327, View in Reaxys 3 of 6

Comment (Pharmacological Data)

physiological behaviour discussed

Heuson, Egon; Storgaard, Morten; Huynh, Tri H. V.; Charmantray, Franck; Gefflaut, Thierry; Bunch, Lennart; Organic and Biomolecular Chemistry; vol. 12; nb. 43; (2014); p. 8689 - 8695, View in Reaxys 4 of 6

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

RD-HGA16 cells expressing human TAAR 1 receptor

Method (Pharmacological Data)

hTAAR1 activation assay; title comp. incubated with test cells in presence of Calcium 3 dye as fluorescent substrate (HAM's F-12 medium, 10percent FBS, 5percent CO2/95percent air, 37 deg C, 1 h); title comp. effect on internal calcium mobilization assessed; fluorimetry

Further Details (Pharmacological Data)

hTAAR1: human trace amine receptor 1; Emax: maximal title comp. efficacy

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

1540 nmol/l

Results

title comp. exhibited Emax 98percent

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys 5 of 6

Effect (Pharmacological Data)

[3H]ketanserin binding; inhibition of

Species or Test-System (Pharmacological Data)

NIH3T3 cell; genetically modified/infected with: 5-HT2A receptor

Further Details (Pharmacological Data)

Ki related to: 5-HT2A receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1770 nmol/l

Location

supporting information

Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.; Journal of Medicinal Chemistry; vol. 51; nb. 21; (2008); p. 6808 - 6828, View in Reaxys 6 of 6

Effect (Pharmacological Data)

[3H]ketanserin binding; inhibition of

Species or Test-System (Pharmacological Data)

NIH3T3 cell; genetically modified/infected with: 5-HT2A receptor

Results

molecular target: 5-HT2A receptor

Location

supporting information

Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.; Journal of Medicinal Chemistry; vol. 51; nb. 21; (2008); p. 6808 - 6828, View in Reaxys

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Reaxys ID 2802715 View in Reaxys

2/43 CAS Registry Number: 65185-58-2 Chemical Name: 2-(2-bromophenyl)ethanamine; 2-(2-bromophenyl)-ethylamine; 2-bromo-phenethylamine; o-bromophenethylamine; N-(2-(2-bromophenyl)ethyl)amine; 2-(2-bromophenyl)ethan-1-amine; 2-(2-bromophen)ethyl-1-amine Linear Structure Formula: C8H10NBr Molecular Formula: C8H10BrN Molecular Weight: 200.078 Type of Substance: isocyclic InChI Key: ITRNQMJXZUWZQL-UHFFFAOYSA-N Note:

Br NH 2

Substance Label (17) Label References 12

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4{19}

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2, n = 2

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Educt,Tab.1,run 2,col 3

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4c-1

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oBrC6H4CH2CH2 NH2

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Boiling Point (2)

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Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

0.4

Tomaszewski, Miroslaw J.; Warkentin, John; Werstiuk, Nick H.; Australian Journal of Chemistry; vol. 48; nb. 2; (1995); p. 291 - 322, View in Reaxys

89 - 91

0.7

Patent; Sahyun Laboratories; US3089826; (1963); Chem.Abstr.; vol. 59; nb. 12706s; (1963), View in Reaxys

Crystal Property Description (3) Colour & Other Location Properties yellow

supporting information

yellow

References Mestichelli, Paola; Scott, Matthew J.; Galloway, Warren R. J. D.; Selwyn, Jamie; Parker, Jeremy S.; Spring, David R.; Organic Letters; vol. 15; nb. 21; (2013); p. 5448 5451, View in Reaxys Haddenham, Dustin; Pasumansky, Lubov; DeSoto, Jamie; Eagon, Scott; Singaram, Bakthan; Journal of Organic Chemistry; vol. 74; nb. 5; (2009); p. 1964 - 1970, View in Reaxys

supporting information

Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 - 9632, View in Reaxys

NMR Spectroscopy (12) 1 of 12

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

13C

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

125

Location

supporting information

Haddenham, Dustin; Pasumansky, Lubov; DeSoto, Jamie; Eagon, Scott; Singaram, Bakthan; Journal of Organic Chemistry; vol. 74; nb. 5; (2009); p. 1964 - 1970, View in Reaxys; Mestichelli, Paola; Scott, Matthew J.; Galloway, Warren R. J. D.; Selwyn, Jamie; Parker, Jeremy S.; Spring, David R.; Organic Letters; vol. 15; nb. 21; (2013); p. 5448 - 5451, View in Reaxys 2 of 12

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

Coupling Nuclei

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

500

Location

supporting information

Mestichelli, Paola; Scott, Matthew J.; Galloway, Warren R. J. D.; Selwyn, Jamie; Parker, Jeremy S.; Spring, David R.; Organic Letters; vol. 15; nb. 21; (2013); p. 5448 - 5451, View in Reaxys 3 of 12

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

Mori,M. et al.; Journal of Organic Chemistry; vol. 43; nb. 9; (1978); p. 1684 - 1687, View in Reaxys; Chang, ChiaFu; Huang, Chu-Yun; Huang, Yu-Chao; Lin, Kuan-Yu; Lee, Yean-Jang; Wang, Chau-Jong; Synthetic Communications; vol. 40; nb. 23; (2010); p. 3452 - 3466, View in Reaxys 4 of 12

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

13C

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Chang, Chia-Fu; Huang, Chu-Yun; Huang, Yu-Chao; Lin, Kuan-Yu; Lee, Yean-Jang; Wang, Chau-Jong; Synthetic Communications; vol. 40; nb. 23; (2010); p. 3452 - 3466, View in Reaxys 5 of 12

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

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

500

Location

supporting information

Haddenham, Dustin; Pasumansky, Lubov; DeSoto, Jamie; Eagon, Scott; Singaram, Bakthan; Journal of Organic Chemistry; vol. 74; nb. 5; (2009); p. 1964 - 1970, View in Reaxys 6 of 12

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

13C

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

100.6

Location

supporting information

Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 - 9632, View in Reaxys 7 of 12

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

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

400

Location

supporting information

Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 - 9632, View in Reaxys; Kubo, Tetsuji; Katoh, Chiharu; Yamada, Ken; Okano, Kentaro; Tokuyama, Hidetoshi; Fukuyama, Tohru; Tetrahedron; vol. 64; nb. 49; (2008); p. 11230 - 11236, View in Reaxys 8 of 12

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

13C

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

100

Location

supporting information

Kubo, Tetsuji; Katoh, Chiharu; Yamada, Ken; Okano, Kentaro; Tokuyama, Hidetoshi; Fukuyama, Tohru; Tetrahedron; vol. 64; nb. 49; (2008); p. 11230 - 11236, View in Reaxys 9 of 12

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

15/53

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Solvents (NMR Spectro- CDCl3 scopy) Bradsher, Charles K.; Hunt, David A.; Journal of Organic Chemistry; vol. 46; nb. 2; (1981); p. 327 - 330, View in Reaxys; Tomaszewski, Miroslaw J.; Warkentin, John; Werstiuk, Nick H.; Australian Journal of Chemistry; vol. 48; nb. 2; (1995); p. 291 - 322, View in Reaxys; Wolfe, John P.; Rennels, Roger A.; Buchwald, Stephen L.; Tetrahedron; vol. 52; nb. 21; (1996); p. 7525 - 7546, View in Reaxys; McClure, Cynthia K.; Kiessling, Anthony J.; Link, Jeffrey S.; Tetrahedron; vol. 54; nb. 25; (1998); p. 7121 - 7126, View in Reaxys 10 of 12

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Tomaszewski, Miroslaw J.; Warkentin, John; Werstiuk, Nick H.; Australian Journal of Chemistry; vol. 48; nb. 2; (1995); p. 291 - 322, View in Reaxys; Wolfe, John P.; Rennels, Roger A.; Buchwald, Stephen L.; Tetrahedron; vol. 52; nb. 21; (1996); p. 7525 - 7546, View in Reaxys; McClure, Cynthia K.; Kiessling, Anthony J.; Link, Jeffrey S.; Tetrahedron; vol. 54; nb. 25; (1998); p. 7121 - 7126, View in Reaxys 11 of 12

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

1H-1H

Bradsher, Charles K.; Hunt, David A.; Journal of Organic Chemistry; vol. 46; nb. 2; (1981); p. 327 - 330, View in Reaxys; Tomaszewski, Miroslaw J.; Warkentin, John; Werstiuk, Nick H.; Australian Journal of Chemistry; vol. 48; nb. 2; (1995); p. 291 - 322, View in Reaxys; Wolfe, John P.; Rennels, Roger A.; Buchwald, Stephen L.; Tetrahedron; vol. 52; nb. 21; (1996); p. 7525 - 7546, View in Reaxys; McClure, Cynthia K.; Kiessling, Anthony J.; Link, Jeffrey S.; Tetrahedron; vol. 54; nb. 25; (1998); p. 7121 - 7126, View in Reaxys 12 of 12

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

Solvents (NMR Spectro- neat (no solvent) scopy) Brunet, Jean-Jacques; Sidot, Christian; Caubere, Paul; Journal of Organic Chemistry; vol. 48; nb. 8; (1983); p. 1166 - 1171, View in Reaxys IR Spectroscopy (5) 1 of 5

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Location

supporting information

Mestichelli, Paola; Scott, Matthew J.; Galloway, Warren R. J. D.; Selwyn, Jamie; Parker, Jeremy S.; Spring, David R.; Organic Letters; vol. 15; nb. 21; (2013); p. 5448 - 5451, View in Reaxys 2 of 5

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3362 - 657 cm**(-1)

Wolfe, John P.; Rennels, Roger A.; Buchwald, Stephen L.; Tetrahedron; vol. 52; nb. 21; (1996); p. 7525 - 7546, View in Reaxys 3 of 5

Description (IR Spectroscopy)

Bands

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Comment (IR Spectroscopy)

3375 - 740 cm**(-1)

Tomaszewski, Miroslaw J.; Warkentin, John; Werstiuk, Nick H.; Australian Journal of Chemistry; vol. 48; nb. 2; (1995); p. 291 - 322, View in Reaxys 4 of 5

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3370 - 1470 cm**(-1)

Bradsher, Charles K.; Hunt, David A.; Journal of Organic Chemistry; vol. 46; nb. 2; (1981); p. 327 - 330, View in Reaxys 5 of 5

Description (IR Spectroscopy)

Bands

Mori,M. et al.; Journal of Organic Chemistry; vol. 43; nb. 9; (1978); p. 1684 - 1687, View in Reaxys Mass Spectrometry (4) Description (Mass Location Spectrometry)

Comment (Mass Spectrometry)

References

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

Mestichelli, Paola; Scott, Matthew J.; Galloway, Warren R. J. D.; Selwyn, Jamie; Parker, Jeremy S.; Spring, David R.; Organic Letters; vol. 15; nb. 21; (2013); p. 5448 - 5451, View in Reaxys

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

Page/Page column 181

Patent; BIOENERGENIX; MCCALL, John, M.; MCKEARN, John; ROMERO, Donnal, L.; CLAIR, Michael; WO2011/28947; (2011); (A2) English, View in Reaxys

HRMS (High resolution mass spectrometry)

mol peak

spectrum; chemical ionization (CI)

Haddenham, Dustin; Pasumansky, Lubov; DeSoto, Jamie; Eagon, Scott; Singaram, Bakthan; Journal of Organic Chemistry; vol. 74; nb. 5; (2009); p. 1964 - 1970, View in Reaxys Tomaszewski, Miroslaw J.; Warkentin, John; Werstiuk, Nick H.; Australian Journal of Chemistry; vol. 48; nb. 2; (1995); p. 291 - 322, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; Scios Nova, Inc.; US5444048; (1995); (A1) English, View in Reaxys; Patent; Scios Nova Inc.; US5541286; (1996); (A1) English, View in Reaxys; Patent; Johnston, Jeffrey N.; Viswanathan, Rajesh; US2002/128490; (2002); (A1) English, View in Reaxys; Patent; Sundermann, Bernd; Koegel, Babette-Yvonne; Buschmann, Helmut; US2002/198251; (2002); (A1) English, View in Reaxys; Mori,M. et al.; Journal of Organic Chemistry; vol. 43; nb. 9; (1978); p. 1684 - 1687, View in Reaxys; Patent; Dendreon Corporation; US2007/232603; (2007); (A1) English, View in Reaxys; Patent; Sahyun Laboratories; US3089826; (1963); Chem.Abstr.; vol. 59; nb. 12706s; (1963), View in Reaxys; Bradsher, Charles K.; Hunt, David A.; Journal of Organic Chemistry; vol. 46; nb. 2; (1981); p. 327 - 330, View in Reaxys; Brunet, Jean-Jacques; Sidot, Christian; Caubere, Paul; Journal of Organic Chemistry; vol. 48; nb. 8; (1983); p. 1166 - 1171, View in Reaxys; Ortwine, Daniel F.; Malone, Thomas C.; Bigge, Christopher F.; Drummond, James T.; Humblet, Christine; et al.; Journal of Medicinal Chemistry; vol. 35; nb. 8; (1992); p. 1345 - 1370, View in Reaxys; Lamas, Carlos; Saa, Carlos; Castedo, Luis; Dominguez, Domingo; Tetrahedron Letters; vol. 33; nb. 38; (1992); p. 5653 - 5654, View in Reaxys; Kihara; Miyake; Iitomi; Kobayashi; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1260 - 1265, View in Reaxys; Tomaszewski, Miroslaw J.; Warkentin, John; Journal of the Chemical Society, Chemical Communications; nb. 11; (1993); p. 966 - 968, View in Reaxys; Kihara, Masaru; Itoh, Joji; Iguchi, Seiichiro; Imakura, Yasuhiro; Kobayashi, Shigeru; Journal of Chemical Research, Miniprint; nb. 1; (1988); p. 157 - 177, View in Reaxys; Tomaszewski, Miroslaw J.; Warkentin, John; Werstiuk, Nick H.; Australian Journal of Chemistry; vol. 48; nb. 2; (1995); p. 291 - 322, View in Reaxys; Wolfe, John P.; Rennels, Roger A.; Buchwald, Stephen L.; Tetrahedron; vol. 52; nb. 21; (1996); p. 7525 - 7546, View in Reaxys; McClure, Cynthia K.; Kiessling, Anthony J.; Link, Jeffrey S.; Tetrahedron; vol. 54; nb. 25; (1998); p. 7121 - 7126, View in Reaxys; Rodriguez, Gema; Castedo, Luis; Dominguez, Domingo; Saa, Carlos; Adam, Waldemar; Saha-Moeller, Chantu R.; Journal of Organic Chemistry; vol. 64; nb. 3; (1999); p. 877 - 883, View in Reaxys; Garcia, Alberto; Rodriguez, David; Castedo, Luis; Saa, Carlos; Dominguez, Domingo; Tetrahedron Letters; vol. 42; nb. 10; (2001); p. 1903 - 1905, View in Reaxys; Johnston, Jeffrey N.; Plotkin, Michael A.;

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Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

RD-HGA16 cells expressing human TAAR 1 receptor

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Method (Pharmacological Data)

Further Details (Pharmacological Data)

hTAAR1: human trace amine receptor 1; Emax: maximal title comp. efficacy

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

57 nmol/l

Results

title comp. exhibited Emax 57percent

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Reaxys ID 2716071 View in Reaxys

3/43 CAS Registry Number: 58971-11-2 Chemical Name: 2-(3-bromophenyl)ethanamine; [2-(3-bromophenyl)ethyl]amine; 2-(3-bromophenyl)ethylamine; 3-bromophenylethylamine; 3-bromophenethyl amine; 3-bromophenethylamine; m-bromophenethylamine Linear Structure Formula: C8H10BrN Molecular Formula: C8H10BrN Molecular Weight: 200.078 Type of Substance: isocyclic InChI Key: ORHRHMLEFQBHND-UHFFFAOYSA-N Note:

NH 2

Substance Label (13) Label References 13d

Boominathan, Muthusamy; Nagaraj, Muthupandi; Muthusubramanian, Shanmugam; Bhuvanesh, Nattamai; RSC Advances; vol. 4; nb. 36; (2014); p. 18549 - 18557, View in Reaxys

Georgsson, Jennie; Bergstroem, Fredrik; Nordqvist, Anneli; Watson, Martin J.; Blundell, Charles D.; Johansson, Magnus J.; Petersson, Annika U.; Yuan, Zhong-Qing; Zhou, Yiqun; Kristensson, Lisbeth; Kakol-Palm, Dorota; Tyrchan, Christian; Wellner, Eric; Bauer, Udo; Brodin, Peter; Svensson Henriksson, Anette; Journal of Medicinal Chemistry; vol. 57; nb. 14; (2014); p. 5935 - 5948, View in Reaxys

Wang, Zhi-Xia; Chen, Jing-Lei; Qiao, Chunhua; Chemical Biology and Drug Design; vol. 82; nb. 2; (2013); p. 216 - 225, View in Reaxys

Pesnot, Thomas; Gershater, Markus C.; Ward, John M.; Hailes, Helen C.; Advanced Synthesis and Catalysis; vol. 354; nb. 16; (2012); p. 2997 - 3008, View in Reaxys

Kumar, Vishal; Sharma, Upendra; Singh, Bikram; Kumar, Neeraj; Australian Journal of Chemistry; vol. 65; nb. 12; (2012); p. 1594 - 1598, View in Reaxys

Patent; HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian; WO2011/47156; (2011); (A1) English, View in Reaxys

I-60

Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); (A1) English, View in Reaxys

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Paillet-Loilier, Magalie; Fabis, Frederic; Lepailleur, Alban; Bureau, Ronan; Butt-Gueulle, Sabrina; Dauphin, Francois; Lesnard, Aurelien; Delarue, Catherine; Vaudry, Hubert; Rault, Sylvain; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 11; (2007); p. 3018 - 3022, View in Reaxys

3-Br-C6H4CH2CH2NH2

Erdelyi, Mate; Karlen, Anders; Gogoll, Adolf; Chemistry - A European Journal; vol. 12; nb. 2; (2006); p. 403 - 412, View in Reaxys

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Patent; ASTRAZENECA AB; WO2004/60882; (2004); (A1) English, View in Reaxys

Patent-Specific Data (3) References Patent; ASTRAZENECA AB; US2008/15237; (2008); (A1) English, View in Reaxys Patent; Laboratorios del Dr. Esteve S.A.; EP1935886; (2008); (A1) English, View in Reaxys Patent; ASTRAZENECA AB; WO2006/73366; (2006); (A1) English, View in Reaxys Derivative (1) Comment (Derivative)

References

Hydrochlorid: F: 226-227grad

Gittos et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1976); p. 33,34,37, View in Reaxys

Boiling Point (1) Boiling Point [°C] 127 - 132

Pressure (Boiling Point) [Torr]

References

Gittos et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1976); p. 33,34,37, View in Reaxys

Crystal Property Description (2) Colour & Other Location Properties colourless

supporting information

colorless

References Pesnot, Thomas; Gershater, Markus C.; Ward, John M.; Hailes, Helen C.; Advanced Synthesis and Catalysis; vol. 354; nb. 16; (2012); p. 2997 - 3008, View in Reaxys Patent; NOVARTIS AG; WO2008/76954; (2008); (A2) English, View in Reaxys

NMR Spectroscopy (4) 1 of 4

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

Solvents (NMR Spectro- water-d2 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

600

Location

supporting information

Pesnot, Thomas; Gershater, Markus C.; Ward, John M.; Hailes, Helen C.; Advanced Synthesis and Catalysis; vol. 354; nb. 16; (2012); p. 2997 - 3008, View in Reaxys 2 of 4

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

13C

Solvents (NMR Spectro- water-d2 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

150

Location

supporting information

Pesnot, Thomas; Gershater, Markus C.; Ward, John M.; Hailes, Helen C.; Advanced Synthesis and Catalysis; vol. 354; nb. 16; (2012); p. 2997 - 3008, View in Reaxys

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3 of 4

Nucleus (NMR Spectroscopy)

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

400

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (400 MHz, CDCl3) δ 7.38-7.30 (m, 2H), 7.20-7.10 (m, 2H), 2.96 (t, 2H), 2.72 (t, 2H), 1.35 (br s, 2H).

Patent; PREDIX PHARMACEUTICALS HOLDINGS, INC.; WO2007/61458; (2007); (A2) English, View in Reaxys 4 of 4

Nucleus (NMR Spectroscopy)

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

1H-NMR (CDCl3): δ 7.38-7. 30 (overlapping s at 7.35 and d, J=7. 2 Hz for d, 2H), 7.207.10 (m, 2H), 2. 96 (t,. J=6. 8 Hz, 2H), 2.72 (t, J=6. 4 Hz, 2H), 1. 35 (br s, 2H)

Comment (NMR Spectroscopy)

Signals given

Patent; ASTRAZENECA AB; WO2004/60882; (2004); (A1) English, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Spectrum

Oki; Mutai; Bulletin of the Chemical Society of Japan; vol. 38; (1965); p. 387,388, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry)

Comment (Mass Spectrometry)

References

high resolution mass spectrometry (HRMS); CI (Chemical ionization); spectrum

supporting information

Pesnot, Thomas; Gershater, Markus C.; Ward, John M.; Hailes, Helen C.; Advanced Synthesis and Catalysis; vol. 354; nb. 16; (2012); p. 2997 - 3008, View in Reaxys

ESI (Electrospray ionisation)

Page/Page column 110

Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); (A1) English, View in Reaxys

ESI (Electrospray ionisation)

Molecular peak

Patent; PREDIX PHARMACEUTICALS HOLDINGS, INC.; WO2007/61458; (2007); (A2) English, View in Reaxys; Patent; ASTRAZENECA AB; WO2004/60882; (2004); (A1) English, View in Reaxys

Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

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Bruce; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 4; (2011); p. 1206 - 1213, View in Reaxys; Patent; HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian; WO2011/47156; (2011); (A1) English, View in Reaxys; Gagnepain, Julien; Moulin, Emilie; Nevado, Cristina; Waser, Mario; Maier, Armin; Kelter, Gerhard; Fiebig, Heinz-Herbert; Fuerstner, Alois; Chemistry - A European Journal; vol. 17; nb. 25; (2011); p. 6973 - 6984, View in Reaxys; Maillard, Michel C.; Brookfield, Frederick A.; Courtney, Stephen M.; Eustache, Florence M.; Gemkow, Mark J.; Handel, Rebecca K.; Johnson, Laura C.; Johnson, Peter D.; Kerry, Mark A.; Krieger, Florian; Meniconi, Mirco; Munoz-Sanjuan, Ignacio; Palfrey, Jordan J.; Park, Hyunsun; Schaertl, Sabine; Taylor, Malcolm G.; Weddell, Derek; Dominguez, Celia; Bioorganic and Medicinal Chemistry; vol. 19; nb. 19; (2011); p. 5833 - 5851, View in Reaxys; Patent; SANOFI; GAO, Zhongli; HARTUNG, Ryan; WO2011/143145; (2011); (A1) English, View in Reaxys; Patent; SANOFI; GAO, Zhongli; HARTUNG, Ryan; WO2011/143155; (2011); (A1) English, View in Reaxys; Ballatore, Carlo; Soper, James H.; Piscitelli, Francesco; James, Michael; Huang, Longchuan; Atasoylu, Onur; Huryn, Donna M.; Trojanowski, John Q.; Lee, Virginia M.-Y.; Brunden, Kurt R.; Smith, Amos B.; Journal of Medicinal Chemistry; vol. 54; nb. 19; (2011); p. 6969 - 6983, View in Reaxys; Selvakumar, Jayaraman; Ramanathan, Chinnasamy Ramaraj; Organic and Biomolecular Chemistry; vol. 9; nb. 22; (2011); p. 7643 - 7646, View in Reaxys; Patent; ALMIRALL, S.A.; VIDAL JUAN, Bernat; FORNS BERENGUEL, Maria Pilar; CASTILLO MCQUADE, Marcos; ERRA SOLA, Montserrat; MIR CEPEDA, Marta; WO2012/41476; (2012); (A1) English, View in Reaxys; Herth, Matthias M.; Hansen, Hanne D.; Ettrup, Anders; Dyssegaard, Agnete; Lehel, Szabolcs; Kristensen, Jesper; Knudsen, Gitte M.; Bioorganic and Medicinal Chemistry; vol. 20; nb. 14; (2012); p. 4574 - 4581, View in Reaxys; Smith, Keith; El-Hiti, Gamal A.; Alshammari, Mohammed B.; Synthesis (Germany); vol. 44; nb. 13; (2012); p. 2013 - 2022; Art.No: SS-2012-Z0143-OP, View in Reaxys; Pesnot, Thomas; Gershater, Markus C.; Ward, John M.; Hailes, Helen C.; Advanced Synthesis and Catalysis; vol. 354; nb. 16; (2012); p. 2997 - 3008, View in Reaxys; Kumar, Vishal; Sharma, Upendra; Singh, Bikram; Kumar, Neeraj; Australian Journal of Chemistry; vol. 65; nb. 12; (2012); p. 1594 1598, View in Reaxys; Patent; Almirall, S.A.; Vidal Juan, Bernat; Forns Berenguel, Maria Pilar; Castillo Mcquade, Marcos; Erra Sola, Montserrat; Mir Cepeda, Marta; EP2441755; (2012); (A1) English, View in Reaxys; Garner, Amanda L.; Fullagar, Jessica L.; Day, Joshua A.; Cohen, Seth M.; Janda, Kim D.; Journal of the American Chemical Society; vol. 135; nb. 27; (2013); p. 10014 - 10017, View in Reaxys; Mei, Tian-Sheng; Leow, Dasheng; Xiao, Han; Laforteza, Brian N.; Yu, Jin-Quan; Organic Letters; vol. 15; nb. 12; (2013); p. 3058 - 3061, View in Reaxys; Wang, Zhi-Xia; Chen, Jing-Lei; Qiao, Chunhua; Chemical Biology and Drug Design; vol. 82; nb. 2; (2013); p. 216 - 225, View in Reaxys; Golubev, Viktor; Zubkov, Fedor; Krasavin, Mikhail; Tetrahedron Letters; vol. 54; nb. 36; (2013); p. 4844 - 4847, View in Reaxys; Boominathan, Muthusamy; Nagaraj, Muthupandi; Muthusubramanian, Shanmugam; Bhuvanesh, Nattamai; RSC Advances; vol. 4; nb. 36; (2014); p. 18549 - 18557,

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View in Reaxys; Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); (A1) English, View in Reaxys; Georgsson, Jennie; Bergstroem, Fredrik; Nordqvist, Anneli; Watson, Martin J.; Blundell, Charles D.; Johansson, Magnus J.; Petersson, Annika U.; Yuan, Zhong-Qing; Zhou, Yiqun; Kristensson, Lisbeth; Kakol-Palm, Dorota; Tyrchan, Christian; Wellner, Eric; Bauer, Udo; Brodin, Peter; Svensson Henriksson, Anette; Journal of Medicinal Chemistry; vol. 57; nb. 14; (2014); p. 5935 - 5948, View in Reaxys; Wang, Chao; Chen, Changpeng; Zhang, Jingyu; Han, Jian; Wang, Qian; Guo, Kun; Liu, Pei; Guan, Mingyu; Yao, Yingming; Zhao, Yingsheng; Angewandte Chemie, International Edition; vol. 53; nb. 37; (2014); p. 9884 - 9888,5; Angewandte Chemie; vol. 126; nb. 37; (2014); p. 10042 - 10046,5, View in Reaxys; Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy; BATES, J. Alex; CHENEY, Daniel L.; WO2014/201073; (2014); (A1) English, View in Reaxys; Li, Zhenyu; Jia, Lejiao; Wang, Jifeng; Wu, Xingkang; Shi, Guowei; Lu, Chunhua; Shen, Yuemao; Chemical Biology and Drug Design; vol. 85; nb. 2; (2015); p. 181 - 188, View in Reaxys; Patent; FUJIFILM CORPORATION; TAKASAKI, Masaru; TSUJINO, Toshiaki; TANABE, Shintarou; OOKUBO, Megumi; SATO, Kimihiko; HIRAI, Atsushi; TERADA, Daisuke; INUKI, Shinsuke; MIZUMOTO, Shinsuke; US2015/45339; (2015); (A1) English, View in Reaxys; Selvakumar, Jayaraman; Rao, Ramana Sreenivasa; Srinivasapriyan, Vijayan; Marutheeswaran, Srinivasan; Ramanathan, Chinnasamy Ramaraj; European Journal of Organic Chemistry; vol. 2015; nb. 10; (2015); p. 2175 - 2188, View in Reaxys; Wang, Kevin H.; Penmatsa, Aravind; Gouaux, Eric; Nature; vol. 521; nb. 7552; (2015); p. 322 - 327, View in Reaxys; Patent; MERCK SHARP and DOHME CORP.; COBURN, Craig; MALETIC, Milana; LUO, Yunfu; QI, Zhiqi; LI, Chun Sing; YU, Tingting; WO2015/70366; (2015); (A1) English, View in Reaxys; Patent; MERCK SHARP and DOHME CORP.; COBURN, Craig, A.; MALETIC, Milana, M.; LUO, Yunfu; QI, Zhiqi; LI, Chun Sing; YU, Tingting; WO2015/73308; (2015); (A1) English, View in Reaxys; Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); (A1) English, View in Reaxys; Guan, Mingyu; Chen, Changpeng; Zhang, Jingyu; Zeng, Runsheng; Zhao, Yingsheng; Chemical Communications; vol. 51; nb. 60; (2015); p. 12103 - 12106, View in Reaxys; Ogiyama, Takashi; Yonezawa, Koichi; Inoue, Makoto; Katayama, Naoko; Watanabe, Toshihiro; Yoshimura, Seiji; Gotoh, Takayasu; Kiso, Tetsuo; Koakutsu, Akiko; Kakimoto, Shuichiro; Shishikura, Jun-Ichi; Bioorganic and Medicinal Chemistry; vol. 23; nb. 15; (2015); p. 4638 - 4648, View in Reaxys; Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANNLA ROCHE INC.; CECERE, Giuseppe; GALLEY, Guido; NORCROSS, Roger; PATINY-ADAM, Angélique; PFLIEGER, Philippe; (68 pag.); WO2016/30306; (2016); (A1) English, View in Reaxys 2 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Wang, Kevin H.; Penmatsa, Aravind; Gouaux, Eric; Nature; vol. 521; nb. 7552; (2015); p. 322 - 327, View in Reaxys 3 of 3

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

RD-HGA16 cells expressing human TAAR 1 receptor

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hTAAR1: human trace amine receptor 1; Emax: maximal title comp. efficacy

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

398 nmol/l

Results

title comp. exhibited Emax 75percent

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Reaxys ID 3240553 View in Reaxys

4/43 CAS Registry Number: 13235-83-1 Chemical Name: 1-(4'-bromo)phenyl-2-propanamine; 1-(4-bromophenyl)-2-aminopropane; 1-(4-bromophenyl)propane-2amine; 2-(4-bromo-phenyl)-1-methyl-ethylamine; 2-(4-Bromphenyl)-1-methyl-aethylamin; 2-Amino-1-(4-brom-phenyl)-propan; 1-(4-bromophenyl)propan-2-amine

NH 2

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Linear Structure Formula: C9H12BrN Molecular Formula: C9H12BrN Molecular Weight: 214.105 Type of Substance: isocyclic InChI Key: SMNXUMMCCOZPPN-UHFFFAOYSA-N Note: Substance Label (6) Label References 12d

Rodrguez, Anna; Guerrero, Angel; Gutierrez-De-Tern, Hugo; Rodrguez, David; Brea, Jos; Loza, Mara I.; Rosell, Gloria; Pilar Bosch; MedChemComm; vol. 6; nb. 6; (2015); p. 1178 - 1185, View in Reaxys

I.1

Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; NOSSE, Bernd; ROTH, Gerald, Juergen; WO2013/98375; (2013); (A1) English, View in Reaxys

Intermediate 29

Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/214785; (2012); (A1) English, View in Reaxys

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun; Journal of Medicinal Chemistry; vol. 35; nb. 4; (1992); p. 734 - 740, View in Reaxys

Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt; Journal of Medicinal Chemistry; vol. 29; nb. 2; (1986); p. 194 - 199, View in Reaxys

Table I, entry 4, prod.

Mourad, M. Soubei; Varma, Rajender S.; Kabalka, George W.; Synthetic Communications; vol. 14; nb. 12; (1984); p. 1099 - 1104, View in Reaxys

Patent-Specific Data (4) Prophetic ComLocation in Patent References pound Page/Page column

Patent; FLECK, Martin; NOSSE, Bernd; ROTH, Gerald Juergen; US2013/172316; (2013); (A1) English, View in Reaxys Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; NOSSE, Bernd; ROTH, Gerald, Juergen; WO2013/98375; (2013); (A1) English, View in Reaxys Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/214785; (2012); (A1) English, View in Reaxys

prophetic product Derivative (1) Derivative 2-(4-bromo-phenyl)-1-methyl-ethylamine; hydrochloride Boiling Point (1) Boiling Point [°C] 123 - 124

Patent; A. H. Robins Company, Incorporated; US4857553; (1989); (A1) English, View in Reaxys References Kabalka, George W.; Laila Guindi; Varma, Rajender S.; Tetrahedron; vol. 46; nb. 21; (1990); p. 7443 7457, View in Reaxys

Pressure (Boiling Point) [Torr]

References

Patrick; McBee; Hass; Journal of the American Chemical Society; vol. 68; (1946); p. 1009, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5569

Patrick; McBee; Hass; Journal of the American Chemical Society; vol. 68; (1946); p. 1009, View in Reaxys

589

Density (1) 1 of 1

Density [g·cm-3]

1.308

Reference Temperature [°C]

Measurement Temperature [°C]

Patrick; McBee; Hass; Journal of the American Chemical Society; vol. 68; (1946); p. 1009, View in Reaxys

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Chromatographic Data (2) Chromatographic Original string data

Location

References

TLC (Thin layer chromatography)

Rf (TLC): 0.3 (sili- Paragraph 0358; ca gel, DCM/ 0359 MeOH 9/1)

Patent; FLECK, Martin; NOSSE, Bernd; ROTH, Gerald Juergen; US2013/172316; (2013); (A1) English, View in Reaxys

TLC (Thin layer chromatography)

Rf (TLC): 0.3 (sili- Page/Page colca gel, DCM/ umn 64 MeOH 9/1 )

Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; NOSSE, Bernd; ROTH, Gerald, Juergen; WO2013/98375; (2013); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

300

Location

supporting information

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel; Organic and Biomolecular Chemistry; vol. 9; nb. 23; (2011); p. 8171 - 8177, View in Reaxys 2 of 2

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

13C

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

Location

supporting information

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel; Organic and Biomolecular Chemistry; vol. 9; nb. 23; (2011); p. 8171 - 8177, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel; Organic and Biomolecular Chemistry; vol. 9; nb. 23; (2011); p. 8171 - 8177, View in Reaxys Mass Spectrometry (5) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

Paragraph 0357; 0359

electrospray ionisation (ESI); spectrum

Page/Page column 64

ESI (Electrospray ionisation)

Page/Page column 58

Comment (Mass Spectrometry)

Peak

References

214 m/z

Molecular peak

214 m/z

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Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/214785; (2012); (A1) English, View in Reaxys

2016-06-12 07:01:14

EI (Electron impact); Spectrum

supporting information

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel; Organic and Biomolecular Chemistry; vol. 9; nb. 23; (2011); p. 8171 - 8177, View in Reaxys

LCMS (Liquid chromatography mass spectrometry)

Page/Page column 97

Patent; INCYTE CORPORATION; ZHANG, Colin; QIAN, Ding-quan; ZHUO, Jincong; YAO, Wenqing; WO2010/75270; (2010); (A1) English, View in Reaxys

Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; A. H. Robins Company, Incorporated; US4857553; (1989); (A1) English, View in Reaxys; Patrick; McBee; Hass; Journal of the American Chemical Society; vol. 68; (1946); p. 1009, View in Reaxys; Kabalka, George W.; Laila Guindi; Varma, Rajender S.; Tetrahedron; vol. 46; nb. 21; (1990); p. 7443 - 7457, View in Reaxys; Glennon, Richard A.; Ismaiel, Abd M.; Smith, J. Doyle; Yousif, Mamoun; El-Ashmawy, Mahmoud; et al.; Journal of Medicinal Chemistry; vol. 34; nb. 6; (1991); p. 1855 - 1859, View in Reaxys; Kabalka, George W.; Varma, Rajender S.; Gai, Yuan-Zhu; Baldwin, Ronald M.; Tetrahedron Letters; vol. 27; nb. 33; (1986); p. 3843 - 3844, View in Reaxys; Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun; Journal of Medicinal Chemistry; vol. 35; nb. 4; (1992); p. 734 - 740, View in Reaxys; Mourad, M. Soubei; Varma, Rajender S.; Kabalka, George W.; Synthetic Communications; vol. 14; nb. 12; (1984); p. 1099 - 1104, View in Reaxys; Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt; Journal of Medicinal Chemistry; vol. 29; nb. 2; (1986); p. 194 - 199, View in Reaxys; Varma, Rajender S.; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 9; (1985); p. 843 - 848, View in Reaxys; Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG; WO2009/52078; (2009); (A1) English, View in Reaxys; Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/103478; (2009); (A1) English, View in Reaxys; Patent; INCYTE CORPORATION; ZHANG, Colin; QIAN, Ding-quan; ZHUO, Jincong; YAO, Wenqing; WO2010/75270; (2010); (A1) English, View in Reaxys; Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel; Organic and Biomolecular Chemistry; vol. 9; nb. 23; (2011); p. 8171 - 8177, View in Reaxys; Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/214785; (2012); (A1) English, View in Reaxys; Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; NOSSE, Bernd; ROTH, Gerald, Juergen; WO2013/98375; (2013); (A1) English, View in Reaxys; Patent; FLECK, Martin; NOSSE, Bernd; ROTH, Gerald Juergen; US2013/172316; (2013); (A1) English, View in Reaxys; Aldous; Barrass; Brewster; Buxton; Green; Pinder; Rich; Skeels; Tutt; Journal of Medicinal Chemistry; vol. 17; nb. 10; (1974); p. 1100 - 1111, View in Reaxys; Glennon; Raghupathi; Bartyzel; Teitler; Leonhardt; Journal of Medicinal Chemistry; vol. 35; nb. 4; (1992); p. 734 - 740, View in Reaxys; Glennon; McKenney; Lyon; Titeler; Journal of medicinal chemistry; vol. 29; nb. 2; (1986); p. 194 - 199, View in Reaxys; SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL; Chemical reviews; vol. 83; nb. 6; (1983); p. 633 - 649, View in Reaxys; Rodrguez, Anna; Guerrero, Angel; Gutierrez-De-Tern, Hugo; Rodrguez, David; Brea, Jos; Loza, Mara I.; Rosell, Gloria; Pilar Bosch; MedChemComm; vol. 6; nb. 6; (2015); p. 1178 - 1185, View in Reaxys 2 of 3

Comment (Pharmacological Data)

binding affinity at 5-HT1C and 5-HT2 serotonin receptors; lack of selectivity

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun; Journal of Medicinal Chemistry; vol. 35; nb. 4; (1992); p. 734 - 740, View in Reaxys 3 of 3

Comment (Pharmacological Data)

binding affinity to 5-HT1 and 5-HT2 sites

Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt; Journal of Medicinal Chemistry; vol. 29; nb. 2; (1986); p. 194 - 199, View in Reaxys

Reaxys ID 3696303 View in Reaxys

5/43 CAS Registry Number: 39260-89-4 Chemical Name: 2-(4-bromophenyl)-1-aminoethane hydrochloride; 2-(4-bromophenyl)ethanamine hydrochloride; 4-bromophenylethylamine hydrochloride; 4-bromo-phenethylamine; hydrochloride; 4-Brom-phenaethylamin; Hydrochlorid; 2-(4-bromophenyl)ethanaminium chloride; 4-bromo-phenethylamine hydrochloride Linear Structure Formula: C8H10BrN*ClH Molecular Formula: C8H10BrN*ClH Molecular Weight: 236.539 Type of Substance: isocyclic

NH 2 Cl

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InChI Key: ZHAWIPAHUYMLDV-UHFFFAOYSA-N Note: Substance Label (2) Label References 2a

Laval, Stephane; Dayoub, Wissam; Pehlivan, Leyla; Metay, Estelle; Favre-Reguillon, Alain; Delbrayelle, Dominique; Mignani, Gerard; Lemaire, Marc; Tetrahedron; vol. 70; nb. 4; (2014); p. 975 - 983, View in Reaxys

I-68

Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); (A1) English, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

239 - 241

Deles,J. et al.; Polish Journal of Chemistry; vol. 53; (1979); p. 1025 - 1032, View in Reaxys 2 of 2

Melting Point [°C]

240 - 243

Comment (Melting Point)

Decomposition.

Benington et al.; Journal of Organic Chemistry; vol. 23; (1958); p. 1979,1980, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.; Journal of Medicinal Chemistry; vol. 51; nb. 21; (2008); p. 6808 - 6828, View in Reaxys

Decomposition (1) 1 of 1

Decomposition [°C]

239 - 241

Solvent (Decomposition) isopropyl alcohol Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.; Journal of Medicinal Chemistry; vol. 51; nb. 21; (2008); p. 6808 - 6828, View in Reaxys NMR Spectroscopy (7) 1 of 7

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

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

400

Location

supporting information

Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 - 2700, View in Reaxys 2 of 7

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

13C

Solvents (NMR Spectro- water scopy) Location

supporting information

Jackson, Douglas M.; Ashley, Robert L.; Brownfield, Callan B.; Morrison, Daniel R.; Morrison, Richard W.; Synthetic Communications; vol. 45; nb. 23; (2015); p. 2691 - 2700, View in Reaxys 3 of 7

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

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

300

Location

supporting information

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

13C

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

100

Location

supporting information

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H-NMR

Location

Page/Page column 112

Comment (NMR Spectroscopy)

Signals given

(400 MHz, DMSO-d6) δ: 7.52 (m, 2H), 7.24 (m, 2H), 3.18 (m, 2H), 2.95 (m, 2H).

Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); (A1) English, View in Reaxys 6 of 7

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

Solvents (NMR Spectro- d(4)-methanol scopy) Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.; Journal of Medicinal Chemistry; vol. 51; nb. 21; (2008); p. 6808 - 6828, View in Reaxys 7 of 7

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

13C

References

CI (Chemical ioni- supporting inforzation); gas chro- mation matography mass

29/53

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spectrometry (GCMS); spectrum ESI (Electrospray ionisation)

Page/Page column 112

Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); (A1) English, View in Reaxys

Reaxys ID 2717969 View in Reaxys

6/43 CAS Registry Number: 4302-85-6 Chemical Name: p-bromomethamphetamine; 4-bromo-N-methylphenylisopropylamine; <1-Methyl-2-(4-bromphenyl)-aethyl>methylamin; [1-Methyl-2-(4-bromphenyl)-aethyl]-methylamin Linear Structure Formula: C10H14BrN Molecular Formula: C10H14BrN Molecular Weight: 228.132 Type of Substance: isocyclic InChI Key: RHHFGACRACGCQS-UHFFFAOYSA-N Note:

H N

Substance Label (5) Label References BMA

Nakahara, Yuji; Hanajiri, Ruri; Life Sciences; vol. 66; nb. 7; (2000); p. 563 - 574, View in Reaxys

Acs, Maria; Kozma, David; Fogassy, Elemer; ACH - Models in Chemistry; vol. 132; nb. 3; (1995); p. 475 478, View in Reaxys

D und L

Patent; Chinoin Gy.es Veg.Term.Gyara Rt.; HU12209; (1974); Chem.Abstr.; vol. 85; nb. 192336p; (1976), View in Reaxys

I, R=H, R1=Br

Patent; Chinoin Gyog. es Veg. Termekek Gyara Rt; AT271436; (1965); Chem.Abstr.; vol. 71; nb. 80910a; (1969), View in Reaxys

Patent; Chinoin; FRAD94906, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product Derivative (3) Comment (Derivative)

Patent; Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.; US2007/27208; (2007); (A1) English, View in Reaxys References

Bromhydrat; F: 174-175grad

Patent; Zoltan et al.; HU154060; (1968); Ref. Zh., Khim.; vol. 6; nb. N444P; (1970), View in Reaxys

HBr-Salz: F: 156-158grad

Patent; Chinoin Gyog. es Veg. Termekek Gyara Rt; AT271436; (1965); Chem.Abstr.; vol. 71; nb. 80910a; (1969), View in Reaxys

Hydrobromid: F: 156-158grad

Patent; Chinoin; FRAD94906, View in Reaxys

Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

72 - 76

0.1

Patent; Zoltan et al.; HU154060; (1968); Ref. Zh., Khim.; vol. 6; nb. N444P; (1970), View in Reaxys

81 - 83

0.2

Patent; Chinoin; FRAD94906, View in Reaxys; Patent; Chinoin Gyog. es Veg. Termekek Gyara Rt; AT271436; (1965); Chem.Abstr.; vol. 71; nb. 80910a; (1969), View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

30/53

2016-06-12 07:01:14

1.5454

589

Patent; Chinoin; FRAD94906, View in Reaxys; Patent; Chinoin Gyog. es Veg. Termekek Gyara Rt; AT271436; (1965); Chem.Abstr.; vol. 71; nb. 80910a; (1969), View in Reaxys

Liquid/Liquid Systems (MCS) (1) 1 of 1

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Comment (Liquid/Liquid Systems (MCS))

ambient temperature

Partner (Liquid/Liquid Systems (MCS))

octanol

Nakahara, Yuji; Hanajiri, Ruri; Life Sciences; vol. 66; nb. 7; (2000); p. 563 - 574, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.; US2007/27208; (2007); (A1) English, View in Reaxys; Patent; Chinoin; FRAD94906, View in Reaxys; Patent; Zoltan et al.; HU154060; (1968); Ref. Zh., Khim.; vol. 6; nb. N444P; (1970), View in Reaxys; Patent; Chinoin Gyog. es Veg. Termekek Gyara Rt; AT271436; (1965); Chem.Abstr.; vol. 71; nb. 80910a; (1969), View in Reaxys; Patent; Chinoin Gy.es Veg.Term.Gyara Rt.; HU12209; (1974); Chem.Abstr.; vol. 85; nb. 192336p; (1976), View in Reaxys; Acs, Maria; Kozma, David; Fogassy, Elemer; ACH - Models in Chemistry; vol. 132; nb. 3; (1995); p. 475 - 478, View in Reaxys; Nakahara, Yuji; Hanajiri, Ruri; Life Sciences; vol. 66; nb. 7; (2000); p. 563 - 574, View in Reaxys 2 of 3

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

Dark-Agouti rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

daily dose

Method (Pharmacological Data)

rats with shaved back hair administered with title comp. for 10 days; newly growing back hair collected 28 days after first injection; title comp. conc. determined by gas chromatography-mass spectrometry analysis

Results

44.6 ng/mg title comp. found in hair of treated rats (table, figure)

Nakahara, Yuji; Hanajiri, Ruri; Life Sciences; vol. 66; nb. 7; (2000); p. 563 - 574, View in Reaxys 3 of 3

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

Dark-Agouti rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

5 mg/kg

Method (Pharmacological Data)

rats administered with title comp.; blood collected 5-360 min after injection; title comp. conc. determined by gas chromatography-mass spectrometry analysis

Further Details (Pharmacological Data)

Cmax: maximal concentration; Tmax: time of maximum concentration; AUC: area under curve

Results

title comp. found in rat plasma with Cmax: 263 ng/ml, Tmax: 30 min and AUC 49.1 μg min/ml (table, figure)

Nakahara, Yuji; Hanajiri, Ruri; Life Sciences; vol. 66; nb. 7; (2000); p. 563 - 574, View in Reaxys

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Reaxys ID 14779284 View in Reaxys

7/43 CAS Registry Number: 785032-26-0 Chemical Name: 2-(3-bromophenyl)-N-methylethanamine; [2(3-bromo-phenyl)-ethyl]-methyl-amine Linear Structure Formula: C9H12BrN Molecular Formula: C9H12BrN Molecular Weight: 214.105 InChI Key: IJCWRWHKCBWPDJ-UHFFFAOYSA-N Note:

H N

Substance Label (3) Label References Example 13A

Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy; BATES, J. Alex; CHENEY, Daniel L.; WO2014/201073; (2014); (A1) English, View in Reaxys

222

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Patent-Specific Data (1) References Patent; Laboratorios del Dr. Esteve S.A.; EP1935886; (2008); (A1) English, View in Reaxys Derivative (1) Derivative N-methyl-2-(3bromophenyl)ethylamine hydrochloride

References Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Crystal Property Description (4) Colour & Other Location Properties colourless

Paragraph 00279

colourless

light-yellow

References Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy; BATES, J. Alex; CHENEY, Daniel L.; WO2014/201073; (2014); (A1) English, View in Reaxys Herth, Matthias M.; Hansen, Hanne D.; Ettrup, Anders; Dyssegaard, Agnete; Lehel, Szabolcs; Kristensen, Jesper; Knudsen, Gitte M.; Bioorganic and Medicinal Chemistry; vol. 20; nb. 14; (2012); p. 4574 - 4581, View in Reaxys

Page/Page column 131

colorless

Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; HUTTUNEN, Kristiina Maria; LYONS, Dani Michelle; TRAPANI, Joseph Albert; SMYTH, Mark John; DENNY, William Alexander; WO2011/75784; (2011); (A1) English, View in Reaxys Patent; Laboratorios del Dr. Esteve S.A.; EP1935886; (2008); (A1) English, View in Reaxys; Patent; Laboratorios del Dr. Esteve S.A.; EP1997493; (2008); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

300

Herth, Matthias M.; Hansen, Hanne D.; Ettrup, Anders; Dyssegaard, Agnete; Lehel, Szabolcs; Kristensen, Jesper; Knudsen, Gitte M.; Bioorganic and Medicinal Chemistry; vol. 20; nb. 14; (2012); p. 4574 - 4581, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

32/53

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

400

Original Text (NMR Spectroscopy)

NMR [400 MHz, CDC13] δ 7.26-7.36 (m, 2 H), 7.22 (s, 1 H), 7.16-7.20 (m, 1 H), 2.76-2.87 (m, 4 H), 2.44 (s, 3 H), 1.52 (bs, 1 H).

Location

Page/Page column 131

Comment (NMR Spectroscopy)

Signals given

Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; HUTTUNEN, Kristiina Maria; LYONS, Dani Michelle; TRAPANI, Joseph Albert; SMYTH, Mark John; DENNY, William Alexander; WO2011/75784; (2011); (A1) English, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

Paragraph 00279

References Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy; BATES, J. Alex; CHENEY, Daniel L.; WO2014/201073; (2014); (A1) English, View in Reaxys

GCMS (Gas chromatography mass spectrometry); EI (Electron impact); Spectrum

CI (Chemical ioni- Page/Page colzation) umn 131

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; Laboratorios del Dr. Esteve S.A.; EP1935886; (2008); (A1) English, View in Reaxys; Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 7423, View in Reaxys; Patent; Laboratorios del Dr. Esteve S.A.; EP1997493; (2008); (A1) English, View in Reaxys; Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; HUTTUNEN, Kristiina Maria; LYONS, Dani Michelle; TRAPANI, Joseph Albert; SMYTH, Mark John; DENNY, William Alexander; WO2011/75784; (2011); (A1) English, View in Reaxys; Herth, Matthias M.; Hansen, Hanne D.; Ettrup, Anders; Dyssegaard, Agnete; Lehel, Szabolcs; Kristensen, Jesper; Knudsen, Gitte M.; Bioorganic and Medicinal Chemistry; vol. 20; nb. 14; (2012); p. 4574 - 4581, View in Reaxys; Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy; BATES, J. Alex; CHENEY, Daniel L.; WO2014/201073; (2014); (A1) English, View in Reaxys 2 of 2

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

RD-HGA16 cells expressing human TAAR 1 receptor

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hTAAR1: human trace amine receptor 1; Emax: maximal title comp. efficacy

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

1070 nmol/l

Results

title comp. exhibited Emax 71percent

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

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Reaxys ID 2717019 View in Reaxys

8/43 CAS Registry Number: 4302-94-7; 14611-60-0 Chemical Name: <1-Methyl-2-(2-bromphenyl)-aethyl>-methylamin; 1-(o-Bromphenyl)-2-methylaminopropan Linear Structure Formula: C10H14BrN Molecular Formula: C10H14BrN Molecular Weight: 228.132 Type of Substance: isocyclic InChI Key: DKQQZKGGVNMTBO-UHFFFAOYSA-N Note:

H N

Substance Label (2) Label References I, R=Br, R1=H

Patent; Chinoin Gyog. es Veg. Termekek Gyara Rt; AT271436; (1965); Chem.Abstr.; vol. 71; nb. 80910a; (1969), View in Reaxys

Patent; Chinoin; FRAD94906, View in Reaxys

Derivative (6) Comment (Derivative)

References

Hydrobromid:F: 174-175gradC

Patent; Chinoin Gyogyszer-es Vegyeszeti Termekek Gyara Rt.; GB1142981; (1969); Chem.Abstr.; vol. 70; nb. 67866; (1969), View in Reaxys

Bromhydrat; F: 89grad

Patent; Zoltan et al.; HU154060; (1968); Ref. Zh., Khim.; vol. 6; nb. N444P; (1970), View in Reaxys

Bromhydrat; F: 159-160grad

Patent; Zoltan et al.; HU154060; (1968); Ref. Zh., Khim.; vol. 6; nb. N444P; (1970), View in Reaxys

HBr: F: 169-170grad

Patent; Chinoin; NL6605956; (1966); Chem.Abstr.; vol. 67; nb. 21611; (1967), View in Reaxys

HBr-Salz: F: 162-164grad

Patent; Chinoin Gyog. es Veg. Termekek Gyara Rt; AT271436; (1965); Chem.Abstr.; vol. 71; nb. 80910a; (1969), View in Reaxys

Hydrobromid: F: 174-175grad

Patent; Chinoin; FRAD94906, View in Reaxys

Boiling Point (5) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

72 - 76

0.1

Patent; Chinoin; FRAD94906, View in Reaxys; Patent; Chinoin Gyogyszer-es Vegyeszeti Termekek Gyara Rt.; GB1142981; (1969); Chem.Abstr.; vol. 70; nb. 67866; (1969), View in Reaxys

110

0.1

Patent; Zoltan et al.; HU154060; (1968); Ref. Zh., Khim.; vol. 6; nb. N444P; (1970), View in Reaxys

84 - 85

0.4

Patent; Zoltan et al.; HU154060; (1968); Ref. Zh., Khim.; vol. 6; nb. N444P; (1970), View in Reaxys

75 - 76

0.1

Patent; Chinoin; NL6605956; (1966); Chem.Abstr.; vol. 67; nb. 21611; (1967), View in Reaxys

85 - 87

0.3

Patent; Chinoin Gyog. es Veg. Termekek Gyara Rt; AT271436; (1965); Chem.Abstr.; vol. 71; nb. 80910a; (1969), View in Reaxys

Refractive Index (2) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5452

589

Patent; Chinoin; FRAD94906, View in Reaxys; Patent; Chinoin Gyogyszer-es Vegyeszeti Termekek Gyara Rt.; GB1142981; (1969); Chem.Abstr.; vol. 70; nb. 67866; (1969), View in Reaxys

1.5495

589

Patent; Chinoin; NL6605956; (1966); Chem.Abstr.; vol. 67; nb. 21611; (1967), View in Reaxys

34/53

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Reaxys ID 2962588 View in Reaxys

9/43 CAS Registry Number: 61610-64-8 Chemical Name: 2-(ortho-bromophenyl)-1-methylethylamine; 1-(ortho-bromomethyl)-2-amino-propane; 2-(2-bromophenyl)-1methylethylamine; 2-(o-bromophenyl)-1-methylethylamine; 2-(2bromo-phenyl)-1-methyl-ethylamine; 2-(2-Brom-phenyl)-1-methyl-aethylamin; 2-Amino-1-(2-brom-phenyl)-propan Linear Structure Formula: C9H12BrN Molecular Formula: C9H12BrN Molecular Weight: 214.105 Type of Substance: isocyclic InChI Key: VGJBPBDFJNFFRO-UHFFFAOYSA-N Note:

Br NH 2

Substance Label (2) Label References 6b

Viswanathan, Rajesh; Prabhakaran, Erode N.; Plotkin, Michael A.; Johnston, Jeffrey N.; Journal of the American Chemical Society; vol. 125; nb. 1; (2003); p. 163 - 168, View in Reaxys

4, R1=H, R2=CH3

Johnston, Jeffrey N.; Plotkin, Michael A.; Viswanathan, Rajesh; Prabhakaran, Erode N.; Organic Letters; vol. 3; nb. 7; (2001); p. 1009 - 1011, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product Boiling Point (1) Boiling Point [°C] 118

Patent; A. H. Robins Company, Incorporated; US4857553; (1989); (A1) English, View in Reaxys Pressure (Boiling Point) [Torr]

References

Patrick; McBee; Hass; Journal of the American Chemical Society; vol. 68; (1946); p. 1009, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5582

Patrick; McBee; Hass; Journal of the American Chemical Society; vol. 68; (1946); p. 1009, View in Reaxys

589

Density (1) 1 of 1

Density [g·cm-3]

1.2984

Reference Temperature [°C]

Measurement Temperature [°C]

Patrick; McBee; Hass; Journal of the American Chemical Society; vol. 68; (1946); p. 1009, View in Reaxys NMR Spectroscopy (3) 1 of 3

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

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

400

Viswanathan, Rajesh; Prabhakaran, Erode N.; Plotkin, Michael A.; Johnston, Jeffrey N.; Journal of the American Chemical Society; vol. 125; nb. 1; (2003); p. 163 - 168, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

35/53

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

400

Viswanathan, Rajesh; Prabhakaran, Erode N.; Plotkin, Michael A.; Johnston, Jeffrey N.; Journal of the American Chemical Society; vol. 125; nb. 1; (2003); p. 163 - 168, View in Reaxys 3 of 3

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

13C

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

100

Viswanathan, Rajesh; Prabhakaran, Erode N.; Plotkin, Michael A.; Johnston, Jeffrey N.; Journal of the American Chemical Society; vol. 125; nb. 1; (2003); p. 163 - 168, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Viswanathan, Rajesh; Prabhakaran, Erode N.; Plotkin, Michael A.; Johnston, Jeffrey N.; Journal of the American Chemical Society; vol. 125; nb. 1; (2003); p. 163 - 168, View in Reaxys

Reaxys ID 4307143 View in Reaxys

10/43 CAS Registry Number: 61610-65-9 Chemical Name: 1-(3-bromophenyl)-2-aminopropane; 1-(3bromophenyl)propan-2-amine; DL-3-bromoamphetamine Linear Structure Formula: C9H12BrN Molecular Formula: C9H12BrN Molecular Weight: 214.105 Type of Substance: isocyclic InChI Key: ATRSAWXXYCBXLI-UHFFFAOYSA-N Note:

NH 2

Patent-Specific Data (2) Prophetic ComLocation in Patent References pound Page/Page column

Patent; HOFFMANN-LA ROCHE INC.; Han, Xingchun; Javanbakht, Hassan; Jiang, Min; Liang, Chungen; Wang, Jianping; Wang, Yongguang; Wang, Zhanguo; Weikert, Robert James; Yang, Song; Zhou, Chengang; US2015/210682; (2015); (A1) English, View in Reaxys

prophetic product

Patent; A. H. Robins Company, Incorporated; US4857553; (1989); (A1) English, View in Reaxys

Reaxys ID 5425402 View in Reaxys Br

11/43 CAS Registry Number: 915025-70-6 Chemical Name: N-methyl-N-(2-(2-bromophenyl)ethyl)amine; 2-(2-bromophenyl)-N-methylethanamine; [2-(2-bromophenyl)ethyl]methylamine Linear Structure Formula: C9H12NBr Molecular Formula: C9H12BrN Molecular Weight: 214.105

H N

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Type of Substance: isocyclic InChI Key: PBWMDNDMVICFTB-UHFFFAOYSA-N Note: Substance Label (2) Label References 64

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Donets, Pavel A.; Van Der Eycken, Erik V.; Organic Letters; vol. 9; nb. 16; (2007); p. 3017 - 3020, View in Reaxys

Derivative (1) Derivative N-methyl-2-(2bromophenyl)ethylamine hydrochloride Boiling Point (1) Boiling Point [°C] 80

References Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Pressure (Boiling Point) [Torr]

Location

References

0.05

supporting information

Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 - 9632, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 - 9632, 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]

400

Location

supporting information

Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 - 9632, 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]

100.6

Location

supporting information

Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 - 9632, View in Reaxys 3 of 4

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

Solvents (NMR Spectro- CDCl3 scopy)

37/53

2016-06-12 07:01:14

Frequency (NMR Spectroscopy) [MHz]

300

Donets, Pavel A.; Van Der Eycken, Erik V.; Organic Letters; vol. 9; nb. 16; (2007); p. 3017 - 3020, View in Reaxys 4 of 4

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

13C

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

Donets, Pavel A.; Van Der Eycken, Erik V.; Organic Letters; vol. 9; nb. 16; (2007); p. 3017 - 3020, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; chemical ionization (CI)

Donets, Pavel A.; Van Der Eycken, Erik V.; Organic Letters; vol. 9; nb. 16; (2007); p. 3017 - 3020, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Sielecki, Thais M.; Meyers, A. I.; Journal of Organic Chemistry; vol. 57; nb. 13; (1992); p. 3673 - 3676, View in Reaxys; Su, Xianbin; Fox, David J.; Blackwell, David T.; Tanaka, Kiyotaka; Spring, David R.; Chemical Communications; nb. 37; (2006); p. 3883 - 3885, View in Reaxys; Donets, Pavel A.; Van Der Eycken, Erik V.; Organic Letters; vol. 9; nb. 16; (2007); p. 3017 - 3020, View in Reaxys; Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys; Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 9632, View in Reaxys 2 of 2

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

RD-HGA16 cells expressing human TAAR 1 receptor

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hTAAR1: human trace amine receptor 1; Emax: maximal title comp. efficacy

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

205 nmol/l

Results

title comp. exhibited Emax 93percent

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Reaxys ID 11228925 View in Reaxys

12/43 CAS Registry Number: 725683-06-7 Chemical Name: 2-(4-bromophenyl)-N-methylethanamine Linear Structure Formula: C9H12BrN Molecular Formula: C9H12BrN Molecular Weight: 214.105 InChI Key: CJLDHHONSQXJTC-UHFFFAOYSA-N Note:

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Substance Label (4) Label References 216

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Junek, Richard; Brunova, Bohumila; Kverka, Miloslav; Panajotova, Vladimira; Jandera, Antonin; Kuchar, Miroslav; European Journal of Medicinal Chemistry; vol. 42; nb. 8; (2007); p. 1084 - 1094, View in Reaxys

23B

Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/76431; (2007); (A1) English, View in Reaxys

Derivative (1) Derivative

References

N-methyl-2-(4bromophenyl)ethylamine hydrochloride

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Crystal Property Description (2) Colour & Other Location Properties yellow

Page/Page column 129

yellow

References Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; HUTTUNEN, Kristiina Maria; LYONS, Dani Michelle; TRAPANI, Joseph Albert; SMYTH, Mark John; DENNY, William Alexander; WO2011/75784; (2011); (A1) English, View in Reaxys Chan, Daniel Shiu-Hin; Yang, Hui; Kwan, Maria Hiu-Tung; Cheng, Zhen; Lee, Paul; Bai, Li-Ping; Jiang, Zhi-Hong; Wong, Chun-Yuen; Fong, Wang-Fun; Leung, ChungHang; Ma, Dik-Lung; Biochimie; vol. 93; nb. 6; (2011); p. 1055 - 1064, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

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

400

Original Text (NMR Spectroscopy)

NMR [400 MHz, CDC13] δ 7.41 (d, J = 8.4 Hz, 2 H), 7.08 (d, J = 8.3 Hz, 2 H), 2.73-2.86 (m, 4 H), 2.43 (s, 3 H), 1.48 (bs, 1 H).

Location

Page/Page column 129

Comment (NMR Spectroscopy)

Signals given

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

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

300

Chan, Daniel Shiu-Hin; Yang, Hui; Kwan, Maria Hiu-Tung; Cheng, Zhen; Lee, Paul; Bai, Li-Ping; Jiang, ZhiHong; Wong, Chun-Yuen; Fong, Wang-Fun; Leung, Chung-Hang; Ma, Dik-Lung; Biochimie; vol. 93; nb. 6; (2011); p. 1055 - 1064, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

Comment (Mass Spectrometry)

References

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CI (Chemical ioni- Page/Page colzation) umn 129

ESI (Electrospray ionisation)

Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/76431; (2007); (A1) English, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/76431; (2007); (A1) English, View in Reaxys; Junek, Richard; Brunova, Bohumila; Kverka, Miloslav; Panajotova, Vladimira; Jandera, Antonin; Kuchar, Miroslav; European Journal of Medicinal Chemistry; vol. 42; nb. 8; (2007); p. 1084 - 1094, View in Reaxys; Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 7423, View in Reaxys; Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; HUTTUNEN, Kristiina Maria; LYONS, Dani Michelle; TRAPANI, Joseph Albert; SMYTH, Mark John; DENNY, William Alexander; WO2011/75784; (2011); (A1) English, View in Reaxys; Chan, Daniel Shiu-Hin; Yang, Hui; Kwan, Maria Hiu-Tung; Cheng, Zhen; Lee, Paul; Bai, Li-Ping; Jiang, Zhi-Hong; Wong, Chun-Yuen; Fong, Wang-Fun; Leung, Chung-Hang; Ma, Dik-Lung; Biochimie; vol. 93; nb. 6; (2011); p. 1055 - 1064, View in Reaxys 2 of 2

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

RD-HGA16 cells expressing human TAAR 1 receptor

Method (Pharmacological Data)

Further Details (Pharmacological Data)

hTAAR1: human trace amine receptor 1; Emax: maximal title comp. efficacy

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

1070 nmol/l

Results

title comp. exhibited Emax 71percent

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Reaxys ID 3703221 View in Reaxys

13/43 CAS Registry Number: 58400-88-7 Chemical Name: 2-(4-bromo-phenyl)-1-methyl-ethylamine; hydrochloride; 2-(4-Brom-phenyl)-1-methyl-aethylamin; Hydrochlorid Linear Structure Formula: C9H12BrN*ClH Molecular Formula: C9H12BrN*ClH Molecular Weight: 250.566 Type of Substance: isocyclic InChI Key: BPCNYQPDJBGATO-UHFFFAOYSA-N Note:

Br Cl

NH 2

Melting Point (2) 1 of 2

Melting Point [°C]

202 - 203

Kabalka, George W.; Laila Guindi; Varma, Rajender S.; Tetrahedron; vol. 46; nb. 21; (1990); p. 7443 - 7457, View in Reaxys 2 of 2

Melting Point [°C]

204 - 206

Patrick; McBee; Hass; Journal of the American Chemical Society; vol. 68; (1946); p. 1009, View in Reaxys

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Reaxys ID 4208176 View in Reaxys

14/43 CAS Registry Number: 119744-48-8 Chemical Name: N-Ethyl-2-(4-bromophenyl)ethylamine hydrochloride Linear Structure Formula: C10H14BrN*ClH Molecular Formula: C10H14BrN*ClH Molecular Weight: 264.593 Type of Substance: isocyclic InChI Key: WKMQEFNPKGIWHT-UHFFFAOYSA-N Note:

H N Cl

Substance Label (1) Label References 5e*HCl

Hardy, George W.; Lowe, Lawrence A.; Mills, Gail; Sang, Pang Yih; Simpkin, Dean S. A.; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 5; (1989); p. 1108 - 1118, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

172 - 174

Kabalka, George W.; Laila Guindi; Varma, Rajender S.; Tetrahedron; vol. 46; nb. 21; (1990); p. 7443 - 7457, View in Reaxys 2 of 2

Melting Point [°C]

223 - 225

Solvent (Melting Point)

dioxane

Hardy, George W.; Lowe, Lawrence A.; Mills, Gail; Sang, Pang Yih; Simpkin, Dean S. A.; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 5; (1989); p. 1108 - 1118, View in Reaxys

Reaxys ID 13820450 View in Reaxys

15/43 Chemical Name: 2-(4-Bromo-phenyl)ethylamine hydrobromide; 4-bromophenethylamine hydrobromide Linear Structure Formula: BrH*C8H10BrN Molecular Formula: BrH*C8H10BrN Molecular Weight: 280.99 InChI Key: IUWPMHYAMOUYKQ-UHFFFAOYSA-N Note:

NH 2 HBr Br

Reaxys ID 14751869 View in Reaxys

16/43 CAS Registry Number: 214209-95-7 Chemical Name: N-methyl-2-(4-bromophenyl)ethylamine hydrochloride; [2-(4-bromophenyl)ethyl]-N-methylamine hydrochloride Linear Structure Formula: C9H12BrN*ClH Molecular Formula: C9H12BrN*ClH Molecular Weight: 250.566 InChI Key: CGKOMNPUEGGUPP-UHFFFAOYSA-N Note:

H N HCl Br

Substance Label (1) Label References 68, hydrochloride

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

196

Solvent (Melting Point)

methanol; diethyl ether

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

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NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys 2 of 2

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

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys Mass Spectrometry (1) Comment (Mass Peak Spectrometry)

References

Molecular peak

Patent; AstraZeneca AB; US6300352; (2001); (B1) English, View in Reaxys

214 m/z

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; AstraZeneca AB; US6300352; (2001); (B1) English, View in Reaxys; Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Reaxys ID 14751870 View in Reaxys

17/43 CAS Registry Number: 214209-94-6 Chemical Name: N-methyl-2-(3-bromophenyl)ethylamine hydrochloride; [2-(3-bromophenyl)ethyl]methylamine hydrochloride Linear Structure Formula: C9H12BrN*ClH Molecular Formula: C9H12BrN*ClH Molecular Weight: 250.566 InChI Key: ZFHNLQQYLVKJBK-UHFFFAOYSA-N Note:

H N HCl

Substance Label (1) Label References 66, hydrochloride

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

124

Solvent (Melting Point)

methanol; diethyl ether

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys NMR Spectroscopy (2)

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1 of 2

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys 2 of 2

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

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

References

Molecular peak

Patent; AstraZeneca AB; US6300352; (2001); (B1) English, View in Reaxys

214 m/z

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 3691223 View in Reaxys

18/43 Chemical Name: 3-bromo-phenethylamine; hydrochloride; 3Brom-phenaethylamin; Hydrochlorid Linear Structure Formula: C8H10BrN*ClH Molecular Formula: C8H10BrN*ClH Molecular Weight: 236.539 Type of Substance: isocyclic InChI Key: JOMPYVLDZUHKSR-UHFFFAOYSA-N Note:

NH 2 Cl

Melting Point (1) 1 of 1

Melting Point [°C]

225

Ishiwata; Yakugaku Zasshi; vol. 51; (1931); p. 755,765, View in Reaxys

Reaxys ID 3696518 View in Reaxys

19/43 Chemical Name: 3-bromo-phenethylamine; hydrobromide; 3Brom-phenaethylamin; Hydrobromid Linear Structure Formula: C8H10BrN*BrH Molecular Formula: BrH*C8H10BrN Molecular Weight: 280.99 Type of Substance: isocyclic

NH 2

Br H

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InChI Key: LTACTYKNGJFBJI-UHFFFAOYSA-N Note: Melting Point (1) 1 of 1

Melting Point [°C]

235 - 236

Ishiwata; Yakugaku Zasshi; vol. 51; (1931); p. 755,765, View in Reaxys

Reaxys ID 3699067 View in Reaxys

20/43 Chemical Name: 2-(2-bromo-phenyl)-1-methyl-ethylamine; hydrochloride; 2-(2-Brom-phenyl)-1-methyl-aethylamin; Hydrochlorid Linear Structure Formula: C9H12BrN*ClH Molecular Formula: C9H12BrN*ClH Molecular Weight: 250.566 Type of Substance: isocyclic InChI Key: JUVADODGTIMLDV-UHFFFAOYSA-N Note:

Br NH 2

Melting Point (1) 1 of 1

Melting Point [°C]

200 - 201

Patrick; McBee; Hass; Journal of the American Chemical Society; vol. 68; (1946); p. 1009, View in Reaxys

Reaxys ID 4230962 View in Reaxys

21/43 CAS Registry Number: 132336-05-1 Linear Structure Formula: C10H14BrN Molecular Formula: C10H14BrN Molecular Weight: 228.132 Type of Substance: isocyclic InChI Key: FIASMMZEENJBED-UHFFFAOYSA-N Note:

H N

Substance Label (1) Label References 9 (R = R'' = H, R'= Kabalka, George W.; Laila Guindi; Varma, Rajender S.; Tetrahedron; vol. 46; nb. 21; (1990); p. 7443 Br) 7457, View in Reaxys Derivative (1) Derivative N-Ethyl-2-(4-bromophenyl)ethylamine hydrochloride

References Kabalka, George W.; Laila Guindi; Varma, Rajender S.; Tetrahedron; vol. 46; nb. 21; (1990); p. 7443 7457, View in Reaxys

Reaxys ID 4398631 View in Reaxys

22/43 CAS Registry Number: 109971-39-3 Chemical Name: N-isopropyl p-bromoamphetamine Linear Structure Formula: C12H18BrN Molecular Formula: C12H18BrN Molecular Weight: 256.186 Type of Substance: isocyclic InChI Key: LRLQTMFGXRRQOB-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References

44/53

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Kabalka, George W.; Varma, Rajender S.; Gai, Yuan-Zhu; Baldwin, Ronald M.; Tetrahedron Letters; vol. 27; nb. 33; (1986); p. 3843 - 3844, View in Reaxys

Reaxys ID 6387398 View in Reaxys

23/43 Linear Structure Formula: C11H16BrN Molecular Formula: C11H16BrN Molecular Weight: 242.159 Type of Substance: isocyclic InChI Key: AAVUCOBJHRAQLW-UHFFFAOYSA-N Note:

H N

Substance Label (1) Label References 4b

Tomioka, Hideo; Tabayashi, Kazuo; Izava, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 13; (1985); p. 906 - 907, View in Reaxys

Reaxys ID 7410545 View in Reaxys

24/43 Linear Structure Formula: C10H14BrN Molecular Formula: C10H14BrN Molecular Weight: 228.132 Type of Substance: isocyclic InChI Key: RHHFGACRACGCQS-UHFFFAOYSA-N Note:

H N

Br (+)-enantiomer

Substance Label (1) Label References (+)-V

Acs, Maria; Kozma, David; Fogassy, Elemer; ACH - Models in Chemistry; vol. 132; nb. 3; (1995); p. 475 478, View in Reaxys

Purification (1) Purification (method) via salt with sodium-hydrogenR,R-tartrate

References Acs, Maria; Kozma, David; Fogassy, Elemer; ACH - Models in Chemistry; vol. 132; nb. 3; (1995); p. 475 478, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

6.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Acs, Maria; Kozma, David; Fogassy, Elemer; ACH - Models in Chemistry; vol. 132; nb. 3; (1995); p. 475 - 478, View in Reaxys

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Reaxys ID 7410546 View in Reaxys

25/43 Linear Structure Formula: C10H14BrN Molecular Formula: C10H14BrN Molecular Weight: 228.132 Type of Substance: isocyclic InChI Key: RHHFGACRACGCQS-UHFFFAOYSA-N Note:

H N

Br (-)-enantiomer

Substance Label (1) Label References (-)-V

Acs, Maria; Kozma, David; Fogassy, Elemer; ACH - Models in Chemistry; vol. 132; nb. 3; (1995); p. 475 478, View in Reaxys

Purification (1) Purification (method) via salt with sodium-hydrogenR,R-tartrate

References Acs, Maria; Kozma, David; Fogassy, Elemer; ACH - Models in Chemistry; vol. 132; nb. 3; (1995); p. 475 478, View in Reaxys

Reaxys ID 9322241 View in Reaxys

26/43 Chemical Name: [15N]2-(2-bromophenyl)ethylamine Linear Structure Formula: C8H10Br(15)N Molecular Formula: C8H10BrN Molecular Weight: 201.071 Type of Substance: isocyclic InChI Key: ITRNQMJXZUWZQL-DETAZLGJSA-N Note:

Br 15NH

Reaxys ID 11129205 View in Reaxys

27/43 CAS Registry Number: 947530-52-1 Chemical Name: [2-(2-bromophenyl)ethyl]isopropylamine Linear Structure Formula: C11H16NBr Molecular Formula: C11H16BrN Molecular Weight: 242.159 InChI Key: JVDZDFXSEQADHL-UHFFFAOYSA-N Note:

Substance Label (1) Label References 2e

Donets, Pavel A.; Van Der Eycken, Erik V.; Organic Letters; vol. 9; nb. 16; (2007); p. 3017 - 3020, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

13C

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

Donets, Pavel A.; Van Der Eycken, Erik V.; Organic Letters; vol. 9; nb. 16; (2007); p. 3017 - 3020, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

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

300

Donets, Pavel A.; Van Der Eycken, Erik V.; Organic Letters; vol. 9; nb. 16; (2007); p. 3017 - 3020, View in Reaxys

Reaxys ID 13684053 View in Reaxys

28/43 Chemical Name: [2-(4-bromophenyl)-1-methylethyl]ethylamine hydrochloride Linear Structure Formula: C11H16BrN*ClH Molecular Formula: C11H16BrN*ClH Molecular Weight: 278.62 InChI Key: HPHJIDVLKJJTQL-UHFFFAOYSA-N Note:

Br HCl N H

Melting Point (1) 1 of 1

Melting Point [°C]

175 - 176

Patent; Syntex (U.S.A.) LLC; US6319920; (2001); (B1) English, View in Reaxys

Reaxys ID 13909570 View in Reaxys

29/43 Chemical Name: [2-(4-bromo-phenyl)-ethyl]-heptyl-amine Linear Structure Formula: C15H24BrN Molecular Formula: C15H24BrN Molecular Weight: 298.266 InChI Key: LBYZFYWWKDJJAY-UHFFFAOYSA-N Note:

H N

Reaxys ID 17720656 View in Reaxys

30/43 Chemical Name: (2-bromophenethyl)ammoniumiodide Linear Structure Formula: I(1-)*H3NCH2CH2C6H4Br(1+)=[H3NCH2CH2C6H4Br]I Molecular Formula: C8H10BrN*HI Molecular Weight: 327.991 InChI Key: VNXQWEHSHCRRLQ-UHFFFAOYSA-N Note:

NH 2 HI

Reaxys ID 18608590 View in Reaxys

31/43

47/53

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H N

CAS Registry Number: 1067237-68-6 Chemical Name: N-methyl-2-(2-bromophenyl)ethylamine hydrochloride Linear Structure Formula: C9H12BrN*ClH Molecular Formula: C9H12BrN*ClH Molecular Weight: 250.566 InChI Key: IBURWEBFFVLKFV-UHFFFAOYSA-N Note:

HCl

Substance Label (1) Label References 64, hydrochloride

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

109

Solvent (Melting Point)

methanol; diethyl ether

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys 2 of 2

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

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Reaxys ID 18858723 View in Reaxys 2H 2H

32/43 CAS Registry Number: 1093176-86-3 Chemical Name: N-(methyl-d3)-N-(2-(2-bromophenyl)ethyl)amine Linear Structure Formula: C9H9 (2)H3BrN Molecular Formula: C9H12BrN Molecular Weight: 217.081 InChI Key: PBWMDNDMVICFTB-FIBGUPNXSA-N Note:

48/53

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Crystal Property Description (1) Colour & Other Location Properties yellow

References

supporting information

Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 - 9632, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

400

Location

supporting information

Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 - 9632, View in Reaxys 2 of 2

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

13C

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

100.6

Location

supporting information

Jarboe, Stephen G.; Terrazas, Michael S.; Beak, Peter; Journal of Organic Chemistry; vol. 73; nb. 24; (2008); p. 9627 - 9632, View in Reaxys

Reaxys ID 19133269 View in Reaxys

33/43 CAS Registry Number: 919347-79-8 Chemical Name: 2-(3-bromophenyl)-N-ethylethanamine Linear Structure Formula: C10H14BrN Molecular Formula: C10H14BrN Molecular Weight: 228.132 InChI Key: XMJPFHUHXYNXDE-UHFFFAOYSA-N Note:

H N

Reaxys ID 19133270 View in Reaxys

34/43 CAS Registry Number: 919347-80-1 Chemical Name: [2-(3-bromophenyl)ethyl]propylamine Linear Structure Formula: C11H16BrN Molecular Formula: C11H16BrN Molecular Weight: 242.159 InChI Key: GTQYYXVOBLVAHK-UHFFFAOYSA-N Note:

H N

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Reaxys ID 19133271 View in Reaxys

35/43 CAS Registry Number: 919347-78-7 Chemical Name: [2-(3-bromophenyl)ethyl](2-methylpropyl)amine Linear Structure Formula: C12H18BrN Molecular Formula: C12H18BrN Molecular Weight: 256.186 InChI Key: ZXDVYWCFFXIAGV-UHFFFAOYSA-N Note:

H N

Reaxys ID 19397601 View in Reaxys

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2 H 2N

Chemical Name: [Cu(2,4-pyridyne dicarboxylic acid H)2(H2O)2][2-(4-bromophenyl)ethylamine)2]*acetone Linear Structure Formula: Cu((CO2)2C5H3NH)2(H2O)2*2NH2C2H4C6H4Br*99CH3COCH3= Cu((CO2)2C5H3NH)2(H2O)2(NH2C2H4C6H4Br)2*99CH3COCH3 Molecular Formula: (x)C3H6O*2C8H10BrN*C14H12CuN2O10 Type of Substance: Coordination compound InChI Key: SHQCGZLDBCUPDF-UHFFFAOYSA-L Note:

(v3)

OH 2 O O

(v2) – O

(v4)

N Cu 2+ O– N (v6)

O -1

(v2)

(v4)

OH 2 (v3)

Conformation (1) Object of Investi- References gation Conformation

Chen, Chun-Long; Beatty, Alicia M.; Journal of the American Chemical Society; vol. 130; nb. 51; (2008); p. 17222 - 17223 ; (from Gmelin), View in Reaxys

Crystal Phase (1) Description (Crys- References tal Phase) Structure of the solid

Chen, Chun-Long; Beatty, Alicia M.; Journal of the American Chemical Society; vol. 130; nb. 51; (2008); p. 17222 - 17223 ; (from Gmelin), View in Reaxys

Reaxys ID 20480577 View in Reaxys

37/43 CAS Registry Number: 1109229-99-3 Chemical Name: N-[2-(2-bromophenyl)ethyl]pentan-1-amine Linear Structure Formula: C13H20BrN Molecular Formula: C13H20BrN Molecular Weight: 270.213 InChI Key: BFIGYXCUZNNTGB-UHFFFAOYSA-N Note:

H N

Crystal Property Description (1) Colour & Other Location Properties

References

white

Patent; SANOFI-AVENTIS; US2010/197725; (2010); (A1) English, View in Reaxys

Page/Page column 15

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

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

29.84

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Original Text (NMR Spectroscopy)

NMR: 0.86 (t, J=7.0 Hz, 3H) 1.21-1.32 (m, 4H) 1.41 (m, 2H) 2.55 (t, J=7.3 Hz, 2H) 2.74 (m, 2H) 2.84 (m, 2H) 3.14 (broad unresolved m, 1H) 7.14 (td, J=7.7, 2.0 Hz, 1H) 7.22-7.39 (m, 2H) 7.56 (dd, J=7.7, 2.0 Hz, 1H)

Location

Page/Page column 15

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

0.86; 1.21 - 1.32; 1.41; 2.55; 2.74; 2.84; 3.14; 7.14; 7.22 - 7.39; 7.56

Kind of signal

t, J=7.0 Hz, 3H; m, 4H; m, 2H; t, J=7.3 Hz, 2H; m, 2H; m, 2H; broad unresolved m, 1H; td, J=7.7, 2.0 Hz, 1H; m, 2H; dd, J=7.7, 2.0 Hz, 1H

Patent; SANOFI-AVENTIS; US2010/197725; (2010); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) ESI (Electrospray ionisation)

Page/Page column 15

Comment (Mass Spectrometry)

Peak

References

Molecular peak

270 m/z

Patent; SANOFI-AVENTIS; US2010/197725; (2010); (A1) English, View in Reaxys

Reaxys ID 20480581 View in Reaxys

CAS Registry Number: 1109229-81-3 Chemical Name: N-[2-(2-bromophenyl)ethyl]heptan-4-amine Linear Structure Formula: C15H24BrN Molecular Formula: C15H24BrN Molecular Weight: 298.266 InChI Key: BRVYDZUOKGYYDJ-UHFFFAOYSA-N Note:

H N

Mass Spectrometry (1) Description (Mass Location Spectrometry) LCMS (Liquid chromatography mass spectrometry)

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References

Page/Page column 10

Patent; SANOFI-AVENTIS; US2010/197725; (2010); (A1) English, View in Reaxys

Reaxys ID 21694898 View in Reaxys

39/43 CAS Registry Number: 30651-67-3 Chemical Name: 4-bromomethamphetamine hydrochloride Linear Structure Formula: C10H14BrN*ClH Molecular Formula: C10H14BrN*ClH Molecular Weight: 264.593 InChI Key: MMAKZISFQORJPJ-UHFFFAOYSA-N Note:

HCl

NMR Spectroscopy (2) 1 of 2

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

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

300

Location

supporting information

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Taniguchi, Masashi; Yamamoto, Yoshio; Nishi, Katsuji; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1473 - 1476, View in Reaxys 2 of 2

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

13C

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

Location

supporting information

Taniguchi, Masashi; Yamamoto, Yoshio; Nishi, Katsuji; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1473 - 1476, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

MALDI-TOF (Ma- supporting infortrix assisted laser mation desorption ionization - time of flight); Spectrum

Taniguchi, Masashi; Yamamoto, Yoshio; Nishi, Katsuji; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1473 - 1476, View in Reaxys

EI (Electron impact); Spectrum

Taniguchi, Masashi; Yamamoto, Yoshio; Nishi, Katsuji; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1473 - 1476, View in Reaxys

Reaxys ID 22198481 View in Reaxys

40/43 CAS Registry Number: 869567-02-2 Chemical Name: (S)-(+)-1-(4'-bromo)phenyl-2-propanamine Linear Structure Formula: C9H12BrN Molecular Formula: C9H12BrN Molecular Weight: 214.105 InChI Key: SMNXUMMCCOZPPN-ZETCQYMHSA-N Note:

NH 2

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.2 g/100ml

Enantiomeric excess [%ee]

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel; Organic and Biomolecular Chemistry; vol. 9; nb. 23; (2011); p. 8171 - 8177, View in Reaxys

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Reaxys ID 22198482 View in Reaxys

41/43 CAS Registry Number: 869567-01-1 Chemical Name: (R)-(-)-1-(4'-bromo)phenyl-2-propanamine Linear Structure Formula: C9H12BrN Molecular Formula: C9H12BrN Molecular Weight: 214.105 InChI Key: SMNXUMMCCOZPPN-SSDOTTSWSA-N Note:

NH 2

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.2 g/100ml

Enantiomeric excess [%ee]

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-28.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel; Organic and Biomolecular Chemistry; vol. 9; nb. 23; (2011); p. 8171 - 8177, View in Reaxys

Reaxys ID 28132893 View in Reaxys

42/43 Linear Structure Formula: C12H18BrN Molecular Formula: C12H18BrN Molecular Weight: 256.186 InChI Key: CYTXCYSKMLBXET-UHFFFAOYSA-N Note:

Reaxys ID 24727031 View in Reaxys

43/43

NH 2

Linear Structure Formula: C6H3N3O7*C8H10BrN*ClH Molecular Formula: C6H3N3O7*C8H10BrN*ClH Molecular Weight: 465.645 InChI Key: IDZNHUWOOAXOEY-UHFFFAOYSA-N Note:

Br HCl

O OH

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