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Names

Lorcaserin
APD-356

IUPAC name

(1R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

ID 2727 · Formula C₁₁H₁₄ClN · Molecular weight 195.689

InChI InChI=1S/C11H14ClN/c1-8-7-13-5-4-9-2-3-10(12)6-11(8)9/h2-3,6,8,13H,4-5,7H2,1H3/t8-/m0/s1

InChI Key XTTZERNUQAFMOF-QMMMGPOBSA-N This stereoisomer Any stereoisomer

SMILES Clc1ccc2c(c1)[C@@H](C)CNCC2

ChemSpider 9833595
PubChem 11658860
Wikidata Q340139
Wikipedia Lorcaserin
swgdrug.org Lorcaserin

Phenethylamine: Von der Strucktur zur Funktion Lorcaserin: 6.2 (49) 384, 385

Thomsen, WJ; Grottick, AJ; Menzaghi, F; Reyes-Saldana, H; Espitia, S; Yuskin, D; Whelan, K; Martin, M; Morgan, M; Chen, W; Al-Shamma, H; Smith, B; Chalmers, D; Behan, D. Lorcaserin, a novel selective human 5-hydroxytryptamine_2C agonist: in vitro and in vivo pharmacological characterization. J. Pharmacol. Exp. Ther., 1 May 2008, 325 (2), 577–587. 491 kB. https://doi.org/10.1124/jpet.107.133348

Smith, BM; Smith, JM; Tsai, JH; Schultz, JA; Gilson, CA; Estrada, SA; Chen, RR; Park, DM; Prieto, EB; Gallardo, CS; Sengupta, D; Thomsen, WJ; Saldana, HR; Whelan, KT; Menzaghi, F; Webb, RR; Beeley, NRA. Discovery and SAR of new benzazepines as potent and selective 5-HT_2C receptor agonists for the treatment of obesity. Bioorg. Med. Chem. Lett., 1 Mar 2005, 15 (5), 1467–1470. 122 kB. https://doi.org/10.1016/j.bmcl.2004.12.080

Smith, BM; Smith, JM; Tsai, JH; Schultz, JA; Gilson, CA; Estrada, SA; Thomsen, WJ. Discovery and Structure−Activity Relationship of (1R)-8-Chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine (Lorcaserin), a Selective Serotonin 5-HT_2C Receptor Agonist for the Treatment of Obesity. J. Med. Chem., 1 Jan 2008, 51 (2), 305–313. 158 kB. https://doi.org/10.1021/jm0709034

Pawar, RS; Grundel, E. Overview of regulation of dietary supplements in the USA and issues of adulteration with phenethylamines (PEAs). Drug Test. Anal., 1 Mar 2017, 9 (3), 500-517. 601 kB. https://doi.org/10.1002/dta.1980

Helm, K. Synthese und funktionelle In-vitro-Pharmakologie neuer Liganden des 5-HT_2A-Rezeptors aus der Klasse. Ph. D. Thesis, Universität Regensburg, Dresden, 1 Jan 2014. 3.2 MB. #15 LC,MS,NMR,IR

Cheng, J; Kozikowski, AP. We need 2C but not 2B: Developing serotonin 2C (5-HT_2C) receptor agonists for the treatment of CNS disorders. ChemMedChem, 1 Dec 2015, 10 (12), 1963–1967. 1.1 MB. https://doi.org/10.1002/cmdc.201500437 #6

Cheng, J; McCorvy, JD; Giguere, PM; Zhu, H; Kenakin, T; Roth, BL; Kozikowski, AP. Design and discovery of functionally selective serotonin 2C (5-HT_2C) receptor agonists. J. Med. Chem., 10 Nov 2016, 59 (21), 9866–9880. 4.8 MB. https://doi.org/10.1021/acs.jmedchem.6b01194

Zhang, G; Cheng, J; McCorvy, JD; Lorello, PJ; Caldarone, BJ; Roth, BL; Kozikowski, AP. Discovery of N-substituted (2-phenylcyclopropyl)methylamines as functionally selective serotonin 2C receptor agonists for potential use as antipsychotic medications. J. Med. Chem., 27 Jul 2017, 60 (14), 6273–6288. 3.5 MB. https://doi.org/10.1021/acs.jmedchem.7b00584 #2

Cheng, J; Giguère, PM; Onajole, OK; Lv, W; Gaisin, A; Gunosewoyo, H; Schmerberg, CM; Pogorelov, VM; Rodriguiz, RM; Vistoli, G; Wetsel, WC; Roth, BL; Kozikowski, AP. Optimization of 2-phenylcyclopropylmethylamines as selective serotonin 2C receptor agonists and their evaluation as potential antipsychotic agents. J. Med. Chem., 26 Feb 2015, 58 (4), 1992–2002. 1.9 MB. https://doi.org/10.1021/jm5019274 #1

Oh, S; Kim, KS; Chung, YS; Shong, M; Park, SB. Anti-obesity agents: A focused review on the structural classification of therapeutic entities. Curr. Top. Med. Chem., 1 Apr 2009, 9 (6), 466–481. 438 kB. https://doi.org/10.2174/156802609788897862

Cheng, J; Giguere, PM; Schmerberg, CM; Pogorelov, VM; Rodriguiz, RM; Huang, X; Zhu, H; McCorvy, JD; Wetsel, WC; Roth, BL; Kozikowski, AP. Further advances in optimizing (2-phenylcyclopropyl)methylamines as novel serotonin 2C agonists: Effects on hyperlocomotion, prepulse inhibition, and cognition models. J. Med. Chem., 28 Jan 2016, 59 (2), 578–591. 2.9 MB. https://doi.org/10.1021/acs.jmedchem.5b01153 #1 MS,NMR

N,N-Me-PCAI

2745

2746

2747

7 Dec 2019 · · Isomer Design