A substituted 3-benzazepine, or simply 3-benzazepine, is a derivative of 3-benzazepine.Shah, J. H., Hindupur, R. M., & N Pati, H. (2015). Pharmacological and biological activities of benzazepines: An overview. Current Bioactive Compounds, 11(3), 170–188. https://doi.org/10.2174/1573407211666150910202200 They are cyclized phenethylamines and are closely related to the tetrahydroisoquinolines. In addition, they are analogous to the cyclized tryptamine ibogalogs and their β-carboline relatives.Iyer, R. N., Favela, D., Zhang, G., & Olson, D. E. (2021). The iboga enigma: the chemistry and neuropharmacology of iboga alkaloids and related analogs. Natural Product Reports, 38(2), 307–329. https://doi.org/10.1039/D0NP00033G
3-Benzazepines are known to act as monoamine receptor modulators, including as dopamine D1-like receptor agonists, dopamine D1 receptor antagonists, and serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptor agonists, among other activities. 3-Benzazepines acting as serotonin 5-HT2 receptor agonists generally show varying degrees of preferential activity at the serotonin 5-HT2C receptor over the serotonin 5-HT2A receptor, with occasional exceptions. One 3-benzazepine, the non-selective serotonin 5-HT2 receptor agonist and previously marketed anorectic lorcaserin (Belviq), is known to produce psychedelic effects at supratherapeutic doses.
List of 3-benzazepines
Structure Name Action Chemical name Ref 3-Benzazepine N/A 3H-3-benzazepine 2,3,4,5-Tetrahydro-1H-3-benzazepine N/A 2,3,4,5-tetrahydro-1H-benzo[d]azepine SKF-39315 D1-like agonist 2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol Lorcaserin 5-HT2 agonist (1R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine 7-Chlorolorcaserin 5-HT2 agonist (1R)-7,8-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine SCHEMBL5334361 5-HT2 agonist 7-[(3-methoxyphenoxy)methyl]-2,3,4,5-tetrahydro-1H-3-benzazepine SKF-38393 D1-like agonist 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol SKF-81297 D1-like agonist (1R)-6-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol Fenoldopam D1-like agonist 6-chloro-1-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol SCH-23390 D1 antagonist (5R)-8-chloro-3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol SKF-83959 D1-like agonist 6-chloro-3-methyl-1-(3-methylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol Trepipam (SCH-12679) D1-like agonist 7,8-dimethoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine SKF-77434 D1-like agonist (1R)-1-phenyl-3-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol SKF-82958 D1-like agonist (1R)-6-chloro-1-phenyl-3-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol 6-Br-APB D1-like agonist (1R)-6-bromo-1-phenyl-3-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol Odapipam (NNC 01–0756) D1 antagonist (5S)-8-chloro-5-(2,3-dihydro-1-benzofuran-7-yl)-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Berupipam (NNC 22–0010) D1 antagonist (5S)-5-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)-8-chloro-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol NNC 01-0687 (ADX-10061, CEE-03-310) D1 antagonist (5S)-5-(2,3-dihydro-1-benzofuran-7-yl)-3-methyl-8-nitro-1,2,4,5-tetrahydro-3-benzazepin-7-ol GSK-189254 H3 antagonist 6-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methylpyridine-3-carboxamide Anilopam (PR 786–723) Opioid 4-[2-(7-methoxy-4-methyl-1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethyl]aniline
Related compounds
Structure Name Action Chemical name Ref PF-04479745 (PF-4479745) 5-HT2 modulator (9S)-2-benzyl-N,9-dimethyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-amine PF-04781340 5-HT2 modulator 3-benzyl-N-methyl-6,7,8,9-tetrahydro-5H-pyrido[3,4-d]azepin-1-amine PF-4522654 (PF-04522654) 5-HT2 modulator 2-[difluoro(phenyl)methyl]-N-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-amine
See also Benzazepine Cyclized phenethylamine Substituted tetrahydroisoquinoline Ibogalog Iboga alkaloid Substituted β-carboline
References