Azepinoindole

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| InChI=1S/C12H14N2/c1-2-4-11-9(3-1)10-5-7-13-8-6-12(10)14-11/h1-3,13H,4-8H2

| InChIKey=WCBKHRWOLLLQSM-UHFFFAOYSA-N

| SMILES = C1CNCCC2=C1N=C3CC=CC=C23

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| C=12 | H=14 | N=2

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Azepinoindole is a tricyclic chemical compound related to tryptamine and having various alkaloid derivatives.{{cite journal | vauthors = Lavaud C, Massiot G | title = The Iboga Alkaloids | journal = Prog Chem Org Nat Prod | series = Progress in the Chemistry of Organic Natural Products | volume = 105 | issue = | pages = 89–136 | date = 2017 | pmid = 28194562 | doi = 10.1007/978-3-319-49712-9_2 | isbn = 978-3-319-49711-2 | url = }}{{cite journal | vauthors = Lindsay AC, Kim SH, Sperry J | title = Non-monoterpenoid azepinoindole alkaloids | journal = Nat Prod Rep | volume = 35 | issue = 12 | pages = 1347–1382 | date = July 2018 | pmid = 30024006 | doi = 10.1039/c8np00047f | url = }} The analogue of azepinoindole with the azepine ring fully hydrogenated, 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole, is a parent compound of the iboga-type alkaloids such as ibogaine, ibogamine, and tabernanthine as well as their simplified "ibogalog" analogues ibogainalog, ibogaminalog, and tabernanthalog.{{cite journal | vauthors = Tae HS, Ortells MO, Tekarli BJ, Manetti D, Romanelli MN, McIntosh JM, Adams DJ, Arias HR | title = DM506 (3-Methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole fumarate), a Novel Derivative of Ibogamine, Inhibits α7 and α9α10 Nicotinic Acetylcholine Receptors by Different Allosteric Mechanisms | journal = ACS Chem Neurosci | volume = 14 | issue = 14 | pages = 2537–2547 | date = July 2023 | pmid = 37386821 | doi = 10.1021/acschemneuro.3c00212 | url = }}{{cite journal | vauthors = Hester JB, Tang AH, Keasling HH, Veldkamp W | title = Azepinoindoles. I. Hexahydroazepino[4,5-b]indoles | journal = J Med Chem | volume = 11 | issue = 1 | pages = 101–106 | date = January 1968 | pmid = 5637151 | doi = 10.1021/jm00307a023 | url = }}

{{Gallery

| title = Chemical structures of selected azepinoindole derivatives

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| File:Ibogamine.svg | Ibogamine

| File:Ibogaine.svg | Ibogaine

| File:Tabernanthine.svg | Tabernanthine

| File:Ibogaminalog.svg | Ibogaminalog

| File:Ibogainalog.svg | Ibogainalog

| File:Tabernanthalog.svg | Tabernanthalog

}}