Azepinoindole

Azepinoindole

Identifiers
3D model (JSmol)	Interactive image
InChI 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 Key: WCBKHRWOLLLQSM-UHFFFAOYSA-N
SMILES C1CNCCC2=C1N=C3CC=CC=C23
Properties
Chemical formula	C12H14N2
Molar mass	186.258 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Azepinoindole is a tricyclic chemical compound related to tryptamine and having various alkaloid derivatives. ^{[1] [2]} The analogue of azepinoindole with the azepine ring fully hydrogenated, noribogaminalog (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. ^{[1] [3] [4]}

Chemical structures of selected azepinoindole derivatives

• 
  Ibogamine
• 
  Ibogaine
• 
  Tabernanthine
• 
  Ibogaminalog
• 
  Ibogainalog
• 
  Tabernanthalog

See also

• Ibogalog
• Iboga-type alkaloid
• Desethylibogamine
• Substituted β-carboline
• PHA-57378
• PNU-22394
• PNU-181731
• Tryptoline

References

1. Lavaud C, Massiot G (2017). "The Iboga Alkaloids". Progress in the Chemistry of Organic Natural Products. Vol. 105. pp. 89–136. doi:10.1007/978-3-319-49712-9_2. ISBN   978-3-319-49711-2. PMID   28194562.
2. Lindsay AC, Kim SH, Sperry J (July 2018). "Non-monoterpenoid azepinoindole alkaloids". Nat Prod Rep. 35 (12): 1347–1382. doi:10.1039/c8np00047f. PMID   30024006.
3. Tae HS, Ortells MO, Tekarli BJ, Manetti D, Romanelli MN, McIntosh JM, Adams DJ, Arias HR (July 2023). "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". ACS Chem Neurosci. 14 (14): 2537–2547. doi:10.1021/acschemneuro.3c00212. PMID   37386821.
4. Hester JB, Tang AH, Keasling HH, Veldkamp W (January 1968). "Azepinoindoles. I. Hexahydroazepino[4,5-b]indoles". J Med Chem. 11 (1): 101–106. doi:10.1021/jm00307a023. PMID   5637151.