Azepino(4,5-b)indole

Azepino[4,5-b]indole
Names
IUPAC name
azepino[4,5-b]indole
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C12H8N2/c1-2-4-11-9(3-1)10-5-7-13-8-6-12(10)14-11/h1-8H
    Key: ZMKPMNLSLLYATH-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C3=CC=NC=CC3=N2
Properties
C12H8N2
Molar mass 180.210 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Azepino[4,5-b]indole is a tricyclic chemical compound related to tryptamine and having various alkaloid derivatives.[1][2] The analogue of azepino[4,5-b]indole 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 as well as of their simplified ibogalog analogues like ibogainalog.[1][3][4]

Chemical structures of selected azepino[4,5-b]indole derivatives

See also

References

  1. ^ a b 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.
allikas: http://en.wikipedia.org/wiki/Azepinoindole