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Azepino(4,5-b)indole

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(Redirected fromAzepinoindole)
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 mass180.210 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Azepino[4,5-b]indole is atricyclicchemical compound related totryptamine and having variousalkaloidderivatives.[1][2] Theanalogue of azepino[4,5-b]indole with theazepinering fullyhydrogenated,noribogaminalog (1,2,3,4,5,6-hexahydroazepino[4,5-b]indole), is aparent compound of theiboga-type alkaloids such asibogaine,ibogamine, andtabernanthine as well as of their simplifiedibogaloganaloguesibogainalog,ibogaminalog, andtabernanthalog.[1][3][4]

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

See also

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References

[edit]
  1. ^abLavaud 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.
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