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Iboga-type alkaloid

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Iboga alkaloids are alkaloid constituents found in Tabernanthe iboga. Iboga alkaloids include ibogamine, substituted ibogamines (see below), and harmaline[citation needed], among others[citation needed].

Naturally-occurring substituted ibogamines
PubChem CID Name R1 R2 R3 R4
100217 Ibogamine H H H H
197060 Ibogaine OMe H H H
3083548 Noribogaine OH H H H
6326116 Tabernanthine H OMe H H
193302 Ibogaline OMe OMe H H
73489 Coronaridine H H COOMe H
73255 Voacangine OMe H COOMe H
363281 Isovoacangine H OMe COOMe H
65572 Conopharyngine OMe OMe COOMe H
11077316 19(S)-Hydroxyibogamine H H OH
71656190 Iboxygaine / Kimvuline OMe H H OH
ND ND H OMe H OH
ND ND OMe OMe H OH
15559732 19(S)-Hydroxycoronaridine H H COOMe OH
196982 Voacristine OMe H COOMe OH
10362598 Isovoacristine H OMe COOMe OH
102004638 19(S)-Hydroxyconopharyngine OMe OMe COOMe OH

Similarly to other ring-constrained tryptamines such as yohimbine[1] and mitragynine (see mitragynine pseudoindoxyl), oxidation and rearrangement products of substituted ibogamines have been reported, such as ibolutein (ibogaine pseudoindoxyl) (CID:21589055) and voaluteine (CID:633439).[2]

Iboluteine (left) and voaluteine (right), putative metabolites of ibogaine and voacangine, respectively.[2]

See also

References

  1. ^ Finch, Neville; Gemenden, C. W.; Hsu, Iva Hsiu-Chu; Kerr, Ann; Sim, G. A.; Taylor, W. I. (May 1965). "Oxidative Transformations of Indole Alkaloids. III. Pseudoindoxyls from Yohimbinoid Alkaloids and Their Conversion to "Invert" Alkaloids 1,2". Journal of the American Chemical Society. 87 (10): 2229–2235. doi:10.1021/ja01088a024. ISSN 0002-7863.
  2. ^ a b The Alkaloids: Chemistry and Physiology V11. Academic Press. 2014-05-14. ISBN 978-0-08-086535-5.
  3. ^ Antonio, Tamara; Childers, Steven R.; Rothman, Richard B.; Dersch, Christina M.; King, Christine; Kuehne, Martin; Bornmann, William G.; Eshleman, Amy J.; Janowsky, Aaron; Simon, Eric R.; Reith, Maarten E. A.; Alper, Kenneth (2013-10-16). "Effect of Iboga Alkaloids on µ-Opioid Receptor-Coupled G Protein Activation". PLOS ONE. 8 (10): e77262. doi:10.1371/journal.pone.0077262. ISSN 1932-6203. PMC 3818563. PMID 24204784.{{cite journal}}: CS1 maint: PMC format (link) CS1 maint: unflagged free DOI (link)
  4. ^ Glick, S. D.; Kuehne, M. E.; Raucci, J.; Wilson, T. E.; Larson, D.; Keller, R. W.; Carlson, J. N. (1994-09-19). "Effects of iboga alkaloids on morphine and cocaine self-administration in rats: relationship to tremorigenic effects and to effects on dopamine release in nucleus accumbens and striatum". Brain Research. 657 (1): 14–22. doi:10.1016/0006-8993(94)90948-2. ISSN 0006-8993.
  5. ^ Cameron, Lindsay P.; Tombari, Robert J.; Lu, Ju; Pell, Alexander J.; Hurley, Zefan Q.; Ehinger, Yann; Vargas, Maxemiliano V.; McCarroll, Matthew N.; Taylor, Jack C.; Myers-Turnbull, Douglas; Liu, Taohui; Yaghoobi, Bianca; Laskowski, Lauren J.; Anderson, Emilie I.; Zhang, Guoliang (January 2021). "A non-hallucinogenic psychedelic analogue with therapeutic potential". Nature. 589 (7842): 474–479. doi:10.1038/s41586-020-3008-z. ISSN 1476-4687. PMC 7874389. PMID 33299186.{{cite journal}}: CS1 maint: PMC format (link)
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