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Iboga-type alkaloids are a set of monoterpene indole alkaloids comprising naturally occurring compounds found in Tabernanthe and Tabernaemontana, as well as synthetic structural analogs. Naturally occurring iboga-type alkaloids include ibogamine, ibogaine, tabernanthine, and other substituted ibogamines (see below). Ibogaine is a hallucinogen and is referred to as an oneirogen. Many iboga-type alkaloids display biological activities such as cardiac toxicity and psychoactive effects, and some have been studied as potential treatments for drug addiction.[1][2]

Naturally-occurring

Substituted ibogamines

Main article: Ibogamine

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 CO2Me H
73255 Voacangine OMe H CO2Me H
363281 Isovoacangine H OMe CO2Me H
65572 Conopharyngine OMe OMe CO2Me H
11077316 19(S)-Hydroxyibogamine H 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 CO2Me OH
196982 Voacristine OMe H CO2Me OH
10362598 Isovoacristine H OMe CO2Me OH
102004638 19(S)-Hydroxyconopharyngine OMe OMe CO2Me OH

Catharanthine is an unsaturated analog of coronaridine.

Oxidation products

Similarly to other ring-constrained tryptamines such as yohimbine[3] and mitragynine (see mitragynine pseudoindoxyl), oxidation and rearrangement products of substituted ibogamines have been reported, such as iboluteine (ibogaine pseudoindoxyl) (CID:21589055) and voaluteine (CID:633439).[4]

Iboluteine (left) and voaluteine (right), putative metabolites of ibogaine and voacangine, respectively.[4]

Other alkaloids

Treatment of drug dependence

Ibogaine and related alkaloids reduce the craving for subsequent doses in individuals experiencing withdrawal symptoms associated with drug addiction. Their use has been investigated in several clinical studies involving individuals dependent on opioids, cocaine, and other substances. While positive effects—such as alleviation of withdrawal symptoms, improvement in depression, and mitigation of post-traumatic symptoms—have been confirmed, severe medical complications, including fatal cases, have also been reported due to neurotoxic and cardiotoxic side effects.[5]

Synthetic analogues

18-MC, ME-18-MC, and 18-MAC are coronaridine analogs with similar anti-addictive effects.[6][7][8][9]

More distantly related synthetic analogs include:

See also

References

  1. ^ 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. PMID 7820611. S2CID 1940631.
  2. ^ 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. Bibcode:2013PLoSO…877262A. doi:10.1371/journal.pone.0077262. ISSN 1932-6203. PMC 3818563. PMID 24204784.
  3. ^ 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. Bibcode:1965JAChS..87.2229F. doi:10.1021/ja01088a024. ISSN 0002-7863. PMID 14290283. Archived from the original on 2023-02-07. Retrieved 2023-08-05.
  4. ^ a b The Alkaloids: Chemistry and Physiology V11. Academic Press. 2014-05-14. ISBN 978-0-08-086535-5. Archived from the original on 2023-08-06. Retrieved 2023-08-06.
  5. ^ Patrick Köck, Katharina Froelich, Marc Walter, Undine Lang, Kenneth M. Dürsteler (July 2022), “A systematic literature review of clinical trials and therapeutic applications of ibogaine”, Journal of Substance Abuse Treatment, vol. 138, doi:10.1016/j.jsat.2021.108717, PMID 35012793, retrieved 2022-07-05{{citation}}: CS1 maint: multiple names: authors list (link)
  6. ^ Kuehne ME, He L, Jokiel PA, Pace CJ, Fleck MW, Maisonneuve IM, et al. (June 2003). “Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents”. Journal of Medicinal Chemistry. 46 (13): 2716–30. doi:10.1021/jm020562o. PMID 12801235.
  7. ^ Pace CJ, Glick SD, Maisonneuve IM, He LW, Jokiel PA, Kuehne ME, Fleck MW (May 2004). “Novel iboga alkaloid congeners block nicotinic receptors and reduce drug self-administration”. European Journal of Pharmacology. 492 (2–3): 159–67. doi:10.1016/j.ejphar.2004.03.062. PMID 15178360.
  8. ^ Glick SD, Kuehne ME, Maisonneuve IM, Bandarage UK, Molinari HH (May 1996). “18-Methoxycoronaridine, a non-toxic iboga alkaloid congener: effects on morphine and cocaine self-administration and on mesolimbic dopamine release in rats”. Brain Research. 719 (1–2): 29–35. doi:10.1016/0006-8993(96)00056-X. PMID 8782860. S2CID 6178161.
  9. ^ Glick SD, Sell EM, Maisonneuve IM (December 2008). “Brain regions mediating alpha3beta4 nicotinic antagonist effects of 18-MC on methamphetamine and sucrose self-administration”. European Journal of Pharmacology. 599 (1–3): 91–5. doi:10.1016/j.ejphar.2008.09.038. PMC 2600595. PMID 18930043.
  10. ^ 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. Bibcode:2021Natur.589..474C. doi:10.1038/s41586-020-3008-z. ISSN 1476-4687. PMC 7874389. PMID 33299186.