Iboga-type alkaloid explained

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 . 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

See main article: Ibogamine.

	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	H	OH
71656190	Iboxygaine / Kimvuline	OMe	H	H	OH
		H	OMe	H	OH
		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

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]

Other alkaloids

• Vobasine
• Ervaticine
• Dregamine
• Vinblastine

Synthetic analogs

18-MC, ME-18-MC, and 18-MAC are coronaridine analogs with similar anti-addictive effects.^{[5] [6] [7] [8]}

More distantly related synthetic analogs include :

• Varenicline, a polycyclic azepine and anti-addictive agent that similarly targets nicotinic acetylcholine receptors, but acts as a partial agonist instead.
• Tabernanthalog is a structural simplification of tabernanthine and "non-hallucinogenic psychoplastogen".^[9]

See also

• Strictosidine
• Bwiti

Notes and 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 . en . 657 . 1 . 14–22 . 10.1016/0006-8993(94)90948-2 . 7820611 . 1940631 . 0006-8993 . 2023-08-06 . 2023-08-06 . https://web.archive.org/web/20230806133833/https://www.sciencedirect.com/science/article/abs/pii/0006899394909482?via%3Dihub . live .
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 . en . 8 . 10 . e77262 . 10.1371/journal.pone.0077262 . 1932-6203 . 3818563 . 24204784 . 2013PLoSO...877262A . free .
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 . en . 87 . 10 . 2229–2235 . 10.1021/ja01088a024 . 14290283 . 0002-7863 . 2023-08-05 . 2023-02-07 . https://web.archive.org/web/20230207112446/https://pubs.acs.org/doi/abs/10.1021/ja01088a024 . live .
4. Book: The Alkaloids: Chemistry and Physiology V11 . 2014-05-14 . Academic Press . 978-0-08-086535-5 . en . 2023-08-06 . 2023-08-06 . https://web.archive.org/web/20230806133758/https://books.google.com/books?id=AacNdaWmf-8C&dq=ibogaine+pseudoindoxyl&pg=PA81 . live .
5. 6 . Kuehne ME, He L, Jokiel PA, Pace CJ, Fleck MW, Maisonneuve IM, Glick SD, Bidlack JM . June 2003 . Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents . Journal of Medicinal Chemistry . 46 . 13 . 2716–30 . 10.1021/jm020562o . 12801235.
6. 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 . 10.1016/j.ejphar.2004.03.062 . 15178360.
7. 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 . 10.1016/0006-8993(96)00056-X . 8782860 . 6178161.
8. 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 . 10.1016/j.ejphar.2008.09.038 . 2600595 . 18930043.
9. 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 . en . 589 . 7842 . 474–479 . 10.1038/s41586-020-3008-z . 1476-4687 . 7874389 . 33299186. 2021Natur.589..474C .