Iboga-type alkaloid
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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 (). 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
| 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 | 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 |
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
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
References
- ^ 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. Archived from the original on 2023-08-06. Retrieved 2023-08-06.
- ^ 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.
- ^ 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. PMID 14290283. Archived from the original on 2023-02-07. Retrieved 2023-08-05.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.