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
[edit]-Ibogaine_Structural_Formula_V2.svg)
-Ibogamine_Structural_Formula_V2.svg)
-Tabernanthine_Structural_Formula_V2.svg)
-Coronaridine_Structural_Formula_V2.svg)
Substituted ibogamines
[edit]
| 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
[edit]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
[edit]Therapy of Drug Dependence
[edit]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 analogs
[edit]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 :
- 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".[10]
See also
[edit]References
[edit]- ^ 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. 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.
- ^ 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.
- ^ 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, p. 108717, doi:10.1016/j.jsat.2021.108717, retrieved 2022-07-05
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ 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.