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[[Category:Alkaloid]]
[[Category:Alkaloider]]
[[Category:Cycloalkylamine]]
[[Category:Tryptaminer]]
[[Category:Tryptamine]]
[[Category:Psykedelika]]
[[Category:Psychedelic]]
[[Category:Enteogener]]
[[Category:Dissociative]]
[[Category:Entheogen]]


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Nuvarande version från 4 november 2025 kl. 18.29

Mall:Headerpanel Mall:SummarySheet Mall:SubstanceBox/Ibogaine 10-Methoxyibogamine (commonly known as ibogaine) is a naturally occurring psychedelic substance of the chemical class::tryptamine class. Ibogaine is an indole alkaloid found in Tabernanthe iboga, while similar alkaloids occur in other plants of the Apocynaceae family, such as Voacanga africana and Tabernaemontana undulata.[1]

In West Central Africa, low dosages of Tabernanthe iboga extracts have been used by indigenous people against fatigue, hunger and thirst. Higher dosages capable of inducing visionary states are used for initiation rituals during religious ceremonies.[2] Ibogaine's medical history in the West began in the early 1900s when it was indicated for use as a neuromuscular stimulant.[3] In the 1940s and 1950s, its suitability as potential cardiovascular drug was studied.[4] Later in the 1960s, the substance received much attention because of its potential applicability as an anti-addiction medication.

The pharmacology of ibogaine is complex and poorly understood. While largely behaving as a serotonergic psychedelic, ibogaine interacts with numerous brain systems including transporters, opioid receptors, sigma receptors, glutamate receptors, and nicotinic receptors.[5] Ibogaine’s complex pharmacology entails a significant potential to generate adverse effects, particularly on the cardiovascular system. Its use has been associated with at least 12 deaths since 1990.[2]

Ibogaine is not currently approved for any medical uses in the United States.[2] Preliminary research in animals indicates that it could potentially be used for treatment of addiction;[2] however, there is a lack of non-anecdotal data in humans.[2] Although not licensed as therapeutic drug and despite safety concerns, ibogaine is currently used as an anti-addiction medication in dozens of clinics worldwide.[2]

History and culture

Mall:HistoryStub The Iboga tree is the central pillar of the Bwiti religion practiced in West-Central Africa, mainly Gabon, Cameroon, and the Republic of the Congo, which uses the alkaloid-containing roots of the plant for its psychoactive properties in a number of ceremonies. Ibogaine is also used by indigenous peoples in low doses to combat fatigue, hunger, and thirst.[5]

Research of ibogaine started in late 19th century. A published description of the ceremonial use of T. iboga in Gabon appears in 1885. Ibogaine was first extracted and crystallized from the T. iboga root in 1901.[5] The total synthesis of ibogaine was described in 1956 and structural elucidation by X-ray crystallography was completed in 1960.[6][7]

Chemistry

Ibogaine, or 12-methoxyibogamine, is an indole alkaloid molecule of the tryptamine chemical class. Tryptamines share a core structure composed of a bicyclic indole heterocycle attached at R3 to an amino group via an ethyl side chain. While ibogaine contains a tryptamine backbone, the structure features substitutions distinct from other hallucinogenic tryptamines.

Ibogaine is substituted at R10 of its structure with a methoxy group. The location of this substitution is identical to other R5 substituted tryptamines, notably 5-MeO-DMT. The traditional amino attached ethyl chain of tryptamine is incorporated into a seven member nitrogenous azepine ring. The azepine ring is fused to three interlocked cyclohexane rings, attached at the integrated tryptamine nitrogen of azepine and two carbons over. Attached to the fusion of cyclohexane rings is an ethyl chain at R7.

Ibogaine is obtained either by extraction from the iboga plant or by semi-synthesis from the precursor compound voacangine,[8] another plant alkaloid.

Pharmacology

Mall:Further Ibogaine is believed to produce its psychedelic effects from its binding efficacy at the 5-HT2A receptor. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

Ibogaine is rapidly metabolized in the human body into noribogaine. Noribogaine acts as a serotonin reuptake inhibitor. It also acts as a moderate κ-opioid receptor agonist[9] and weak µ-opioid receptor agonist[9] or weak partial agonist.[10] It is possible that the action of ibogaine at the kappa opioid receptor may contribute significantly to the psychoactive effects. Salvia divinorum is another plant recognized for its strong hallucinogenic properties; it contains the chemical salvinorin A which is also a highly selective kappa opioid agonist.

Both ibogaine and noribogaine have a plasma half-life of around two hours in rats,[11] although the half-life of noribogaine is slightly longer than that of the parent compound. It is proposed that ibogaine is deposited in fat and metabolized into noribogaine as it is released. [12] After ibogaine ingestion in humans, noribogaine shows higher plasma levels than ibogaine and is detected for a longer period than ibogaine.[13] Noribogaine is also more potent than ibogaine in rat drug discrimination assays when tested for the subjective effects of ibogaine.[14]

Ibogaine also has activity as an NMDA receptor antagonist.[15]

Subjective effects

Mall:Preamble/SubjectiveEffects Mall:Effects/base

Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:

Natural sources

Ibiogaine can be found within a variety of natural sources which are primarily found on the African continent.

The most common of these are listed below.

Fil:Tabernaemontana-undulata-upload.jpg
Tabernaemontana undulata
Tabernanthe iboga
Fil:Voacanga-africana-upload.jpg
Voacanga africana

Research

Addiction treatment

Research suggests that ibogaine may be useful in treating dependence on other substances such as alcohol, methamphetamine, and nicotine and may affect compulsive behavioral patterns not involving substance abuse or chemical dependence. Researchers note that there remains a "need for systematic investigation in a conventional clinical research setting."[16]

Many users of ibogaine report experiencing visual phenomena during a waking dream state, such as instructive replays of life events that led to their addiction, while others report therapeutic shamanic visions that help them conquer the fears and negative emotions that might drive their addiction. It is proposed that intensive counseling, therapy and aftercare during the interruption period following treatment is of significant value. Some individuals require a second or third treatment session with ibogaine over the course of the next 12 to 18 months. A minority of individuals relapse completely into opiate addiction within days or weeks. A comprehensive article on the subject of ibogaine therapy detailing the procedure, effects and aftereffects is found in "Ibogaine in the Treatment of Chemical Dependence Disorders: Clinical Perspectives".[17] Ibogaine has also been reported in multiple small-study cohorts to reduce cravings for methamphetamine.[18]

There is also evidence that this type of treatment works with LSD, which has been shown to have a therapeutic effect on alcoholism. Both ibogaine and LSD appear to be effective for encouraging introspection and giving the user occasion to reflect on the sources of their addiction, while also producing an intense, transformative experience that can put established patterns of behaviour into perspective;[19] ibogaine has the added benefit of preventing withdrawal effects.[16]

Neuroplasticity

In 2018, a study demonstrated neuroplasticity induced by noribogaine, an active metabolite of ibogaine, and other psychedelics through TrkB, mTOR, and 5-HT2A signaling.[20]

Toxicity and harm potential

Mall:Toxicity Mall:Further Ibogaine has been associated with life-threatening heart complications, such as QT prolongation.[21] It can be taken safely, but only under the supervision of trained medical professionals.

Tolerance and addiction potential

Ibogaine is Addiction potential::not habit-forming, and the desire to use it can actually decrease with regular consumption. Like most psychedelics, it is most often thought to be self-regulating.

Legal status

Ibogaine is unregulated and unlicensed in most countries.[22][23] Some exceptions are listed below.

  • Brazil: On January 14, 2016, Ibogaine was legalized for prescription use.[24]
  • Canada: Ibogaine is prescription drug since 2017.[25]
  • Germany: Ibogaine is not a controlled substance under the BtMG[26] (Narcotics Act) or the NpSG[27] (New Psychoactive Substances Act). Technically it would fall under the definition of a medicine by §2 AMG (Medicines Act) because it induces a pharmacological effect.[28] By a decision of the European Court of Justice, this definition was declared ineffective because it was not compatible with EU law.[29] Ibogaine can be considered unregulated.
  • Mexico: As of 2009, ibogaine is unregulated.[30]
  • New Zealand: Ibogaine was gazetted in 2009 as a non-approved prescription medicine.[31]
  • Norway: Ibogaine is illegal (as are all tryptamine derivatives).[32]
  • Sweden: Ibogaine is a schedule I drug.[33]
  • Switzerland: Ibogaine is a controlled substance specifically named under Verzeichnis D.[34]
  • United Kingdom: It is illegal to produce, supply, or import this drug under the Psychoactive Substance Act, which came into effect on May 26th, 2016.[35]
  • United States: Ibogaine is classified as a Schedule I drug,[36] and is not currently approved for addiction treatment (or any other therapeutic use) because of its hallucinogenic, cardiovascular and possibly neurotoxic side effects, as well as the scarcity of safety and efficacy data in human subjects.[37]

See also

External links

Discussion

Literature

  • Mačiulaitis, R., Kontrimavičiūtė, V., Bressolle, F. M. M., & Briedis, V. (2008). Ibogaine, an anti-addictive drug: pharmacology and time to go further in development. A narrative review. Human & experimental toxicology, 27(3), 181-194. https://doi.org/10.1177/0960327107087802.
  • Koenig, X., & Hilber, K. (2015). The anti-addiction drug ibogaine and the heart: a delicate relation. Molecules, 20(2), 2208-2228. https://doi.org/10.3390/molecules20022208

References

Mall:Reflist

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  1. ↑ Leite, Marcelo (2022). Psiconautas: viagens com a ciência psicodélica brasileira. Fósforo. Sid. 161. 
  2. ↑ 2,0 2,1 2,2 2,3 2,4 2,5 Koenig, X.; Hilber, K. (2015). ”The Anti-Addiction Drug Ibogaine and the Heart: A Delicate Relation”. Molecules 20 (2): sid. 2208–2228. doi:10.3390/molecules20022208. ISSN 1420-3049. OCLC 641147188. PMID 25642835. 
  3. ↑ Alper, K. R. (2001). ”Chapter 1 Ibogaine: A review”. The Alkaloids: Chemistry and Biology 56: sid. 1–38. doi:10.1016/S0099-9598(01)56005-8. ISSN 1099-4831. 
  4. ↑ Schneider, J. A.; Rinehart, R. K. (1957). ”Analysis of the cardiovascular action of ibogaine hydrochlorid”. Archives internationales de Pharmacodynamie et de Thérapie 110: sid. 92–102. ISSN 0003-9780. OCLC 5806034. PMID 13425751. 
  5. ↑ 5,0 5,1 5,2 Mačiulaitis, R.; Kontrimavičiūtė, V.; Bressolle, F. M. M.; Briedis, V. (2008). ”Ibogaine, an anti-addictive drug: pharmacology and time to go further in development. A narrative review”. Human & Experimental Toxicology 27 (3): sid. 181-194. doi:10.1177/0960327107087802. ISSN 0960-3271. OCLC 21307548. PMID 18650249. 
  6. ↑ Soriano-García, M.; Walls, F.; Rodríguez, A.; López Celis, I. (1988). ”Crystal and molecular structure of ibogaine: An alkaloid from Stemmadenia galeottiana”. Journal of Crystallographic and Spectroscopic Research 18: sid. 197–206. doi:10.1007/BF01181911. ISSN 1074-1542. OCLC 43954962. 
  7. ↑ Arai, G.; Coppola, J.; Jeffrey, G. A. (1960). ”The structure of ibogaine”. Acta Crystallographica 13: sid. 553-564. doi:10.1107/S0365110X60001369. ISSN 0365-110X. OCLC 1460867. 
  8. ↑ Dr. Chris Jenks (2009). ”Iboga Extraction Manual”. Iboga Extraction Manual. http://www.puzzlepiece.org/ibogaine/literature/iboga_extraction_manual.pdf. 
  9. ↑ 9,0 9,1 Maillet, E. L.; Milon, N.; Heghinian, M. D.; Fishback, J.; Schürer, S. C.; Garamszegi, N.; Mash, D. C. (2015). ”Noribogaine is a G-protein biased κ-opioid receptor agonist”. Neuropharmacology 99: sid. 675-688. doi:10.1016/j.neuropharm.2015.08.032. ISSN 0028-3908. OCLC 01796748. PMID 26302653. 
  10. ↑ Antonio, T.; Childers, S. R.; Rothman, R. B.; Dersch, C. M.; King, C.; Kuehne, M.; Bornmann, W. G.; Eshleman, A. J.; et al. (2013). ”Effect of Iboga Alkaloids on µ-Opioid Receptor-Coupled G Protein Activation”. PLOS ONE 8 (10): sid. e77262. doi:10.1371/journal.pone.0077262. PMID 24204784. 
  11. ↑ Baumann, M. H.; Rothman, R. B.; Pablo, J. P.; Mash, D. C. (2001). ”In vivo neurobiological effects of ibogaine and its O-desmethyl metabolite, 12-hydroxyibogamine (noribogaine), in rats”. Journal of Pharmacology and Experimental Therapeutics 297 (2): sid. 531-539. ISSN 0022-3565. OCLC 1606914. PMID 11303040. 
  12. ↑ Hough, L. B.; Bagal, A. A.; Glick, S. D. (2000). ”Pharmacokinetic characterization of the indole alkaloid ibogaine in rats”. Methods and Findings in Experimental and Clinical Pharmacology 22 (2): sid. 77-81. doi:10.1358/mf.2000.22.2.796066. ISSN 0379-0355. OCLC 5586831. PMID 10849889. 
  13. ↑ Mash, D. C.; Kovera, C. A.; Pablo, J.; Tyndale, R. F.; Ervin, F. D.; Williams, I. C.; Singleton, E. G.; Mayor, M. (2000). ”Ibogaine: Complex Pharmacokinetics, Concerns for Safety, and Preliminary Efficacy Measures”. Annals of the New York Academy of Sciences 914 (1): sid. 394-401. doi:10.1111/j.1749-6632.2000.tb05213.x. ISSN 0077-8923. OCLC 01306678. PMID 11085338. 
  14. ↑ Zubaran, C.; Shoaib, M.; Stolerman, I. P.; Pablo, J.; Mash, D. C. (1999). ”Noribogaine Generalization to the Ibogaine Stimulus: Correlation with Noribogaine Concentration in Rat Brain”. Neuropsychopharmacology 21 (1): sid. 119-126. doi:10.1016/S0893-133X(99)00003-2. ISSN 0893-133X. OCLC 815994337. PMID 10379526. 
  15. ↑ Chen K, Kokate TG, Donevan SD, Carroll FI, Rogawski MA. Ibogaine block of the NMDA receptor: in vitro and in vivo studies. Neuropharmacology. 1996 Apr;35(4):423-31. doi: 10.1016/0028-3908(96)84107-4. PMID: 8793904.
  16. ↑ 16,0 16,1 Alper, K. R.; Lotsof, H. S.; Frenken, G. M.; Luciano, D. J.; Bastiaans, J. (1999). ”Treatment of Acute Opioid Withdrawal with Ibogaine”. The American Journal on Addictions 8 (3): sid. 234-242. doi:10.1080/105504999305848. ISSN 1055-0496. OCLC 225097764. PMID 10506904. 
  17. ↑ Referensfel: Ogiltig <ref>-tagg; ingen text har angivits för referensen med namnet NewsletterMAPS
  18. ↑ A. James Giannini (1997). Drugs of Abuse (2). California, United States: Practice Management Information Corporation. ISBN 1-57066-053-0. OCLC 34906127. 
  19. ↑ Ludwig, A.; Levine, J.; Stark, L.; Lazar, R. (1969). ”A Clinical Study of LSD Treatment in Alcoholism”. The American Journal of Psychiatry 126 (1): sid. 59-69. doi:10.1176/ajp.126.1.59. ISSN 0002-953X. OCLC 1480183. PMID 5798383. 
  20. ↑ Ly, Calvin; Greb, Alexandra C.; Cameron, Lindsay P.; Wong, Jonathan M.; Barragan, Eden V.; Wilson, Paige C.; Burbach, Kyle F.; Soltanzadeh Zarandi, Sina; et al. (2018). ”Psychedelics Promote Structural and Functional Neural Plasticity”. Cell Reports 23 (11): sid. 3170–3182. doi:10.1016/j.celrep.2018.05.022. ISSN 2211-1247. 
  21. ↑ Steinberg C, Deyell MW. Cardiac arrest after ibogaine intoxication. J Arrhythm. 2018 Jun 12;34(4):455-457. doi: 10.1002/joa3.12061. PMID: 30167018; PMCID: PMC6111465.
  22. ↑ Stephanie Hegarty (April 13, 2012). ”Can a hallucinogen from Africa cure addiction?”. BBC News. http://www.bbc.com/news/magazine-17666589. 
  23. ↑ Keegan Hamilton (November 13, 2013). ”The Shaman Will See You Now”. The Village Voice. http://www.villagevoice.com/news/the-shaman-will-see-you-now-6440113. 
  24. ↑ ”CONSELHO ESTADUAL DE POLÍTICAS SOBRE DROGAS” (på português). Diário Oficial Poder Executivo - Seção I quinta. January 14, 2016. https://www.ibogainealliance.org/wp-content/uploads/2016/01/CONSELHO-ESTADUAL-DE-POLI%CC%81TICAS-SOBRE-DROGAS.pdf. 
  25. ↑ Notice - Prescription Drug List (PDL): Multiple additions
  26. ↑ ”BtMG - Gesetz über den Verkehr mit Betäubungsmitteln” (på Deutsch). BtMG - Gesetz über den Verkehr mit Betäubungsmitteln. Bundesamt für Justiz [Federal Office of Justice]. https://www.gesetze-im-internet.de/btmg_1981/BJNR106810981.html. 
  27. ↑ ”NpSG - Neue-psychoaktive-Stoffe-Gesetz” (på Deutsch). NpSG - Neue-psychoaktive-Stoffe-Gesetz. Bundesministerium der Justiz und für Verbraucherschutz. https://www.gesetze-im-internet.de/npsg/BJNR261510016.html. 
  28. ↑ ”§ 2 AMG” (på Deutsch). § 2 AMG. Bundesamt für Justiz [Federal Office of Justice]. https://www.gesetze-im-internet.de/amg_1976/__2.html. 
  29. ↑ Prof. Dr. Helmut Pollähne (July 11, 2014). ”Cannabinoide Kräutermischungen vor dem EuGH: Legal Highs bleiben legal” (på Deutsch). LTO. https://www.lto.de/recht/hintergruende/h/eugh-urteil-c35813-c18114-legal-highs-kein-arzneimittel-strafbar-amg-btmg/. 
  30. ↑ Keegan Hamilton (November 17, 2010). ”Ibogaine: Can it Cure Addiction Without the Hallucinogenic Trip?”. The Village Voice. https://www.villagevoice.com/2010/11/17/ibogaine-can-it-cure-addiction-without-the-hallucinogenic-trip/. 
  31. ↑ ”Minutes of the 42nd meeting of the Medicines Classification Committee”. Minutes of the 42nd meeting of the Medicines Classification Committee. New Zealand Medicines and Medical Devices Safety Authority. November 3, 2009. http://www.medsafe.govt.nz/profs/class/mccMin03Nov2009.htm. 
  32. ↑ ”Forskrift om narkotika (narkotikaforskriften)” (på norsk). Forskrift om narkotika (narkotikaforskriften). Lovdata. February 14, 2013. https://lovdata.no/dokument/SF/forskrift/2013-02-14-199. 
  33. ↑ ”Läkemedelsverkets föreskrifter om förteckningar över narkotika”. Läkemedelsverkets författningssamling. Läkemedelsverket [Swedish Medical Products Agency]. June 4, 1997. https://lakemedelsverket.se/upload/lvfs/LVFS%201997-12.pdf. 
  34. ↑ ”Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien” (på Deutsch). Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien. Bundeskanzlei [Federal Chancellery of Switzerland]. https://www.admin.ch/opc/de/classified-compilation/20101220/index.html. 
  35. ↑ ”Psychoactive Substances Act 2016”. Psychoactive Substances Act 2016. UK Government. http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted. 
  36. ↑ ”Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals”. Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals. Drug Enforcement Administration (DEA). August 2020. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf. 
  37. ↑ ”Ibogaine”. Drug War Facts. Common Sense for Drug Policy. June 9, 2020. http://www.drugwarfacts.org/cms/Ibogaine#sthash.sKX0AVkG.acvAqx4Q.dpbs. 
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