Ibogaine

Ibogaine

Ibogaine

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Description

Ibogaine

Also known as:

  • (–)-12-Methoxyibogamine
  • (-)-Ibogaine
  • 12-Methoxyibogamin[German][ACD/IUPAC Name]
  • 12-Methoxyibogamine[ACD/IUPAC Name]
  • 12-Méthoxyibogamine[French][ACD/IUPAC Name]
  • 3S814I130U
  • Endabuse
  • Ibogain
  • Ibogaine (8CI)
  • Ibogamine, 12-methoxy-[ACD/Index Name]
  • 12-methoxy-ibogamine[ACD/IUPAC Name]
  • 7-ethyl-2-methoxy-6,6a,7,8,9,10,12,13-octahydro-5H-6,9-methano-pyrido[1',2':1,2]azepino[4,5-b]indole
  • 7-Ethyl-6,6β,7,8,9,10,12,13-octahydro-2-methoxy-6,9-methano-5H-pyrido(1',2':1,2)azepino(5,4-b)indole
  • UNII:3S814I130U

An alkaloid found in many African plants most famously Iboga, with psychedelic and hallucinogenic properties. May be unpleasant. Traditionally used in tribal environments for coming-of-age rituals, it has recently been used as an alternative treatment for drug addiction although this usage has not been backed by conclusive data in humans. Has killed in overdose.

Summary

Ibogaine is an indole alkaloid found in some plants of the Apocynaceae family such as Tabernanthe iboga, Voacanga africana and Tabernaemontana undulata. 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.

Ibogaine’s medical history in the West began in the early 1900s when it was indicated for use as a neuromuscular stimulant. In the 1940s and 1950s, its suitability as potential cardiovascular drug was studied. 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. 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. Ibogaine is not currently approved for any medical uses in the United States. Preliminary research in animals indicates that it could potentially be used for treatment of addiction; however, there is a lack of non-anecdotal data in humans.

Although not licensed as therapeutic drug and despite safety concerns, ibogaine is currently used as an anti-addiction medication in dozens of clinics worldwide.

History

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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. 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.

The total synthesis of ibogaine was described in 1956 and structural elucidation by X-ray crystallography was completed in 1960.

Chemistry

Ibogaine

Ibogaine

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, another plant alkaloid.

Common NameIbogaine
Systematic nameIbogaine
FormulaC_{20}H_{26}N_{2}O
SMILESCC[[email protected]]1C[[email protected]@H]2C[[email protected]@H]3[[email protected]]1N(C2)CCc4c3[nH]c5c4cc(cc5)OC
Std. InChiInChI=1S/C20H26N2O/c1-3-13-8-12-9-17-19-15(6-7-22(11-12)20(13)17)16-10-14(23-2)4-5-18(16)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3/t12-,13+,17+,20+/m1/s1
Std. InChiKeyHSIBGVUMFOSJPD-CFDPKNGZSA-N
Avg. Mass310.4332 Da
Molecular Weight310.4332
Monoisotopic Mass310.204498 Da
Nominal Mass310
ChemSpider ID170667

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Dosing Guide

Oral
Common16-22mg/kg
NOTEDoses

Duration

Ibogaine Duration Data
Onset45-180 minutes
Duration24-30 hours
After-effects24-72 hours

Interactions and Synergies

Caution

  1. PCP
    • PCP can reduce opioid tolerance, increasing the risk of overdose
  2. N2O
    • Both substances potentiate the ataxia and sedation caused by the other and can lead to unexpected loss of consciousness at high doses. While unconscious, vomit aspiration is a risk if not placed in the recovery position. Memory blackouts are likely.
  3. Amphetamines
    • Stimulants increase respiration rate allowing a higher dose of opiates. If the stimulant wears off first then the opiate may overcome the patient and cause respiratory arrest.
  4. MAOIs
    • Coadministration of monoamine oxidase inhibitors (MAOIs) with certain opioids has been associated with rare reports of severe and fatal adverse reactions. There appear to be two types of interaction, an excitatory and a depressive one. Symptoms of the excitatory reaction may include agitation, headache, diaphoresis, hyperpyrexia, flushing, shivering, myoclonus, rigidity, tremor, diarrhea, hypertension, tachycardia, seizures, and coma. Death has occurred in some cases.

Dangerous

    Low Synergy

      No Synergy

      1. Mushrooms
      2. LSD
      3. DMT
      4. Mescaline
      5. DOx
        • No unexpected interactions.
      6. NBOMes
      7. 2C-x
      8. 2C-T-x
        • No expected interactions, some opioids have serotonin action, and could lead to Serotonin Syndrome or a seizure. These are pretty much only to Pentazocine, Methadone, Tramadol, Tapenatdol.
      9. αMT
        • No unexpected interactions
      10. 5-MeO-xxT
      11. MDMA
      12. Caffeine
      13. SSRIs
        • There have been very infrequent reports of a risk of serotonin syndrome with this combination, though this should not be a practical concern.

      High Synergy

      1. Cannabis

      General Information

      Experiences
      Oral
      Vaporization
      Come up
      Dosage
      EffectsAddiction help, Euphoria, empathy, insight, brightened colour, Closed/Open eye visuals, enhanced tactile sensation, mental/physical stimulation, decreased appetite, pupil constriction, restlessness, change in perception, ego softening, sweating/chills, muscle tension, confusion, insomnia.
      After Effects
      Avoid
      Warning
      Risks
      Test Kits
      Marguis Test Result
      Tolerance
      Detection
      Half-life
      Advice
      Note
      Note 2:
      Note 3:

      Effects

      Pharmacological Effects

      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 and weak µ-opioid receptor agonist or weak partial agonist. 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, 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. After ibogaine ingestion in humans, noribogaine shows higher plasma levels than ibogaine and is detected for a longer period than ibogaine. Noribogaine is also more potent than ibogaine in rat drug discrimination assays when tested for the subjective effects of ibogaine. Ibogaine also has activity as an NMDA receptor antagonist.

      Subjective Effects

      Physical Effects

      Psychological Effects

      Visual Effects

      Enhancements

      Distortions

      Geometry

      Hallucinatory states

      Auditory Effects

      Sensory Effects

      Transpersonal Effects

      Anecdotally, these components are generally considered to be most consistent with the naturally-occurring entheogenic tryptamines such as ayahuasca, ibogaine and psilocybin.

      Legal Status

      Ibogaine is unregulated and unlicensed in most countries. Some exceptions are listed below.

    1. Brazil: On January 14, 2016, Ibogaine was legalized for prescription use.
    2. Canada: As of 2009, ibogaine is unregulated.
    3. Germany: Ibogaine is not a controlled substance under the BtMG (Narcotics Act) or the NpSG (New Psychoactive Substances Act)) It is legal, as long as it is not sold for human consumption, according to §2 AMG.
    4. Mexico: As of 2009, ibogaine is unregulated.
    5. New Zealand: Ibogaine was gazetted in 2009 as a non-approved prescription medicine.
    6. Norway: Ibogaine is illegal (as are all tryptamine derivatives).
    7. Sweden: Ibogaine is schedule I.
    8. 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.
    9. United States: Ibogaine is classified as a Schedule I drug, 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.

    10. References

      1. 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
      2. Koenig, X., & Hilber, K. (2015). The anti-addiction drug ibogaine and the heart: a delicate relation. Molecules, 20(2), 2208-2228.
      3. Alper, K.R. Ibogaine: A review. Alkaloids Chem. Biol. 2001, 56, 1–38.
      4. Schneider, J.A.; Rinehart, R.K. Analysis of the cardiovascular action of ibogaine hydrochlorid. Arch. Int. Pharmacodyn. Ther. 1957, 110, 92–102.
      5. 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.
      6. Koenig, Xaver; Hilber, Karlheinz (2015). "The Anti-Addiction Drug Ibogaine and the Heart: A Delicate Relation". Molecules. 20 (2): 2208–2228. :10.3390/molecules20022208.  1420-3049.
      7. 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.
      8. Crystal and molecular structure of ibogaine: An alkaloid from Stemmadenia galeottiana | http://link.springer.com/article/10.1007/BF01181911
      9. The structure of ibogaine | http://scripts.iucr.org/cgi-bin/paper?S0365110X60001369
      10. Iboga Extraction Manual | http://www.puzzlepiece.org/ibogaine/literature/iboga_extraction_manual.pdf
      11. Noribogaine is a G-protein biased κ-opioid receptor agonist | https://www.ncbi.nlm.nih.gov/pubmed/26302653
      12. Noribogaine is a G-protein biased κ-opioid receptor agonist | https://www.ncbi.nlm.nih.gov/pubmed/26302653?dopt=Abstract
      13. Effect of Iboga alkaloids on µ-opioid receptor-coupled G protein activation | https://www.ncbi.nlm.nih.gov/pubmed/24204784
      14. In vivo neurobiological effects of ibogaine and its O-desmethyl metabolite, 12-hydroxyibogamine (noribogaine), in rats | https://www.ncbi.nlm.nih.gov/pubmed/11303040
      15. Pharmacokinetic characterization of the indole alkaloid ibogaine in rats | https://www.ncbi.nlm.nih.gov/pubmed/10849889
      16. Ibogaine: complex pharmacokinetics, concerns for safety, and preliminary efficacy measures | https://www.ncbi.nlm.nih.gov/pubmed/11085338
      17. Noribogaine generalization to the ibogaine stimulus: correlation with noribogaine concentration in rat brain | https://www.ncbi.nlm.nih.gov/pubmed/10379526
      18. ibogaine in the treatment of chemical dependence disorders: clinical perspectives | http://www.maps.org/news-letters/v05n3/05316ibo.html
      19. Treatment of acute opioid withdrawal with ibogaine | https://www.ncbi.nlm.nih.gov/pubmed/10506904
      20. ibogaine in the treatment of chemical dependence disorders: clinical perspectives | http://www.maps.org/news-letters/v05n3/05316ibo.html
      21. Giannini, A. James (1997). Drugs of Abuse (2 ed.). Practice Management Information Corporation. ISBN 1-57066-053-0.
      22. A clinical study of LSD treatment in alcoholism | https://www.ncbi.nlm.nih.gov/pubmed/5798383
      23. Treatment of acute opioid withdrawal with ibogaine | https://www.ncbi.nlm.nih.gov/pubmed/10506904
      24. Ly, Calvin; Greb, Alexandra C.; Cameron, Lindsay P.; Wong, Jonathan M.; Barragan, Eden V.; Wilson, Paige C.; Burbach, Kyle F.; Soltanzadeh Zarandi, Sina; Sood, Alexander; Paddy, Michael R.; Duim, Whitney C.; Dennis, Megan Y.; McAllister, A. Kimberley; Ori-McKenney, Kassandra M.; Gray, John A.; Olson, David E. (2018). "Psychedelics Promote Structural and Functional Neural Plasticity". Cell Reports. 23 (11): 3170–3182. :10.1016/j.celrep.2018.05.022.  2211-1247.
      25. Can a hallucinogen from Africa cure addiction? | http://www.bbc.com/news/magazine-17666589
      26. The Shaman Will See You Now | http://www.villagevoice.com/news/the-shaman-will-see-you-now-6440113
      27. https://www.ibogainealliance.org/wp-content/uploads/2016/01/CONSELHO-ESTADUAL-DE-POLÍTICAS-SOBRE-DROGAS.pdf
      28. http://www.straight.com/article-116274/ibogaine-a-one-way-trip-to-sobriety-pot-head-says
      29. http://laws-lois.justice.gc.ca/eng/acts/C-38.8/
      30. "BtMG - Gesetz über den Verkehr mit Betäubungsmitteln" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
      31. "NpSG - Neue-psychoaktive-Stoffe-Gesetz" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
      32. "§ 2 AMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
      33. http://www.villagevoice.com/news/ibogaine-can-it-cure-addiction-without-the-hallucinogenic-trip-6437311
      34. http://www.medsafe.govt.nz/profs/class/mccMin03Nov2009.htm
      35. https://lovdata.no/dokument/SF/forskrift/2013-02-14-199
      36. https://lakemedelsverket.se/upload/lvfs/LVFS 1997-12.pdf
      37. Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted
      38. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf
      39. http://www.drugwarfacts.org/cms/Ibogaine#sthash.sKX0AVkG.acvAqx4Q.dpbs

      Sources

      Information made possible with:

      1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
      2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
      3. PubChem National Center for Bio Informatics
      4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
      5. Wikipedia

      Additional APIs were used to construct this information. Thanks for ChemSpider, NCBI, PubChem etc.

      Data is constantly updated so please check back later to see if there is any more available information on this substance.