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Ibogaine information


Ibogaine
Clinical data
Other names12-Methoxyibogamine
Routes of
administration
Oral
ATC code
  • None
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: Prescription only[1]
  • NZ: Prescription only[2]
  • UK: Under Psychoactive Substances Act
  • US: Schedule I
  • UN: Unscheduled
Identifiers
IUPAC name
  • (1R,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene
CAS Number
  • 83-74-9 checkY
PubChem CID
  • 197060
ChemSpider
  • 170667 checkY
UNII
  • 3S814I130U
ChEBI
  • CHEBI:5852
ChEMBL
  • ChEMBL1215855 checkY
CompTox Dashboard (EPA)
  • DTXSID20894069 Edit this at Wikidata
ECHA InfoCard100.001.363 Edit this at Wikidata
Chemical and physical data
FormulaC20H26N2O
Molar mass310.441 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point152 to 153 °C (306 to 307 °F)
SMILES
  • CC[C@H]1C[C@@H]2C[C@H]3c4[nH]c5ccc(OC)cc5c4CC[N@@](C2)[C@@H]13
InChI
  • InChI=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 checkY
  • Key:HSIBGVUMFOSJPD-CFDPKNGZSA-N checkY
  (verify)

Ibogaine is a naturally occurring psychoactive substance found in plants in the family Apocynaceae such as Tabernanthe iboga, Voacanga africana, and Tabernaemontana undulata. It is a psychedelic with dissociative properties.

During an eighteen year timeline, a total of 19 fatalities temporally associated with the ingestion of ibogaine were reported, from which six subjects died of acute heart failure or cardiopulmonary arrest. Its prohibition in many countries has slowed scientific research.[3] Various derivatives of ibogaine designed to lack psychedelic properties (such as 18-MC) are under preliminary research.

The psychoactivity of the root bark of the iboga tree (Tabernanthe iboga), from which ibogaine is extracted, was first discovered by the Pygmy tribes of Central Africa, who passed the knowledge to the Bwiti tribe of Gabon. French explorers in turn learned of it from the Bwiti tribe and brought ibogaine back to Europe in 1899–1900, where it was subsequently marketed in France as a stimulant under the trade name Lambarène. Although ibogaine's anti-addictive properties were first widely promoted in 1962 by Howard Lotsof, its Western medical use predates that by at least a century.

Ibogaine is an indole alkaloid obtained either by extraction from the iboga plant or by semi-synthesis from the precursor compound voacangine, another plant alkaloid. The total synthesis of ibogaine was described in 1956.[4] Structural elucidation by X-ray crystallography was completed in 1960.[5][6][7]

  1. ^ "Notice - Prescription Drug List (PDL): Multiple additions". Health Canada. Government of Canada, Health. 12 May 2017.
  2. ^ Galea S, Lorusso M, Newcombe D, Walters C, Williman J, Wheeler A (March 2011). Goodyear-Smith F (ed.). "Ibogaine--be informed before you promote or prescribe" (PDF). Journal of Primary Health Care. 3 (1): 86–7. PMID 21359272. Retrieved 4 December 2015.
  3. ^ Alper KR, Lotsof HS, Kaplan CD (January 2008). "The ibogaine medical subculture". Journal of Ethnopharmacology. 115 (1): 9–24. doi:10.1016/j.jep.2007.08.034. PMID 18029124. Archived from the original on 6 February 2008.
  4. ^ US patent 2813873, Morrice-Marie Janot & Robert Goutarel, "Derivatives of the ibogaine alkaloids", issued 19 November 1957, assigned to Les Laboratoires Gobey 
  5. ^ Soriano-García M (1992). "Structure of ibogaine". Acta Crystallogr. C. 48 (11): 2055–2057. Bibcode:1992AcCrC..48.2055S. doi:10.1107/S0108270192002786.
  6. ^ Soriano-García M, Walls F, Rodríguez A, Celis IL (1988). "Crystal and molecular structure of ibogamine: An alkaloid from Stemmadenia galeottiana". Journal of Crystallographic and Spectroscopic Research. 18 (2): 197–206. doi:10.1007/BF01181911. S2CID 97519993.
  7. ^ Arai G, Coppola J, Jeffrey GA (1960). "The structure of ibogaine". Acta Crystallographica. 13 (7): 553–564. Bibcode:1960AcCry..13..553A. doi:10.1107/S0365110X60001369.

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This is an overview of the legality of ibogaine by country. Ibogaine is not included on the UN International Narcotics Control Board's Green List, or...

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and near-death outcomes, with some fatalities occurring. In high doses, ibogaine is considered to be toxic, and has caused serious comorbidities when used...

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alkaloid ibogaine, which is a psychedelic drug which may help with drug addiction, but which has significant adverse effects, with ibogaine being both...

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known for his efforts to legalize marijuana and to promote the benefits of Ibogaine as an addiction treatment. He is a founder and long-term activist in the...

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occurring psychoactive compounds. Ibogaine is used in pain management and to treat opiate addiction. In low dosages, ibogaine is a stimulant and aphrodisiac...

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differ significantly from saline control". While the related alkaloids ibogaine (20–40 mg/kg), harmaline (10–40 mg/kg) and desethylcoronaridine (10–40 mg/kg)...

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Dimitri Mobengo Mugianis

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his drug use, Mugianis traveled to the Netherlands for ibogaine treatment. During his ibogaine-induced hallucinations, he saw his Greek ancestors, his...

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Howard Lotsof

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American scientific researcher who discovered and pioneered the use of ibogaine as an approach in Western medicine in the treatment of substance addictions...

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Jeremy Weate

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and now runs an ibogaine-assisted retreat centre - Tabula Rasa Retreat - in Portugal. He is also Executive Director of the Global Ibogaine Therapy Alliance...

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for the semi-synthesis of ibogaine. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates...

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Coronaridine

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(under the now obsolete synonym Ervatamia coronaria) it was named. Like ibogaine, (R)-coronaridine and (S)-coronaridine can decrease intake of cocaine and...

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Max Cantor

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student director Peter Sellars. Cantor wrote for The Village Voice about ibogaine as a cure for heroin addiction, and had taken an interest in the cult surrounding...

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Oneirophrenia

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as prolonged sleep deprivation, sensory deprivation, or drugs (such as ibogaine). Oneirophrenia is often confused with an acute case of schizophrenia due...

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depression. 5-MeO-DMT is being studied for depression and eating disorders. Ibogaine and Noribogaine are being studied for addiction. Tryptamines: Psilocin...

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Voacanga africana

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semi-synthesis of ibogaine. Voacamidine and voacamine cleavage can be used to increase voacangine yield. While small amounts of ibogaine are found in Voacanga...

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drugs" include tramadol, chlorpromazine, olanzapine, dextromethorphan, ibogaine, and ethanol, all of which bind to multiple receptors or influence multiple...

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Peter Youngblood Hills

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substance abuse rehabilitation: Evaluating treatments with LSD, Peyote, Ibogaine and Ayahuasca". Current Drug Abuse Reviews. 7 (2): 101–16. doi:10...

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specified quantities of psilocybin, psilocyn, dimethyltryptamine (DMT), ibogaine, mescaline, lysergic acid diethylamide (LSD), and 3,4-methylenedioxymethamphetamine...

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day are: LSD, DMT, psilocybin, mescaline, 2C-B, 2C-I, 5-MeO-DMT, AMT, ibogaine and DOM. In general, the mechanism of action of how these drugs have therapeutic...

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