ibogaine

Also known as 12-methoxyibogamine

Ibogaine is a psychoactive indole alkaloid derived from plants such as Tabernanthe iboga, characterized by hallucinogenic and oneirogenic effects. Traditionally used by Central African foragers, it has undergone controversial research for the treatment of substance use disorders. Ibogaine exhibits complex pharmacology by interacting with multiple neurotransmitter systems, notably affecting opioid, serotonin, sigma, and NMDA receptors, while its metabolite noribogaine primarily acts as a serotonin reuptake inhibitor and κ-opioid receptor agonist.

Key facts

Drug.Watchedfields: verified
Drug.verifiedrevid: 443866754
Drug.image: Ibogaine.svg
Drug.image_class: skin-invert-image
Drug.width: 250px
Drug.image2: Ibogaine-from-xtal-Mercury-3D-bs.png
Drug.image_class2: bg-transparent
Drug.width2: 250px
Drug.routes_of_administration: Oral
Drug.class: Hallucinogen; Oneirogen; Stimulant
Drug.ATC_prefix: None
Drug.legal_AU: S4
Drug.legal_CA: Prescription only
Drug.legal_NZ: Prescription only
Drug.legal_UK: PSA
Drug.legal_UN: Unscheduled
Drug.legal_US: Schedule I
Drug.metabolites: Noribogaine (major active metabolite)

via Wikipedia infobox

Chemical data

Formula: C20H26N2O
Molecular weight: 310.4 g/mol
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
SMILES: CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC
InChIKey: HSIBGVUMFOSJPD-CFDPKNGZSA-N
XLogP: 3.9
Polar surface area: 28.3 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

676 papers

Ibogaine treatment outcomes for opioid dependence from a twelve-month follow-up observational study.The American journal of drug and alcohol abuse · 2018
A systematic literature review of clinical trials and therapeutic applications of ibogaine.Journal of substance abuse treatment · 2022
Magnesium-ibogaine therapy in veterans with traumatic brain injuries.Nature medicine · 2024
How toxic is ibogaine?Clinical toxicology (Philadelphia, Pa.) · 2016
Ibogaine: a review.The Alkaloids. Chemistry and biology · 2001

via PubMed

Wikidata facts

Mass: 310.205

Show 5 more facts

chemical formula: C₂₀H₂₆N₂O
canonical SMILES: CCC1CC2CC3C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC
Commons category: Ibogaine
isomeric SMILES: CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC
hashtag: ibogaine

Sources (2)

via Wikidata · CC0

~36 min read

Article

28 sections

Contents

Use and effects
Adverse effects
Neurotoxicity
Interactions
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
Synthesis
Analogues and derivatives
Biosynthesis
Natural occurrence
History
Society and culture
Legal status
Treatment clinics
Media
Documentary films
Print media
Television drama
Radio and podcasts
Research
Psychotherapy
Addiction treatment
Texas research initiative
See also
References
External links

The psychoactivity of the root bark of the iboga tree, T. iboga, one of the plants from which ibogaine is extracted, was first discovered by forager tribes in Central Africa, who passed the knowledge to the Bwiti tribe of Gabon. It was first documented in the 19th century for its spiritual use, later isolated and synthesized for its psychoactive properties, briefly marketed in Europe as a stimulant, and ultimately researched—and often controversial—for its potential in treating addiction despite being classified as a controlled substance.