Compound: IBOGAINE
SMILES: O(c1cc2c([nH]c3c2CCN4C[C@H]5C[C@@H]3[C@@H]4[C@H](C5)CC)cc1)C
InChIKey: HSIBGVUMFOSJPD-CFDPKNGZSA-N
Synonyms: IBOGAINE, 83-74-9, Endabuse, (-)-Ibogaine, NIH 10567, 3S814I130U, CHEBI:5852, DTXSID20894069, NSC-249764, (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, (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, 12 Methoxyibogamine, RefChem:147568, DTXCID401324112, NIH10567, 201-498-4, 12-Methoxyibogamine, Ibogain, (5beta)-12-methoxyibogamine, CHEMBL1215855, Tabernanthe iboga, EINECS 201-498-4, NSC 249764, DEA No. 7260, UNII-3S814I130U, HSDB 8180, HJM, IBOGAINE [MI], IBOGAINE [VANDF], IBOGAINE [MART.], IBOGAINE [WHO-DD], (6xi)-12-Methoxyibogamine, (18R)-12-methoxyibogamine, SCHEMBL113571, SCHEMBL31738807, GTPL13148, HSIBGVUMFOSJPD-CFDPKNGZSA-N, BDBM50308247, FS-9083, 7-Ethyl-6,6beta,7,8,9,10,12,13-octahydro-2-methoxy-6,9-methano-5H-pyrido(1',2':1,2)azepino(5,4-b)indole, FI159190, NS00041096, Q409455, (6R,6aS,7S,9R,11S)-7-ethyl-2-methoxy-6,6a,7,8,9,10,12,13-octahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole
Theoretical properties:
molecular_formula: C20H26N2O
molecular_weight: 310.4 g/mol
exact_mass: 310.204513457 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 23
topological_polar_surface_area: 28.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 148 °C
solubility: Soluble in chloroform
Descriptions:
{"pubchem": "Ibogaine is an organic heteropentacyclic compound that is ibogamine in which the indole hydrogen para to the indole nitrogen has been replaced by a methoxy group. It has a role as a oneirogen, an inhibitor, a hallucinogen and a plant metabolite. It is an aromatic ether, an organic heteropentacyclic compound and a monoterpenoid indole alkaloid. It is functionally related to an ibogamine. It is a conjugate base of an ibogaine(1+).", "chebi": "An organic heteropentacyclic compound that is ibogamine in which the indole hydrogen <em>para</em> to the indole nitrogen has been replaced by a methoxy group.", "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "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, NMDA, and nicotinic acetylcholine receptors; its metabolite noribogaine primarily acts as a serotonin reuptake inhibitor and \u03ba-opioid receptor agonist.\nThe 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 controversially researched for its potential in treating addiction despite being classified as a controlled substance. Ibogaine can be semisynthetically produced from voacangine, with its total synthesis achieved in 1956 and its structure confirmed by X-ray crystallography in 1960. Its clinical use and development have been limited due to regulatory barriers and serious safety risks, such as toxicity to the heart.\nIbogaine produces a two-phase experience\u2014initially visionary and dream-like with vivid imagery and altered perception, followed by an introspective period marked by lingering side effects, such as nausea and mood disturbances, which may persist for days. Long-term risks include mania and heart issues such as long QT syndrome, and potentially fatal interactions with other drugs.\nOnly two randomized controlled trials have been conducted on ibogaine and noribogaine for substance use disorders, and while they show preliminary anti-addictive potential, their safety and efficacy are unconfirmed, with significant risks including cardiotoxicity and fatalities. Ibogaine is federally illegal in the United States. It is used in treatment clinics abroad under legal gray areas, with growing media attention. It has inspired the development of non-hallucinogenic, non-cardiotoxic analogues like 18-MC and tabernanthalog for therapeutic use. In 2025, Texas allocated $50 million for clinical research on ibogaine to develop FDA-approved treatments for opioid use disorder, co-occurring substance use disorders, and other ibogaine-responsive conditions."}