CHEBI:146264 - noribogaine

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ChEBI Name noribogaine
ChEBI ID CHEBI:146264
Definition An organic heteropentacyclic compound that is ibogamine in which the indole hydrogen para to the indole nitrogen has been replaced by a hydroxy group. It is the primary (and long-lived) metabolite of ibogaine, the psychoactive indole alkaloid found in the African rainforest shrub Tabernanthe iboga.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H24N2O
Net Charge 0
Average Mass 296.414
Monoisotopic Mass 296.18886
InChI InChI=1S/C19H24N2O/c1-2-12-7-11-8-16-18-14(5-6-21(10-11)19(12)16)15-9-13(22)3-4-17(15)20-18/h3-4,9,11-12,16,19-20,22H,2,5-8,10H2,1H3/t11-,12+,16+,19+/m1/s1
InChIKey RAUCDOKTMDOIPF-RYRUWHOVSA-N
SMILES [C@@]12([C@@]3([C@H](C[C@](C1)(CN3CCC=4C5=C(C=CC(=C5)O)NC42)[H])CC)[H])[H]
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
NMDA receptor antagonist
Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
kappa-opioid receptor agonist
A compound that exhibits agonist activity at the kappa-opioid receptor.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
kappa-opioid receptor agonist
A compound that exhibits agonist activity at the kappa-opioid receptor.
psychotropic drug
A loosely defined grouping of drugs that have effects on psychological function.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing noribogaine (CHEBI:146264) has functional parent ibogaine (CHEBI:5852)
noribogaine (CHEBI:146264) has role κ-opioid receptor agonist (CHEBI:59282)
noribogaine (CHEBI:146264) has role NMDA receptor antagonist (CHEBI:60643)
noribogaine (CHEBI:146264) has role psychotropic drug (CHEBI:35471)
noribogaine (CHEBI:146264) has role serotonin uptake inhibitor (CHEBI:50949)
noribogaine (CHEBI:146264) is a monoterpenoid indole alkaloid (CHEBI:65323)
noribogaine (CHEBI:146264) is a organic heteropentacyclic compound (CHEBI:38164)
noribogaine (CHEBI:146264) is a secondary amino compound (CHEBI:50995)
noribogaine (CHEBI:146264) is a tertiary amino compound (CHEBI:50996)
noribogaine (CHEBI:146264) is conjugate base of noribogaine(1+) (CHEBI:146258)
Incoming noribogaine(1+) (CHEBI:146258) is conjugate acid of noribogaine (CHEBI:146264)
IUPAC Name
(18R)-ibogamine-12-ol
Synonyms Sources
12-hydroxyibogamine ChemIDplus
ibogamin-12-ol ChemIDplus
O-demethylibogaine ChemIDplus
O-desmethylibogaine ChEBI
O-noribogaine ChemIDplus
Manual Xref Database
Noribogaine Wikipedia
View more database links
Registry Number Type Source
481-88-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
06 March 2020