ibogamine (CHEBI:5853)

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ChEBI Name	ibogamine

ChEBI ID	CHEBI:5853

Definition	A monoterpenoid indole alkaloid with formula C₁₉H₂₄N₂. It is isolated from the flowering plant genus, Tabernaemontana and exhibits anti-addictive properties.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C19H24N2

Net Charge

Average Mass

280.415

Monoisotopic Mass

280.19395

InChI

InChI=1S/C19H24N2/c1-2-13-9-12-10-16-18-15(7-8-21(11-12)19(13)16)14-5-3-4-6-17(14)20-18/h3-6,12-13,16,19-20H,2,7-11H2,1H3/t12-,13+,16+,19+/m1/s1

InChIKey

LRLCVRYKAFDXKU-YGOSVGOTSA-N

SMILES

[C@H]12[C@@]3([C@H](C[C@](C1)(CN3CCC=4C5=C(C=CC=C5)NC42)[H])CC)[H]

Metabolite of Species	Details
Tabernaemontana australis (IPNI:315554-2)	Isolated from stalk. See: PubMed
Ervatamia hainanensis (IPNI:78925-1)	Found in rhizome (BTO:0001181). See: PubMed
Stemmadenia galeottiana (IPNI:81804-1)	Found in wood (BTO:0005516). See: DOI
Tabernaemontana alba (IPNI:81985-1)	Found in bark (BTO:0001301). Isolated from root bark. See: PubMed
Tabernaemontana johnstonii (IPNI:82167-1)	Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Tabernanthe iboga (NCBI:txid141617)	See: DOI
Tabernaemontana catharinensis (NCBI:txid403124)	Found in stem (BTO:0001300). See: PubMed
Tabernaemontana hystrix (NCBI:txid761074)	See: PubMed

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):	EC 3.1.1.7 (acetylcholinesterase) inhibitor An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. 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):	oneirogen Any substance that produces or enhances dream-like states of consciousness.

ChEBI Ontology
Outgoing	ibogamine (CHEBI:5853) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462) ibogamine (CHEBI:5853) has role oneirogen (CHEBI:146270) ibogamine (CHEBI:5853) has role plant metabolite (CHEBI:76924) ibogamine (CHEBI:5853) is a indole alkaloid fundamental parent (CHEBI:38482) ibogamine (CHEBI:5853) is a monoterpenoid indole alkaloid (CHEBI:65323) ibogamine (CHEBI:5853) is a organic heteropentacyclic compound (CHEBI:38164) ibogamine (CHEBI:5853) is a tertiary amino compound (CHEBI:50996) ibogamine (CHEBI:5853) is conjugate base of ibogamine(1+) (CHEBI:146257)

Incoming	ibogaine (CHEBI:5852) has functional parent ibogamine (CHEBI:5853) ibogamine(1+) (CHEBI:146257) is conjugate acid of ibogamine (CHEBI:5853)

IUPAC Name

ibogamine

Last Modified

06 March 2020