CHEBI:10093 - yohimbine

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ChEBI Name yohimbine
ChEBI ID CHEBI:10093
Definition An indole alkaloid with α2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H26N2O3
Net Charge 0
Average Mass 354.44282
Monoisotopic Mass 354.194
InChI InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
InChIKey BLGXFZZNTVWLAY-SCYLSFHTSA-N
SMILES [H][C@@]12CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@]1([H])N(CCc3c1[nH]c1ccccc31)C2
Roles Classification
Biological Role(s): dopamine receptor D2 antagonist
An antagonist that binds to and deactivates the dopamine receptor D2, the main receptor for all antipsychotic drugs.
alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
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): alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
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ChEBI Ontology
Outgoing yohimbine (CHEBI:10093) has functional parent yohimbic acid (CHEBI:35633)
yohimbine (CHEBI:10093) has role α-adrenergic antagonist (CHEBI:37890)
yohimbine (CHEBI:10093) has role dopamine receptor D2 antagonist (CHEBI:131787)
yohimbine (CHEBI:10093) has role serotonergic antagonist (CHEBI:48279)
yohimbine (CHEBI:10093) is a methyl 17-hydroxy-20ξ-yohimban-16-carboxylate (CHEBI:48565)
IUPAC Name
methyl 17α-hydroxyyohimban-16α-carboxylate
Synonyms Sources
(+)-yohimbine NIST Chemistry WebBook
(16α,17α)-17-hydroxyyohimban-16-carboxylic acid methyl ester NIST Chemistry WebBook
17α-hydroxyyohimban-16α-carboxylic acid methyl ester NIST Chemistry WebBook
aphrodine ChemIDplus
corynine ChemIDplus
Johimbin ChEBI
Quebrachin ChemIDplus
quebrachine ChemIDplus
yohimbic acid methyl ester ChemIDplus
Yohimbin ChemIDplus
Yohimbine KEGG COMPOUND
Database Links Databases
3659 DrugCentral
C00001789 KNApSAcK
C09256 KEGG COMPOUND
D08685 KEGG DRUG
DB01392 DrugBank
LSM-2779 LINCS
View more database links
Registry Numbers Types Sources
146-48-5 CAS Registry Number ChemIDplus
146-48-5 CAS Registry Number NIST Chemistry WebBook
4720812 Beilstein Registry Number Beilstein
97276 Beilstein Registry Number Beilstein
Last Modified
22 February 2017