CHEBI:3084 - bethanechol

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ChEBI Name bethanechol
ChEBI ID CHEBI:3084
Definition The carbamic acid ester of 2-methylcholine. A slowly hydrolysed muscarinic agonist with no nicotinic effects, it is used as its chloride salt to increase smooth muscle tone, as in the gastrointestinal tract following abdominal surgery, treatment of gastro-oesophageal reflux disease, and as an alternative to catheterisation in the treatment of non-obstructive urinary retention.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:506520
Supplier Information
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Formula C7H17N2O2
Net Charge +1
Average Mass 161.22150
Monoisotopic Mass 161.129
InChI InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1
InChIKey NZUPCNDJBJXXRF-UHFFFAOYSA-O
SMILES CC(C[N+](C)(C)C)OC(N)=O
Roles Classification
Biological Role(s): muscarinic agonist
Any drug that binds to and activates a muscarinic cholinergic receptor.
Application(s): muscarinic agonist
Any drug that binds to and activates a muscarinic cholinergic receptor.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bethanechol (CHEBI:3084) has role muscarinic agonist (CHEBI:38325)
bethanechol (CHEBI:3084) is a carbamate ester (CHEBI:23003)
bethanechol (CHEBI:3084) is a quaternary ammonium ion (CHEBI:35267)
Incoming bethanechol chloride (CHEBI:3085) has part bethanechol (CHEBI:3084)
(R)-bethanechol (CHEBI:59260) is a bethanechol (CHEBI:3084)
(S)-bethanechol (CHEBI:59261) is a bethanechol (CHEBI:3084)
IUPAC Name
2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium
Synonyms Sources
(2-hydroxypropyl)trimethylammonium carbamate ChemIDplus
2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium ChEMBL
2-carbamoyloxypropyl-trimethylazanium DrugBank
amidopropyldimethylbetaine ChemIDplus
Bethanechol KEGG COMPOUND
carbamoyl-β-methylcholine ChemIDplus
carbamyl-β-methylcholine ChemIDplus
Database Links Databases
358 DrugCentral
C06850 KEGG COMPOUND
DB01019 DrugBank
LSM-5196 LINCS
View more database links
Registry Numbers Types Sources
1773706 Beilstein Registry Number Beilstein
674-38-4 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
17889543 PubMed citation ChEMBL
Last Modified
22 February 2017