CHEBI:2814 - arecoline

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ChEBI Name arecoline
ChEBI ID CHEBI:2814
Definition A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C8H13NO2
Net Charge 0
Average Mass 155.19430
Monoisotopic Mass 155.095
InChI InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
InChIKey HJJPJSXJAXAIPN-UHFFFAOYSA-N
SMILES COC(=O)C1=CCCN(C)C1
Roles Classification
Biological Role(s): muscarinic agonist
Any drug that binds to and activates a muscarinic cholinergic 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): muscarinic agonist
Any drug that binds to and activates a muscarinic cholinergic receptor.
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ChEBI Ontology
Outgoing arecoline (CHEBI:2814) has role metabolite (CHEBI:25212)
arecoline (CHEBI:2814) has role muscarinic agonist (CHEBI:38325)
arecoline (CHEBI:2814) is a enoate ester (CHEBI:51702)
arecoline (CHEBI:2814) is a methyl ester (CHEBI:25248)
arecoline (CHEBI:2814) is a pyridine alkaloid (CHEBI:26416)
arecoline (CHEBI:2814) is a tetrahydropyridine (CHEBI:26921)
IUPAC Name
methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
Synonyms Sources
arecaidine methyl ester ChEBI
arecaline ChEBI
arecholine ChEBI
arekolin ChEBI
methylarecaiden ChEBI
methylarecaidin ChEBI
Database Links Databases
Arecoline Wikipedia
C00002020 KNApSAcK
C10129 KEGG COMPOUND
CN101411705 Patent
CN102464607 Patent
DB04365 DrugBank
HMDB0030353 HMDB
LSM-15214 LINCS
US2506458 Patent
View more database links
Registry Numbers Types Sources
123045 Reaxys Registry Number Reaxys
63-75-2 CAS Registry Number KEGG COMPOUND
63-75-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21809341 PubMed citation Europe PMC
22493525 PubMed citation Europe PMC
23525646 PubMed citation Europe PMC
23895157 PubMed citation Europe PMC
Last Modified
25 February 2016