CHEBI:18723 - nicotine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways
ChEBI Name nicotine
ChEBI ID CHEBI:18723
Definition An N-alkylpyrrolidine that consists of N-methylpyrrolidine bearing a pyridin-3-yl substituent at position 2. It has been isolated from Nicotiana tabacum.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C10H14N2
Net Charge 0
Average Mass 162.23160
InChI InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3
InChIKey SNICXCGAKADSCV-UHFFFAOYSA-N
SMILES CN1CCCC1c1cccnc1
Metabolite of Species Details
Nicotiana tabacum (NCBI:4097) See: PubMed
Roles Classification
Biological Role(s): mitogen
A chemical substance that encourages a cell to commence cell division, triggering mitosis.
nicotinic acetylcholine receptor agonist
An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
neurotoxin
A poison that interferes with the functions of the nervous system.
teratogenic agent
A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
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): peripheral nervous system drug
A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
nicotinic acetylcholine receptor agonist
An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
biomarker
A substance used as an indicator of a biological state.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
psychotropic drug
A loosely defined grouping of drugs that have effects on psychological function.
anxiolytic drug
Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nicotine (CHEBI:18723) has role anxiolytic drug (CHEBI:35474)
nicotine (CHEBI:18723) has role biomarker (CHEBI:59163)
nicotine (CHEBI:18723) has role immunomodulator (CHEBI:50846)
nicotine (CHEBI:18723) has role mitogen (CHEBI:52290)
nicotine (CHEBI:18723) has role neurotoxin (CHEBI:50910)
nicotine (CHEBI:18723) has role nicotinic acetylcholine receptor agonist (CHEBI:47958)
nicotine (CHEBI:18723) has role peripheral nervous system drug (CHEBI:49110)
nicotine (CHEBI:18723) has role plant metabolite (CHEBI:76924)
nicotine (CHEBI:18723) has role psychotropic drug (CHEBI:35471)
nicotine (CHEBI:18723) has role teratogenic agent (CHEBI:50905)
nicotine (CHEBI:18723) is a N-alkylpyrrolidine (CHEBI:46775)
nicotine (CHEBI:18723) is a pyridine alkaloid (CHEBI:26416)
nicotine (CHEBI:18723) is a pyrrolidine alkaloid (CHEBI:26456)
Incoming 6-hydroxynicotine (CHEBI:24729) has functional parent nicotine (CHEBI:18723)
nicotine N1'-oxide (CHEBI:30734) has parent hydride nicotine (CHEBI:18723)
nornicotine (CHEBI:28313) has parent hydride nicotine (CHEBI:18723)
(R)-nicotine (CHEBI:39162) is a nicotine (CHEBI:18723)
(S)-nicotine (CHEBI:17688) is a nicotine (CHEBI:18723)
IUPAC Name
3-(1-methylpyrrolidin-2-yl)pyridine
Synonyms Sources
(±)-nicotine ChemIDplus
(+-)-3-(1-Methyl-2-pyrrolidinyl)pyridine KEGG COMPOUND
(R,S)-nicotine ChemIDplus
(RS)-nicotine UM-BBD
Nicotin ChEBI
Nikotin ChEBI
Database Links Databases
C00002057 KNApSAcK
c0468 UM-BBD
C16150 KEGG COMPOUND
DB00184 DrugBank
HMDB14330 HMDB
Nicotine Wikipedia
View more database links
Registry Numbers Types Sources
22083-74-5 CAS Registry Number ChemIDplus
82108 Reaxys Registry Number Reaxys
82108 Beilstein Registry Number Beilstein
82111 Beilstein Registry Number Beilstein
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Last Modified
23 October 2015
General Comment
2007-08-13 The term 'nicotine' usually refers to the (S) stereomer (CHEBI:17688).