CHEBI:28313 - (S)-nornicotine

ChEBI IDCHEBI:28313
ChEBI Name(S)-nornicotine
Stars
ASCII Name(S)-nornicotine
DefinitionA pyridine alkaloid that is nicotine lacking the methyl group on the pyrrolidine nitrogen.
Secondary ChEBI IDsCHEBI:7634, CHEBI:25594
Last Modified17 June 2025
DownloadsMolfile
FormulaC9H12N2
Net Charge0
Average Mass148.209
Monoisotopic Mass148.10005
SMILES[H][C@@]1(c2cccnc2)CCCN1
InChIInChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m0/s1
InChIKeyMYKUKUCHPMASKF-VIFPVBQESA-N
Roles Classification
Biological Roles:
nicotinic acetylcholine receptor agonist  An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
nicotinic acetylcholine receptor agonist  An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
phytogenic insecticide  An insecticide compound naturally occurring in plants.
ChEBI Ontology
Outgoing Relation(s)
(S)-nornicotine (CHEBI:28313) has parent hydride nicotine (CHEBI:18723)
(S)-nornicotine (CHEBI:28313) has role metabolite (CHEBI:25212)
(S)-nornicotine (CHEBI:28313) has role nicotinic acetylcholine receptor agonist (CHEBI:47958)
(S)-nornicotine (CHEBI:28313) has role phytogenic insecticide (CHEBI:22917)
(S)-nornicotine (CHEBI:28313) is a pyridine alkaloid (CHEBI:26416)
(S)-nornicotine (CHEBI:28313) is a pyrrolidine alkaloid (CHEBI:26456)
(S)-nornicotine (CHEBI:28313) is conjugate base of (S)-nornicotine(1+) (CHEBI:190184)
(S)-nornicotine (CHEBI:28313) is enantiomer of (+)-Nornicotine (CHEBI:37)
Incoming Relation(s)
[(2-{4-[(2S)-2-(pyridin-3-yl)pyrrolidin-1-yl]butanamido}ethyl)sulfanyl]acetic acid (CHEBI:234459) has functional parent (S)-nornicotine (CHEBI:28313)
(S)-nornicotine(1+) (CHEBI:190184) is conjugate acid of (S)-nornicotine (CHEBI:28313)
(+)-Nornicotine (CHEBI:37) is enantiomer of (S)-nornicotine (CHEBI:28313)
IUPAC Name 
3-[(2S)-pyrrolidin-2-yl]pyridine
Synonyms  Source
NornicotineKEGG COMPOUND
1'-demethyl nicotineChemIDplus
l-nor-nicotineChemIDplus
S-(−)-nornicotineNIST Chemistry WebBook
(S)-1'-demethylnicotineNIST Chemistry WebBook
(−)-nornicotineChEBI
Manual XrefsDatabases
C06524KEGG COMPOUND
2560PPDB
nornicotineAlan Wood's Pesticides
C00042792KNApSAcK
Registry NumbersSources
Reaxys:81966Reaxys
CAS:494-97-3KEGG COMPOUND
CAS:494-97-3ChemIDplus
CAS:494-97-3NIST Chemistry WebBook
Citations