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CHEBI:178585 - norcocaine

ChEBI IDCHEBI:178585
ChEBI Namenorcocaine
Stars
DefinitionA tropane alkaloid that is cocaine in which the N-methyl group has been demethylated. It is a metabolite of cocaine.
Last Modified24 June 2025
SubmitterMetaboLights
DownloadsMolfile
FormulaC16H19NO4
Net Charge0
Average Mass289.331
Monoisotopic Mass289.13141
SMILES[H][C@@]12CC[C@@]([H])(N1)[C@@H](C(=O)OC)[C@@H](OC(=O)c1ccccc1)C2
InChIInChI=1S/C16H19NO4/c1-20-16(19)14-12-8-7-11(17-12)9-13(14)21-15(18)10-5-3-2-4-6-10/h2-6,11-14,17H,7-9H2,1H3/t11-,12+,13-,14+/m0/s1
InChIKeyAYDBLCSLKNTEJL-RFQIPJPRSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
norcocaine (CHEBI:178585) has role drug metabolite (CHEBI:49103)
norcocaine (CHEBI:178585) is a benzoate ester (CHEBI:36054)
norcocaine (CHEBI:178585) is a methyl ester (CHEBI:25248)
norcocaine (CHEBI:178585) is a secondary amino compound (CHEBI:50995)
norcocaine (CHEBI:178585) is a tropane alkaloid (CHEBI:37332)
Incoming Relation(s)
N-succinyl norcocaine (CHEBI:234506) has functional parent norcocaine (CHEBI:178585)
IUPAC Name 
methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate
Synonyms  Source
methyl (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2-carboxylateChEBI
(−)-norcocaineChEBI
N-demethylcocaineChEBI
(1R,2R,3S,5S)-3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl esterChEBI
[1R-(exo,exo)]-3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl esterChEBI
Manual XrefsDatabases
559083ChemSpider
NorcocaineWikipedia
HMDB0041955HMDB
Registry NumbersSources
CAS:18717-72-1ChEBI
Citations