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CHEBI:2168 - 6-acetylmorphine

Default Structure
ChEBI IDCHEBI:2168
ChEBI Name6-acetylmorphine
Stars
DefinitionA morphinane alkaloid that is morphine in which the hydroxy group at position 3 is replaced by an acetyloxy group. It is a metabolite of heroin.
Last Modified15 May 2025
DownloadsMolfile
FormulaC19H21NO4
Net Charge0
Average Mass327.380
Monoisotopic Mass327.14706
SMILES[H][C@@]12C=C[C@H](OC(C)=O)[C@@H]3Oc4c(O)ccc5c4[C@@]31CCN(C)[C@@H]2C5
InChIInChI=1S/C19H21NO4/c1-10(21)23-15-6-4-12-13-9-11-3-5-14(22)17-16(11)19(12,18(15)24-17)7-8-20(13)2/h3-6,12-13,15,18,22H,7-9H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
InChIKeyJJGYGPZNTOPXGV-SSTWWWIQSA-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)
6-acetylmorphine (CHEBI:2168) has functional parent morphine (CHEBI:17303)
6-acetylmorphine (CHEBI:2168) has role drug metabolite (CHEBI:49103)
6-acetylmorphine (CHEBI:2168) is a acetate ester (CHEBI:47622)
6-acetylmorphine (CHEBI:2168) is a morphinane alkaloid (CHEBI:25418)
6-acetylmorphine (CHEBI:2168) is a organic heteropentacyclic compound (CHEBI:38164)
6-acetylmorphine (CHEBI:2168) is a tertiary amino compound (CHEBI:50996)
IUPAC Name 
3-hydroxy-17-methyl-5α-7,8-didehydro-4,5-epoxymorphinan-6α-yl acetate
Synonyms  Source
6-AMChEBI
6-O-acetylmorphineChEBI
6-O-monoacetylmorphineKEGG COMPOUND
6-MAMChEBI
6-monoacetylmorphineChEBI
O6-acetylmorphineChEBI
Manual XrefsDatabases
6-MonoacetylmorphineWikipedia
C11781KEGG COMPOUND
HMDB0041812HMDB
Registry NumbersSources
CAS:2784-73-8NIST Chemistry WebBook
Citations