Structure via PubChem · Public domain (PubChem)
3-O-acetylmorphine
Sign in to saveAlso known as O(3)-Monoacetylmorphine
3-Monoacetylmorphine (3-MAM) or 3-acetylmorphine is a less active metabolite of heroin (diacetylmorphine), the other two being morphine and more active 6-monoacetylmorphine (6-MAM).
Chemical data
- Formula
- C19H21NO4
- Molecular weight
- 327.4 g/mol
- IUPAC name
- [(4R,4aR,7S,7aR,12bS)-7-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] acetate
- SMILES
- CC(=O)OC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4C)[C@@H](O2)[C@H](C=C5)O)C=C1
- InChIKey
- GMLREHXYJDLZOU-LEPYJNQMSA-N
- XLogP
- 0.9
- Polar surface area
- 59 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 327.147058
Show 4 more facts
- chemical formula
- C₁₉H₂₁NO₄
- canonical SMILES
- CC(=O)OC1=C2C3=C(CC4C5C3(CCN4C)C(O2)C(C=C5)O)C=C1
- isomeric SMILES
- CC(=O)OC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4C)[C@@H](O2)[C@H](C=C5)O)C=C1
- Commons category
- 3-Monoacetylmorphine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
3-Monoacetylmorphine (3-MAM) or 3-acetylmorphine is a less active metabolite of heroin (diacetylmorphine), the other two being morphine and more active 6-monoacetylmorphine (6-MAM).
Because of the acetyl-group in 3-position, 3-MAM has relatively weak affinity to μ-opioid receptors.
Excerpted from Wikipedia’s “3-O-acetylmorphine” article, available under the CC BY-SA 4.0 licence.