3-Monoacetylmorphine

3-Monoacetylmorphine
Systematic (IUPAC) name
3-acetyl-6-hydroxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan
Clinical data
Pregnancy cat.  ?
Legal status Prohibited (S9) (AU) ? (UK) Schedule I (US)
Routes Intravenous
Identifiers
CAS number 5140-28-3 Y
ATC code None
PubChem CID 5462504
ChemSpider 4575431 Y
Synonyms 3-Acetylmorphine, O(3)-monoacetylmorphine
Chemical data
Formula C19H21NO4 
Mol. mass 327.1471 g/mol
SMILES eMolecules & PubChem
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3-Monoacetylmorphine (3-MAM) or 3-acetylmorphine is 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.

As 3-O-acetylmorphine-6-O-sulfate (C19H23NO7S), where 6-OH is changed to 6-O-SO3, it can act as potent, centrally acting morphine derivative and has important analgesic properties. [1] [2] [3]

References

  1. ^ 3-O-Acetylmorphine-6-O-sulfate: A potent, centrally acting morphine derivative
  2. ^ 3-O-Acetylmorphine-6-O-sulfate
  3. ^ Dihydromorphine-6-O-sulfate