3-Monoacetylmorphine

3-Monoacetylmorphine

Systematic (IUPAC) name
3-acetyl-6-hydroxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan
Clinical data
Routes of administration	Intravenous
Legal status
Legal status	AU: S9 (Prohibited) UK: Class A US: Schedule I
Identifiers
CAS Number	5140-28-3
ATC code	none
PubChem	CID 5462504
ChemSpider	4575431
Synonyms	3-Acetylmorphine, O(3)-monoacetylmorphine
Chemical data
Formula	C19H21NO4
Molar mass	327.1471 g/mol
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
InChI InChI=1S/C19H21NO4/c1-10(21)23-15-6-3-11-9-13-12-4-5-14(22)18-19(12,7-8-20(13)2)16(11)17(15)24-18/h3-6,12-14,18,22H,7-9H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1 Key:GMLREHXYJDLZOU-LEPYJNQMSA-N
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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.

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]}

3-MAM-6-Sulfate (M3A6S)

Acetyl groups of heroin. In 3-MAM lower group is changed to hydrogen making hydroxyl-group in 6-position.

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