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).

3-Monoacetylmorphine

Clinical data
Other names	3-Acetylmorphine, O(3)-monoacetylmorphine
Routes of administration	Intravenous
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) UK: Class A US: Schedule I
Identifiers
IUPAC name 3-acetyl-6-hydroxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan
CAS Number	5140-28-3^Y
PubChem CID	5462504
ChemSpider	4575431^Y
UNII	9N7243EY5T
CompTox Dashboard (EPA)	DTXSID30183774
ECHA InfoCard	100.208.392
Chemical and physical data
Formula	C19H21NO4
Molar mass	327.380 g·mol^−1
3D model (JSmol)	Interactive image
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^Y Key:GMLREHXYJDLZOU-LEPYJNQMSA-N^Y
(verify)

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 a 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. Houdi AA, Kottayil S, Crooks PA, Butterfield DA (March 1996). "3-O-acetylmorphine-6-O-sulfate: a potent, centrally acting morphine derivative". Pharmacology, Biochemistry, and Behavior. 53 (3): 665–71. doi:10.1016/0091-3057(95)02067-5. PMID 8866970.
2. "3-O-Acetylmorphine-6-O-sulfate". BindingDB.
3. Brock CP, Kottayil S, Butterfield DA, Crooks PA (January 1996). "A Dihydromorphine-6-O-sulfate". Acta Crystallographica Section C: Crystal Structure Communications. 52 (1): 122–5. doi:10.1107/S0108270195010250.