3-Monoacetylmorphine

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 ;
PubChem CID	5462504;
ChemSpider	4575431 ;
CompTox Dashboard (EPA)	DTXSID30183774 ;
ECHA InfoCard	100.208.392
Chemical and physical data
Formula	C19H21NO4
Molar mass	327.1471 g/mol 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 ; Key:GMLREHXYJDLZOU-LEPYJNQMSA-N ;
	(verify)

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]

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

[1]

[2]

[3]