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
Structural formula
Ball-and-stick model
Clinical data
Other names3-Acetylmorphine, O(3)-monoacetylmorphine
Routes of
administration		Intravenous
ATC code
  • none
Legal status
Legal status
Identifiers
  • 3-acetyl-6-hydroxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.208.392
Chemical and physical data
FormulaC19H21NO4
Molar mass327.380 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:GMLREHXYJDLZOU-LEPYJNQMSA-N checkY
  (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. S2CID 14870642.
  2. Crooks, Peter A.; Kottayil, Santosh G.; Al-Ghananeem, Abeer M.; Byrn, Stephen R.; Butterfield, D. Allan (15 August 2006). "3-O-Acetylmorphine-6-O-sulfate". BindingDB. 16 (16): 4291–4295. doi:10.1016/j.bmcl.2006.05.060. PMID 16777416.
  3. Brock CP, Kottayil S, Butterfield DA, Crooks PA (January 1996). "A Dihydromorphine-6-O-sulfate". Acta Crystallographica Section C. 52 (1): 122–5. doi:10.1107/S0108270195010250.
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