3-Monoacetylmorphine

3-Monoacetylmorphine
Structural formula
Ball-and-stick model
Clinical data
Synonyms 3-Acetylmorphine, O(3)-monoacetylmorphine
Routes of
administration		 Intravenous
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
ECHA InfoCard 100.208.392 Edit this at Wikidata
Chemical and physical data
Formula C19H21NO4
Molar mass 327.1471 g/mol
3D model (JSmol)
  (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 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, Abdulghani A.; Kottayil, Santosh; Crooks, Peter A.; Butterfield, D.Alan (1996). "3-O-Acetylmorphine-6-O-sulfate: A potent, centrally acting morphine derivative". Pharmacology Biochemistry and Behavior. 53: 665–671. doi:10.1016/0091-3057(95)02067-5.
  2. ↑ 3-O-Acetylmorphine-6-O-sulfate
  3. ↑ Dihydromorphine-6-O-sulfate
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