3-monoacetylmorphine

3-Monoacetylmorphine

3-Monoacetylmorphine

Chemical compound

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).

Quick Facts Clinical data, Other names ...

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. [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): 665–671. doi:10.1016/0091-3057(95)02067-5. PMID 8866970. S2CID 14870642.
  2. [2]
    Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA (August 2006). "Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners". Bioorganic & Medicinal Chemistry Letters. 16 (16): 4291–4295. doi:10.1016/j.bmcl.2006.05.060. PMID 16777416.
  3. [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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