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3-Monoacetylmorphine

Chemical compound

3-Monoacetylmorphine

Chemical compound

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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.

3-MAM-6-Sulfate (M3A6S)

References

References

  1. (March 1996). "3-O-acetylmorphine-6-O-sulfate: a potent, centrally acting morphine derivative". Pharmacology, Biochemistry, and Behavior.
  2. (August 2006). "Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners". Bioorganic & Medicinal Chemistry Letters.
  3. (January 1996). "A Dihydromorphine-6-''O''-sulfate". Acta Crystallographica Section C.
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heroin opioid-metabolites recreational-drug-metabolites human-drug-metabolites
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