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
^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.
PMID8866970.
S2CID14870642.