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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.

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  • 3-Monoacetylmorphine (en)
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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. (en)
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  • http://commons.wikimedia.org/wiki/Special:FilePath/Acetyl_groups_of_heroin.svg
  • http://commons.wikimedia.org/wiki/Special:FilePath/3-MAM-6-Sulphur.svg
  • http://commons.wikimedia.org/wiki/Special:FilePath/3-MAM.svg
  • http://commons.wikimedia.org/wiki/Special:FilePath/3-Monoacetylmorphine_molecule_ball.png
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  • Ball-and-stick model (en)
  • Structural formula (en)
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  • none (en)
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  • Class A (en)
legal US
  • Schedule I (en)
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O
PubChem
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  • Intravenous (en)
SMILES
  • CCOC1=C2C3=CC=C1 (en)
StdInChI
StdInChIKey
  • GMLREHXYJDLZOU-LEPYJNQMSA-N (en)
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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. (en)
legal AU
  • S9 (en)
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page length (characters) of wiki page
CAS number
  • 5140-28-3
FDA UNII code
  • 9N7243EY5T
PubChem
  • 5462504
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