Acetylmorphone

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Acetylmorphone
Acetylmorphone.svg
Systematic (IUPAC) name
3-acetoxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-6-one
Clinical data
Legal status ?
Identifiers
CAS number 14696-22-1 N
ATC code None
PubChem CID 625177
ChemSpider 21106250 YesY
Synonyms Acetylmorphone, Dihydromorphinone acetate, 3-acetyl-7,8-dihydromorphin-6-one
Chemical data
Formula C19H21NO4 
Mol. mass 327.374 g/mol
 N (what is this?)  (verify)

Acetylmorphone (Dihydromorphinone acetate) is an opiate analogue that is an acetylated derivative of hydromorphone which was developed in the early 1900s as a potential cough suppressant and analgesic. It is prepared by the acetylation of hydromorphone using either acetyl chloride or acetic anhydride. It was banned internationally in 1930 by the Health Committee of the League of Nations, in order to prevent its sale as an analogue of heroin.[1]

Acetylmorphone is not currently used in medicine, but may have a higher bioavailability than hydromorphone due to its greater lipid solubility,[2] and hence is likely to be more potent than the parent drug, although probably slower acting due to the requirement for deacetylation to the active metabolite hydromorphone. It can be expected to have similar side effects to other opiates, which would include itching, nausea and respiratory depression.

References[edit]

  1. ^ Esters of Morphine. UNODC Bulletin on Narcotics, 1953; Issue 2:36-38.
  2. ^ US patent application 2011/0015398, Gary L. Cantrell, Robert E. Halvachs, Frank W. Moser, David W. Berberich, Peter X. Wang, "3-Oxy-Hydromorphone Derivatives", published July 9, 2010