Acetylmorphone

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
Clinical data
Other namesAcetylmorphone, Dihydromorphinone acetate, 3-acetyl-7,8-dihydromorphin-6-one
ATC code
  • none
Identifiers
IUPAC name
  • 3-acetoxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-6-one
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC19H21NO4
Molar mass327.380 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)Oc4ccc5C[C@H]1[N@](C)CC[C@@]23c5c4O[C@H]3C(=O)CC[C@@H]12
InChI
  • InChI=1S/C19H21NO4/c1-10(21)23-15-6-3-11-9-13-12-4-5-14(22)18-19(12,7-8-20(13)2)16(11)17(15)24-18/h3,6,12-13,18H,4-5,7-9H2,1-2H3/t12-,13+,18-,19-/m0/s1 Y
  • Key:QVIUKMVKLLVCDU-ATNYCFDYSA-N Y
 NY (what is this?)  (verify)

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
  1. "UNODC - Bulletin on Narcotics - 1953 Issue 2 - 008". United Nations : Office on Drugs and Crime.
  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


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