Acetylmorphone

Acetylmorphone

Systematic (IUPAC) name
3-acetoxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-6-one
Identifiers
CAS Number	14696-22-1
ATC code	none
PubChem	CID 625177
ChemSpider	21106250
Synonyms	Acetylmorphone, Dihydromorphinone acetate, 3-acetyl-7,8-dihydromorphin-6-one
Chemical data
Formula	C19H21NO4
Molar mass	327.374 g/mol
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 Key:QVIUKMVKLLVCDU-ATNYCFDYSA-N
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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

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