Dipropanoylmorphine

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Dipropanoylmorphine
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Clinical data
SynonymsDipropanoylmorphine
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
E number{{#property:P628}}
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Chemical and physical data
FormulaC23H27NO5
Molar mass397.464 g/mol

Dipropanoylmorphine is an opiate derivative, the 3,6-dipropanoyl ester of morphine. It was developed in the 1970s as an analgesic. [1] It is rarely used in some countries for the relief of severe pain such as that caused by terminal cancer, as an alternative to diamorphine (heroin) and morphine.

Dipropanoylmorphine is slightly slower acting than diamorphine, but longer lasting, and is slightly more potent due to its relatively higher lipophilicity. [2] Side effects are similar to those of other opioids and include itching, nausea and respiratory depression.

Dipropanoylmorphine is prepared by reacting morphine with propanoic anhydride, in an analogous manner to how heroin is produced by reacting morphine with acetic anhydride.

While acetic anhydride is a restricted chemical around the world due to its potential uses in making heroin, it is used in vast amounts by the chemical industry for the manufacture of drugs such as aspirin. Propanoic anhydride however is much less widely used. Although it is used in the manufacture of a range of pharmaceuticals, none of these are produced in nearly as large quantities, and sales of propanoic anhydride in quantities larger than one gram must be reported in many countries because of its potential use in making fentanyl type synthetic opiates.

References

  1. May EL, Jacobson AE. Chemistry and pharmacology of homologs of 6-acetyl-and 3,6-diacetylmorphine. Journal of Pharmaceutical Sciences. 1977 Feb;66(2):285-6.
  2. Owen JA, Nakatsu K. Morphine diesters. II. Blood metabolism and analgesic activity in the rat. Canadian Journal of Physiology and Pharmacology. 1984 Apr;62(4):452-6.

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