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Dibenzoylmorphine

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Dibenzoylmorphine

Dibenzoylmorphine
Systematic (IUPAC) name
3,6-dibenzoyl-(5α,6α)-7,8-didehydro-4,5-epoxy-17-methylmorphinan
Clinical data
Legal status
  • Illegal under UN drug conventions as "ester of morphine"
Identifiers
ATC code ?
Chemical data
Formula C31H27NO5 
Mol. mass 493.549 g/mol
 YesY   

Dibenzoylmorphine is an designer drugs" for around five years following the introduction of the first international restrictions on the sale of heroin in 1925. It is described as being virtually identical to heroin and morphine in its effects, and consequently was itself banned internationally in 1930 by the Health Committee of the League of Nations, in order to prevent its sale as an unscheduled alternative to diacetylmorphine.[1]

It is produced in the same fashion as other esters of morphine -- treating morphine with an acid anhydride (or some acids or other relatives of acids like acetyl chloride) to get a mono-, di-, tri-, or tetra-ester. Specifically, the original 1875 synthesis was effected by boiling morphine for 2 hours in benzoic acid at 130°C, as was heroin made by using acetic anhydride.

See also

References

  1. ^ Esters of Morphine. UNODC Bulletin on Narcotics, 1953; Issue 2:36-38.



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