Dihydrodesoxymorphine

Dihydrodesoxymorphine

Clinical data
Synonyms	Desomorphine, Dihydrodesoxymorphine, Permonid
Legal status
Legal status	US: Schedule I
Identifiers
IUPAC name 4,5-α-epoxy-17-methyl-morphinan-3-ol
CAS Number	427-00-9
PubChem CID	5362456
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C17H21NO2
Molar mass	271.354 g/mol
3D model (JSmol)	Interactive image
SMILES CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3CCC4

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Desomorphine (Dihydrodesoxymorphine, Permonid) is an opiate analogue invented in 1933 in the United States, that is a derivative of morphine, where the 6-hydroxy group has been removed and the 7,8 double bond has been saturated. It has sedative and analgesic effects, and is around 10 times more potent than morphine. It was used in Switzerland under the brand name Permonid, and was described as having a fast onset and a short duration of action, with relatively little nausea or respiratory depression compared to equivalent doses of morphine. This drug has attracted recent attention in Russia due to an upsurge in clandestine production, presumably due to its relatively simple synthesis from codeine. It is prepared from α-chlorocodide, which is itself obtained by reacting thionyl chloride with codeine. By catalytic reduction, α-chlorocodide gives dihydrodesoxycodeine, which yields desomorphine on demethylation.

References

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