Desomorphine

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Desomorphine
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Systematic (IUPAC) name
4,5-α-epoxy-17-methylmorphinan-3-ol
Legal status
Legal status
Identifiers
CAS Number 427-00-9
ATC code none
PubChem CID 5362456
ChemSpider 4515044
Synonyms Desomorphine, Dihydrodesoxymorphine, Permonid
Chemical data
Formula C17H21NO2
Molar mass 271.354 g/mol[[Script error: No such module "String".]]
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Desomorphine (Dihydrodesoxymorphine, Permonid) is an opiate analogue invented in 1932 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.[1][2][3] 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.[4] 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.[5][6]


References

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  1. ↑ Bognar R, Makleit S. New method for the preparation of dihydro-6-desoxymorphine. (German). Arzneimittelforschung. 1958 Jun;8(6):323-5. PMID 13546093
  2. ↑ Janssen PA. A review of the chemical features associated with strong morphine-like activity. British Journal of Anaesthesia. 1962 Apr;34(4):260-268. PMID 14451235
  3. ↑ Sargent LJ, May EL. Agonists--antagonists derived from desomorphine and metopon. Journal of Medicinal Chemistry. 1970 Nov;13(6):1061-3. PMID 4098039
  4. ↑ Drug police RB is alarmed with growth of Desomorphine usage
  5. ↑ Mosettig E, Cohen FL, Small LF. Desoxycodeine Studies. III. The Constitution of the So-Called Alpha-Dehydrodesoxycodeine: Bis-Di-hydrodesoxycodeine. Journal of the American Chemical Society 1932; 54:793-801.
  6. ↑ Eddy NB, Howes HA. Studies of Morphine, Codeine and their Derivatives X. Desoxymorphine-C, Desoxycodeine-C and their Hydrogenated Derivatives. Journal of Pharmacology And Experimental Therapeutics. 1935; 55(3):257-267.
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