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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.<ref>Bognar R, Makleit S. New method for the preparation of dihydro-6-desoxymorphine. (German). ''Arzneimittelforschung''. 1958 Jun;8(6):323-5. PMID 13546093</ref><ref>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</ref><ref>Sargent LJ, May EL. Agonists--antagonists derived from desomorphine and metopon. ''Journal of Medicinal Chemistry''. 1970 Nov;13(6):1061-3. PMID 4098039</ref> 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.<ref>[http://eng.bashinform.ru/index.php?id=12434 Drug police RB is alarmed with growth of Desomorphine usage]</ref> It is prepared from α-chlorocodide, which is itself obtained by reacting [[thionyl chloride]] with codeine. By [[reduction (chemistry)|catalytic reduction]], α-chlorocodide gives dihydrodesoxycodeine, which yields desomorphine on [[demethylation]].<ref>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.</ref><ref>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.</ref> |
'''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.<ref>Bognar R, Makleit S. New method for the preparation of dihydro-6-desoxymorphine. (German). ''Arzneimittelforschung''. 1958 Jun;8(6):323-5. PMID 13546093</ref><ref>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</ref><ref>Sargent LJ, May EL. Agonists--antagonists derived from desomorphine and metopon. ''Journal of Medicinal Chemistry''. 1970 Nov;13(6):1061-3. PMID 4098039</ref> 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.<ref>[http://eng.bashinform.ru/index.php?id=12434 Drug police RB is alarmed with growth of Desomorphine usage]</ref> It is prepared from α-chlorocodide, which is itself obtained by reacting [[thionyl chloride]] with codeine. By [[reduction (chemistry)|catalytic reduction]], α-chlorocodide gives dihydrodesoxycodeine, which yields desomorphine on [[demethylation]].<ref>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.</ref><ref>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.</ref> |
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== References == |
== References == |
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Revision as of 15:42, 27 July 2010
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| Clinical data | |
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| Other names | Desomorphine, Dihydrodesoxymorphine, Permonid |
| ATC code |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.006.406 |
| Chemical and physical data | |
| Formula | C17H21NO2 |
| Molar mass | 271.354 g/mol g·mol−1 |
| 3D model (JSmol) | |
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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
- ^ Bognar R, Makleit S. New method for the preparation of dihydro-6-desoxymorphine. (German). Arzneimittelforschung. 1958 Jun;8(6):323-5. PMID 13546093
- ^ 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
- ^ Sargent LJ, May EL. Agonists--antagonists derived from desomorphine and metopon. Journal of Medicinal Chemistry. 1970 Nov;13(6):1061-3. PMID 4098039
- ^ Drug police RB is alarmed with growth of Desomorphine usage
- ^ 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.
- ^ 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.