Desomorphine

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Desomorphine
Systematic (IUPAC) name
4,5-α-epoxy-17-methylmorphinan-3-ol
Clinical data
Pregnancy cat. ?
Legal statusSchedule I (US)
Identifiers
CAS number427-00-9 N
ATC codeNone
PubChemCID 5362456
ChemSpider4515044 YesY
UNII7OP86J5E33 YesY
SynonymsDesomorphine, Dihydrodesoxymorphine, Permonid
Chemical data
FormulaC17H21NO2 
Mol. mass271.354 g/mol
 N (what is this?)  (verify)
 
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Desomorphine
Systematic (IUPAC) name
4,5-α-epoxy-17-methylmorphinan-3-ol
Clinical data
Pregnancy cat. ?
Legal statusSchedule I (US)
Identifiers
CAS number427-00-9 N
ATC codeNone
PubChemCID 5362456
ChemSpider4515044 YesY
UNII7OP86J5E33 YesY
SynonymsDesomorphine, Dihydrodesoxymorphine, Permonid
Chemical data
FormulaC17H21NO2 
Mol. mass271.354 g/mol
 N (what is this?)  (verify)

Desomorphine (dihydrodesoxymorphine, Permonid) is an opioid invented in 1932 in the United States that is a derivative of morphine, where the 6-hydroxyl group has been removed and the 7,8 double bond has been reduced.[1] It has sedative and analgesic effects, and is around 8-10 times more potent than morphine.[2][3][4][5] 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. The traditional synthesis of desomorphine starts 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.[6][7]

Contents

"Krokodil"

Desomorphine attracted attention in 2010 in Russia due to an increase in clandestine production, presumably due to its relatively simple synthesis from codeine. The drug is easily made from codeine, iodine and red phosphorus,[8] in a process similar to the manufacture of methamphetamine from pseudoephedrine; like methamphetamine, desomorphine made this way is often highly impure and is contaminated with various toxic and corrosive byproducts. The street name in Russia for home-made desomorphine is "krokodil" (крокодил, crocodile), reportedly due to the scale-like appearance of skin of its users and the derivation from chlorocodide.[9] Due to difficulties in procuring heroin, combined with easy and cheap access to over-the-counter pharmacy products containing codeine in Russia, use of "krokodil" has been on the increase. The high associated with krokodil is akin to that of heroin, but lasts a much shorter period. While the effects of heroin use can last four to eight hours, the effects of krokodil do not usually extend past one and one half hours, with the symptoms of withdrawal setting in soon after. Krokodil takes roughly 30 minutes to an hour to prepare with over-the-counter ingredients in a kitchen.[10] Since the home-made mix is routinely injected immediately with little or no further purification, "krokodil" has become notorious for producing severe tissue damage, phlebitis and gangrene, sometimes requiring limb amputation in long-term users.[11] The amount of tissue damage is so high that addicts' life expectancies are said to be as low as two to three years, especially as they are often highly susceptible to infections and gangrene due to widespread HIV infection among injecting drug users in Russia.[12][13][14][15]

Abuse of home-made desomorphine was first reported in middle and eastern Siberia in 2002, but has since spread throughout Russia and the neighboring former Soviet republics. In October 2011, indications of "krokodil" use were found in Germany, with some media outlets claiming several dead users.[16] One death in Poland in December 2011 was also believed to be caused by "krokodil" use, and its use has been confirmed among Russian expatriate communities in a number of other European countries.[17]

Other ingredients

While crude amateur attempts to make krokodil will almost invariably still contain some remaining codeine as well as other, "accidentally produced" synthetic opioids such as iodocodeine, some of the krokodil produced also contains other drugs. For example, the codeine pills sold in Russia may also contain ingredients such as caffeine, paracetamol, or diphenhydramine (coincidentally an opioid potentiator); while chemicals such as tropicamide, found in over the counter eyedrops, may also be added to the mixture in attempt to prolong or enhance the experience. [18]

Synthesis of desomorphine from codeine.


See also

References

  1. ^ US patent 1980972, Lyndon Frederick Small, "MORPHINE DERIVATIVE AND PROCESSES", published 1934-19-07, issued 1934-13-11 
  2. ^ Casy, Alan F.; Parfitt, Robert T. (1986). Opioid analgesics: chemistry and receptors. New York: Plenum Press. p. 32. ISBN 978-0-306-42130-3.
  3. ^ Bognar, R; Makleit, S (1958). "Neue Methode für die Vorbereitung von dihydro-6-desoxymorphine [New method for the preparation of dihydro-6-desoxymorphine]" (in German). Arzneimittel-Forschung 8 (6): 323–5. PMID 13546093.
  4. ^ Janssen, Paul A. J. (1962). "A Review of the Chemical Features Associated with Strong Morphine-Like Activity". British Journal of Anaesthesia 34 (4): 260–8. doi:10.1093/bja/34.4.260. PMID 14451235.
  5. ^ Sargent, Lewis J.; May, Everette L. (1970). "Agonists-antagonists derived from desomorphine and metopon". Journal of Medicinal Chemistry 13 (6): 1061–3. doi:10.1021/jm00300a009. PMID 4098039.
  6. ^ Mosettig, Erich; Cohen, Frank L.; Small, Lyndon F. (1932). Journal of the American Chemical Society 54 (2): 793–801. doi:10.1021/ja01341a051.
  7. ^ Eddy, Nathan B.; Howes, Homer A. (1935). "Studies of Morphine, Codeine and their Derivatives X. Desoxymorphine-C, Desoxycodeine-C and their Hydrogenated Derivatives". Journal of Pharmacology and Experimental Therapeutics 55 (3): 257–67. http://jpet.aspetjournals.org/content/55/3/257.short.
  8. ^ Savchuk, S. A.; Barsegyan, S. S.; Barsegyan, I. B.; Kolesov, G. M. (2011). "Chromatographic study of expert and biological samples containing desomorphine". Journal of Analytical Chemistry 63 (4): 361–70. doi:10.1134/S1061934808040096.
  9. ^ Priymak, Arthur (June 23, 2011). "Desomorphine, drug for the poor, kills all of its victims". Pravda. http://english.pravda.ru/hotspots/crimes/23-06-2011/118296-desomorphine-0/.
  10. ^ Veronese, Keith. "Krokodil: Russia’s Designer Drug That Will Eat Your Flesh". http://io9.com/5859291/krokodil-russias-designer-drug-that-will-eat-your-flesh. Retrieved 11/27/2012.
  11. ^ http://mosmedservice.com/index/dezomorfin/0-80
  12. ^ Walker, Shaun (June 22, 2011). "Krokodil: The drug that eats junkies". The Independent. http://www.independent.co.uk/news/world/europe/krokodil-the-drug-that-eats-junkies-2300787.html.
  13. ^ Shuster, Simon (June 20, 2011). "The Curse of the Crocodile: Russia's Deadly Designer Drug". Time. http://www.time.com/time/world/article/0,8599,2078355,00.html.
  14. ^ "Дезоморфин последствия – фото [Desomorphine consequences - photo]" (in Russian). February 9, 2011. http://stopnarkotik.com.ua/obschaya/dezomorfin-posledstviya-foto/.[self-published source?]
  15. ^ Snap goes the Crocodile. Marina Akhmedova, 3 August 2012. Russky Reporter Magazine
  16. ^ "Deutschland kämpft gegen neue todesdroge [Germany fights new death-drug]" (in German). Bild. October 14, 2011. http://www.bild.de/news/inland/ueberdosis/deutschland-kaempft-gegen-neue-todesdroge-20456878.bild.html. Retrieved 2011-11-10.
  17. ^ Skowronek, R.; Celiński, R.; Chowaniec, C. A. (2012). ""Crocodile" – new dangerous designer drug of abuse from the East". Clinical Toxicology 50 (4): 269. doi:10.3109/15563650.2012.660574. PMID 22385107. edit
  18. ^ "Siberia: Krokodil Tears - Full Length". http://www.vice.com/vice-news/siberia-krokodil-tears-full-length. Retrieved May 14, 2012.