Desomorphine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Desomorphine
Permonid.svg
Systematic (IUPAC) name
4,5-α-Epoxy-17-methylmorphinan-3-ol
Clinical data
Legal status Prohibited (S9) (AU) Schedule I (US)
Dependence liability Very High
Identifiers
CAS number 427-00-9 N
ATC code None
PubChem CID 5362456
ChemSpider 4515044 YesY
UNII 7OP86J5E33 YesY
ChEMBL CHEMBL2106274 N
Synonyms Desomorphine, Dihydrodesoxymorphine, Permonid
Chemical data
Formula C17H21NO2 
Mol. mass 271.354 g/mol
 N (what is this?)  

Desomorphine (dihydrodesoxymorphine, Permonid, street name krokodil) is a derivative from morphine (an opioid) with powerful, fast-acting sedative and analgesic effects.[1][2][3][4] Patented in 1932,[5] Desomorphine was used in Switzerland under the brand name Permonid[6] 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.

Desomorphine is derived from morphine where the 6-hydroxyl group and the 7,8 double bond have been reduced.[5] 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.[7][8]

Recreational use

Desomorphine abuse in Russia attracted international attention in 2010 due to an increase in clandestine production, presumably due to its relatively simple synthesis from codeine available over-the-counter. Abuse of homemade desomorphine was first reported in Siberia in 2003 when Russia started a major crackdown on heroin production and trafficking, but has since spread throughout Russia and the neighboring former Soviet republics.[9]

The drug can be made from codeine and iodine derived from OTC medications and red phosphorus from match strikers,[10] in a process similar to the manufacture of methamphetamine from pseudoephedrine. Like methamphetamine, desomorphine made this way is often contaminated with various agents. The street name in Russia for homemade desomorphine is krokodil (Russian: крокодил, crocodile), possibly related to the chemical name of the precursor α-chlorocodide, or similarity of a skin, damaged by the drug use, to crocodile leather.[11]

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 increased. It has been estimated that around 100,000 people use krokodil in Russia and around 20,000 in Ukraine.[12] 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.[13]

Effects

Russian sources report homemade krokodil producing severe tissue damage, phlebitis and gangrene, sometimes requiring limb amputation in long-term users.[14]

Regulation

In Russia, desomorphine was declared illegal narcotic analgesic in 1998. However, while codeine-containing drugs generally have been prescription products in Europe, in Russia they were not until June 2012.[15]

References

  1. ^ Casy, Alan F.; Parfitt, Robert T. (1986). Opioid analgesics: chemistry and receptors. New York: Plenum Press. p. 32. ISBN 978-0-306-42130-3. 
  2. ^ Bognar, R; Makleit, S (1958). "Neue Methode für die Vorbereitung von dihydro-6-desoxymorphine" [New method for the preparation of dihydro-6-desoxymorphine]. Arzneimittel-Forschung (in German) 8 (6): 323–5. PMID 13546093. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ a b US patent 1980972, Lyndon Frederick Small, "Morphine Derivative and Processes", published 1934-19-07, issued 1934-13-11 
  6. ^ "Krokodil". New York State Office of Alcoholism and Substance Abuse Services. 
  7. ^ Mosettig, Erich; Cohen, Frank L.; Small, Lyndon F. (1932). "Desoxycodeine Studies. III. The Constitution of the So-Called α-Dihydrodesoxycodeine: Bis-Dihydrodesoxycodeine". Journal of the American Chemical Society 54 (2): 793–801. doi:10.1021/ja01341a051. 
  8. ^ 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. 
  9. ^ Gahr, M; Freudenmann, C; Hiemke, C; Gunst, IM; Connemann, BJ; Schönfeldt-Lecuona, Carlos (2012). "Desomorphine goes "crocodile"". Journal of Addictive Diseases 31 (4): 407–12. doi:10.1080/10550887.2012.735570. PMID 23244560. 
  10. ^ 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. 
  11. ^ "Flesh-rotting 'krokodil' drug emerges in USA". USA Today. 
  12. ^ Grund, J. P. C.; Latypov, A.; Harris, M. (2013). "Breaking worse: The emergence of krokodil and excessive injuries among people who inject drugs in Eurasia". International Journal of Drug Policy 24 (4): 265–274. doi:10.1016/j.drugpo.2013.04.007. PMID 23726898. 
  13. ^ 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. 
  14. ^ "Дезоморфин. Последствия употребления. Лечение" (in Russian). mosmedservice.com. 
  15. ^ Берсенева А. (23 June 2011). "Без рецепта не обезболят". Gazeta.ru. Retrieved 12 January 2014.