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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?)  (verify)

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 1934,[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[edit]

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.[12] It has been estimated that around 100,000 people use krokodil in Russia and around 20,000 in Ukraine.[13] One death in Poland in December 2011 was also believed to have been caused by krokodil use, and its use has been confirmed among Russian expatriate communities in a number of other European countries.[14]

Test results[edit]

Test subjects were subjected to desomorphine intake. The completed tests on animal subjects produced results that contrast desomorphine to morphine; Compared to morphine, the results show increased toxicity, more potent relief of pain, higher levels of depression, increased respiration, and increased digestive activity. Early medical trials of humans taking desomorphine have resulted in the finding that small amounts are highly addictive. As of 1936, there are no legal uses of desomorphine in the U.S.[15]

Street prices[edit]

In 2011, a study showed that 120 Rubles worth of desomorphine is enough to equal 500 Rubles worth of heroin.[16] This is a difference of about 12 U.S. Dollars. Young Russian adults' abuse of desomorphine was increasing in reports from 2009. Due to its cheaper cost, desomorphine was an attractive alternative for these young Russians compared to the high cost of heroin.

Health effects[edit]

Desomorphine typically has large amounts of toxic substances due to it being "cooked" and used without any significant effort to remove the byproducts and leftovers from synthesis. Injecting such mixture can cause serious damage of the skin, blood vessels, bone, and muscles, sometimes requiring limb amputation in long-term users.[17] Causes of this damage are from iodine and phosphorus (and other toxic substances) that are present after synthesis. The large volume of tissue damage/infection is what gained the drug its nickname of the flesh-eating drug.[16] Gangrene, phlebitis, and HIV are also common amongst users of desomorphine. Sometimes, the user will miss the vein when injecting the desomorphine, creating abscess and causing death of the flesh surrounding the entry-point.[18]

Composition[edit]

Desomorphine is made from codeine mixed with other substances. The codeine is retrieved from over-the-counter medicine and is then mixed with alcohol, gasoline, red phosphorus, iodine, hydrochloric acid and paint thinner.[18][19] Toxic nitrogen oxides fumes emerge from the drug when heated.[20]

Western media coverage[edit]

The media in the U.S. and Canada have brought awareness to desomorphine. There have been incidents reported where desomorphine had supposedly been present within either country but all incidents have not been confirmed by any drug-testing reports.[21]

History[edit]

Desomorphine was patented on November 13, 1934. Lyndon Frederick Small filed for the patent, under the subject titled "Morphine Derivative and Processes".[22] 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 sold freely over-the-counter until June 2012.[23]

In 2005, Russia's drug-enforcement agencies reported instances of desomorphine being used. By 2011, 65 million doses of desomorphine were confiscated by these agencies.[24] Amount of users in Russia was estimated to have reached the one million mark at the peak of the drug's popularity.[25]

In June 2012, Russia provided stricter controls over sales of medication with codeine.[24]

References[edit]

  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. ^ Siberia: Krokodil Tears
  13. ^ 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.  edit
  14. ^ 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
  15. ^ "DESOMORPHINE (Dihydrodesoxymorphine; dihydrodesoxymorphine-D; Street Name: Krokodil, Crocodil". Drug Enforcement Administration. Retrieved 3 April 2014. 
  16. ^ a b "Desomorphine (Krokodil) Basics". Erowid. Retrieved 3 April 2014. 
  17. ^ "Дезоморфин. Последствия употребления. Лечение" (in Russian). mosmedservice.com. 
  18. ^ a b Kankudti, Affirunisa (27 September 2013). "Flesh-Rotting Drug 'Desomorphine' Found in Arizona". Nature World News. Retrieved 3 April 2014. 
  19. ^ "Desomorphine Aka Krokodil". DARA Thailand. Retrieved 4 April 2014. 
  20. ^ "Desomorphine". Specialized Information Services. Retrieved 3 April 2014. 
  21. ^ No Confirmed Reports of Desomorphine ( "Krokodil" / "Crocodile" ) in Canada. Canadian Centre on Substance Abuse. November 21, 2013. ISBN 978-1-77178-052-0. 
  22. ^ Bellis, Mary. "History of Krokodil". about.com. Retrieved 4 April 2014. 
  23. ^ Берсенева А. (23 June 2011). "Без рецепта не обезболят". Gazeta.ru. Retrieved 12 January 2014. 
  24. ^ a b Shuster, Simon. "The World's Deadliest Drug: Inside a Krokodil Cookhouse". TIME. Retrieved 4 April 2014. 
  25. ^ "Krokodil". New York State Office of Alcoholism and Substance Abuse Services. Retrieved 3 April 2014. 

Original courtesy of Wikipedia: http://en.wikipedia.org/wiki/Desomorphine — Please support Wikipedia.
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5 news items

 
Morris Daily Herald
Mon, 24 Mar 2014 19:03:45 -0700

House Bill 5531 declares desomorphine, a drug stemming from morphine, as a “specified illegal drug.” This bill increases the penalties for manufacturing or delivering desomorphine, a recreational drug that has recently been growing in popularity ...
 
WXIX
Wed, 02 Apr 2014 14:45:10 -0700

There are no reported cases of krokodil use in Northeast Ohio as of now. But there have been reports of its use in Franklin and Athens counties. However, law enforcement can't confirm that it's actually krokodil, or desomorphine, until they can get ...

Metro

Metro
Sun, 23 Mar 2014 14:11:15 -0700

... two years and the drug has already killed thousands of addicts in Russia and eastern Europe. Glasgow city council said: 'The city's addiction services are aware of the existence of krokodil, a poorly made form of desomorphine often used in eastern ...

Bangor Daily News

Bangor Daily News
Thu, 27 Mar 2014 02:22:30 -0700

It's a homemade version of the painkiller desomorphine, but it's laced with corrosive chemicals and can cause gangrene, Wilson said. “If you do a Google search on krokodil, be prepared for some gross pictures,” he added. Because of requests from some ...

Index.hr

Index.hr
Sat, 29 Mar 2014 13:08:14 -0700

"Krokodil", poznat i kao "droga za siromašne", izaziva katastrofalne posljedice na organizam - tijelo se doslovno počinje raspadati, koža se ljušti (odatle i kolokvijalni naziv za drogu), organi propadaju. "Ta je droga po svom kemijskom sastavu ...
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