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Desomorphine

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Desomorphine
Clinical data
Other namesDesomorphine, Dihydrodesoxymorphine, Permonid
ATC code
  • none
Legal status
Legal status
Identifiers
  • 4,5-α-epoxy-17-methylmorphinan-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.006.406 Edit this at Wikidata
Chemical and physical data
FormulaC17H21NO2
Molar mass271.354 g/mol g·mol−1
3D model (JSmol)
  • Oc2c1O[C@@H]5[C@@]34c1c(cc2)C[C@@H](N(CC3)C)[C@@H]4CCC5
  • InChI=1S/C17H21NO2/c1-18-8-7-17-11-3-2-4-14(17)20-16-13(19)6-5-10(15(16)17)9-12(11)18/h5-6,11-12,14,19H,2-4,7-9H2,1H3/t11-,12+,14-,17+/m0/s1 checkY
  • Key:LNNWVNGFPYWNQE-GMIGKAJZSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Desomorphine (dihydrodesoxymorphine, Permonid) is an opiate analogue 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]

"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; but desomorphine made this way is 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. 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.[10] 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.[11][12][13][14]

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.[15] 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.[16][17] In September 2012 the drug was reported in use by Norwegian heroin addicts in Tromsø. [18]

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. [19]

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". Arzneimittel-Forschung (in German). 8 (6): 323–5. PMID 13546093. {{cite journal}}: Unknown parameter |trans_title= ignored (|trans-title= suggested) (help)
  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. {{cite journal}}: Missing or empty |title= (help)
  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.
  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 (23 June 2011). "Desomorphine, drug for the poor, kills all of its victims". Pravda.
  10. ^ http://mosmedservice.com/index/dezomorfin/0-80
  11. ^ Walker, Shaun (22 June 2011). "Krokodil: The drug that eats junkies". The Independent.
  12. ^ Shuster, Simon (20 June 2011). "The Curse of the Crocodile: Russia's Deadly Designer Drug". Time.
  13. ^ "Дезоморфин последствия – фото" (in Russian). 9 February 2011. {{cite web}}: Unknown parameter |trans_title= ignored (|trans-title= suggested) (help)[self-published source?]
  14. ^ Snap goes the Crocodile. Marina Akhmedova, 3 August 2012. Russky Reporter Magazine
  15. ^ "Deutschland kämpft gegen neue todesdroge". Bild (in German). 14 October 2011. Retrieved 10 November 2011. {{cite news}}: Unknown parameter |trans_title= ignored (|trans-title= suggested) (help)
  16. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 22385107, please use {{cite journal}} with |pmid=22385107 instead.
  17. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 22468632, please use {{cite journal}} with |pmid=22468632 instead.
  18. ^ Jepsen, Helene (7 September 2012). "Dødsnarko: Her er det norske tilfælde". Ekstrabladet (in Danish). {{cite news}}: Unknown parameter |trans_title= ignored (|trans-title= suggested) (help)
  19. ^ "Siberia: Krokodil Tears - Full Length". Retrieved 14 May 2012.

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