Desomorphine

Desomorphine

Systematic (IUPAC) name
4,5-α-epoxy-17-methylmorphinan-3-ol
Clinical data
Pregnancy cat.	?
Legal status	Schedule I (US)
Identifiers
CAS number	427-00-9 N
ATC code	None
PubChem	CID 5362456
ChemSpider	4515044 Y
UNII	7OP86J5E33 Y
Synonyms	Desomorphine, Dihydrodesoxymorphine, Permonid
Chemical data
Formula	C17H21NO2
Mol. mass	271.354 g/mol
SMILES	eMolecules & PubChem
InChI 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 Y Key:LNNWVNGFPYWNQE-GMIGKAJZSA-N Y
N(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 saturated.^[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 upsurge in clandestine production, presumably due to its relatively simple synthesis from codeine.^{[citation needed]} The drug is easily made from codeine, iodine and red phosphorus,^[8] in a similar process to the manufacture of methamphetamine from pseudoephedrine, but desomorphine made this way is highly impure and contaminated with various toxic and corrosive byproducts. The street name in Russia for home-made Desomorphine made in this way is "krokodil" (crocodile), reportedly due to the scale-like appearance of skin of its users, and it is used as a cheaper alternative to heroin, as codeine tablets are available without a prescription.^[9] Since this 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. The amount of tissue damage is so high that addicts' life expectancies are said to be as low as two to three years.^[10][11][12]

Abuse of home-made desomorphine was first reported in 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.^[13]

Synthesis of desomorphine from codeine.

See also

• Methyldesorphine - sometimes also found in samples of "Krokodil" seized by police
• N-Phenethylnordesomorphine - a more complexly modified derivative

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. ^ 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. 
11. ^ 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. 
12. ^ "Дезоморфин последствия – фото [Desomorphine consequences - photo]" (in Russian). February 9, 2011. http://stopnarkotik.com.ua/obschaya/dezomorfin-posledstviya-foto/. ^{[self-published source?]}
13. ^ "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.