Desomorphine

"Crocodil" redirects here. Not to be confused with Crocodile.
Desomorphine
Clinical data
Trade namesPermonid
Other namesDesomorphine, krokodil, dihydrodesoxymorphine, Permonid
Addiction
liability		Very High
ATC code
  • none
Legal status
Legal status
Identifiers
  • 4,5α-Epoxy-17-methylmorphinan-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.406 Edit this at Wikidata
Chemical and physical data
FormulaC17H21NO2
Molar mass271.360 g·mol−1
3D model (JSmol)
  • OC1=C2O[C@@H]3[C@@]45C2=C(C[C@H]([C@@H]5CCC3)N(C)CC4)C=C1
  • 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[note 1] is a semi-synthetic opioid commercialized by Roche, with powerful, fast-acting effects, such as sedation and analgesia.[3][4][5][6] It was first discovered and patented in Germany by a German team working for Knoll in 1920[7] but was not generally recognized. It was later synthesized in 1932 by American chemist Lyndon Frederick Small. Small also successfully patented it in 1934 in the United States.[8] Desomorphine was used in Germany, Austria, and Switzerland under the brand name Permonid[9] and was described as having a fast onset and a short duration of action, with relatively little nausea compared to equivalent doses of morphine. Dose for dose it is roughly ten times more potent than morphine, with 1 mg desomorphine being equivalent 10 mg morphine, via the intravenous (IV) or intramuscular (IM) routes.[10]

Desomorphine is a morphine analogue where the 6-hydroxyl group and the 7,8 double bond have been reduced.[8] The traditional synthesis of desomorphine starts from α-chlorocodide, which is itself obtained by treating codeine with thionyl chloride. By catalytic reduction, α-chlorocodide gives dihydrodesoxycodeine, which yields desomorphine on demethylation.[11][12]

A desomorphine product, usually based on codeine, has been developed as a recreational drug.[13] The product in question is typically a highly impure variant of desomorphine. The scaly sores and necrosis that develop around the injection site has prompted the name krokodil (Russian for crocodile).

  1. ^ Shuster S (5 December 2013). "The World's Deadliest Drug: Inside a Krokodil Cookhouse". Time.
  2. ^ Christensen J (18 October 2013). "Flesh-eating 'zombie' drug 'kills you from the inside out'". CNN.
  3. ^ Casy AF, Parfitt RT (1986). Opioid analgesics: chemistry and receptors. New York: Plenum Press. p. 32. ISBN 978-0-306-42130-3.
  4. ^ Bognar R, Makleit S (June 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.
  5. ^ Janssen PA (April 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.
  6. ^ Sargent LJ, May EL (November 1970). "Agonists--antagonists derived from desomorphine and metopon". Journal of Medicinal Chemistry. 13 (6): 1061–3. doi:10.1021/jm00300a009. PMID 4098039.
  7. ^ DE Patent 414598C 'Verfahren zur Herstellung von Dihydrodesoxymorphin und Dihydrodesoxycodein'
  8. ^ a b US patent 1980972, Lyndon Frederick Small, "Morphine Derivative and Processes", published 1934-19-07, issued 1934-13-11 
  9. ^ "Krokodil". New York State Office of Alcoholism and Substance Abuse Services. Archived from the original on 13 February 2014. Retrieved 27 September 2013.
  10. ^ Cite error: The named reference lifsci was invoked but never defined (see the help page).
  11. ^ Mosettig E, Cohen FL, Small LF (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.
  12. ^ Eddy NB, Howes HA (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.
  13. ^ Alves EA (December 2020). "DARK Classics in Chemical Neuroscience: Krokodil". ACS Chemical Neuroscience. 11 (23): 3968–3978. doi:10.1021/acschemneuro.0c00495. PMID 32877160. S2CID 221476977.


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