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[DeSwiss]

15. Desomorphine arrived in 1932.....

Desomorphine

Systematic (IUPAC) name
4,5-α-Epoxy-17-methylmorphinan-3-ol

Legal status: Prohibited (S9) (AU) Schedule I (US)
Dependence liability: Very High
Identifiers:
CAS number: 427-00-9
ATC code: None
PubChem CID: 5362456
ChemSpider: 4515044 Yes
UNII 7OP86J5E33 Yes
Synonyms Desomorphine, Dihydrodesoxymorphine, Permonid
Chemical data -
Formula: C17H21NO2
Mol. mass: 271.354 g/mol

Desomorphine (dihydrodesoxymorphine, Permonid) is an opioid first patented 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. It has sedative and analgesic effects, and is around 8-10 times more potent than morphine. It was used[clarification needed] 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.

"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; like methamphetamine, desomorphine made this way is often 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. 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. The high associated with krokodil is akin to that of heroin, but lasts a much shorter period. While the effects of heroin use can last four to eight hours, the effects of krokodil do not usually extend past one and a half hours, with the symptoms of withdrawal setting in soon after. Krokodil takes roughly 30 minutes to an hour to prepare with over-the-counter ingredients in a kitchen. 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. 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.

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