|Systematic (IUPAC) name|
|Legal status||Prohibited (S9) (AU) Class A (UK) Schedule I (US)|
|Dependence liability||Very High|
|Synonyms||Desomorphine, Dihydrodesoxymorphine, Permonid|
|Mol. mass||271.354 g/mol|
|14px (what is this?)|
Desomorphine (dihydrodesoxymorphine, former brand name Permonid, street name krokodil) is a derivative of morphine with powerful, fast-acting opioid effects, such as sedation and analgesia. First synthesized in 1932 and patented in 1934, desomorphine 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. Dose-by-dose it is eight to ten times more potent than morphine.
Desomorphine is derived from morphine where the 6-hydroxyl group and the 7,8 double bond have been reduced. 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.
It was previously used in Switzerland for the treatment of severe pain; although for many years up to 1981, when its use was terminated, it was being used to treat a single person in Bern, Switzerland with a rare illness.
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 2013, there are no legal uses of desomorphine in the U.S., where it has been a Schedule 1 controlled substance since 1936.
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 any such mixture can cause serious damage of the skin, blood vessels, bone and muscles, sometimes requiring limb amputation in long-term users. 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. Gangrene, phlebitis, thrombosis (blood clots), pneumonia, meningitis, septicaemia (blood infection), rotting bones, osteomyelitis (bone infection), liver & kidney damage, brain damage 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.
Physical and chemical properties
Desomorphine has a molecular weight of 271.35 g/mol and three salts are used: hydrobromide (free-base conversion ratio 0.770), hydrochloride (0.881) and sulfate (0.802). Its freebase form is slightly soluble in water (1.425 g/L at 25 °C), although its salts are very water soluble; its freebase form is also very soluble in most polar organic solvents (like acetone, ethanol and ethyl acetate). Its melting point is 189°C. It has a pKa of 9.69.
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. Toxic nitrogen oxides fumes emerge from the drug when heated.
Desomorphine was first synthesised in the U.S. in 1932 and patented on November 13, 1934. In Russia, desomorphine was declared an 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. The number of users in Russia was estimated to have reached around one million at the peak of the drug's popularity.
Society and culture
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.
The drug can be made from codeine and iodine derived from OTC medications and red phosphorus from match strikers, 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. 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. It has been estimated that around 100,000 people use krokodil in Russia and around 20,000 in Ukraine. 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.
Western media coverage
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.
|40x40px||Wikimedia Commons has media related to Desomorphine.|
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