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Desomorphine

From Wikipedia, the free encyclopedia

 

 

 

Desomorphine

 

http://upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Permonid.svg/200px-Permonid.svg.png

 

Systematic (IUPAC) name

 

4,5-α-Epoxy-17-methylmorphinan-3-ol

 

Clinical data

 

Pregnancy cat.

 

 ?

 

Legal status

 

Prohibited (S9) (AU)Schedule I (US)

 

Dependence liability

 

Very High

 

Identifiers

 

CAS number

 

427-00-9 ^{http://upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png}

 

ATC code

 

None

 

PubChem

 

CID 5362456

 

ChemSpider

 

4515044 ^{http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png}

 

UNII

 

7OP86J5E33 ^{http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png}

 

Synonyms

 

Desomorphine, Dihydrodesoxymorphine, Permonid

 

Chemical data

 

Formula

 

C₁₇H₂₁NO₂ 

 

Mol. mass

 

271.354 g/mol

 

SMILES[show]

 

 

InChI[show]

 

 

 http://upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png (what is this?)  (verify)

Desomorphine (dihydrodesoxymorphine, Permonid, street namekrokodil) is an opioid first patented in 1932 in the United States that is a derivative of morphine, where the 6-hydroxyl group and the 7,8 double bond have been reduced.^[1] It has sedative and analgesiceffects, and is around 8-10 times more potent than morphine.^[2][3][4][5] It was used in Switzerland under the brand name Permonid^[6] 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. Bycatalytic reduction, α-chlorocodide gives dihydrodesoxycodeine, which yields desomorphine on demethylation.^[7][8]

 

Contents

  [hide] 

• 1 "Krokodil"
  • 1.1 Other ingredients

2 See also

3 References

 

"Krokodil"[edit]

Desomorphine attracted attention in 2010 in Russia due to an increase in clandestine production, presumably due to its relatively simple synthesis from codeine. Reports of its use there date back to 2003.^[9] The drug is easily made from codeine, iodine and red phosphorus,^[10] in a process similar to the manufacture ofmethamphetamine 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 homemade desomorphine is "krokodil" (Russian:крокодил, crocodile), reportedly due to the scale-like appearance of skin of its users and the derivation from chlorocodide.^[11] 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. 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,^[12] 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.^[13] Since the homemade 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.^[14] Although there are not many, addicts' life expectancies are said to be as low as two to three years due to injecting drug users' high susceptablitity to infections and gangrene.^[15][16][17]

Abuse of homemade desomorphine was first reported in middle and eastern Siberia in 2002, but has since spread throughout Russia and the neighboring former Soviet republics. 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.^[18]

Possibly the first discovery of use of the drug in the United States was reported by the Banner Poison Control Center inPhoenix, Arizona, in September 2013.^[19][20]

 

Other ingredients[edit]

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, ordiphenhydramine (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.^[21]

http://upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Synthesis_of_Desomorphine_from_Codein.svg/700px-Synthesis_of_Desomorphine_from_Codein.svg.png

http://bits.wikimedia.org/static-1.22wmf20/skins/common/images/magnify-clip.png

Synthesis of desomorphine from codeine.

 

[ethnoman]

I saw a video once of a person who had such bad gangrene from desomorphine that the flesh had rotted away completely from the thigh, leaving the femur bones exposed. They sawed through the bones with the leg sitting in a garbage can until the leg dropped in. Full on!!! :sick :sick

[Skunkxxx]

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