Desomorphine
Encyclopedia
Desomorphine 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. It has sedative
and analgesic
effects, and is around 8-10 times more potent than morphine. 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
.
due to an upsurge in clandestine production, presumably due to its relatively simple synthesis from codeine
. The drug is easily made from codeine
, iodine
and red phosphorus, 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. 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.
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.
Opiate
In medicine, the term opiate describes any of the narcotic opioid alkaloids found as natural products in the opium poppy plant.-Overview:Opiates are so named because they are constituents or derivatives of constituents found in opium, which is processed from the latex sap of the opium poppy,...
analogue invented in 1932 in the United States that is a derivative of morphine
Morphine
Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...
, where the 6-hydroxyl group has been removed and the 7,8 double bond has been saturated. It has sedative
Sedative
A sedative or tranquilizer is a substance that induces sedation by reducing irritability or excitement....
and analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
effects, and is around 8-10 times more potent than morphine. 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
Nausea
Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...
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
Thionyl chloride
Thionyl chloride is an inorganic compound with the formula SOCl2. It is a reactive chemical reagent used in chlorination reactions. It is a colorless, distillable liquid at room temperature and pressure that decomposes above 140 °C. Thionyl chloride is sometimes confused with sulfuryl...
with codeine
Codeine
Codeine or 3-methylmorphine is an opiate used for its analgesic, antitussive, and antidiarrheal properties...
. By catalytic reduction, α-chlorocodide gives dihydrodesoxycodeine, which yields desomorphine on demethylation
Demethylation
Demethylation is the chemical process resulting in the removal a of methyl group from a molecule.A common way of demethylation is the replacement of a methyl group by a hydrogen atom, resulting in a net loss of one carbon and two hydrogen atoms....
.
"Krokodil"
Desomorphine attracted attention in 2010 in RussiaRussia
Russia or , officially known as both Russia and the Russian Federation , is a country in northern Eurasia. It is a federal semi-presidential republic, comprising 83 federal subjects...
due to an upsurge in clandestine production, presumably due to its relatively simple synthesis from codeine
Codeine
Codeine or 3-methylmorphine is an opiate used for its analgesic, antitussive, and antidiarrheal properties...
. The drug is easily made from codeine
Codeine
Codeine or 3-methylmorphine is an opiate used for its analgesic, antitussive, and antidiarrheal properties...
, iodine
Iodine
Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....
and red phosphorus, in a similar process to the manufacture of methamphetamine
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...
from pseudoephedrine
Pseudoephedrine
Pseudoephedrine is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It is used as a nasal/sinus decongestant and stimulant, or as a wakefulness-promoting agent....
, 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. Since this mix is routinely injected immediately with little or no further purification, "Krokodil" has become notorious for producing severe tissue damage, phlebitis
Phlebitis
Phlebitis is an inflammation of a vein, usually in the legs.When phlebitis is associated with the formation of blood clots , usually in the deep veins of the legs, the condition is called thrombophlebitis...
and gangrene
Gangrene
Gangrene is a serious and potentially life-threatening condition that arises when a considerable mass of body tissue dies . This may occur after an injury or infection, or in people suffering from any chronic health problem affecting blood circulation. The primary cause of gangrene is reduced blood...
, 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.
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.
See also
- MethyldesorphineMethyldesorphineMethyldesorphine is an opioid analgesic. First synthesized in Germany in 1940 and patented in the USA in 1952, it has a high potential for abuse as with any potent opioid agonist, and is sometimes found along with desomorphine as a component of the home-made opioid mixture known as "Krokodil" used...
- sometimes also found in samples of "Krokodil" seized by police - N-PhenethylnordesomorphineN-PhenethylnordesomorphineN-Phenethylnordesomorphine is an opiate analgesic drug derived from desomorphine by replacing the N-methyl group with β-phenethyl. Since desomorphine is already around eight times more potent than morphine, the additional boost in binding affinity produced by using the larger phenethyl group makes...
- a more complexly modified derivative