6-Monoacetylcodeine
Encyclopedia
6-Monoacetylcodeine is a toxic acetate
ester
of codeine
in which the hydroxyl group on the 6 position has been acetylated. It is occasionally present as an impurity in street heroin and is typically created when attempting to create heroin from a solution of morphine
in which some of the codeine from the original opium
solution still remains. It is formed either through the addition of acetic anhydride
, which will only acetylate the 6 position on the codeine or as a result of the addition of acetic acid
with a catalyst in an attempt to create 6-monoacetylmorphine, the equivalent ester of morphine which is slightly more potent than heroin itself. Administration of 6-MAC through any route results in the rapid release of histamine
into the blood stream which can lead to potentially fatal anaphylactic shock. 6-monoacetylcodeine is eventually metabolised into codeine and then into morphine. Since only illegally produced heroin is likely to contain 6-MAC, testing for the presence of it in the urine can be used as a fairly reliable method of detecting the use of illicit heroin, as opposed to prescription painkillers.
Acetate
An acetate is a derivative of acetic acid. This term includes salts and esters, as well as the anion found in solution. Most of the approximately 5 billion kilograms of acetic acid produced annually in industry are used in the production of acetates, which usually take the form of polymers. In...
ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
of codeine
Codeine
Codeine or 3-methylmorphine is an opiate used for its analgesic, antitussive, and antidiarrheal properties...
in which the hydroxyl group on the 6 position has been acetylated. It is occasionally present as an impurity in street heroin and is typically created when attempting to create heroin from a solution 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...
in which some of the codeine from the original opium
Opium
Opium is the dried latex obtained from the opium poppy . Opium contains up to 12% morphine, an alkaloid, which is frequently processed chemically to produce heroin for the illegal drug trade. The latex also includes codeine and non-narcotic alkaloids such as papaverine, thebaine and noscapine...
solution still remains. It is formed either through the addition of acetic anhydride
Acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula 2O. Commonly abbreviated Ac2O, it is the simplest isolatable acid anhydride and is a widely used reagent in organic synthesis...
, which will only acetylate the 6 position on the codeine or as a result of the addition of acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...
with a catalyst in an attempt to create 6-monoacetylmorphine, the equivalent ester of morphine which is slightly more potent than heroin itself. Administration of 6-MAC through any route results in the rapid release of histamine
Histamine
Histamine is an organic nitrogen compound involved in local immune responses as well as regulating physiological function in the gut and acting as a neurotransmitter. Histamine triggers the inflammatory response. As part of an immune response to foreign pathogens, histamine is produced by...
into the blood stream which can lead to potentially fatal anaphylactic shock. 6-monoacetylcodeine is eventually metabolised into codeine and then into morphine. Since only illegally produced heroin is likely to contain 6-MAC, testing for the presence of it in the urine can be used as a fairly reliable method of detecting the use of illicit heroin, as opposed to prescription painkillers.
See also
- 6-Monoacetylmorphine, the equivalent form of morphineMorphineMorphine 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...
- CodeineCodeineCodeine or 3-methylmorphine is an opiate used for its analgesic, antitussive, and antidiarrheal properties...
- Poppy teaPoppy teaPoppy tea is an infusion brewed from poppy straw or seeds of several species of poppy. The species most commonly used for this purpose is Papaver somniferum, which contains opium....