Clinical data | |
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Other names | 6-acetylcodeine |
Routes of administration | Intravenous (if present in heroin) |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.169.473 |
Chemical and physical data | |
Formula | C20H23NO4 |
Molar mass | 341.407 g·mol−1 |
3D model (JSmol) | |
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6-Monoacetylcodeine (6-MAC) is an 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 can 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. 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. [1] 6-MAC is the precursor for 14-hydroxycodeinenone which was the original precursor to oxycodone. The 7-8 double-bond was reduced using the hyposulfite ion to reduce the 6-7 double-bond. [2] While the acute toxicity of 6-monoacetylcodeine has not been studied in man, animal studies have shown that in animal models its convulsant effects have been proved and when mixed with mono- or di- acetyl morphine, lowers the convulsant threshold of the mixture still further. [3]
Heroin, also known as diacetylmorphine and diamorphine among other names, is a morphinan opioid substance synthesized from the dried latex of the Papaver somniferum plant; it is mainly used as a recreational drug for its euphoric effects. Medical-grade diamorphine is used as a pure hydrochloride salt. Various white and brown powders sold illegally around the world as heroin are routinely diluted with cutting agents. Black tar heroin is a variable admixture of morphine derivatives—predominantly 6-MAM (6-monoacetylmorphine), which is the result of crude acetylation during clandestine production of street heroin. Heroin is used medically in several countries to relieve pain, such as during childbirth or a heart attack, as well as in opioid replacement therapy.
Morphine is a strong opiate that is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies. It is mainly used as an analgesic. There are numerous methods used to administer morphine: oral; sublingual; via inhalation; injection into a muscle, injection under the skin, or injection into the spinal cord area; transdermal; or via rectal suppository. It acts directly on the central nervous system (CNS) to induce analgesia and alter perception and emotional response to pain. Physical and psychological dependence and tolerance may develop with repeated administration. It can be taken for both acute pain and chronic pain and is frequently used for pain from myocardial infarction, kidney stones, and during labor. Its maximum effect is reached after about 20 minutes when administered intravenously and 60 minutes when administered by mouth, while the duration of its effect is 3–7 hours. Long-acting formulations of morphine are available as MS-Contin, Kadian, and other brand names as well as generically.
Clandestine chemistry is chemistry carried out in secret, and particularly in illegal drug laboratories. Larger labs are usually run by gangs or organized crime intending to produce for distribution on the black market. Smaller labs can be run by individual chemists working clandestinely in order to synthesize smaller amounts of controlled substances or simply out of a hobbyist interest in chemistry, often because of the difficulty in ascertaining the purity of other, illegally synthesized drugs obtained on the black market. The term clandestine lab is generally used in any situation involving the production of illicit compounds, regardless of whether the facilities being used qualify as a true laboratory.
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.
The Convention for Limiting the Manufacture and Regulating the Distribution of Narcotic Drugs was a drug control treaty promulgated in Geneva on 13 July 1931 that entered into force on 9 July 1933.
Black tar heroin, also known as black dragon, is a form of heroin that is sticky like tar or hard like coal. Its dark color is the result of crude processing methods that leave behind impurities. Despite its name, black tar heroin can also be dark orange or dark brown in appearance.
Etonitazene, also known as EA-4941 or CS-4640, is a benzimidazole opioid, first reported in 1957, that has been shown to have approximately 1,000 to 1,500 times the potency of morphine in animals.
6-Monoacetylmorphine is an opioid and also one of three active metabolites of heroin (diacetylmorphine), the others being morphine and the much less active 3-monoacetylmorphine (3-MAM).
Drug injection is a method of introducing a drug into the bloodstream via a hollow hypodermic needle, which is pierced through the skin into the body. Intravenous therapy, a form of drug injection, is universally practiced in modernized medical care. As of 2004, there were 13.2 million people worldwide who self-administered injection drugs outside of medical supervision, of which 22% are from developed countries.
Thebacon, or dihydrocodeinone enol acetate, is a semisynthetic opioid that is similar to hydrocodone and is most commonly synthesised from thebaine. Thebacon was invented in Germany in 1924, four years after the first synthesis of hydrocodone. Thebacon is a derivative of acetyldihydrocodeine, where only the 6–7 double bond is saturated. Thebacon is marketed as its hydrochloride salt under the trade name Acedicon, and as its bitartrate under Diacodin and other trade names. The hydrochloride salt has a free base conversion ratio of 0.846. Other salts used in research and other settings include thebacon's phosphate, hydrobromide, citrate, hydroiodide, and sulfate.
Nicomorphine is the 3,6-dinicotinate ester of morphine. It is a strong opioid agonist analgesic two to three times as potent as morphine with a side effect profile similar to that of dihydromorphine, morphine, and diamorphine.
Nicocodeine is an opioid analgesic and cough suppressant, an ester of codeine closely related to dihydrocodeine and the codeine analogue of nicomorphine. It is not commonly used in most countries, but has activity similar to other opiates. Nicocodeine and nicomorphine were synthesized in 1904, and introduced in 1957 by Lannacher Heilmittel of Austria. Nicocodeine is metabolised in the liver by demethylation to produce nicomorphine, also known as 6-nicotinoylmorphine, and subsequently further metabolised to morphine. Side effects are similar to those of other opiates and include itching, nausea and respiratory depression. Related opioid analogues such as nicomorphine and nicodicodeine were first synthesized. The definitive synthesis, which involves treating anhydrous codeine base with nicotinic anhydride at 130 °C, was published by Pongratz and Zirm in Monatshefte für Chemie in 1957, simultaneously with the two analogues in an article about amides and esters of various organic acids.
Dipropanoylmorphine is an opiate derivative, the 3,6-dipropanoyl ester of morphine. It was developed in 1972 as an analgesic. It is rarely used in some countries for the relief of severe pain such as that caused by terminal cancer, as an alternative to diamorphine (heroin) and morphine. The drug was first synthesised circa or about 1875 in Great Britain along with many other esters of morphine, all of which were shelved at the time, some of which were later developed such as heroin (1898), acetylpropionylmorphine (1924), dibenzoylmorphine, and so on. The name of this drug is also given as 3,6-dipropanoylmorphine and its 6-mono-acetylated homologue is also a longer-acting heroin-like drug, as are 3,6-diformylmorphine and 6-formylmorphine.
"Polish" heroin is a crude preparation of heroin made from poppy straw. It is an opiate, used recreationally as a psychoactive drug. Poppy straw, like opium, is harvested from the opium poppy. Polish heroin was used mainly in Central and Eastern Europe prior to the dissolution of the Soviet Union and the end of communist control of the countries of the Warsaw Pact or Eastern Bloc.
Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is also commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, Papaver somniferum. It is typically used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children or adults. In Europe, it is not recommended as a cough medicine in those under 12 years of age. It is generally taken by mouth. It typically starts working after half an hour, with maximum effect at two hours. Its effects last for about four to six hours. Codeine exhibits abuse potential similar to other opioid medications, including a risk of habituation and overdose.
Benzylmorphine (Peronine) is a semi-synthetic opioid narcotic introduced to the international market in 1896 and that of the United States very shortly thereafter. It is much like codeine, containing a benzyl group attached to the morphine molecule just as the methyl group creates codeine and the ethyl group creates ethylmorphine or dionine. It is about 90% as strong as codeine by weight.
Desomorphine is a semi-synthetic opioid commercialized by Roche, with powerful, fast-acting effects, such as sedation and analgesia. It was first discovered and patented by a German team working for Knoll in 1920 but was not generally recognized. It was later synthesized in 1932 by Lyndon Frederick Small. Small also successfully patented it in 1934 in the United States. 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 compared to equivalent doses of morphine. Dose for dose it is eight to ten times more potent than morphine.
3-Monoacetylmorphine (3-MAM) or 3-acetylmorphine is a less active metabolite of heroin (diacetylmorphine), the other two being morphine and more active 6-monoacetylmorphine (6-MAM).
3,14-Diacetyloxymorphone is an opioid analgesic which has never been marketed. It is an acetyl derivative of oxymorphone. It is related to other acetylated morphone derivatives, including 3,6-diacetyloxymorphone, 3,8,14-triacetyloxymorphone, 3,6,8,14-tetraacetyloxymorphone, noroxymorphone analogs of all or most of the above, and 3,6,14-triacetyloxymorphone, a derivative of oxymorphone whose structure-activity relationship suggests is 800% the potency of the parent drug versus 250% for 3,14-diacetyoxymorphone. Both were developed in Austria in the 1920s along with other derivatives of the strong dihydromorphinones and these drugs are generated by reacting oxymorphone with either acetic anhydride or acetyl chloride at various temperatures in the 80-160 °C for several hours; 3,6,14-triacetyloxymorphone may be more easily made when a catalyst is used but elevated pressure or reaction in vacuo or under a nitrogen or noble gas atmosphere is not required.[Citation Needed]
Dibutyrylmorphine is the 3,6-dibutyryl ester of morphine, first synthesized by the CR Alders Wright organization in the United Kingdom in 1875.