6-Monoacetylcodeine

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6-Monoacetylcodeine
6-MAC.svg
Clinical data
Other names6-acetylcodeine
Routes of
administration
Intravenous (if present in heroin)
ATC code
  • none
Identifiers
  • 3-methoxy-6-acetoxy-(5α,6α)-7,8-didehydro-4,5-epoxy-17-methylmorphinan
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.169.473 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H23NO4
Molar mass 341.407 g·mol−1
3D model (JSmol)
  • O=C(O[C@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(OC)ccc3C4)C)C
  • InChI=1S/C20H23NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4-7,13-14,16,19H,8-10H2,1-3H3/t13-,14+,16-,19-,20-/m0/s1 Yes check.svgY
  • Key:MFXFQKMUCYHPFQ-BKRJIHRRSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

See also

Related Research Articles

<span class="mw-page-title-main">Heroin</span> Opioid used as an analgesic and a recreational drug for its euphoric effects

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.

<span class="mw-page-title-main">Morphine</span> Pain medication of the opiate family

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<span class="mw-page-title-main">6-Monoacetylmorphine</span> Metabolite of Heroin

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<span class="mw-page-title-main">Drug injection</span> Method of introducing a drug

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<span class="mw-page-title-main">Nicomorphine</span> Opioid analgesic drug

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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.

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<span class="mw-page-title-main">Benzylmorphine</span> Opioid analgesic and cough suppressant drug

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<span class="mw-page-title-main">Desomorphine</span> Semi-synthetic opioid, morphine analogue

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<span class="mw-page-title-main">3-Monoacetylmorphine</span> Chemical compound

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).

<span class="mw-page-title-main">3,14-Diacetyloxymorphone</span> Chemical compound

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<span class="mw-page-title-main">Dibutyrylmorphine</span> Chemical compound

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References

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  2. Freund M, Speyer E (24 November 1916). "Über die Umwandlung von Thebain in Oxycodeinon und dessen Derivate" [On the conversion of thebaine into oxycodeinone and its derivatives]. Journal für Praktische Chemie (in German). Leipzig. 94 (1): 135–178, 156–157. doi:10.1002/prac.19160940112.
  3. O'Neal CL, Poklis A, Lichtman AH (December 2001). "Acetylcodeine, an impurity of illicitly manufactured heroin, elicits convulsions, antinociception, and locomotor stimulation in mice". Drug and Alcohol Dependence. 65 (1): 37–43. doi:10.1016/s0376-8716(01)00145-4. PMID   11714588.