6-Monoacetylcodeine

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6-Monoacetylcodeine
6-MAC.svg
Systematic (IUPAC) name
3-methoxy-6-acetyl-(5α,6α)-7,8-didehydro-4,5-epoxy-
Clinical data
Legal status ?
Routes Intravenous (if present in heroin)
Identifiers
CAS number 6703-27-1 N
ATC code None
PubChem CID 5745725
ChemSpider 4588962 YesY
Synonyms 6-acetylcodeine
Chemical data
Formula C20H23NO4 
Mol. mass 341.4 g/mol
 N (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 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. 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]

See also[edit]

References[edit]

  1. ^ * Detection of Acetylcodeine in Urine
  2. ^ Journal fuer Praktische Chemie (Leipzig), 1916 , vol. <2> 94, p. 156,157

External links[edit]