6-Monoacetylcodeine

6-Monoacetylcodeine

Clinical data
Other names	6-acetylcodeine
Routes of administration	Intravenous (if present in heroin)
ATC code	none
Identifiers
IUPAC name 3-methoxy-6-acetyl-(5α,6α)-7,8-didehydro-4,5-epoxy-
CAS Number	6703-27-1 Y
PubChem CID	5745725
ChemSpider	4588962 Y
CompTox Dashboard (EPA)	DTXSID50213224
ECHA InfoCard	100.169.473
Chemical and physical data
Formula	C20H23NO4
Molar mass	341.4 g/mol g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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 Y Key:MFXFQKMUCYHPFQ-BKRJIHRRSA-N Y
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6-Monoacetylcodeine (6-MAC) 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.

See also

• 6-Monoacetylmorphine, the equivalent form of morphine
• Codeine
• Poppy tea

External links

• Acetylcodeine, an impurity of illicitly manufactured heroin Pubmed