| Revision as of 18:38, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 461017800 of page 6-Monoacetylcodeine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 14:39, 8 February 2024 edit VastV0idInSpace0 (talk | contribs)Extended confirmed users2,406 edits Fixed spacing between stub template and category templates.Tag: 2017 wikitext editor |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 451725956 |
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| verifiedrevid = 477226104 |
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| IUPAC_name = 3-methoxy-6-acetyl-(5α,6α)-7,8-didehydro-4,5-epoxy- |
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| IUPAC_name = 3-methoxy-6-acetoxy-(5α,6α)-7,8-didehydro-4,5-epoxy-17-methylmorphinan |
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| image = 6-MAC.svg |
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| image = 6-MAC.svg |
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| width = 180 |
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| width = 180 |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 6703-27-1 --> |
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| CAS_number = 6703-27-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = U59401ETXH |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_suffix = |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=20 | H=23 | N=1 | O=4 |
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| C=20 | H=23 | N=1 | O=4 |
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| molecular_weight = 341.4 g/mol |
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| smiles = O=C(O2\C=C/54N(CC51c3c(O12)c(OC)ccc3C4)C)C |
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| smiles = O=C(O2\C=C/54N(CC51c3c(O12)c(OC)ccc3C4)C)C |
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| InChI = 1/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 |
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| InChIKey = MFXFQKMUCYHPFQ-BKRJIHRRBK |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey = MFXFQKMUCYHPFQ-BKRJIHRRSA-N |
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| StdInChIKey = MFXFQKMUCYHPFQ-BKRJIHRRSA-N |
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}} |
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}} |
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'''6-Monoacetylcodeine''' (6-MAC) is an ] ] of ] in which the ] on the 6 position has been ]. It is occasionally present as an impurity in ] and is typically created when attempting to create heroin from a solution of ] in which some of the codeine from the original ] solution still remains. It is formed either through the addition of ], which can only acetylate the 6 position on the codeine or as a result of the addition of ] with a ] in an attempt to create ], 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.<ref name="pmid11159779">{{cite journal | vauthors = Staub C, Marset M, Mino A, Mangin P | title = Detection of acetylcodeine in urine as an indicator of illicit heroin use: method validation and results of a pilot study | journal = Clinical Chemistry | volume = 47 | issue = 2 | pages = 301–7 | date = February 2001 | pmid = 11159779 | doi = 10.1093/clinchem/47.2.301| doi-access = free }}</ref> 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.<ref>{{cite journal | vauthors = Freund M, Speyer E |title=Über die Umwandlung von Thebain in Oxycodeinon und dessen Derivate | trans-title = On the conversion of thebaine into oxycodeinone and its derivatives |journal=Journal für Praktische Chemie | language = de | location = Leipzig |date=24 November 1916 |volume=94 |issue=1 |pages=135–178, 156–157 |doi=10.1002/prac.19160940112|url=https://zenodo.org/record/1428060 }}</ref> |
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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.<ref>{{cite journal | vauthors = O'Neal CL, Poklis A, Lichtman AH | title = Acetylcodeine, an impurity of illicitly manufactured heroin, elicits convulsions, antinociception, and locomotor stimulation in mice | journal = Drug and Alcohol Dependence | volume = 65 | issue = 1 | pages = 37–43 | date = December 2001 | pmid = 11714588 | doi = 10.1016/s0376-8716(01)00145-4 }}</ref> |
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== See also == |
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* ], the equivalent form of ] |
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* ] |
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* ] |
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== References == |
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{{Reflist|2}} |
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== External links== |
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* Pubmed |
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{{Opioidergics}} |
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{{DEFAULTSORT:Monoacetylcodeine, 6-}} |
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] |
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] |
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] |
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{{analgesic-stub}} |