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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-M

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rdfs:label
  • 6-Monoacetylcodeine (en)
  • 6-モノアセチルコデイン (ja)
  • 6-Monoacetilcodeína (pt)
rdfs:comment
  • 6-モノアセチルコデイン(6-Monoacetylcodeine、6-MAC)は、コデインの酢酸エステルで、6位の水酸基がアセチル化している。原料となるアヘンのコデインが残ったモルヒネ溶液からヘロインを生成しようとするときに生じ、しばしばヘロインに不純物として含まれる。6-MACは、ヘロイン自体よりも効き目が強いため、無水酢酸の付加か、または触媒による酢酸の付加によって形成される。6-MACは最終的にコデイン、そしてモルヒネに代謝される。6-MACは、痛み緩和のために処方されたヘロインには含まれず、不法に製造されたヘロインだけに含まれるため、尿中の6-MACの存在確認が不法モルヒネ使用の検出法として用いられる。6-MACは、オキシコドンの前駆体であるの前駆体となる。6-7二重結合を還元するために用いる次亜硫酸イオンによって、7-8二重結合も還元される。 (ja)
  • 6-Monoacetilcodeína (6-MAC) é um éster acetato tóxico da codeína na qual o grupo hidroxila da posição 6 tenha sido acetilado. Está ocasionalmente presente como uma impureza na heroína traficada nas ruas e geralmente é produzida quando se tenta obter a heroína de uma solução de morfina na qual alguma codeína da solução de ópio original ainda resta. É formado através da adição de anidrido acético, que só acetila a posição 6 na codeína ou como resultado da adição de ácido acético com um catalisador em uma tentativa de criar , o éster equivalente de morfina que é um pouco mais potente que a heroína em si.< (pt)
  • 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-M (en)
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  • http://commons.wikimedia.org/wiki/Special:FilePath/6-MAC.svg
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  • none (en)
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  • Intravenous (en)
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  • O=CC (en)
StdInChI
StdInChIKey
  • MFXFQKMUCYHPFQ-BKRJIHRRSA-N (en)
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UNII
  • U59401ETXH (en)
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  • changed (en)
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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. 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.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. (en)
  • 6-モノアセチルコデイン(6-Monoacetylcodeine、6-MAC)は、コデインの酢酸エステルで、6位の水酸基がアセチル化している。原料となるアヘンのコデインが残ったモルヒネ溶液からヘロインを生成しようとするときに生じ、しばしばヘロインに不純物として含まれる。6-MACは、ヘロイン自体よりも効き目が強いため、無水酢酸の付加か、または触媒による酢酸の付加によって形成される。6-MACは最終的にコデイン、そしてモルヒネに代謝される。6-MACは、痛み緩和のために処方されたヘロインには含まれず、不法に製造されたヘロインだけに含まれるため、尿中の6-MACの存在確認が不法モルヒネ使用の検出法として用いられる。6-MACは、オキシコドンの前駆体であるの前駆体となる。6-7二重結合を還元するために用いる次亜硫酸イオンによって、7-8二重結合も還元される。 (ja)
  • 6-Monoacetilcodeína (6-MAC) é um éster acetato tóxico da codeína na qual o grupo hidroxila da posição 6 tenha sido acetilado. Está ocasionalmente presente como uma impureza na heroína traficada nas ruas e geralmente é produzida quando se tenta obter a heroína de uma solução de morfina na qual alguma codeína da solução de ópio original ainda resta. É formado através da adição de anidrido acético, que só acetila a posição 6 na codeína ou como resultado da adição de ácido acético com um catalisador em uma tentativa de criar , o éster equivalente de morfina que é um pouco mais potente que a heroína em si.< (pt)
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page length (characters) of wiki page
CAS number
  • 6703-27-1
FDA UNII code
  • U59401ETXH
PubChem
  • 5745725
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