6-Monoacetylcodeine

Chemical compound related to codeine

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6-Monoacetylcodeine (6-MAC) is an opioid derivative and a minor metabolite of codeine. It is chemically related to 6-Monoacetylmorphine (6-MAM), which is a metabolite of heroin.

Chemical Structure and Properties

6-Monoacetylcodeine is an acetylated form of codeine, specifically acetylated at the 6-position of the molecule. The chemical structure of 6-MAC is similar to that of codeine, with the addition of an acetyl group. This modification alters its pharmacokinetic and pharmacodynamic properties compared to codeine.

Pharmacology

6-Monoacetylcodeine acts on the central nervous system by binding to opioid receptors, similar to other opioids. However, its potency and efficacy as an analgesic are generally lower than those of more potent opioids like morphine and heroin. The presence of the acetyl group at the 6-position may influence its ability to cross the blood-brain barrier and its subsequent conversion to active metabolites.

Metabolism

In the body, 6-Monoacetylcodeine is metabolized primarily in the liver. It undergoes deacetylation to form codeine, which can then be further metabolized to morphine and other metabolites. The metabolic pathway of 6-MAC is similar to that of other acetylated opioids, involving enzymes such as cytochrome P450.

Legal Status

The legal status of 6-Monoacetylcodeine varies by country. In many jurisdictions, it is classified as a controlled substance due to its potential for abuse and dependence. It is not commonly used in clinical practice and is primarily of interest in forensic and toxicological studies.

Synthesis

The synthesis of 6-Monoacetylcodeine involves the acetylation of codeine. This chemical reaction typically requires an acetylating agent, such as acetic anhydride, under controlled conditions. The process is similar to the synthesis of other acetylated opioids, such as heroin.

Applications and Research

While 6-Monoacetylcodeine is not widely used in medicine, it is of interest in research settings. Studies may focus on its pharmacological properties, metabolism, and potential as a biomarker for codeine use. It is also relevant in the context of drug testing and forensic analysis.

Related Pages

• Codeine
• 6-Monoacetylmorphine
• Heroin
• Opioid
• Metabolism