6-Monoacetylmorphine

6-Monoacetylmorphine

Chemical structure of 6-Monoacetylmorphine

Ball-and-stick model of 6-Monoacetylmorphine

6-Monoacetylmorphine (6-MAM) is an opioid and a metabolite of heroin. It is one of the three active metabolites of heroin, the others being morphine and 3-monoacetylmorphine.

Chemical Structure

6-Monoacetylmorphine is an acetylated form of morphine. It is specifically the 6-acetyl derivative of morphine, meaning that an acetyl group is attached to the 6-position of the morphine molecule. This modification increases the lipophilicity of the compound, allowing it to cross the blood-brain barrier more rapidly than morphine itself.

Pharmacology

6-Monoacetylmorphine is a potent agonist of the mu-opioid receptor, which is responsible for its analgesic and euphoric effects. It is more potent than morphine due to its increased ability to penetrate the central nervous system. Once in the brain, 6-MAM is rapidly deacetylated to morphine, which then exerts the majority of the opioid effects.

Metabolism

Heroin is metabolized in the body to 6-monoacetylmorphine and 3-monoacetylmorphine, with 6-MAM being the primary active metabolite. This conversion occurs rapidly, and 6-MAM is further metabolized to morphine. The presence of 6-MAM in the body is a definitive indicator of heroin use, as it is not a metabolite of any other opioid.

Detection

6-Monoacetylmorphine can be detected in urine and blood samples as part of drug testing protocols. Its presence is used to confirm heroin use, as it is not found in the metabolism of other opioids.

Related Pages

• Heroin
• Morphine
• Opioid
• Blood-brain barrier

Gallery

• 

  Black tar heroin, a form of heroin that metabolizes to 6-MAM.

• 

  Diagram showing the acetyl groups in heroin.

• 

  2D structure of 6-Monoacetylmorphine

• 

  Ball-and-stick model of 6-Monoacetylmorphine

• 

  Black tar heroin

• 

  Acetyl groups of heroin