Alpha-Methyldopamine

Alpha-Methyldopamine (α-Methyldopamine) is a metabolite of the neurotoxic amphetamine derivative, methylenedioxymethamphetamine (MDMA), commonly known as ecstasy. It is formed in the body during the metabolism of MDMA by the enzyme CYP2D6.

Chemistry

Alpha-Methyldopamine is a catecholamine and a phenethylamine. Its chemical structure is similar to that of other natural catecholamines in the body, such as dopamine, norepinephrine, and epinephrine. It is formed by the addition of a methyl group to the nitrogen atom of dopamine.

Pharmacology

Alpha-Methyldopamine is thought to contribute to the neurotoxic effects of MDMA. It is metabolized by the enzyme catechol-O-methyl transferase (COMT) to form alpha-methylnorepinephrine, which is then further metabolized to form alpha-methylepinephrine. These metabolites are thought to be responsible for the neurotoxic effects of MDMA.

Toxicity

The neurotoxicity of alpha-methyldopamine is thought to be due to the formation of quinone species, which can form adducts with cellular proteins and DNA, leading to cell death. This is thought to be the mechanism by which MDMA causes damage to serotonin neurons in the brain.

See also

• Methylenedioxymethamphetamine
• Neurotoxicity
• Catechol-O-methyl transferase