3,4-Dihydroxymethamphetamine

Chemical compound related to methamphetamine

3,4-Dihydroxymethamphetamine (also known as HHMA) is a catecholamine and a metabolite of the psychoactive drug MDMA (3,4-methylenedioxymethamphetamine). It is structurally related to dopamine and norepinephrine, which are important neurotransmitters in the central nervous system.

Chemical Structure and Properties

Chemical structure of 3,4-Dihydroxymethamphetamine

3,4-Dihydroxymethamphetamine is characterized by the presence of two hydroxyl groups attached to the benzene ring, which classifies it as a catechol. The chemical formula is C10H15NO2, and it has a molecular weight of 181.23 g/mol. The presence of the hydroxyl groups makes it more polar than its parent compound, MDMA, affecting its solubility and interaction with biological systems.

Biological Activity

3,4-Dihydroxymethamphetamine is primarily formed in the body as a result of the metabolism of MDMA. It is produced through the action of the enzyme CYP2D6, which demethylenates MDMA to form HHMA. This metabolite is further metabolized to form 3,4-dihydroxyamphetamine (DHA) and other compounds.

In terms of biological activity, HHMA is known to have some effects on the central nervous system, although it is less potent than MDMA itself. It is thought to contribute to the overall pharmacological profile of MDMA by interacting with monoamine transporters and receptors.

Pharmacokinetics

The pharmacokinetics of 3,4-Dihydroxymethamphetamine involve its rapid formation following the ingestion of MDMA. It is further metabolized by catechol-O-methyltransferase (COMT) to form 3-methoxy-4-hydroxymethamphetamine (HMMA), which is then excreted in the urine. The presence of HHMA and its metabolites in the urine can be used as a biomarker for MDMA use.

Toxicity and Safety

The toxicity of 3,4-Dihydroxymethamphetamine is not well characterized, but it is believed to contribute to the neurotoxic effects associated with MDMA use. The formation of reactive oxygen species (ROS) during its metabolism may lead to oxidative stress, which can damage neurons and other cells.

Research and Implications

Research into 3,4-Dihydroxymethamphetamine is ongoing, with studies focusing on its role in the pharmacology and toxicology of MDMA. Understanding the metabolism and effects of HHMA is important for developing strategies to mitigate the adverse effects of MDMA and for the potential therapeutic use of MDMA in controlled settings.

Related Pages

• MDMA
• Dopamine
• Norepinephrine
• Catecholamine
• Neurotransmitter