4-Hydroxy-3-methoxymethamphetamine

Chemical compound

4-Hydroxy-3-methoxymethamphetamine (HMMA) is a chemical compound that is a metabolite of the psychoactive drug methamphetamine. It is structurally related to 4-hydroxy-3-methoxyamphetamine (HMA), which is a metabolite of 3,4-methylenedioxyamphetamine (MDA).

Chemical structure

4-Hydroxy-3-methoxymethamphetamine is a phenethylamine derivative, characterized by a methoxy group at the 3-position and a hydroxy group at the 4-position of the benzene ring. The presence of these functional groups influences its pharmacokinetics and pharmacodynamics.

Metabolism

HMMA is formed in the body as a result of the biotransformation of methamphetamine. The liver enzymes, particularly those in the cytochrome P450 family, play a crucial role in this metabolic pathway. The conversion involves demethylation and hydroxylation processes.

Pharmacology

The pharmacological effects of HMMA are not as well-studied as those of its parent compound, methamphetamine. However, it is believed to have a lower psychoactive potential. The presence of the hydroxy and methoxy groups may alter its ability to cross the blood-brain barrier, thus affecting its central nervous system activity.

Toxicology

The toxicological profile of HMMA is not fully understood. As a metabolite, it is generally considered to be less toxic than methamphetamine itself. However, its accumulation in the body could potentially contribute to the overall toxicity of methamphetamine use.

Related compounds

• 4-Hydroxy-3-methoxyamphetamine (HMA)
• 3,4-Methylenedioxyamphetamine (MDA)
• Methamphetamine
• Amphetamine

See also

• Metabolite
• Psychoactive drug
• Biotransformation

Gallery

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  Chemical structure of 4-Hydroxy-3-methoxymethamphetamine

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  4-Hydroxy-3-methoxymethamphetamine