4-Hydroxy-3-methoxymethamphetamine

4-Hydroxy-3-methoxymethamphetamine (HMM) is a metabolite of the psychoactive drug methamphetamine. It is formed in the body after ingestion of methamphetamine and is excreted in the urine. The presence of HMM in urine can be used as an indicator of methamphetamine use.

Chemistry

HMM is a phenethylamine and amphetamine derivative. It is structurally similar to methamphetamine, with the addition of a hydroxy group at the 4 position and a methoxy group at the 3 position of the phenyl ring.

Pharmacology

The pharmacological effects of HMM are not well studied. However, it is known that it is less potent than methamphetamine. It is believed to be largely inactive, but may contribute to the overall effects of methamphetamine through unknown mechanisms.

Metabolism

HMM is one of several metabolites of methamphetamine. It is formed in the body by the action of cytochrome P450 enzymes, specifically CYP2D6. The formation of HMM is a step in the metabolic breakdown of methamphetamine, which also includes the formation of amphetamine, 4-hydroxyamphetamine, and norpseudoephedrine.

Detection

The presence of HMM in urine can be used as an indicator of methamphetamine use. It can be detected using gas chromatography-mass spectrometry (GC-MS) or liquid chromatography-mass spectrometry (LC-MS). The detection of HMM, along with other methamphetamine metabolites, can help to confirm a diagnosis of methamphetamine abuse or poisoning.

See also

• Methamphetamine
• Drug metabolism
• Drug testing

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