phydroxyamphetamine

4-hydroxyamphetamine, also known as p-hydroxyamphetamine or 4-HA, is a substituted phenethylamine that shares the core structure of amphetamine but carries a hydroxy group at the para position of the benzene ring. Its systematic name is 4-hydroxy-α-methylphenethylamine.

Chemical characteristics and related compounds

As a para-hydroxy analogue of amphetamine, 4-hydroxyamphetamine is a relatively small, lipophilic amine with a single hydroxyl group on the aromatic ring. This modification typically affects lipophilicity, aromatic ring interactions, and the compound’s pharmacokinetic properties compared with amphetamine.

Occurrence and metabolism

4-Hydroxyamphetamine is not a widely used pharmaceutical agent. In humans, it has been reported as a metabolite or a trace byproduct in investigations of amphetamine metabolism. It may be formed in vivo by phase I hydroxylation of amphetamine or related pathways, and it can appear in biological samples alongside other amphetamine-type compounds.

Pharmacology

Compared with amphetamine, the pharmacological profile of 4-hydroxyamphetamine is less well characterized. Available data suggest reduced potency at monoamine transporters (dopamine, norepinephrine, and serotonin) and potentially lower central nervous system penetration due to increased polarity from the hydroxyl group. The substance is primarily of interest to researchers and clinical toxicology rather than as a therapeutic agent.

Legal status and detection

4-Hydroxyamphetamine is not commonly scheduled as a standalone pharmaceutical in many jurisdictions. In forensic toxicology, it may be monitored as a potential marker in the broader analysis of amphetamine use, often detected using LC-MS or GC-MS methods in urine or plasma samples.

See also

4-hydroxyphenethylamine, amphetamine, forensic toxicology.