4hydroxyamphetamine

4-hydroxyamphetamine, also known as p-hydroxyamphetamine or 4-HA, is a phenethylamine and a structural analog of amphetamine. Its IUPAC name is 4-hydroxy-1-phenylpropan-2-amine, and its chemical formula is C9H13NO2. The molecule features a phenyl ring substituted at the 4-position with a hydroxyl group and a side chain that confers amphetamine-like activity.

Pharmacology and effects reported in the literature suggest that 4-hydroxyamphetamine can act as a monoamine releasing agent, with activity at dopamine and norepinephrine transporters and, to a lesser extent, the serotonin transporter. In vitro studies and limited in vivo data indicate stimulant-like effects at higher doses, though the potency and duration are not as well characterized as those of amphetamine. The compound is primarily of interest in research and forensic contexts rather than as a medicine.

Occurrence and context: 4-hydroxyamphetamine has been described as a minor metabolite in pharmacokinetic studies of amphetamine and methamphetamine in humans. It may also be encountered in analytical settings that target phenethylamines in drug testing panels, often as part of broader investigations into amphetamine-related compounds.

Regulatory status and use: There are no approved medical uses for 4-hydroxyamphetamine. Regulatory treatment varies by jurisdiction; some countries classify hydroxy-substituted phenethylamines as controlled substances or as illegal analogs of amphetamine, while others may not explicitly schedule them. Safety concerns include stimulant-like cardiovascular and central nervous system effects, with risks associated with misuse or high-dose exposure.

See also: related hydroxy-substituted phenethylamines and the broader class of amphetamine analogs.