3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers.
3,4-DMA has been tested in humans at doses of up to 700mg intravenously, with mescaline-like effects reported. It is also orally active and has produced sympathomimetic effects at a dose of 160mg orally. The drug's duration is unknown.
3,4-DMA has been assessed in various biochemical and preclinical studies.
Its affinity (K<sub>i</sub>) for the rat serotonin 5-HT<sub>2A</sub> receptor has been assessed and was found to be 43,300nM. For comparison, the affinity of para-methoxyamphetamine (PMA) was 33,600nM, of 2,5-dimethoxyamphetamine (2,5-DMA) was 5,200nM, and of 2,5-dimethoxy-4-methylamphetamine (DOM) was 100nM in the same study. 3,4-DMA also showed affinity for the 5-HT<sub>1</sub> receptor (K<sub>i</sub> = 64,600nM).
The drug has additionally been found to be a monoamine oxidase inhibitor (MAOI), with an of 20,000nM for monoamine oxidase A (MAO-A), whereas it was inactive at monoamine oxidase B (MAO-B) ( > 100,000nM).
3,4-DMA fails to produce stimulus generalization to dextroamphetamine in rodent drug discrimination tests, suggesting that it lacks psychostimulant- or amphetamine-like effects.
3,4-DMA produces 3-methoxy-4-hydroxyamphetamine (MHA) as its major metabolite in dogs and monkeys.
The chemical synthesis of 3,4-DMA has been described.
3,4-DMA was first described in the scientific literature by Alexander Shulgin and colleagues by at least 1967. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.
3,4-DMA is a controlled substance in Canada under amphetamine blanket-ban language. It is not an explicitly controlled substance in the United States, but may be considered scheduled as an isomer of 2,5-dimethoxyamphetamine (2,5-DMA).