3,5-Dimethoxyamphetamine

3,5-Dimethoxyamphetamine (3,5-DMA), also known as DMA-6, is a drug of the amphetamine family and a positional isomer of dimethoxyamphetamine (DMA). It is the parent structure of the 3C (4-substituted 3,5-dimethoxyamphetamine) family of compounds (also known as 3C-scalines).

Use and effects

The effects of 3,5-DMA in humans have not been reported.

Pharmacology

Pharmacodynamics

In an early study, it showed similar affinity for serotonin receptors as mescaline (3,4,5-trimethoxyphenethylamine) but had more than an order of magnitude lower affinity than DOx (4-substituted 2,5-dimethoxyamphetamine) drugs like DOM, DOET, and DOB. However, in a later study, it showed no or very low affinity for the serotonin 5-HT_2A and 5-HT_2C receptors (K_i = >10,000nM), whereas DOB showed high affinity for these receptors (K_i = 32nM and 64nM, respectively).

3,5-DMA's effects on monoamine reuptake and efflux have also been studied. It appeared to be weak or inactive as a norepinephrine reuptake inhibitor and norepinephrine releasing agent. Likewise, it was a very weak serotonin reuptake inhibitor ( = 18,500nM) and serotonin releasing agent (active at ≥10,000nM).

3,5-DMA was inactive in substituting for DOM in rodent drug discrimination tests (4–14% appropriate responding for 5–12.5mg/kg), suggesting that it would not be hallucinogenic in humans. However, it has shown other pharmacological effects in mice and with similar potency as mescaline, whereas it was inactive in rats.

Chemistry

Synthesis

The chemical synthesis of 3,5-DMA has been described.

History

3,5-DMA was first described in the scientific literature by F. Benington and colleagues by at least 1968. It was not included as an entry in Alexander Shulgin's 1991 book PiHKAL (Phenethylamines I Have Known and Loved), but was subsequently included as an entry in his 2011 book '. The drug has been detected as an adulterant in forensic drug samples.