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Other names | 3,5-DMA; DMA-6 |
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Formula | C11H17NO2 |
Molar mass | 195.262 g·mol−1 |
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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). [1] It is the parent structure of the 3C (4-substituted 3,5-dimethoxyamphetamine) family of compounds (also known as 3C-scalines). [1]
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. [1] [2] However, in a later study, it showed no or very low affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = >10,000 nM), whereas DOB showed high affinity for these receptors (Ki = 32 nM and 64 nM, respectively). [3] 3,5-DMA's effects on monoamine reuptake and efflux have also been studied. [1] [4] [5] [6] It appeared to be weak or inactive as a norepinephrine reuptake inhibitor and norepinephrine releasing agent. [4] [5] Likewise, it was a very weak serotonin reuptake inhibitor (IC50 = 18,500 nM) and serotonin releasing agent (active at ≥10,000 nM). [6]
3,5-DMA was inactive in substituting for DOM in rodent drug discrimination tests (4–14% appropriate responding for 5–12.5 mg/kg), suggesting that it would not be hallucinogenic in humans. [1] [7] However, it has shown other pharmacological effects in mice and with similar potency as mescaline, whereas it was inactive in rats. [8] The effects of 3,5-DMA in humans have not been reported. [1] [8] 3,5-DMA has been detected as an adulterant in forensic drug samples. [9] As a positional isomer of 2,5-dimethoxyamphetamine (2,5-DMA; DMA-4), 3,5-DMA is a Schedule I controlled substance in the United States. [1]
A derivative of 3,5-DMA, 4-bromo-3,5-dimethoxyamphetamine (4-Br-3,5-DMA), showed relatively high affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 210 nM and 570 nM, respectively). [3] However, it was not active as a psychedelic at the assessed doses (4–10 mg). [10]