2,4-Dimethoxyamphetamine
Pharmaceutical compound
From Wikipedia, the free encyclopedia
2,4-Dimethoxyamphetamine (2,4-DMA), also known as DMA-3, is a psychoactive drug of the phenethylamine and amphetamine families.[1][2] It is one of the dimethoxyamphetamine (DMA) series of positional isomers.[1][2]
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| Other names | 2,4-DMA; 2,4-Dimethoxy-α-methylphenethylamine; DMA-3 |
| Routes of administration | Oral[1] |
| Drug class | Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Psychoactive drug; Stimulant, Serotonergic psychedelic; Hallucinogen |
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| Duration of action | "Short"[1] |
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| Formula | C11H17NO2 |
| Molar mass | 195.262 g·mol−1 |
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In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2,4-DMA's dose as greater than 60 mg orally and its duration as "short".[1][2] At a dose of 60 mg orally, the effects of 2,4-DMA were reported to include definite threshold effects or even a bit more, a lot of amphetamine-like effects, some euphoria, and a psychedelic-like "diffusion of association".[1][2] The drug's effects started to wear off after 3 hours.[1][2] According to Shulgin, 2,4-DMA could be a full stimulant and/or a full psychedelic at sufficiently high doses, but higher doses were not tested.[1]
2,4-DMA has been found to act as a low-potency full agonist of the serotonin 5-HT2A receptor, with an EC50 of 2,950 nM and an Emax of 117%.[3] It fully substitutes for DOM in rodent drug discrimination tests.[4][5] The drug is less potent in this regard than 2,4,5-trimethoxyamphetamine (2,4,5-TMA or TMA-2), but is more potent than 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1).[4] 2,4-DMA fails to produce stimulus generalization to dextroamphetamine in rodent drug discrimination tests, suggesting that it lacks psychostimulant- or amphetamine-like effects.[6]
The chemical synthesis of 2,4-DMA has been described.[1]
2,4-DMA was first described in the scientific literature by Alexander Shulgin and colleagues by at least 1967.[7][8] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]