Methyl-DMA
Pharmaceutical compound
From Wikipedia, the free encyclopedia
Methyl-DMA, also known as 2,5-dimethoxy-N-methylamphetamine or as N-methyl-2,5-DMA, is a psychoactive drug of the phenethylamine, amphetamine, and DOx families.[1] It is the N-methyl derivative of 2,5-dimethoxyamphetamine (2,5-DMA; DOH).[1]
- None
 | |
| Clinical data | |
|---|---|
| Other names | METHYL-DMA; N-Methyl-3,4-DMA; 2,5-Dimethoxy-N-methylamphetamine; N-Methyl-DMA; N-Methyl-2,5-dimethoxyamphetamine; N-Methyl-DOH; Methyl-DOH; 2,5-DMMA; DMMA; EA-1322 |
| Routes of administration | Oral, intravenous[1][2] |
| Drug class | Serotonin receptor modulator; Psychoactive drug |
| ATC code |
|
| Pharmacokinetic data | |
| Duration of action | Unknown[1] |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C12H19NO2 |
| Molar mass | 209.289 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists methyl-DMA's dose as above 250 mg orally and its duration as unknown.[1] The drug produced slight paresthesia and no other effects at tested doses of up to 250 mg orally.[1] Other mixed and inconsistent anecdotal reports have also been described, with effects including nothing at all, threshold effects, "complete and thorough experiences", real awareness [of effects], tingling in genitalia, strange presence in the spine, and increased body temperature and blood pressure.[1] These effects were said to persist for many hours.[1] No clear hallucinogenic effects were described.[1]
Methyl-DMA shows affinity for serotonin receptors in the rat stomach fundus strip (A2 = 316 nM).[1] Its affinity in this assay was about 2-fold lower than that of 2,5-DMA and about 4-fold lower than that of DOM.[1]
The chemical synthesis of methyl-DMA has been described.[1] Analogues of methyl-DMA include Beatrice (N-methyl-DOM), methyl-TMA-2 (N-methyl-TMA-2), methyl-TMA (N-methyl-TMA), and para-methoxyamphetamine (PMMA; methyl-MA), among others.[1] N-Methylation of psychedelic phenethylamines is well-known to greatly reduce or abolish their hallucinogenic activity.[1]
Methyl-DMA was studied at Edgewood Arsenal under the code name EA‐1322 in the early 1950s.[2] It was first described in the scientific literature by Richard Glennon and colleagues by 1978.[3] Subsequently, the drug was described in greater detail by Shulgin in PiHKAL in 1991.[1] Methyl-DMA has reportedly been encountered as a novel designer drug.[4] It is a controlled substance in Canada under phenethylamine blanket-ban language.[5]