Methyl-DMA

Methyl-DMA
Clinical data
Other namesMETHYL-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 classSerotonin receptor modulator; Psychoactive drug
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 1-(2,5-dimethoxyphenyl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO2
Molar mass209.289 g·mol−1
3D model (JSmol)
  • O(c1ccc(OC)cc1CC(NC)C)C
  • InChI=1S/C12H19NO2/c1-9(13-2)7-10-8-11(14-3)5-6-12(10)15-4/h5-6,8-9,13H,7H2,1-4H3 Y
  • Key:RSDBPMOXIPCTPN-UHFFFAOYSA-N Y
  (verify)

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]

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]

See also

References

  1. ^ a b c d e f g h i j k l m n o Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. Methyl-DMA entryL
  2. ^ a b Passie T, Benzenhöfer U (January 2018). "MDA, MDMA, and other "mescaline-like" substances in the US military's search for a truth drug (1940s to 1960s)". Drug Test Anal. 10 (1): 72–80. doi:10.1002/dta.2292. PMID 28851034. In November 1952, the Army Chemical Corps delivered the following substances to the NYSPI for human tests: MDPEA, MDA, MDE, DMA and 2,5‐dimethoxy‐N‐methylamphetamine (DMMA) (Table 1).29 (p. 2) None of these had been previously tested in humans. Animal testing was grossly deficient. "The five ... compounds were tested only on mice, for less than one month and only to determine the LD (lethal dose) 50." 29 (p.3) Nevertheless, "within a month of receiving the drugs, NYSPI experimenters began injecting them into patients." 31 quoted in ref. 2 (p. 500) (Table 2), without their informed consent.
  3. ^ Glennon RA, Liebowitz SM, Mack EC (August 1978). "Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues". J Med Chem. 21 (8): 822–825. doi:10.1021/jm00206a022. PMID 278843.
  4. ^ King LA (2014). "New phenethylamines in Europe". Drug Test Anal. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.
  5. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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