2,4-Dimethoxyamphetamine

2,4-Dimethoxyamphetamine
Clinical data
Other names2,4-DMA; 2,4-Dimethoxy-α-methylphenethylamine; DMA-3
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Psychoactive drug; Stimulant, Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action"Short"[1]
Identifiers
  • 1-(2,4-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C=C(C=C1)OC)OC)N
  • InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)7-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3
  • Key:DQWOZMUBHQPFFF-UHFFFAOYSA-N

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]

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 EC50Tooltip half-maximal effective concentration of 2,950 nM and an EmaxTooltip half-maximal effective concentration 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]

See also

References

  1. ^ a b c d e f g h i j Shulgin AT, Shulgin A (1991). "#53 2,4-DMA; 2,4-DIMETHOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 9780963009609. OCLC 25627628.
  2. ^ a b c d e Shulgin A, Manning T, Daley PF (2011). "#35. 2,4-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  3. ^ Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD (April 2021). "Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore". ACS Pharmacol Transl Sci. 4 (2): 488–502. doi:10.1021/acsptsci.0c00063. PMC 8033619. PMID 33860179.
  4. ^ a b Glennon RA, Young R (October 1982). "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacol Biochem Behav. 17 (4): 603–607. doi:10.1016/0091-3057(82)90330-6. PMID 6965276.
  5. ^ Marcher-Rørsted E, Halberstadt AL, Klein AK, Chatha M, Jademyr S, Jensen AA, Kristensen JL (May 2020). "Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists". ACS Chem Neurosci. 11 (9): 1238–1244. doi:10.1021/acschemneuro.0c00129. PMID 32212672. Removal of the 2- or 5-position methoxy group in 2,4,5-substituted compounds is also detrimental for their in vivo activity. For example, 2,4-dimethoxyamphetamine (13, Figure 2) and 3,4-dimethoxyamphetamine (14, Figure 2) are less potent than 8 in humans and in rats trained to discriminate 9. 14,15
  6. ^ Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships" (PDF). NIDA Res Monogr. 94: 43–67. PMID 2575229. Archived from the original (PDF) on May 11, 2023.
  7. ^ Alexander T. Shulgin, Thornton Sargent, Claudio Naranjo (1967). "The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines". In Efron DH, Holmstedt B, Kline NS (eds.). Ethnopharmacologic Search for Psychoactive Drugs: Proceedings of a Symposium Held in San Francisco, California, January 28–30, 1967. New York: Raven Press. pp. 202–214. ISBN 978-0-89004-047-8. OCLC 14498182. OL 14623132M. Archived from the original on 12 July 2025.
  8. ^ Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure–activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. Bibcode:1969Natur.221..537S. doi:10.1038/221537a0. PMID 5789297. Archived from the original on 2025-07-12.
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