| Width | 250px |
|---|---|
| Width 2 | 225px |
| Routes of administration | Oral[1] |
| Class | Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Psychoactive drug; Stimulant, Serotonergic psychedelic; Hallucinogen |
| Atc prefix | None |
| Duration of action | "Short"[1] |
| Cas number | 23690-13-3 |
| Cas supplemental | 52850-81-4 |
| Pubchem | 141047 |
| Chemspiderid | 124411 |
| Unii | GT33R7Q58G |
| Chembl | 282734 |
| Synonyms | 2,4-DMA; 2,4-Dimethoxy-α-methylphenethylamine; DMA-3 |
| Iupac name | 1-(2,4-dimethoxyphenyl)propan-2-amine |
| C | 11 |
| H | 17 |
| N | 1 |
| O | 2 |
| Smiles | CC(CC1=C(C=C(C=C1)OC)OC)N |
| Stdinchi | 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 |
| Stdinchikey | 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 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]
See also
- Dimethoxyamphetamine
- Substituted methoxyphenethylamine
- 2,4,5-Trimethoxyamphetamine (TMA-2)
- 2,4,6-Trimethoxyamphetamine (TMA-6; ψ-TMA-2)
- 2,4-Dimethoxyphenethylamine
References
- ^ 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
- ^ 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.
- ^ 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
- ^ 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
- ^ 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
- ^ Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships". NIDA Res Monogr. 94: 43–67. PMID 2575229. Archived from the original on May 11, 2023.
- ^ Alexander T. Shulgin; Thornton Sargent; Claudio Naranjo (1967). "The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines". 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. Archived 12 July 2025 at the Wayback Machine.
- ^ 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 2025-07-12 at the Wayback Machine.