Chemistry:2,4-Dimethoxyamphetamine

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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

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 "#53 2,4-DMA; 2,4-DIMETHOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. 1991. ISBN 9780963009609. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/pihkal053.shtml. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "#35. 2,4-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0. https://archive.org/details/shulgin-index-vol-1/page/54/mode/1up?view=theater. 
  3. ↑ "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. April 2021. doi:10.1021/acsptsci.0c00063. PMID 33860179. 
  4. ↑ 4.0 4.1 "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacol Biochem Behav 17 (4): 603–607. October 1982. doi:10.1016/0091-3057(82)90330-6. PMID 6965276. 
  5. ↑ "Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists". ACS Chem Neurosci 11 (9): 1238–1244. May 2020. 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. ↑ "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships". NIDA Res Monogr 94: 43–67. 1989. PMID 2575229. https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54. 
  7. ↑ 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. https://bibliography.maps.org/resources/download/15578. 
  8. ↑ "Structure–activity relationships of one-ring psychotomimetics". Nature 221 (5180): 537–541. February 1969. doi:10.1038/221537a0. PMID 5789297. Bibcode: 1969Natur.221..537S. https://bibliography.maps.org/resources/download/11267. 



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