{{Infobox drug | drug_name = | image = 2,4-DMA.svg | image_class = skin-invert-image | width = 250px | image2 = DMA-3d-sticks.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = Serotonin receptor modulator; Serotonin 5-HT<sub>2A</sub> receptor agonist; Psychoactive drug; Stimulant, Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = "Short"<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number = 23690-13-3 | CAS_supplemental = <br />52850-81-4 | PubChem = 141047 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 124411 | UNII = GT33R7Q58G | KEGG = | ChEBI = | ChEMBL = 282734 | NIAID_ChemDB = | PDB_ligand = | synonyms = 2,4-DMA; 2,4-Dimethoxy-α-methylphenethylamine; DMA-3
<!-- Chemical data --> | 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.<ref name="PiHKAL">{{Cite book | vauthors = Shulgin AT, Shulgin A | chapter = #53 2,4-DMA; 2,4-DIMETHOXYAMPHETAMINE | title = PiHKAL: A Chemical Love Story | date = 1991 | publisher = Transform Press | isbn = 9780963009609 | edition = 1st | location = Berkeley, CA | oclc = 25627628 | chapter-url = https://www.erowid.org/library/books_online/pihkal/pihkal053.shtml }}</ref><ref name="ShulginManningDaley2011">{{cite book | vauthors = Shulgin A, Manning T, Daley PF | chapter=#35. 2,4-DMA | title=The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | publisher=Transform Press | location=Berkeley | volume=1 | year=2011 | isbn=978-0-9630096-3-0 | chapter-url=https://archive.org/details/shulgin-index-vol-1/page/54/mode/1up?view=theater }}</ref> It is one of the dimethoxyamphetamine (DMA) series of positional isomers.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" />
In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists 2,4-DMA's dose as greater than 60{{nbsp}}mg orally and its duration as "short".<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /> At a dose of 60{{nbsp}}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".<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /> The drug's effects started to wear off after 3{{nbsp}}hours.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /> 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.<ref name="PiHKAL" />
2,4-DMA has been found to act as a low-potency full agonist of the serotonin 5-HT<sub>2A</sub> receptor, with an {{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} of 2,950{{nbsp}}nM and an {{Abbrlink|E<sub>max</sub>|half-maximal effective concentration}} of 117%.<ref name="FlanaganBillacLandry2021">{{cite journal | vauthors = Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD | title = Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore | journal = ACS Pharmacol Transl Sci | volume = 4 | issue = 2 | pages = 488–502 | date = April 2021 | pmid = 33860179 | pmc = 8033619 | doi = 10.1021/acsptsci.0c00063 | url = }}</ref> It fully substitutes for DOM in rodent drug discrimination tests.<ref name="GlennonYoung1982">{{cite journal | vauthors = Glennon RA, Young R | title = Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines | journal = Pharmacol Biochem Behav | volume = 17 | issue = 4 | pages = 603–607 | date = October 1982 | pmid = 6965276 | doi = 10.1016/0091-3057(82)90330-6 | url = }}</ref><ref name="Marcher-RørstedHalberstadtKlein2020">{{cite journal | vauthors = Marcher-Rørsted E, Halberstadt AL, Klein AK, Chatha M, Jademyr S, Jensen AA, Kristensen JL | title = Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists | journal = ACS Chem Neurosci | volume = 11 | issue = 9 | pages = 1238–1244 | date = May 2020 | pmid = 32212672 | doi = 10.1021/acschemneuro.0c00129 | url = | quote = 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}}</ref> 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).<ref name="GlennonYoung1982" /> 2,4-DMA fails to produce stimulus generalization to dextroamphetamine in rodent drug discrimination tests, suggesting that it lacks psychostimulant- or amphetamine-like effects.<ref name="Glennon1989">{{cite journal | vauthors = Glennon RA | title = Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships | journal = NIDA Res Monogr | volume = 94 | issue = | pages = 43–67 | date = 1989 | pmid = 2575229 | doi = | url = https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54| archive-url = https://web.archive.org/web/20230511144224/https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54| url-status = dead| archive-date = May 11, 2023}}</ref>
The chemical synthesis of 2,4-DMA has been described.<ref name="PiHKAL" />
2,4-DMA was first described in the scientific literature by Alexander Shulgin and colleagues by at least 1967.<ref name="ShulginSargentNaranjo1967">{{cite book | author1=Alexander T. Shulgin | author2=Thornton Sargent | author3=Claudio Naranjo | chapter=The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines | pages=202–214 | veditors=Efron DH, Holmstedt B, Kline NS | title=Ethnopharmacologic Search for Psychoactive Drugs: Proceedings of a Symposium Held in San Francisco, California, January 28–30, 1967 | publisher=Raven Press | location=New York | date=1967 | isbn=978-0-89004-047-8 | oclc=14498182 | ol=OL14623132M | chapter-url=https://bibliography.maps.org/resources/download/15578 | url=https://books.google.com/books?id=IvfBDethZkYC | archive-url=https://web.archive.org/web/20250712212357/https://bibliography.maps.org/resources/download/15578 | archive-date=12 July 2025 }}</ref><ref name="ShulginSargentNaranjo1969">{{cite journal | vauthors = Shulgin AT, Sargent T, Naranjo C | title = Structure–activity relationships of one-ring psychotomimetics | journal = Nature | volume = 221 | issue = 5180 | pages = 537–541 | date = February 1969 | pmid = 5789297 | doi = 10.1038/221537a0 | bibcode = 1969Natur.221..537S | url = https://bibliography.maps.org/resources/download/11267 | archive-url = https://web.archive.org/web/20250712213646/https://bibliography.maps.org/resources/download/11267 | archive-date = 2025-07-12}}</ref> Subsequently, it was described in greater detail by Shulgin in ''PiHKAL'' in 1991.<ref name="PiHKAL" />
==See also== * Dimethoxyamphetamine * Substituted methoxyphenethylamine * 2,4,5-Trimethoxyamphetamine (TMA-2) * 2,4,6-Trimethoxyamphetamine (TMA-6; ψ-TMA-2) * 2,4-Dimethoxyphenethylamine
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/53 2,4-DMA - Isomer Design] * [https://erowid.org/library/books_online/pihkal/pihkal053.shtml 2,4-DMA - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/53 2,4-DMA - PiHKAL - Isomer Design] * [https://archive.org/details/shulgin-index-vol-1/page/54/mode/1up 2,4-DMA - The Shulgin Index]
{{Stimulants}} {{Psychedelics}} {{Serotonin receptor modulators}} {{Monoamine releasing agents}} {{Phenethylamines}}
{{DEFAULTSORT:Dimethoxyamphetamine, 2,4-}}
Category:5-HT2A agonists Category:Methoxyphenethylamines Category:Monoamine releasing agents Category:PiHKAL Category:Psychedelic phenethylamines Category:Stimulants Category:Substituted amphetamines Category:2,4-Substituted phenethylamines