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2,4-Dimethoxyamphetamine

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2,4-Dimethoxyamphetamine
Clinical data
Other names2,4-DMA; 2,4-Dimethoxy-α-methylphenethylamine; DMA-3
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 drug of the phenethylamine and amphetamine families.[1][2] It is one of the dimethoxyamphetamine (DMA) series of positional isomers.[1][2]

It was reported by Alexander Shulgin to be active at a dose of 60 mg orally and to produce threshold amphetamine-like stimulant and euphoric effects.[1][2] However, there was also a "diffusion of association" and Shulgin stated that it was more than just a stimulant.[1] The duration was described as short and effects subsiding at 3 hours.[1][2] Per Shulgin, the drug could be a full stimulant and/or a full psychedelic at sufficiently high doses, but higher doses were not pursued.[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]

See also

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References

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  1. ^ a b c d e f 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 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
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