2,4-Dimethoxyamphetamine

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]

2,4-Dimethoxyamphetamine

Clinical data
Other names	2,4-DMA; 2,4-Dimethoxy-α-methylphenethylamine; DMA-3
Identifiers
IUPAC name 1-(2,4-dimethoxyphenyl)propan-2-amine
CAS Number	23690-13-3 52850-81-4
PubChem CID	141047
ChemSpider	124411
UNII	GT33R7Q58G
ChEMBL	ChEMBL282734
CompTox Dashboard (EPA)	DTXSID90874252
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=C(C=C(C=C1)OC)OC)N
InChI 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

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-HT_2A receptor, with an EC₅₀Tooltip half-maximal effective concentration of 2,950 nM and an E_maxTooltip 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]

See also

• 2,4,5-Trimethoxyamphetamine (TMA-2)