2,4-Dimethoxyamphetamine

2,4-Dimethoxyamphetamine
Clinical data
Other names	2,4-DMA; 2,4-Dimethoxy-α-methylphenethylamine; DMA-3
Routes of; administration	Oral
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Psychoactive drug; Stimulant, Serotonergic psychedelic; Hallucinogen
ATC code	None;
Pharmacokinetic data
Duration of action	"Short"
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;

2,4-Dimethoxyamphetamine (2,4-DMA), also known as DMA-3, is a psychoactive drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers.

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". 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". The drug's effects started to wear off after 3 hours. 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.

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%. It fully substitutes for DOM in rodent drug discrimination tests. 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). 2,4-DMA fails to produce stimulus generalization to dextroamphetamine in rodent drug discrimination tests, suggesting that it lacks psychostimulant- or amphetamine-like effects.

The chemical synthesis of 2,4-DMA has been described.

2,4-DMA was first described in the scientific literature by Alexander Shulgin and colleagues by at least 1967. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.