2,3-Dimethoxyamphetamine

2,3-Dimethoxyamphetamine
Clinical data
Other names	2,3-DMA; DMA-2; NSC-172189
Drug class	Serotonin receptor modulator
ATC code	None;
Identifiers
	IUPAC name 1-(2,3-dimethoxyphenyl)propan-2-amine;
CAS Number	15402-81-0;
PubChem CID	91255;
ChemSpider	82404;
UNII	P5Z6ZU6N7S;
ChEMBL	ChEMBL280855;
CompTox Dashboard (EPA)	DTXSID20934898 ;
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=C(C(=CC=C1)OC)OC)N;
	InChI InChI=1S/C11H17NO2/c1-8(12)7-9-5-4-6-10(13-2)11(9)14-3/h4-6,8H,7,12H2,1-3H3; Key:DHLWJXGSZDJWKK-UHFFFAOYSA-N;

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

2,3-DMA does not appear to have been tested in humans.

The drug showed weak affinity for serotonin receptors in rat stomach fundus strips (A₂ = 2,880 nM). In a subsequent study, 2,3-DMA showed very low affinity for the serotonin 5-HT_2A and 5-HT_2C receptors (K_i = 4,280 nM and >10,000 nM, respectively). It did not show activity as a norepinephrine releasing agent in vitro. The drug is behaviorally active in mice. 2,3-DMA did not substitute for DOM in rodent drug discrimination tests. However, it did partially substitute for 5-MeO-DMT in these tests. As with DOM, the drug did not substitute for dextroamphetamine in drug discrimination tests. It produced behavioral disruption at higher doses.

The chemical synthesis of 2,3-DMA has been described.

2,3-DMA was first described in the scientific literature by F. Benington and colleagues by 1968. Alexander Shulgin first described 2,3-DMA in 1969 but had not yet synthesized it and did not report its effects.