2,6-Dimethoxyamphetamine

2,6-Dimethoxyamphetamine
Clinical data
Other names	2,6-DMA; DMA-5
Drug class	Serotonin receptor modulator
ATC code	None;
Identifiers
	IUPAC name 1-(2,6-dimethoxyphenyl)propan-2-amine;
CAS Number	23690-14-4;
PubChem CID	141048;
ChemSpider	124412;
UNII	GCG9F6BC2R;
ChEMBL	ChEMBL30577;
CompTox Dashboard (EPA)	DTXSID40946493 ;
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=C(C=CC=C1OC)OC)N;
	InChI InChI=1S/C11H17NO2/c1-8(12)7-9-10(13-2)5-4-6-11(9)14-3/h4-6,8H,7,12H2,1-3H3; Key:OHGNLLDQBKOWJW-UHFFFAOYSA-N;

2,6-Dimethoxyamphetamine (2,6-DMA), also known as DMA-5, is a drug of the phenethylamine and amphetamine families. It is one of the positional isomers of dimethoxyamphetamine.

The drug has not been tested in humans and its effects in humans are unknown.

2,6-DMA showed very low affinity for serotonin receptors in rat stomach fundus strips (A₂ = 8,130 nM). In a subsequent study, it showed no affinity for the serotonin 5-HT_2A or 5-HT_2C receptors (K_i = >10,000 nM). 2,6-DMA only partially substituted for DOM in rodent drug discrimination tests, with a maximum responding of 41% and behavioral disruption at higher doses. It did not substitute for dextroamphetamine in these tests.

The chemical synthesis of 2,6-DMA has been described.

2,6-DMA was first described in the scientific literature by Alexander Shulgin by 1969. At that time, he had not yet synthesized it and did not report its effects. 2,6-DMA is a positional isomer of 2,5-dimethoxyamphetamine (2,5-DMA) and hence is a Schedule I controlled substance in the United States.