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.^[1] It is one of the positional isomers of dimethoxyamphetamine.^[1]

Other names2,6-DMA; DMA-5

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The drug has not been tested in humans and its effects in humans are unknown.^[1]

2,6-DMA showed very low affinity for serotonin receptors in rat stomach fundus strips (A₂ = 8,130 nM).^[1]^[2] In a subsequent study, it showed no affinity for the serotonin 5-HT_2A or 5-HT_2C receptors (K_i = >10,000 nM).^[3] 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.^[4]^[5] It did not substitute for dextroamphetamine in these tests.^[5]^[6]

The chemical synthesis of 2,6-DMA has been described.^[1]

2,6-DMA was first described in the scientific literature by Alexander Shulgin by 1969.^[7] At that time, he had not yet synthesized it and did not report its effects.^[7] 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.^[1]

See also