2,6-Dimethoxyamphetamine

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]

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

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

• Substituted methoxyphenethylamine
• Dimethoxyamphetamine
• 2,6-Dimethoxyphenethylamine