3,4-Dimethoxyamphetamine

3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families.^[1][2] It is one of the dimethoxyamphetamine (DMA) series of positional isomers.^[1][2]

3,4-Dimethoxyamphetamine

Clinical data
Other names	3,4-DMA; Dimethoxyamphetamine; DMA; 3,4-Dimethoxy-α-methylphenethylamine; α-Methylhomoveratrylamine; EA-1316; NSC-144717
Drug class	Serotonergic psychedelic; Hallucinogen
Identifiers
IUPAC name 1-(3,4-dimethoxyphenyl)propan-2-amine
CAS Number	120-26-3
PubChem CID	8423
ChemSpider	8116
UNII	EMH5PUB78V
ChEMBL	ChEMBL277540
CompTox Dashboard (EPA)	DTXSID50902787
ECHA InfoCard	100.003.985
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC(=C(C=C1)OC)OC)N
InChI InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)11(7-9)14-3/h4-5,7-8H,6,12H2,1-3H3 Key:KAZPHAGSWZTKDW-UHFFFAOYSA-N

The drug has been assessed in various biochemical and preclinical studies.^[2] It has been tried in humans at doses of up to 700 mg intravenously, with mescaline-like effects reported.^[2][1] 3,4-DMA is also orally active and has produced sympathomimetic effects at a dose of 160 mg.^[2][1] Its duration of action is unknown.^[2][1]

Its affinity (K_i) for the rat serotonin 5-HT_2A receptor has been assessed^[2] and was found to be 43,300 nM.^[3] For comparison, the affinity of para-methoxyamphetamine (PMA) was 33,600 nM, of 2,5-dimethoxyamphetamine (2,5-DMA) was 5,200 nM, and of 2,5-dimethoxy-4-methylamphetamine (DOM) was 100 nM in the same study.^[3] 3,4-DMA has been found to be a monoamine oxidase inhibitor (MAOI), with an IC₅₀Tooltip half-maximal inhibitory concentration of 20,000 nM for monoamine oxidase A (MAO-A), whereas it was inactive at monoamine oxidase B (MAO-B) (IC₅₀ > 100,000 nM).^[4][5]

3,4-DMA fails to produce stimulus generalization to dextroamphetamine in rodent drug discrimination tests, suggesting that it lacks psychostimulant- or amphetamine-like effects.^[6]

3,4-DMA produces 3-methoxy-4-hydroxyamphetamine (MHA) as its major metabolite in dogs and monkeys.^[2]

See also

• 3,4-Methylenedioxyamphetamine (MDA)
• 3,4-Ethylenedioxyamphetamine (EDMA)
• 3-Methoxyamphetamine (3-MA)
• 4-Methoxyamphetamine (PMA)
• 3,4,5-Trimethoxyamphetamine (TMA)
• 3,4-Dihydroxyamphetamine (DHA; α-methyldopamine)