3,4-Dimethoxyamphetamine

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3,4-Dimethoxyamphetamine
Clinical data
Other names3,4-DMA; Dimethoxyamphetamine; DMA; 3,4-Dimethoxy-α-methylphenethylamine; α-Methylhomoveratrylamine; EA-1316; NSC-144717
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen; Sympathomimetic
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 1-(3,4-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=C(C=C1)OC)OC)N
  • 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

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]

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 is unknown.[2][1]

Its affinity (Ki) for the rat serotonin 5-HT2A receptor has been assessed and was found to be 43,300 nM.[3][4][2] 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][4] 3,4-DMA also showed affinity for the 5-HT1 receptor (Ki = 64,600 nM).[3][4] The drug has additionally 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).[5][6]

3,4-DMA fails to produce stimulus generalization to dextroamphetamine in rodent drug discrimination tests, suggesting that it lacks psychostimulant- or amphetamine-like effects.[7]

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

See also

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References

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