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3,4-Dimethoxyamphetamine

Pharmaceutical compound From Wikipedia, the free encyclopedia

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]

Other names3,4-DMA; Dimethoxyamphetamine; DMA; 3,4-Dimethoxy-α-methylphenethylamine; O,O-Dimethyl-α-methyldopamine; α-Methylhomoveratrylamine; EA-1316; NSC-144717
Routes of
administrationOral[1]
Drug classSerotonergic psychedelic; Hallucinogen; Sympathomimetic
ATC code
  • None
Quick facts Clinical data, Other names ...
3,4-Dimethoxyamphetamine
Clinical data
Other names3,4-DMA; Dimethoxyamphetamine; DMA; 3,4-Dimethoxy-α-methylphenethylamine; O,O-Dimethyl-α-methyldopamine; 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
CompTox Dashboard (EPA)
ECHA InfoCard100.003.985 Edit this at Wikidata
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
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Use and effects

3,4-DMA has been tested in humans at doses of up to 700 mg intravenously, with mescaline-like effects reported.[2][1] It is also orally active and has produced sympathomimetic effects at a dose of 160 mg orally.[2][1] The drug's duration is unknown.[2][1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

3,4-DMA has been assessed in various biochemical and preclinical studies.[2]

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]

Pharmacokinetics

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

Chemistry

Synthesis

The chemical synthesis of 3,4-DMA has been described.[1]

History

3,4-DMA was first described in the scientific literature by Alexander Shulgin and colleagues by at least 1967.[8] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]

Society and culture

3,4-DMA is a controlled substance in Canada under amphetamine blanket-ban language.[9] It is not an explicitly controlled substance in the United States, but may be considered scheduled as an isomer of 2,5-dimethoxyamphetamine (2,5-DMA).[10][11]

See also

References

External links

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