3,4-Dimethoxyamphetamine

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
CompTox Dashboard (EPA)
ECHA InfoCard100.003.985
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]

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

  1. ^ a b c d e f g h i Shulgin AT, Shulgin A (1991). "#55 3,4-DMA; 3,4-DIMETHOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 9780963009609. OCLC 25627628.
  2. ^ a b c d e f g h Shulgin A, Manning T, Daley PF (2011). "#38. DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  3. ^ a b c Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID 3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites [...]
  4. ^ a b c Shannon M, Battaglia G, Glennon RA, Titeler M (June 1984). "5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA)". Eur J Pharmacol. 102 (1): 23–29. doi:10.1016/0014-2999(84)90333-9. PMID 6479216.
  5. ^ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10: 1590. doi:10.3389/fphar.2019.01590. PMC 6989591. PMID 32038257.
  6. ^ Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE (April 2005). "Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling". J Med Chem. 48 (7): 2407–2419. doi:10.1021/jm0493109. PMID 15801832.
  7. ^ Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships" (PDF). NIDA Res Monogr. 94: 43–67. PMID 2575229. Archived from the original (PDF) on May 11, 2023.
  8. ^ Alexander T. Shulgin, Thornton Sargent, Claudio Naranjo (1967). "The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines". In Efron DH, Holmstedt B, Kline NS (eds.). Ethnopharmacologic Search for Psychoactive Drugs: Proceedings of a Symposium Held in San Francisco, California, January 28–30, 1967. New York: Raven Press. pp. 202–214. ISBN 978-0-89004-047-8. OCLC 14498182. OL 14623132M. Archived from the original on 12 July 2025.
  9. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  10. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
  11. ^ Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances". Federal Register.
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