Chemistry:3,4-Dimethoxyamphetamine

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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

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 IC50 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. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "#55 3,4-DMA; 3,4-DIMETHOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. 1991. ISBN 9780963009609. OCLC 25627628. https://erowid.org/library/books_online/pihkal/pihkal055.shtml. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 "#38. DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0. https://archive.org/details/shulgin-index-vol-1/page/65/mode/1up?view=theater. 
  3. ↑ 3.0 3.1 3.2 "Central serotonin receptors as targets for drug research". J Med Chem 30 (1): 1–12. January 1987. doi:10.1021/jm00384a001. PMID 3543362. "Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites [...]". 
  4. ↑ 4.0 4.1 4.2 "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. June 1984. doi:10.1016/0014-2999(84)90333-9. PMID 6479216. 
  5. ↑ "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol 10: 1590. 2019. doi:10.3389/fphar.2019.01590. PMID 32038257. 
  6. ↑ "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. April 2005. doi:10.1021/jm0493109. PMID 15801832. 
  7. ↑ "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships". NIDA Res Monogr 94: 43–67. 1989. PMID 2575229. https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54. 
  8. ↑ Alexander T. Shulgin; Thornton Sargent; Claudio Naranjo (1967). "The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines". 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. https://bibliography.maps.org/resources/download/15578. 
  9. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  10. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 
  11. ↑ Drug Enforcement Administration (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances". https://www.federalregister.gov/documents/2007/12/03/E7-23413/definition-of-positional-isomer-as-it-pertains-to-the-control-of-schedule-i-controlled-substances. 



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