Chemistry:MMDA-2

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MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families.[1] It is closely related to MMDA and MDA.[1]

Alexander Shulgin was likely the first to synthesize MMDA-2.[1] In his book PiHKAL (Phenethylamines I Have Known and Loved), the dose is listed as 25 to 50 mg, and the duration is listed as 8 to 12 hours.[1] Shulgin reports that MMDA-2 produces effects such as enhanced awareness, empathy, and visual facilitation and distortion, as well as some side effects like gastrointestinal upset and appetite loss.[1] He states that 30 mg is very similar to 80 mg of MDA, and also remarks that it would be impossible for anyone to have a bad experience on the drug at that dose.[1]

It has been found that MMDA-2, unlike MMDA but similarly to 6-methyl-MDA, is very weak or negligible at inducing the release of serotonin or dopamine,[2] and accordingly, does not produce amphetamine-like responses in animals in drug discrimination studies.[3] Instead, MMDA-2 is likely to act as a pure serotonin 5-HT2 receptor agonist similarly to the DOx series of compounds, with activation of the serotonin 5-HT2A receptor conferring its psychedelic effects.[4]

MMDA-2 has been sold as a designer drug in Japan.[5] It may be a controlled substance in Canada under phenethylamine blanket-ban language.[6] The drug is not an explicitly controlled substance in the United States, but may be considered scheduled as an isomer of MMDA.[7][8]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 "MMDA-2 (2-Methoxy-4,5-methylenedioxyamphetamine)". Pihkal: A Chemical Love Story. Transform Press. 13 May 2016. ISBN 978-0-9630096-0-9. http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=133. 
  2. ↑ "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacology, Biochemistry, and Behavior 38 (3): 505–512. March 1991. doi:10.1016/0091-3057(91)90005-M. PMID 1829838. 
  3. ↑ "Methcathinone: a new and potent amphetamine-like agent". Pharmacology, Biochemistry, and Behavior 26 (3): 547–551. March 1987. doi:10.1016/0091-3057(87)90164-X. PMID 3575369. 
  4. ↑ "QSAR of benzene derivatives: comparison of classical descriptors, quantum theoretic parameters and flip regression, exemplified by phenylalkylamine hallucinogens". Journal of Computer-Aided Molecular Design 16 (8–9): 611–633. 2002. doi:10.1023/A:1021966231380. PMID 12602954. Bibcode: 2002JCAMD..16..611C. 
  5. ↑ "Simultaneous determination of 11 designated hallucinogenic phenethylamines by ultra-fast liquid chromatography with fluorescence detection". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 873 (2): 187–194. October 2008. doi:10.1016/j.jchromb.2008.08.020. PMID 18789774. 
  6. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  7. ↑ 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 
  8. ↑ 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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