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][2] It is the 6-methoxy derivative of MDA and is a positional isomer of MMDA (5-methoxy-MDA).[1][2]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MMDA-2's dose as 25 to 50 mg orally and its duration as 8 to 12 hours.[1][2] The effects of MMDA-2 have been reported to include enhanced awareness, empathy, and visual facilitation and distortion, as well as some side effects like gastrointestinal upset and appetite loss.[1] Shlgin states that MMDA-2 at a dose of 30 mg orally is very similar to MDA at a dose of 80 mg orally, and also remarks that it would be impossible for anyone to have a bad experience on the drug at that dose.[1] MMDA-2 is approximately 4- or 5-fold more potent than MMDA, which has a listed dose range of 100 to 250 mg orally.[1]

Interactions

Pharmacology

Pharmacodynamics

MMDA-2 is a moderately potent serotonin receptor agonist in the rat stomach fundus assay (A2 = 224 nM).[3] These serotonin receptors may correspond specifically to the serotonin 5-HT2B receptor.[4][5]

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 in vitro.[6] Accordingly, it does not produce amphetamine-like responses in animals in drug discrimination studies.[7] 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 believed to be responsible for its psychedelic effects.[8]

Chemistry

Synthesis

The chemical synthesis of MMDA-2 has been described.[1]

Analogues

Analogues of MMDA-2 include 2C-MMDA-2 (MMDPEA-2; 6-methoxy-MDPEA), MDA, MMDA (5-methoxy-MDA), MMDA-3a (2-methoxy-MDA), DMMDA-2 (5,6-dimethoxy-MDA; 5-methoxy-MMDA-2), methyl-MMDA-2 (N-methyl-MMDA-2; 6-methoxy-MDMA), EMDA-2 (6-ethoxy-MDA; 6-ethoxy-MMDA-2), 2C2-NBOMe (2C-MMDA-2-NBOMe; NBOMe-MMDPEA-2), F (5-methoxy-6-APDB), 4T-MMDA-2 (4-thio-MMDA-2), 6-methyl-MDA, 6-bromo-MDA (2-Br-4,5-MDA), and 6-chloro-MDA (2-Cl-4,5-MDA), among others.[1][2]

History

MMDA-2 was first described in the scientific literature by Alexander Shulgin in 1964.[9] Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[1] MMDA-2 was encountered as a novel designer drug by the 1990s.[10][11]

Society and culture

Canada

MMDA-2 may be a controlled substance in Canada under phenethylamine blanket-ban language.[12]

United States

MMDA-2 is not an explicitly controlled substance in the United States, but may be considered scheduled as an isomer of MMDA.[13][14]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 "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. ↑ 2.0 2.1 2.2 2.3 Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013) (in de). Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  3. ↑ "Serotonin receptor affinities of psychoactive phenalkylamine analogues". J Med Chem 23 (3): 294–299. March 1980. doi:10.1021/jm00177a017. PMID 7365744. 
  4. ↑ "Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle". British Journal of Pharmacology 112 (1): 323–331. May 1994. doi:10.1111/j.1476-5381.1994.tb13072.x. PMID 8032658. 
  5. ↑ "Unreliability of the rat stomach fundus as a predictor of hallucinogenic activity in substituted phenethylamines". Life Sciences 35 (13): 1343–1348. September 1984. doi:10.1016/0024-3205(84)90390-4. PMID 6482656. 
  6. ↑ "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. 
  7. ↑ "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. 
  8. ↑ "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. 
  9. ↑ "Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines". Experientia 20 (7): 366–367. July 1964. doi:10.1007/BF02147960. PMID 5855670. https://bibliography.maps.org/resources/download/8691. 
  10. ↑ "Designer drugs related to amphetamine (1990-1996).". J Clan Lab Invest Chem Assoc 6 (3): 15–16. 1996. https://isomerdesign.com/bitnest/external/JCLIC/6.3.15-16. 
  11. ↑ "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. 
  12. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  13. ↑ 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 
  14. ↑ 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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