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MMDA-2
Clinical data
Routes of
administration
Oral, Insufflated, Rectal
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(6-Methoxy-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard ( EPA)
Chemical and physical data
FormulaC11H15NO3
Molar mass209.245 g·mol−1
3D model ( JSmol)
  • O1c2cc(c(OC)cc2OC1)CC(N)C

MMDA-2 (2-methoxy-4,5-methylenedioxyamphetamine) is a psychedelic drug of the amphetamine class. [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, the dose is listed as 25–50 mg, and the duration is listed as 8–12 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]

Scientific research has shown that MMDA-2, unlike MMDA, but similarly to 6-methyl-MDA, is only very weak 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 5-HT2 receptor agonist similarly to the DOx series of compounds, with activation of the 5-HT2A receptor conferring its psychedelic effects. [4]

MMDA-2 has been sold as a designer drug in Japan. [5]

See also

References

  1. ^ a b c d e f Shulgin A, Shulgin A (13 May 2016). "MMDA-2 (2-Methoxy-4,5-methylenedioxyamphetamine)". Pihkal: A Chemical Love Story. Transform Press. ISBN  978-0-9630096-0-9.
  2. ^ McKenna DJ, Guan XM, Shulgin AT (March 1991). "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. doi: 10.1016/0091-3057(91)90005-M. PMID  1829838. S2CID  2740262.
  3. ^ Glennon RA, Yousif M, Naiman N, Kalix P (March 1987). "Methcathinone: a new and potent amphetamine-like agent". Pharmacology, Biochemistry, and Behavior. 26 (3): 547–551. doi: 10.1016/0091-3057(87)90164-X. PMID  3575369. S2CID  5890314.
  4. ^ Clare BW (2002). "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. Bibcode: 2002JCAMD..16..611C. doi: 10.1023/A:1021966231380. PMID  12602954. S2CID  9948738.
  5. ^ Min JZ, Shimizu Y, Toyo'oka T, Inagaki S, Kikura-Hanajiri R, Goda Y (October 2008). "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. doi: 10.1016/j.jchromb.2008.08.020. PMID  18789774.

External links