MMDA-2

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]

MMDA-2
Clinical data
Routes of
administration		Oral, Insufflated, Rectal
ATC code
  • none
Legal status
Legal status
  • CA: Schedule I
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Identifiers
IUPAC name
  • 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)
SMILES
  • O1c2cc(c(OC)cc2OC1)CC(N)C

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]

References
  1. Ann Shulgin; Alexander Shulgin (1991). 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): 505–12. 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): 547–51. 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" (PDF). Journal of Computer-aided Molecular Design. 16 (8–9): 611–33. 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. 873 (2): 187–94. doi:10.1016/j.jchromb.2008.08.020. PMID 18789774.
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