MMDA-2

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MMDA-2
MMDA-2-structure.png
Systematic (IUPAC) name
1-(6-methoxy-1,3-benzodioxol-5-yl)propan-2-amine
Clinical data
Legal status Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Routes Oral, Insufflated, Rectal
Identifiers
CAS number 23693-18-7
ATC code None
PubChem CID 90966
ChemSpider 82147
Chemical data
Formula C11H15NO3 
Mol. mass 209.24 g/mol

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-appropriate responding 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]

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References[edit]

  1. ^ a b c d e f Ann Shulgin; Alexander Shulgin (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5. 
  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. 
  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. 
  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): 611–33. doi:10.1023/A:1021966231380. PMID 12602954. 
  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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