Chemistry:MMAI

From HandWiki
Short description: Chemical compound
MMAI
5-methoxy-6-methyl-2-aminoindane.svg
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC11H15NO
Molar mass177.247 g·mol−1
3D model (JSmol)

5-Methoxy-6-methyl-2-aminoindane (MMAI) is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University.[1] It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) and produces entactogen effects in humans.[1][2][3][4] It has been sold as a designer drug and research chemical online since 2010.

MMAI has been shown to relieve stress-induced depression in rats more robustly than sertraline,[5] and as a result it has been suggested that SSRAs like MMAI and 4-MTA could be developed as novel antidepressants with a faster onset of therapeutic action and superior efficacy to current antidepressants such as the selective serotonin reuptake inhibitors (SSRIs).[6]

References

  1. 1.0 1.1 "Behavioral effects of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan". European Journal of Pharmacology 258 (1–2): 1–13. June 1994. doi:10.1016/0014-2999(94)90051-5. PMID 7925587. 
  2. "Neuroendocrine pharmacology of three serotonin releasers: 1-(1,3-benzodioxol-5-yl)-2-(methylamino)butane (MBDB), 5-methoxy-6-methyl-2-aminoindan (MMAi) and p-methylthioamphetamine (MTA)". The Journal of Pharmacology and Experimental Therapeutics 279 (3): 1261–1267. December 1996. PMID 8968349. 
  3. "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Molecular Pharmacology 43 (2): 271–276. February 1993. PMID 8429828. 
  4. "Pharmacological profile of mephedrone analogs and related new psychoactive substances". Neuropharmacology 134 (Pt A): 4–12. May 2018. doi:10.1016/j.neuropharm.2017.07.026. PMID 28755886. https://edoc.unibas.ch/57357/1/20170920120908_59c23e44b5f0e.pdf. 
  5. "The Effect of Selective Serotonin Releasing Agents in the Chronic Mild Stress Model of Depression in Rats". Stress 2 (2): 91–100. December 1997. doi:10.3109/10253899709014740. PMID 9787258. 
  6. "Effects of 5-HT-releasing agents on the extracellullar hippocampal 5-HT of rats. Implications for the development of novel antidepressants with a short onset of action". Neuropharmacology 38 (7): 1055–1061. July 1999. doi:10.1016/S0028-3908(99)00023-4. PMID 10428424.