MMAI

Last updated
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
  • 5-Methoxy-6-methyl-2,3-dihydro-1H-inden-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H15NO
Molar mass 177.247 g·mol−1
3D model (JSmol)
  • Cc1cc2CC(N)Cc2cc1OC
  • InChI=1S/C11H15NO/c1-7-3-8-4-10(12)5-9(8)6-11(7)13-2/h3,6,10H,4-5,12H2,1-2H3
  • Key:JLESVLCTIOAHPT-UHFFFAOYSA-N

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]

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References

  1. 1 2 Marona-Lewicka D, Nichols DE (1994). "Behavioral effects of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan". Eur J Pharmacol. 258 (1–2): 1–13. CiteSeerX   10.1.1.688.1895 . doi:10.1016/0014-2999(94)90051-5. PMID   7925587.
  2. Li Q, Murakami I, Stall S, Levy AD, Brownfield MS, Nichols DE, Van de Kar LD (1996). "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)". J Pharmacol Exp Ther. 279 (3): 1261–1267. PMID   8968349.
  3. Rudnick G, Wall SC (1993). "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Mol. Pharmacol. 43 (2): 271–276. PMID   8429828.
  4. Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME (2018). "Pharmacological profile of mephedrone analogs and related new psychoactive substances" (PDF). Neuropharmacology. 15 (134): 4–12. doi:10.1016/j.neuropharm.2017.07.026. PMID   28755886. S2CID   28786127.
  5. Marona-Lewicka D, Nichols DE (1997). "The Effect of Selective Serotonin Releasing Agents in the Chronic Mild Stress Model of Depression in Rats". Stress. 2 (2): 91–100. doi:10.3109/10253899709014740. PMID   9787258.
  6. Neuropharmacology; Silveira, R; Nichols, DE; Reyes-Parada, M (1999). "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. doi:10.1016/S0028-3908(99)00023-4. PMID   10428424. S2CID   13714807.