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Methoxymethylaminoindane: Wikis

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5-Methoxy-6-methyl-2-aminoindane
Systematic (IUPAC) name
5-methoxy-6-methyl-2,3-dihydro-1H-inden-2-amine
Identifiers
CAS number 132980-16-6
ATC code  ?
PubChem 131575
Chemical data
Formula C 11H15NO 
Mol. mass 177.242 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status legal
Routes  ?

5-Methoxy-6-methyl-2-aminoindane (MMAI), is a drug and research chemical developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic highly selective serotonin releasing agent (SSRA) in animals and a putative empathogen in humans.[1][2][3] It has been shown to relieve stress-induced depression in rats more robustly than sertraline.[4] It has been suggested that SSRAs like MMAI and 4-MTA could be developed as novel antidepressants with a faster onset of action and superior efficacy to current antidepressants such as the selective serotonin reuptake inhibitors (SSRIs).[5] MMAI is closely related to MDAI, MDMAI, and MDAT.

References

  1. ^ 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. 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. ^ 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. PMID 9787258.  
  5. ^ Neuropharmacology. (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. PMID 10428424.  
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