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. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) and produces entactogen effects in humans. It has been sold as a designer drug and research chemical online since 2010.
|Chemical and physical data|
|Molar mass||177.242 g/mol g·mol−1|
|3D model (JSmol)|
MMAI has been shown to relieve stress-induced depression in rats more robustly than sertraline, 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).
- 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.
- 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.
- Rudnick G, Wall SC (1993). "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Mol. Pharmacol. 43 (2): 271–276. PMID 8429828.
- 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.
- 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.