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| Other names | MMAI; MMAi; 5-Methoxy-6-methyl-2-aminoindan |
| Drug class | Selective serotonin releasing agent;Entactogen |
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| Formula | C11H15NO |
| Molar mass | 177.247 g·mol−1 |
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5-Methoxy-6-methyl-2-aminoindane (MMAI) is adrug of the2-aminoindane family developed in the 1990s by a team led byDavid E. Nichols atPurdue University.[1] It acts as a lessneurotoxic and highlyselectiveserotonin releasing agent (SSRA) and producesentactogenic effects in humans.[1][2][3][4] The drug has been sold as adesigner drug andresearch chemical online since 2010.
The drug is one of the only knownmonoamine releasing agents (MRAs) with greater than 100-foldselectivity for theserotonin transporter (SERT) over thedopamine transporter (DAT).[5]Receptor interaction data for MMAI have also been reported.[6][7]
MMAI has been shown to relieve stress-induceddepression in rats more robustly thansertraline,[8] and as a result it has been suggested that SSRAs like MMAI and4-methylthioamphetamine (4-MTA) could be developed as novelantidepressants with a fasteronset of therapeutic action and superioreffectiveness to current antidepressants such as theselective serotonin reuptake inhibitors (SSRIs).[9]
MMAI alone does not appear to produceserotonergic neurotoxicity with either acute or chronic administration in animals.[10][11] However, subsequent research found that a single high dose of MMAI could produce significant serotonergic neurotoxicity.[10][11] In addition, combination of MMAI with thedopamine releasing agentdextroamphetamine has been found to producedose-dependent serotonergic neurotoxicity in animals.[10] Hence, MMAI is not a fully non-neurotoxicMDMAanalogue.[10][11]
| Compound | Monoamine release (EC50Tooltip half-maximal effective concentration, nM) | Ref | ||
|---|---|---|---|---|
| Serotonin | Norepinephrine | Dopamine | ||
| 2-AI | >10,000 | 86 | 439 | [6] |
| MDAI | 114 | 117 | 1,334 | [6] |
| MMAI | 31 | 3,101 | >10,000 | [6] |
| MEAI | 134 | 861 | 2,646 | [6] |
| d-Amphetamine | 698–1,765 | 6.6–7.2 | 5.8–24.8 | [12][13][14][15][16] |
| MDA | 160–162 | 47–108 | 106–190 | [17][14][18] |
| MDMA | 50–85 | 54–110 | 51–278 | [12][19][20][17][18] |
| 3-MA | ND | 58.0 | 103 | [14] |
| Notes: The smaller the value, the more strongly the compound produces the effect. Theassays were done in rat brainsynaptosomes and humanpotencies may be different. See alsoMonoamine releasing agent § Activity profiles for a larger table with more compounds.Refs:[6] | ||||
MMAI is the2-aminoindaneanalogue of3-methoxy-4-methylamphetamine (MMA).[21][3]
RESULTS. Methamphetamine and amphetamine potently released NE (IC50s = 14.3 and 7.0 nM) and DA (IC50s = 40.4 nM and 24.8 nM), and were much less potent releasers of 5-HT (IC50s = 740 nM and 1765 nM). [...]
