MMAI
Chemical compound
From Wikipedia, the free encyclopedia
5-Methoxy-6-methyl-2-aminoindane (MMAI) is a drug of the 2-aminoindane family developed in the 1990s by a team led by David E. Nichols at Purdue University.[1] It acts as a less neurotoxic and highly selective serotonin releasing agent (SSRA) and produces entactogenic effects in humans.[1][2][3][4] The drug has been sold as a designer drug and research chemical online since 2010.
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- In general: uncontrolled
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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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Interactions
Pharmacology
Pharmacodynamics
MMAI is one of the only known monoamine releasing agents (MRAs) with greater than 100-fold selectivity for the serotonin transporter (SERT) over the dopamine transporter (DAT).[5] Receptor interaction data for MMAI have also been reported.[6][4]
The drug has been found to dose-dependently and robustly increase oxytocin levels in rodents similarly to MDMA.[7][2] It also increases prolactin and adrenocorticotropic hormone (ACTH) secretion in rodents.[7][2] The ACTH secretion induced by MMAI could only be partially blocked by the serotonin reuptake inhibitor fluoxetine, suggesting that MMAI also has some other unknown mechanism to increase ACTH levels.[7][2] This is unlikely to be dopamine or norepinephrine release as MMAI shows very low potency in such regards.[2] In addition, fluoxetine did not block the renin response to MMAI, suggesting an additional mechanism for this effect as well.[7][2]
MMAI has been shown to relieve stress-induced depression in rats more robustly than sertraline,[8] and as a result it has been suggested that SSRAs like MMAI and 4-methylthioamphetamine (4-MTA) could be developed as novel antidepressants with a faster onset of therapeutic action and superior effectiveness to current antidepressants such as the selective serotonin reuptake inhibitors (SSRIs).[9]
MMAI alone does not appear to produce serotonergic 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 the dopamine releasing agent dextroamphetamine has been found to produce dose-dependent serotonergic neurotoxicity in animals.[10] Hence, MMAI is not a fully non-neurotoxic MDMA analogue.[10][11]
| Compound | Monoamine release (EC50, nM) | Ref | ||
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| 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. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: [6] | ||||
Chemistry
MMAI is the 2-aminoindane analogue of 3-methoxy-4-methylamphetamine (MMA).[21][3]