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| Other names | HMMA; 4-Hydroxy-3-methoxy-N-methylamphetamine; 3-Methoxy-4-hydroxymethamphetamine; 3-Methoxy-4-hydroxy-N-methylamphetamine |
| Drug class | Serotonin–norepinephrine–dopamine releasing agent |
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| Chemical and physical data | |
| Formula | C11H17NO2 |
| Molar mass | 195.262 g·mol−1 |
| 3D model (JSmol) | |
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4-Hydroxy-3-methoxymethamphetamine (HMMA) is anactive metabolite of3,4-methylenedioxymethamphetamine (MDMA).[1][2][3] It is a slightly more potentstimulant than MDMA in rodents.[4] The drug is substantially less potent than MDMA as amonoamine releasing agentin vitro.[5][6] Nonetheless, HMMA has been found to induce the release ofserotonin,norepinephrine, anddopamine withEC50Tooltip half-maximal effective concentration values of 589 nM, 625 nM, and 607–2884 nM, respectively, and hence acts as a lower-potencyserotonin–norepinephrine–dopamine releasing agent (SNDRA).[5][6] The predictedlog P of HMMA is 1.2.[7]
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