4-Methylephedrine
Pharmaceutical compound
From Wikipedia, the free encyclopedia
4-Methylephedrine (4-ME), also known as dihydromephedrone (DHMMC) or as β-hydroxy-4-methylmethamphetamine, is a putative stimulant drug of the phenethylamine, amphetamine, and β-hydroxyamphetamine families. It is the β-hydroxy analogue of mephedrone and is a known metabolite of mephedrone. The drug acts as a monoamine reuptake inhibitor and monoamine releasing agent, albeit with relatively low potency and far less than that of mephedrone.[1][2][3][4][5][6][7]
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| Pronunciation | /ˌfɔːr mɛθəlɪˈfɛdrɪn/ |
| Other names | 4-ME; Dihydromephedrone; DHMMC; β-Hydroxy-4-methylmethamphetamine; 4-Methyl-β-hydroxymethamphetamine |
| Drug class | Stimulant; Monoamine releasing agent |
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| Formula | C11H17NO |
| Molar mass | 179.263 g·mol−1 |
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| Density | 0.987 to 1.00 g/cm3 |
| Melting point | 56.1 to 89.0 °C (133.0 to 192.2 °F) |
| Boiling point | 269 to 281 °C (516 to 538 °F) |
| Solubility in water | 1.61e-2 to 0.110 (water) mg/mL (20 °C) |
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Pharmacology
Pharmacodynamics
4-Methylephedrine acts as a monoamine reuptake inhibitor and monoamine releasing agent in vitro, with potency far lower than that of its parent drug mephedrone.[8][1]
The drug is a weak reuptake inhibitor of norepinephrine, dopamine, and serotonin, with IC50 values of 64.98 μM, 23.97 μM, and 23.53 μM for the serotonin, norepinephrine, and dopamine transporters, respectively.[8] The values for individual enantiomers of 4-methylephedrine have also been reported.[8] In addition, data for induction of monoamine release in the HEK293 system have been reported.[8]
| Compound | NE | DA | SERT | Ref |
|---|---|---|---|---|
| Dihydromephedrone | 23.97 | 23.53 | 64.98 | [8][1] |
| Mephedrone | 0.77 | 2.77 | 7.83 | [8] |
| Normephedrone | 6.35 | 5.46 | 10.61 | [8][1] |
| 4-Hydroxymephedrone | 2.92 | 4.85 | 73.53 | [8][1] |
| Notes: The smaller the value, the more avidly the drug releases the neurotransmitter. | ||||