Chemistry:4-Methylephedrine
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]
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. | ||||
See also
- Substituted β-hydroxyamphetamine
References
- ↑ 1.0 1.1 1.2 1.3 1.4 "Stereochemistry of phase-1 metabolites of mephedrone determines their effectiveness as releasers at the serotonin transporter". Neuropharmacology 148: 199–209. April 2019. doi:10.1016/j.neuropharm.2018.12.032. PMID 30610839.
- ↑ "Metabolic profile of mephedrone: Identification of nor-mephedrone conjugates with dicarboxylic acids as a new type of xenobiotic phase II metabolites". Toxicology Letters 240 (1): 114–121. January 2016. doi:10.1016/j.toxlet.2015.10.025. PMID 26541208.
- ↑ "The Electroanalytical Sensing of Mephedrone Metabolites". Forensic Electrochemistry: The Voltammetry for Sensing and Analysis. ACS Symposium Series. 1481. 2024. pp. 121–149. doi:10.1021/bk-2024-1481.ch006. ISBN 978-0-8412-9675-6. https://pubs.acs.org/action/cookieAbsent. Retrieved 2026-03-21.
- ↑ "Mephedrone and Its Metabolites: A Narrative Review". International Journal of Molecular Sciences 26 (15): 7656. August 2025. doi:10.3390/ijms26157656. PMID 40806784.
- ↑ "Excretion of mephedrone and its phase I metabolites in urine after a controlled intranasal administration to healthy human volunteers". Drug Testing and Analysis 14 (4): 741–746. April 2022. doi:10.1002/dta.3214. PMID 34984836.
- ↑ "Investigation of Biotransformation Products of p-Methoxymethylamphetamine and Dihydromephedrone in Wastewater by High-Resolution Mass Spectrometry". Metabolites 11 (2): 66. January 2021. doi:10.3390/metabo11020066. PMID 33503865.
- ↑ "Phase I metabolites of mephedrone display biological activity as substrates at monoamine transporters". British Journal of Pharmacology 173 (17): 2657–2668. September 2016. doi:10.1111/bph.13547. PMID 27391165.
- ↑ 8.0 8.1 8.2 8.3 8.4 8.5 8.6 8.7 "Pharmacological characterization of the metabolites of methylone and mephedrone". Journal of Psychoactive Drugs 48 (4): 237–246. 2016. doi:10.1080/02791072.2016.1200486. PMID 27337194.
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