4-Methylephedrine

4-Methylephedrine
Clinical data
Pronunciation/ˌfɔːr mɛθəlɪˈfɛdrɪn/
Other names4-ME; Dihydromephedrone; DHMMC; β-Hydroxy-4-methylmethamphetamine; 4-Methyl-β-hydroxymethamphetamine
Drug classStimulant; Monoamine releasing agent
ATC code
  • None
Legal status
Legal status
  • Generally not controlled
Identifiers
  • 2-(methylamino)-1-(4-methylphenyl)propan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17NO
Molar mass179.263 g·mol−1
3D model (JSmol)
Density0.987 to 1.00 g/cm3
Melting point56.1 to 89.0 °C (133.0 to 192.2 °F)
Boiling point269 to 281 °C (516 to 538 °F)
Solubility in water1.61e-2 to 0.110 (water) mg/mL (20 °C)
  • CC1=CC=C(C=C1)C(C(C)NC)O
  • InChI=1S/C11H17NO/c1-8-4-6-10(7-5-8)11(13)9(2)12-3/h4-7,9,11-13H,1-3H3
  • Key:DUESQFQLBNOCIT-UHFFFAOYSA-N

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 IC50Tooltip half-maximal inhibitory concentration 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]

Monoamine reuptake inhibition of 4-methylephedrine and related compounds (IC50Tooltip Half maximal inhibitory concentration, μM)
Compound NETooltip Norepinephrine DATooltip Dopamine SERTTooltip Serotonin transporter 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

References

  1. ^ a b c d e Mayer FP, Cintulova D, Pittrich DA, Wimmer L, Luethi D, Holy M, et al. (April 2019). "Stereochemistry of phase-1 metabolites of mephedrone determines their effectiveness as releasers at the serotonin transporter". Neuropharmacology. 148: 199–209. doi:10.1016/j.neuropharm.2018.12.032. PMID 30610839.
  2. ^ Linhart I, Himl M, Židková M, Balíková M, Lhotková E, Páleníček T (January 2016). "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. doi:10.1016/j.toxlet.2015.10.025. PMID 26541208.
  3. ^ Keles G, Yerli YI, Atay I, Kurbanoglu S (2024). "The Electroanalytical Sensing of Mephedrone Metabolites". Forensic Electrochemistry: The Voltammetry for Sensing and Analysis. ACS Symposium Series. Vol. 1481. pp. 121–149. doi:10.1021/bk-2024-1481.ch006. ISBN 978-0-8412-9675-6. Retrieved 2026-03-21.
  4. ^ Michal O, Daria T, Izabela J, Gorecka W, Tadeusz N, Elzbieta M, et al. (August 2025). "Mephedrone and Its Metabolites: A Narrative Review". International Journal of Molecular Sciences. 26 (15): 7656. doi:10.3390/ijms26157656. PMC 12347919. PMID 40806784.
  5. ^ Czerwinska J, Parkin MC, George C, Kicman AT, Dargan PI, Abbate V (April 2022). "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. doi:10.1002/dta.3214. PMC 9306721. PMID 34984836.
  6. ^ Kinyua J, Psoma AK, Rousis NI, Nika MC, Covaci A, van Nuijs AL, et al. (January 2021). "Investigation of Biotransformation Products of p-Methoxymethylamphetamine and Dihydromephedrone in Wastewater by High-Resolution Mass Spectrometry". Metabolites. 11 (2): 66. doi:10.3390/metabo11020066. PMC 7912097. PMID 33503865.
  7. ^ Mayer FP, Wimmer L, Dillon-Carter O, Partilla JS, Burchardt NV, Mihovilovic MD, et al. (September 2016). "Phase I metabolites of mephedrone display biological activity as substrates at monoamine transporters". British Journal of Pharmacology. 173 (17): 2657–2668. doi:10.1111/bph.13547. PMC 4978154. PMID 27391165.
  8. ^ a b c d e f g h "Pharmacological characterization of the metabolites of methylone and mephedrone". Journal of Psychoactive Drugs. 48 (4): 237–246. 2016. doi:10.1080/02791072.2016.1200486 (inactive 22 March 2026). PMC 4978154. PMID 27337194.{{cite journal}}: CS1 maint: DOI inactive as of March 2026 (link)
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