4-Methylephedrine

Pharmaceutical compound From Wikipedia, the free encyclopedia

4-Methylephedrine (4-ME) — an organic compound, a substituted amphetamine and a derivative of methamphetamine, it is a metabolite of mephedrone. It belongs to the group of central nervous system stimulants and monoamine-releasing agents, although it did not increase extracellular dopamine levels.[1][2][3][4][5][6][4][7][1]

Other namesDihydromephedrone
ATC code
  • none
Quick facts Clinical data, Pronunciation ...
4-Methylephedrine
Clinical data
Pronunciation/ˌfɔːr mɛθəlɪˈfɛdrɪn/
Other namesDihydromephedrone
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
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
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Pharmacology

Pharmacodynamics

In vitro, 4-methylephedrine acts as a weak monoamine releaser, with potency significantly lower than that of the parent drug mephedrone. This agent is a weak releaser of norepinephrine, dopamine, and serotonin (SNDRA), with IC50Tooltip half-maximal inhibitory concentration values ​​of 64.98 nM, 23.97 nM, and 23.53 nM for the serotonin, norepinephrine, and dopamine transporters, respectively.[7][8]

More information Compound, NETooltip Norepinephrine ...
Monoamine release of 4-methylephedrine and related compounds (IC50Tooltip Half maximal inhibitory concentration, nM)
CompoundNETooltip NorepinephrineDATooltip DopamineSERTTooltip Serotonin transporterRef
Dihydromephedrone23.97 (8.65–66.46)23.53 (19.8–27.97)64.98 (50.66–83.37)[8][1]
Mephedrone0.77 (0.53–1.08)2.77 (1.92–3.97)7.83 (6.32–9.75)[8]
Normephedrone6.35 (4.66–8.64)5.46 (3.58–8.31)10.61 (9.06–12.43)[8][1]
4-hydroxymephedrone2.92 (2.35–3.6)4.85 (3.28–7.17)73.53 (62.5–86.51)[8][1]
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter.
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References

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