4-Methylcathinone

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4-Methylcathinone
File:4-Methylcathinone.png
File:4-MethylCathinone.png
Clinical data
Other names4-MC; Normephedrone; NSC-60487
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
  • 2-amino-1-(4-methylphenyl)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC10H13NO
Molar mass163.220 g·mol−1
3D model (JSmol)
  • CC1=CC=C(C=C1)C(=O)C(C)N
  • InChI=1S/C10H13NO/c1-7-3-5-9(6-4-7)10(12)8(2)11/h3-6,8H,11H2,1-2H3
  • Key:OHULHWHSUJEYIT-UHFFFAOYSA-N

4-Methylcathinone (4-MC), also known as normephedrone is a stimulant drug of the cathinone group. It is an active metabolite of the better known drug mephedrone (4-methylmethcathinone or 4-MMC).[1][2][3][4]

4-MC is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) similarly to mephedrone.[5][6][7] It displays a 2.4-fold selectivity to promote monoamine release via DAT over SERT as opposed to 309-fold selectivity for cathinone.[6] It also releases norepinephrine.[6]

Monoamine release of 4-methylcathinone and related agents (EC50Tooltip Half maximal effective concentration, nM)
Compound NETooltip Norepinephrine DATooltip Dopamine 5-HTTooltip Serotonin Ref
Dextroamphetamine 6.6–7.2 5.8–24.8 698–1,765 [8][9]
Dextromethamphetamine 12.3–13.8 8.5–24.5 736–1,292 [8][10]
4-Methylamphetamine 22.2 44.1 53.4 [11][12][13]
4-Methylmethamphetamine 66.9 41.3 67.4 [14][15]
MDMA 54.1–110 51.2–278 49.6–72 [8][10][16][17][13][18]
Cathinone 23.6–25.6 34.8–83.1 6,100–7,595 [13][19][20]
Methcathinone 22–26.1 12.5–49.9 2,592–5,853 [13][19][21][22][20]
Normephedrone 100 220 210 [5][6][7]
  R(+)-Normephedrone 89 150 179 [7][6]
  S(–)-Normephedrone 115 391 1,592 [7][6]
Mephedrone 58–62.7 49.1–51 118.3–122 [10][9][19][22][23]
  S(–)-Mephedrone ND 74 61 [7][24]
  R(+)-Mephedrone ND 31 1,470 [7][24]
Methylone 140–270 117–220 234–708 [10][9][15][25][26]
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: [27][28]

See also

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References

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