4-Methylcathinone

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-Methylcathinone

Clinical data
Other names	4-MC; Normephedrone; NSC-60487
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name 2-amino-1-(4-methylphenyl)propan-1-one
CAS Number	31952-47-3 HCl: 6941-17-9
PubChem CID	414532
ChemSpider	367058
UNII	CY9HK59OK6
CompTox Dashboard (EPA)	DTXSID801032529
Chemical and physical data
Formula	C10H13NO
Molar mass	163.220 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC=C(C=C1)C(=O)C(C)N
InChI 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-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

• 4-Methylbuphedrone
• 4-Methylethcathinone