4-Chloromethcathinone

4-Chloromethcathinone (also known as 4-CMC and clephedrone) is a stimulant drug of the cathinone class that has been sold online as a designer drug.^[1][2]

4-Chloromethcathinone

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics) DE: Anlage I (Authorized scientific use only) UK: Class B UN: Psychotropic Schedule II Illegal in China and Sweden
Identifiers
IUPAC name 1-(4-chlorophenyl)-2-(methylamino)-1-propanone
CAS Number	1225843-86-6
PubChem CID	82100418
ChemSpider	25630416
UNII	PTAYYYZMMT
KEGG	C22721
CompTox Dashboard (EPA)	DTXSID201014163
ECHA InfoCard	100.257.446
Chemical and physical data
Formula	C10H12ClNO
Molar mass	197.66 g·mol−1
3D model (JSmol)	Interactive image
Melting point	198 °C (388 °F)
SMILES ClC1=CC=C(C(C(C)NC)=O)C=C1
InChI InChI=1S/C10H12ClNO/c1-7(12-2)10(13)8-3-5-9(11)6-4-8/h3-7,12H,1-2H3 Key:UEJBEYOXRNGPEI-UHFFFAOYSA-N

4-CMC produces similar effects to mephedrone, and has been sold as an alternative in countries where mephedrone was scheduled.

Adverse effects

Short-term

4-CMC produces similar side effects to mephedrone, including: increased blood pressure, tachycardia, hyperthermia, and anxiety.^[3]

Neurotoxicity

Its chemical structure closely resembles para-chloromethamphetamine, raising concerns about its potential to readily induce cell death of serotoninergic neurons. However, no neurotoxicity of this kind has been found to occur, but studies involving mice do indicate that it is neurotoxic through other mechanisms, similarly to other cathinones. 4-CMC is cytotoxic and induces oxidative stress, more so than 4-MMC.^[4]

Pharmacology

Pharmacodynamics

Similar to mephedrone, 4-CMC mainly acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), and partially as a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI) with similar potency.^[3]

Effects of 4-CMC and mephedrone on neurotransmitter release^[3]

Drug	Release at DAT EC50 (nM)	Release at NET EC50 (nM)	Release at SERT EC50 (nM)
Mephedrone (4-MMC)	103 ± 16	83 ± 20	188 ± 22
4-CMC	91 ± 11	99 ± 18	169 ± 20

Effects of 4-CMC and mephedrone on inhibition of neurotransmitter uptake^[3]

Drug	Uptake Inhibition at DAT IC50 (nM)	Uptake Inhibition at NET IC50 (nM)	Uptake Inhibition at SERT IC50 (nM)
Mephedrone (4-MMC)	769 ± 106	319 ± 40	600 ± 99
4-CMC	1014 ± 78	559 ± 57	542 ± 38

Legality

4-CMC is an Anlage I controlled drug in Germany.

Sweden's public health agency suggested classifying 4-Chloromethcathinone (klefedron) as illegal narcotic on June 1, 2015.^[5]

As of October 2015, 4-CMC is a controlled substance in China.^[6]

4-CMC is considered a Schedule 1 substance in Virginia.^[7]

In December 2019, the UNODC announced scheduling recommendations placing 4-CMC into Schedule II.^[8]

See also

• 3-Chloromethcathinone
• 3-Methylmethcathinone
• 4-Bromomethcathinone
• 4-Chloroamphetamine
• 4-Cl-3-MMC
• 4Cl-PVP
• 4-Ethylmethcathinone
• 4-Methylmethcathinone
• Substituted cathinone