Para-Chloromethamphetamine

Not to be confused with para-Chloroamphetamine.

para-Chloromethamphetamine (also known as 4-chloromethamphetamine and 4-CMA; code name Ro 4-6861) is a stimulant that is the N-methyl derivative and prodrug of the neurotoxic drug para-chloroamphetamine (4-CA).^[1][2][3] It has been found to decrease serotonin in rats.^[4][5][6] Further investigation into the long-term effects of chloroamphetamines discovered that administration of 4-CMA caused a prolonged reduction in the levels of serotonin and the activity of tryptophan hydroxylase in the brain one month after injection of a single dose of the drug.^[7]

para-Chloromethamphetamine

Clinical data
Other names	Ro 4-6861; PCMA; CMA; 4-Chloromethamphetamine; 4-CMA
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name 1-(4-Chlorophenyl)-N-methylpropan-2-amine
CAS Number	30572-91-9 Y
PubChem CID	3128
ChemSpider	3016
UNII	IXP5G5WMYA
CompTox Dashboard (EPA)	DTXSID00897230
Chemical and physical data
Formula	C10H14ClN
Molar mass	183.68 g·mol−1
3D model (JSmol)	Interactive image
SMILES ClC1=CC=C(C=C1)CC(C)NC
InChI InChI=1S/C10H14ClN/c1-8(12-2)7-9-3-5-10(11)6-4-9/h3-6,8,12H,7H2,1-2H3 Key:XXLWNLKEOWWHDC-UHFFFAOYSA-N

Another study on rats found that 4-chloromethamphetamine was more potent at inducing conditioned taste aversion than methamphetamine.^[8]

4-Chloromethamphetamine was further investigated in the 1960s along with 4-CA and it was noted that they differed from their parent amphetamine and methamphetamine substances by exhibiting only a slight central stimulant effect in both animals and humans and that they acted like antidepressants rather than stimulants.^{[9][10][11][12]}

Tablet containing 4-chloromethamphetamine, found in 2015 in Belgium.

Studies in the 1970s found that a single dose of 10 mg/1 kg 4-CMA resulted in a decreased level of 5-hydroxytryptamine in the brain for several weeks.^[13]

4-Chloromethamphetamine was identified outside of the laboratory for the first time at the Tomorrowland festival edition 2015, where a tablet was found in possession of a drug dealer (see picture).^[14] In the following year, tablets with 4–CMA were also found in Romania, Austria and Croatia. Fortuitously, and for unknown reasons, 4-CMA disappeared briefly from the European rave scene after the Spring of 2016. However, a 2019 study of participants of a dance music festival in Belgium reported detection of 4-CMA in pills (out of 178 analyzed samples only one was mostly 4-CMA, while in one other 4-CMA was a minor ingredient).^[15]

See also

• 3-Chloromethamphetamine
• 4-Bromoamphetamine
• 4-Bromomethamphetamine
• 4-Fluoroamphetamine
• 4-Fluoromethamphetamine
• 4-Iodoamphetamine