Para-chloromethamphetamine

Para-Chloromethamphetamine

Legal status
Legal status	UK: Class B
Identifiers
IUPAC name 1-(4-Chlorophenyl)-N-methylpropan-2-amine
CAS Number	30572-91-9 Y
PubChem CID	3128
ChemSpider	3016
ECHA InfoCard	100.164.347
Chemical and physical data
Formula	C10H14ClN
Molar mass	183.68 g·mol−1
3D model (Jmol)	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

para-Chloromethamphetamine (also known as 4-Chloromethamphetamine and 4-CMA) is a stimulant that is the N-methyl derivative and prodrug of the neurotoxic drug para-Chloroamphetamine. It has been found to decrease serotonin in rats. Further investigation into the long-term effects of chloroamphetamines discovered that administration of 4-CMA caused a prolonged reduction in the levels of 5-HT and the activity of tryptophan hydroxylase in the brain one month after injection of a single dose of the drug.

Another study on rats found that 4-Chloromethamphetamine was more potent at inducing conditioned taste aversion than methamphetamine.

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.