para-Chloroamphetamine

Not to be confused with para-Chloromethamphetamine.

para-Chloroamphetamine

Systematic (IUPAC) name
1-(4-Chlorophenyl)propan-2-amine
Identifiers
CAS Number	64-12-0 N
PubChem	CID: 3127
IUPHAR/BPS	4592
ChemSpider	3015 Y
ChEMBL	CHEMBL358967 Y
Chemical data
Formula	C9H12ClN
Molecular mass	169.651 g/mol
SMILES Clc1ccc(cc1)CC(N)C
InChI InChI=1S/C9H12ClN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3 Y Key:WWPITPSIWMXDPE-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

para-Chloroamphetamine (PCA), also known as 4-chloroamphetamine (4-CA), is an amphetamine derivative and monoamine releaser similar to MDMA, but with substantially higher neurotoxicity, thought to be due to the unrestrained release of both serotonin and dopamine by a metabolite. It is used as a neurotoxin by neurobiologists to selectively kill serotonergic neurons for research purposes, in the same way that 6-hydroxydopamine is used to kill dopaminergic neurons.

However, the effects of the compound on experimental animals appear less encouraging. It has been detected as an apparent designer drug, along with the related 3-chloroamphetamine, which is even more potent as a releaser of dopamine and serotonin but slightly less neurotoxic.

The closely related N-methylated derivative, para-Chloromethamphetamine (CMA), which is metabolised to para-chloroamphetamine in vivo, has neurotoxic properties as well.

Legal Status

China

As of October 2015 4-CA is a controlled substance in China.

See also

• para-Chloromethamphetamine
• Substituted amphetamines
• 3,4-Dichloroamphetamine (DCA)
• 4-Fluoroamphetamine (4-FA)
• 4-Methylamphetamine (4-MA)
• 5,7-Dihydroxytryptamine (5,7-DHT)
• para-Bromoamphetamine (PBA)
• para-Chlorophenylalanine (PCPA)
• para-Iodoamphetamine (PIA)
• 6-CAT