para-Chloroamphetamine

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Not to be confused with para-Chloromethamphetamine.
para-Chloroamphetamine
Parachloroamphetamine.png
4-CA44.jpg
Systematic (IUPAC) name
1-(4-Chlorophenyl)propan-2-amine
Identifiers
CAS Number 64-12-0 N
PubChem CID: 3127
IUPHAR/BPS 4592
ChemSpider 3015 YesY
ChEMBL CHEMBL358967 YesY
Chemical data
Formula C9H12ClN
Molecular mass 169.651 g/mol
  • Clc1ccc(cc1)CC(N)C
  • InChI=1S/C9H12ClN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3 YesY
  • Key:WWPITPSIWMXDPE-UHFFFAOYSA-N YesY
 NYesY (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.[1] 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.[2][3][4][5]

However, the effects of the compound on experimental animals appear less encouraging.[6] It has been detected as an apparent designer drug,[7] along with the related 3-chloroamphetamine, which is even more potent as a releaser of dopamine and serotonin but slightly less neurotoxic.[8][9][10][11][12]

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.[13]

See also

References

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