para-Chloroamphetamine

para-chloroamphetamine
Systematic (IUPAC) name
1-(4-chlorophenyl)propan-2-amine
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 64-12-0
ATC code  ?
PubChem CID 3127
ChemSpider 3015 YesY
Chemical data
Formula C9H12ClN 
Mol. mass 169.651
SMILES eMolecules & PubChem
 YesY(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 as with MDMA itself.[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]

This compound does have a history of being used daily as an antidepressant in humans with no mentionable side effects that are particularly worrysome. However, the effects of the compound on experimental animals appear less encouraging.[6]

See also

References

  1. ^ Johnson MP, Huang XM, Oberlender R, Nash JF, Nichols DE. Behavioral, biochemical and neurotoxicological actions of the alpha-ethyl homologue of p-chloroamphetamine. European Journal of Pharmacology. 1990 Nov 20;191(1):1-10. PMID 1982656
  2. ^ Gal EM, Cristiansen PA, Yunger LM. Effect of p-chloroamphetamine on cerebral tryptophan-5-hydroxylase in vivo: a reexamination. Neuropharmacology. 1975 Jan;14(1):31-9. PMID 125387
  3. ^ Curzon G, Fernando JC, Marsden CA. 5-Hydroxytryptamine: the effects of impaired synthesis on its metabolism and release in rat. British Journal of Pharmacology. 1978 Aug;63(4):627-34. PMID 80243
  4. ^ Colado MI, Murray TK, Green AR. 5-HT loss in rat brain following 3,4-methylenedioxymethamphetamine (MDMA), p-chloroamphetamine and fenfluramine administration and effects of chlormethiazole and dizocilpine. British Journal of Pharmacology. 1993 Mar;108(3):583-9. PMID 7682129
  5. ^ Freo U, Pietrini P, Pizzolato G, Furey M, Merico A, Ruggero S, Dam M, Battistin L. Cerebral metabolic responses to clomipramine are greatly reduced following pretreatment with the specific serotonin neurotoxin para-chloroamphetamine (PCA). A 2-deoxyglucose study in rats. Neuropsychopharmacology. 1995 Nov;13(3):215-22. PMID 8602894
  6. ^ http://www.erowid.org/archive/rhodium/chemistry/shulgin.pea.sar.hop.html#35



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