From Wikipedia, the free encyclopedia

Jump to: navigation, search
Systematic (IUPAC) name
Clinical data
Legal status
CAS number 64-12-0 N
ATC code ?
PubChem CID 3127
ChemSpider 3015 YesY
Chemical data
Formula C9H12ClN 
Mol. mass 169.651
 N (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]

An interesting analog that was prepared by Horrom, et al. is the N-cyclopropyl and N-cyclopropylmethyl analogs. The 3,4-methylenedioxy analogs were also prepared.[13]

See also[edit]


  1. ^ Miller, K. J.; Anderholm, D. C.; Ames, M. M. (1986). "Metabolic activation of the serotonergic neurotoxin para-chloroamphetamine to chemically reactive intermediates by hepatic and brain microsomal preparations". Biochemical Pharmacology 35 (10): 1737–1742. doi:10.1016/0006-2952(86)90332-1. PMID 3707603.  edit
  2. ^ Gal, E. M.; Cristiansen, P. A.; Yunger, L. M. (1975). "Effect of p-chloroamphetamine on cerebral tryptophan-5-hydroxylase in vivo: A reexamination". Neuropharmacology 14 (1): 31–9. PMID 125387. 
  3. ^ Curzon, G; Fernando, J. C.; Marsden, C. A. (1978). "5-Hydroxytryptamine: The effects of impaired synthesis on its metabolism and release in rat". British journal of pharmacology 63 (4): 627–34. PMC 1668117. PMID 80243. 
  4. ^ Colado, M. I.; Murray, T. K.; Green, A. R. (1993). "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 108 (3): 583–9. PMC 1908028. PMID 7682129. 
  5. ^ Freo, U; Pietrini, P; Pizzolato, G; Furey, M; Merico, A; Ruggero, S; Dam, M; Battistin, L (1995). "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 13 (3): 215–22. doi:10.1016/0893-133X(95)00053-G. PMID 8602894. 
  6. ^ Alexander T. Shulgin (1978). Leslie L. Iversen, Susan D. Iversen, and Solomon H. Snyder, ed. Handbook of Psychopharmacology. 11: Stimulants. New York: Plenum Press. 
  7. ^ Lin TC, Lin DL, Lua AC; Lin; Lua (2011). "Detection of p-chloroamphetamine in urine samples with mass spectrometry". Journal of Analytical Toxicology 35 (4): 205–210. PMID 21513613. 
  8. ^ Fuller, R.; Schaffer, R. J.; Roush, B. W.; Molloy, B. B. (1972). "Drug disposition as a factor in the lowering of brain serotonin by chloroamphetamines in the rat". Biochemical Pharmacology 21 (10): 1413–1417. doi:10.1016/0006-2952(72)90365-6. PMID 5029422.  edit
  9. ^ Ögren, S. O.; Ross, S. B. (2009). "Substituted Amphetamine Derivatives. II. Behavioural Effects in Mice Related to Monoaminergic Neurones". Acta Pharmacologica et Toxicologica 41 (4): 353–368. doi:10.1111/j.1600-0773.1977.tb02674.x. PMID 303437.  edit
  10. ^ Ross, S. B.; Kelder, D. (2009). "Inhibition of 3H-Dopamine Accumulation in Reserpinized and Normal Rat Striatum". Acta Pharmacologica et Toxicologica 44 (5): 329–335. doi:10.1111/j.1600-0773.1979.tb02339.x. PMID 474143.  edit
  11. ^ Fuller, R. W.; Baker, J. C. (1974). "Long-lasting reduction of brain 5-hydroxytryptamine concentration by 3-chloroamphetamine and 4-chloroamphetamine in iprindole-treated rats". Journal of Pharmacy and Pharmacology 26 (11): 912–914. doi:10.1111/j.2042-7158.1974.tb09206.x. PMID 4156568.  edit
  12. ^ Ross, S. B.; Ögren, S. O.; Renyi, A. L. (2009). "Substituted Amphetamine Derivatives. I. Effect on Uptake and Release of Biogenic Monoamines and on Monoamine Oxidase in the Mouse Brain". Acta Pharmacologica et Toxicologica 41 (4): 337–352. doi:10.1111/j.1600-0773.1977.tb02673.x. PMID 579062.  edit
  13. ^ U.S. Patent 3,689,504