para-Chloroamphetamine
Para-Chloroamphetamine Structure.svg
4-CA44.jpg
Clinical data
Other namesPCA; 4-Chloroamphetamine; 4-CA
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • 1-(4-Chlorophenyl)propan-2-amine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC9H12ClN
Molar mass169.65 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:WWPITPSIWMXDPE-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

para-Chloroamphetamine (PCA), also known as 4-chloroamphetamine (4-CA), is a substituted amphetamine 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]

para-Chloroamphetamine has been detected as an apparent designer drug,[6] along with the related 3-chloroamphetamine, which is even more potent as a releaser of dopamine and serotonin but slightly less neurotoxic.[7][8][9][10][11]

The closely related N-methylated derivative, para-chloromethamphetamine (CMA), which is metabolized 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.[12]

See also

References

  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.
  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. doi:10.1016/0028-3908(75)90063-5. PMID 125387. S2CID 1068793.
  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. doi:10.1111/j.1476-5381.1978.tb17275.x. 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. doi:10.1111/j.1476-5381.1993.tb12846.x. 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. ^ Lin TC, Lin DL, Lua AC (2011). "Detection of p-chloroamphetamine in urine samples with mass spectrometry". Journal of Analytical Toxicology. 35 (4): 205–210. doi:10.1093/anatox/35.4.205. PMID 21513613.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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. S2CID 41833796.
  11. ^ 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.
  12. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
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