para-Chloroamphetamine

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para-chloroamphetamine
Parachloroamphetamine.png
Systematic (IUPAC) name
1-(4-chlorophenyl)propan-2-amine
Clinical data
Legal status
?
Identifiers
CAS number 64-12-0 N
ATC code ?
PubChem CID 3127
ChemSpider 3015 YesY
ChEMBL CHEMBL358967 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]

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] 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]

Analog[edit]

Rigid PCA analog (6-CAT)

According to Nichols et al.,[13] the above depicted compound is non-neurotoxic analog of PCA. It's actually called 6-Chloro-2-aminotetralin.[14][15]

See Org 6582 also.

6-CAT

See also[edit]

References[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 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
  7. ^ Lin TC, Lin DL, Lua AC. Detection of p-chloroamphetamine in urine samples with mass spectrometry. Journal of Analytical Toxicology. 2011 May;35(4):205-10. 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. ^ Johnson, M. P.; Frescas, S. P.; Oberlender, R.; Nichols, D. E. (1991). "Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: Similarities to 3,4-(methylenedioxy)methamphetamine (MDMA)". Journal of Medical Chemistry 34 (5): 1662–1668. doi:10.1021/jm00109a020. PMID 1674539.  edit
  14. ^ Fuller, R. W.; Perry, K. W.; Baker, J. C.; Molloy, B. B. (1974). "6-Chloro-2-aminotetralin, a rigid Conformational analog of 4-chloroamphetamine: Pharmacologic properties of it and related compounds in rats". Archives internationales de pharmacodynamie et de therapie 212 (1): 141–153. PMID 4455127.  edit
  15. ^ Fuller, R. W.; Wong, D. T.; Snoddy, H. D.; Bymaster, F. P. (1977). "Comparison of the effects of 6-chloro-2-aminotetralin and of Org 6582, a related chloroamphetamine analog, on brain serotonin metabolism in rats". Biochemical Pharmacology 26 (14): 1333. doi:10.1016/0006-2952(77)90094-6.  edit