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Title: Para-Chloromethamphetamine  
Author: World Heritage Encyclopedia
Language: English
Subject: Methamphetamines, Neurotoxins, Stimulants, Heptaminol, 2-Propanoyl-3-(4-isopropylphenyl)-tropane
Publisher: World Heritage Encyclopedia


Systematic (IUPAC) name
Clinical data
Legal status
CAS Registry Number  Y
PubChem CID:
Chemical data
Formula C10H14ClN
Molecular mass 183.68 g·mol−1

para-Chloromethamphetamine (also known as 4-Chloromethamphetamine and 4-CMA) is a stimulant that is the N-methyl derivative and prodrug of the neurotoxic drug para-Chloroamphetamine.[1][2] It has been found to decrease serotonin in rats.[3][4][5] Further investigation into the long-term effects of chloroamphetamines discovered that administration of 4-CMA caused a prolonged reduction in the levels of 5-HT and the activity of tryptophan hydroxylase in the brain one month after injection of a single dose of the drug.[6]

Another study on rats found that 4-Chloromethamphetamine was more potent at inducing conditioned taste aversion than methamphetamine.[7]

4-Chloromethamphetamine was further investigated in the 1960's along with 4-CA and it was noted that they differed from their parent amphetamine and methamphetamine substances by exhibiting only a slight central stimulant effect in both animals and humans and that they acted like antidepressants rather than stimulants.[8][9][10][11]

See also


  1. ^ Johnson MP, Conarty PF, Nichols DE (July 1991). H]Monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetaimne and p-chloroamphetamine analogues"3"[. European Journal of Pharmacology 200 (1): 9–16.  
  2. ^ R.W. Fuller, J.C. Baker, K.W. Perry, B.B. Molloy (October 1975). "Comparison of 4-chloro-, 4-bromo- and 4-fluoroamphetamine in rats: Drug levels in brain and effects on brain serotonin metabolism". Neuropharmacology 14 (10): 739–746.  
  3. ^ Kevin Sean Murnane, Shane Alan Perrine, Brendan James Finton, Matthew Peter Galloway, Leonard Lee Howell, William Edward Fantegrossi (April 2012). "Effects of exposure to amphetamine derivatives on passive avoidance performance and the central levels of monoamines and their metabolites in mice: Correlations between behavior and neurochemistry". Psychopharmacology 220 (3): 495–508.  
  4. ^ A. Pletscher, W.P. Burkard, H. Bruderer, K.F. Gey (November 1963). "Decrease of cerebral 5-hydroxytryptamine and 5-hydroxyindolacetic acid by an arylalkylamine". Life Sciences 2 (11): 828–833.  
  5. ^ Ray W. Fuller, C.W. Hines, J. Mills (April 1965). "Lowering of brain serotonin level by chloramphetamines". Biochemical Pharmacology 14 (4): 483–488.  
  6. ^ E Sanders-Bush, J A Bushing, and F Sulser (January 1975). "Long-term effects of p-chloroamphetamine and related drugs on central serotonergic mechanisms.". Journal of Pharmacology and Experimental Therapeutics 192 (1): 33–41.  
  7. ^ D.A. Booth, C.W.T. Pilcher, G.D. D'Mello, I.P. Stolerman (December 1977). "Comparative potencies of amphetamine, fenfluramine and related compounds in taste aversion experiments in rats". British Journal of Pharmacology 61 (4): 669–677.  
  8. ^ H. M. van Praagtory, J. Korf, F. van Woudenberg, T. P. Kits (July 1968). "Influencing the human indoleamine metabolism by means of a chlorinated amphetamine derivative with antidepressive action (p-Chloro-N-Methylamphetamine)". Psychopharmacologia 13 (2): 145–160.  
  9. ^ Kits TP, van Praag HM. (1970). "A controlled study of the antidepressant effect of p-Chloro-N-methylamphetamine, a compound with a selective effect on the central 5-hydroxytryptamine metabolism.". Acta Psychiatrica Scandinavica 46 (4): 365–373.  
  10. ^ H. M. van Praag, J. Korf, F. van Woudenberg (December 1970). "Investigation into the possible influence of chlorinated amphetamine derivatives on 5-hydroxytryptamine synthesis in man". Psychopharmacologia 18 (4): 412–420.  
  11. ^ H. M. van Praag, T. Schut, E. Bosma, R. van den Bergh (March 1971). "A comparative study of the therapeutic effects of some 4-chlorinated amphetamine derivatives in depressive patients". Psychopharmacologia 20 (1): 66–76.  
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