para-Chloromethamphetamine

Not to be confused with para-Chloroamphetamine.
Para-Chloromethamphetamine
Systematic (IUPAC) name
1-(4-Chlorophenyl)-N-methylpropan-2-amine
Clinical data
Legal status
Identifiers
CAS Number 30572-91-9 YesY
PubChem CID 3128
ChemSpider 3016
Chemical data
Formula C10H14ClN
Molar 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 1960s 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

References

  1. ↑ Johnson MP, Conarty PF, Nichols DE (July 1991). "[3H]Monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetaimne and p-chloroamphetamine analogues". European Journal of Pharmacology 200 (1): 9–16. doi:10.1016/0014-2999(91)90659-E. PMID 1685125.
  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. doi:10.1016/0028-3908(75)90099-4. PMID 1196472.
  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. doi:10.1007/s00213-011-2504-0. PMC 3289749. PMID 21993877.
  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. doi:10.1016/0024-3205(63)90094-8.
  5. ↑ Ray W. Fuller, C.W. Hines, J. Mills (April 1965). "Lowering of brain serotonin level by chloramphetamines". Biochemical Pharmacology 14 (4): 483–488. doi:10.1016/0006-2952(65)90221-2. PMID 14322972.
  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. PMID 1123726.
  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. doi:10.1111/j.1476-5381.1977.tb07560.x. PMC 1668069. PMID 597669.
  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. doi:10.1007/BF00404812.
  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. doi:10.1111/j.1600-0447.1970.tb02126.x. PMID 5502782.
  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. doi:10.1007/BF00402767. PMID 4923523.
  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. doi:10.1007/BF00404060. PMID 5565748.

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