para-Chloromethamphetamine

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 (4-CA).[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 serotonin and the activity of tryptophan hydroxylase in the brain one month after injection of a single dose of the drug.[6]

para-Chloromethamphetamine
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
IUPAC name
  • 1-(4-Chlorophenyl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H14ClN
Molar mass183.68 g·mol−1
3D model (JSmol)
SMILES
  • ClC1=CC=C(C=C1)CC(C)NC
InChI
  • InChI=1S/C10H14ClN/c1-8(12-2)7-9-3-5-10(11)6-4-9/h3-6,8,12H,7H2,1-2H3
  • Key:XXLWNLKEOWWHDC-UHFFFAOYSA-N

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]

Tablet containing 4-chloromethamphetamine, found in 2015 in Belgium.

4-Chloromethamphetamine was identified outside of the laboratory for the first time at the Tomorrowland festival edition 2015, where a tablet was found in possession of a drug dealer (see picture).[12]

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. S2CID 9620299.
  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. PMID 14078137.
  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 & 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. PMID 5678577. S2CID 30028917.
  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. S2CID 2211532.
  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. S2CID 27509683.
  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. S2CID 5581.
  12. Blanckaert, Peter; Vanquekelberghe, Stijn; Coopman, Vera; Risseeuw, Martijn D.P.; Van Calenbergh, Serge; Cordonnier, Jan (2018-07-01). "Identification and characterization of 4-chloromethamphetamine (4-CMA) in seized ecstacy — a risk to public health". Forensic Science International. 288: 173–180. doi:10.1016/j.forsciint.2018.04.023. hdl:1854/LU-8569680. ISSN 0379-0738. PMID 29753935. S2CID 21720366.
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