Para-Chloromethamphetamine Explained

Para-Chloromethamphetamine should not be confused with para-Chloroamphetamine.

Drug Name:para-Chloromethamphetamine
Iupac Name:1-(4-Chlorophenyl)-N-methylpropan-2-amine
Width:220
Legal De:NpSG
Legal Uk:Class B
Cas Number:30572-91-9
Unii:IXP5G5WMYA
Pubchem:3128
Chemspiderid:3016
C:10
H:14
Cl:1
N:1
Smiles:ClC1=CC=C(C=C1)CC(C)NC
Stdinchi:1S/C10H14ClN/c1-8(12-2)7-9-3-5-10(11)6-4-9/h3-6,8,12H,7H2,1-2H3
Stdinchikey:XXLWNLKEOWWHDC-UHFFFAOYSA-N

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]

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]

Studies in the 1970s found that a single dose of 10 mg/1 kg 4-CMA resulted in a decreased level of 5-hydroxytryptamine in the brain for several weeks.[12]

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).[13] In the following year, tablets with 4–CMA were also found in Romania, Austria andCroatia. Fortituously, and for unknown reasons, 4-CMA disappeared briefly from the European rave scene after the Spring of 2016. However, a 2019 study of participants of a dance music festival in Belgium reported detection of 4-CMA in pills (out of 178 analyzed samples only one was mostly 4-CMA, while in one other 4-CMA was a minor ingredient).[14]

See also

Notes and References

  1. Johnson MP, Conarty PF, Nichols DE . [3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues . European Journal of Pharmacology . 200 . 1 . 9–16 . July 1991 . 1685125 . 10.1016/0014-2999(91)90659-E .
  2. Fuller RW, Baker JC, Perry KW, Molloy BB . 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 . October 1975 . 1196472 . 10.1016/0028-3908(75)90099-4 . 9620299 .
  3. Murnane KS, Perrine SA, Finton BJ, Galloway MP, Howell LL, Fantegrossi WE . 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 . April 2012 . 21993877 . 3289749 . 10.1007/s00213-011-2504-0 .
  4. Pletscher A, Burkard WP, Bruderer H, Gey KF . Decrease of cerebral 5-hydroxytryptamine and 5-hydroxyindolacetic acid by an arylalkylamine . Life Sciences . 2 . 11 . 828–833 . November 1963 . 14078137 . 10.1016/0024-3205(63)90094-8 .
  5. Fuller RW, Hines CW, Mills J . Lowering of brain serotonin level by chloramphetamines . Biochemical Pharmacology . 14 . 4 . 483–488 . April 1965 . 14322972 . 10.1016/0006-2952(65)90221-2 .
  6. Sanders-Bush E, Bushing JA, Sulser F . Long-term effects of p-chloroamphetamine and related drugs on central serotonergic mechanisms . The Journal of Pharmacology and Experimental Therapeutics . 192 . 1 . 33–41 . January 1975 . 1123726 .
  7. Booth DA, Pilcher CW, D'Mello GD, Stolerman IP . Comparative potencies of amphetamine, fenfluramine and related compounds in taste aversion experiments in rats . British Journal of Pharmacology . 61 . 4 . 669–677 . December 1977 . 597669 . 1668069 . 10.1111/j.1476-5381.1977.tb07560.x .
  8. van Praag HM, Korf J, van Woudenberg F, Kits TP . Influencing the human indoleamine metabolism by means of a chlorinated amphetamine derivative with antidepressive action (p-chloro-N-methylamphetamine) . Psychopharmacologia . 13 . 2 . 145–160 . July 1968 . 5678577 . 10.1007/BF00404812 . 30028917 .
  9. Kits TP, van Praag HM . 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 . 1970 . 5502782 . 10.1111/j.1600-0447.1970.tb02126.x . 2211532 .
  10. van Praag HM, Korf J, van Woudenberg F . Investigation into the possible influence of chlorinated amphetamine derivatives on 5-hydroxytryptamine synthesis in man . Psychopharmacologia . 18 . 4 . 412–420 . December 1970 . 4923523 . 10.1007/BF00402767 . 27509683 .
  11. van Praag HM, Schut T, Bosma E, van den Bergh R . A comparative study of the therapeutic effects of sone 4-chlorinated amphetamine derivatives in depressive patients . Psychopharmacologia . 20 . 1 . 66–76 . March 1971 . 5565748 . 10.1007/BF00404060 . 5581 .
  12. Long-term effects of p-chloroamphetamine and related drugs on central serotonergic mechanisms. 1975. Journal of Pharmacology and Experimental Therapeutics. 192/1, 33-41. E. Sanders-Bush, J.A. Bushing, F. Sulser.
  13. Blanckaert P, Vanquekelberghe S, Coopman V, Risseeuw MD, Van Calenbergh S, Cordonnier J . Identification and characterization of 4-chloromethamphetamine (4-CMA) in seized ecstacy - a risk to public health . Forensic Science International . 288 . 173–180 . July 2018 . 29753935 . 10.1016/j.forsciint.2018.04.023 . free . 21720366 . 1854/LU-8569680 .
  14. Lessons to be learned from toxicological analyses in intoxicated patients and seized materials at an electronic music dance festival. 2019. Forensic Sci Int. 299/174-9. P. Calle, K. Maudens, S. Lemoyne, S. Geerts, D. Van Sassenbroeck, P. Jensen, et al. doi: 10.1016/j.forsciint.2019.03.047.

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