Para-Chloromethamphetamine: Difference between revisions

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Another study on rats found that 4-chloromethamphetamine was more potent at inducing conditioned taste aversion than [[methamphetamine]].<ref>{{cite journal | title=Comparative potencies of amphetamine, fenfluramine and related compounds in taste aversion experiments in rats |author1=D.A. Booth |author2=C.W.T. Pilcher |author3=G.D. D'Mello |author4=I.P. Stolerman | journal=British Journal of Pharmacology |date=December 1977 | volume=61 | issue=4 | pages=669–677 | doi=10.1111/j.1476-5381.1977.tb07560.x | pmid=597669 | pmc=1668069}}</ref>
Another study on rats found that 4-chloromethamphetamine was more potent at inducing conditioned taste aversion than [[methamphetamine]].<ref>{{cite journal | title=Comparative potencies of amphetamine, fenfluramine and related compounds in taste aversion experiments in rats |author1=D.A. Booth |author2=C.W.T. Pilcher |author3=G.D. D'Mello |author4=I.P. Stolerman | journal=British Journal of Pharmacology |date=December 1977 | volume=61 | issue=4 | pages=669–677 | doi=10.1111/j.1476-5381.1977.tb07560.x | pmid=597669 | pmc=1668069}}</ref>


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 [[antidepressant]]s rather than stimulants.<ref>{{cite journal | url=https://link.springer.com/article/10.1007%2FBF00404812 | title=Influencing the human indoleamine metabolism by means of a chlorinated amphetamine derivative with antidepressive action (p-Chloro-N-Methylamphetamine) |author1=H. M. van Praagtory |author2=J. Korf |author3=F. van Woudenberg |author4=T. P. Kits | journal=Psychopharmacologia |date=July 1968 | volume=13 | issue=2 | pages=145–160 | doi=10.1007/BF00404812}}</ref><ref>{{cite journal | url=http://onlinelibrary.wiley.com/doi/10.1111/j.1600-0447.1970.tb02126.x/abstract | title=A controlled study of the antidepressant effect of p-Chloro-N-methylamphetamine, a compound with a selective effect on the central 5-hydroxytryptamine metabolism. |vauthors=Kits TP, van Praag HM | journal=Acta Psychiatrica Scandinavica | year=1970 | volume=46 | issue=4 | pages=365–373 | doi=10.1111/j.1600-0447.1970.tb02126.x | pmid=5502782}}</ref><ref>{{cite journal | url=https://link.springer.com/article/10.1007%2FBF00402767 | title=Investigation into the possible influence of chlorinated amphetamine derivatives on 5-hydroxytryptamine synthesis in man |author1=H. M. van Praag |author2=J. Korf |author3=F. van Woudenberg | journal=Psychopharmacologia |date=December 1970 | volume=18 | issue=4 | pages=412–420 | doi=10.1007/BF00402767 | pmid=4923523}}</ref><ref>{{cite journal | url=https://link.springer.com/article/10.1007%2FBF00404060 | title=A comparative study of the therapeutic effects of some 4-chlorinated amphetamine derivatives in depressive patients |author1=H. M. van Praag |author2=T. Schut |author3=E. Bosma |author4=R. van den Bergh | journal=Psychopharmacologia |date=March 1971 | volume=20 | issue=1 | pages=66–76 | doi=10.1007/BF00404060 | pmid=5565748}}</ref>
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 [[antidepressant]]s rather than stimulants.<ref>{{cite journal | title=Influencing the human indoleamine metabolism by means of a chlorinated amphetamine derivative with antidepressive action (p-Chloro-N-Methylamphetamine) |author1=H. M. van Praagtory |author2=J. Korf |author3=F. van Woudenberg |author4=T. P. Kits | journal=Psychopharmacologia |date=July 1968 | volume=13 | issue=2 | pages=145–160 | doi=10.1007/BF00404812}}</ref><ref>{{cite journal | title=A controlled study of the antidepressant effect of p-Chloro-N-methylamphetamine, a compound with a selective effect on the central 5-hydroxytryptamine metabolism. |vauthors=Kits TP, van Praag HM | journal=Acta Psychiatrica Scandinavica | year=1970 | volume=46 | issue=4 | pages=365–373 | doi=10.1111/j.1600-0447.1970.tb02126.x | pmid=5502782}}</ref><ref>{{cite journal | title=Investigation into the possible influence of chlorinated amphetamine derivatives on 5-hydroxytryptamine synthesis in man |author1=H. M. van Praag |author2=J. Korf |author3=F. van Woudenberg | journal=Psychopharmacologia |date=December 1970 | volume=18 | issue=4 | pages=412–420 | doi=10.1007/BF00402767 | pmid=4923523}}</ref><ref>{{cite journal | title=A comparative study of the therapeutic effects of some 4-chlorinated amphetamine derivatives in depressive patients |author1=H. M. van Praag |author2=T. Schut |author3=E. Bosma |author4=R. van den Bergh | journal=Psychopharmacologia |date=March 1971 | volume=20 | issue=1 | pages=66–76 | doi=10.1007/BF00404060 | pmid=5565748}}</ref>
[[File:Tablet containing 4-chloromethamphetamine.jpg|frame|Tablet containing 4-chloromethamphetamine, found in 2015 in Belgium.]]
[[File:Tablet containing 4-chloromethamphetamine.jpg|frame|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)<ref>{{Cite journal|date=2018-07-01|title=Identification and characterization of 4-chloromethamphetamine (4-CMA) in seized ecstacy — a risk to public health|url=https://www.sciencedirect.com/science/article/pii/S0379073818301816|journal=Forensic Science International|language=en|volume=288|pages=173–180|doi=10.1016/j.forsciint.2018.04.023|issn=0379-0738}}</ref>.
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)<ref>{{Cite journal|date=2018-07-01|title=Identification and characterization of 4-chloromethamphetamine (4-CMA) in seized ecstacy — a risk to public health|url=https://www.sciencedirect.com/science/article/pii/S0379073818301816|journal=Forensic Science International|language=en|volume=288|pages=173–180|doi=10.1016/j.forsciint.2018.04.023|pmid=29753935|issn=0379-0738|last1=Blanckaert|first1=Peter|last2=Vanquekelberghe|first2=Stijn|last3=Coopman|first3=Vera|last4=Risseeuw|first4=Martijn D.P.|last5=Van Calenbergh|first5=Serge|last6=Cordonnier|first6=Jan}}</ref>.


== See also ==
== See also ==

Revision as of 17:08, 16 January 2019

Not to be confused with para-Chloroamphetamine.
para-Chloromethamphetamine
Legal status
Legal status
Identifiers
  • 1-(4-Chlorophenyl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H14ClN
Molar mass183.68 g·mol−1
3D model (JSmol)
  • ClC1=CC=C(C=C1)CC(C)NC
  • 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

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]

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.
  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; 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. {{cite journal}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)
  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.
  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. ISSN 0379-0738. PMID 29753935.
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