Chemistry:3-Chloroamphetamine

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3-Chloroamphetamine (3-CA; code name PAL-304), also known as meta-chloroamphetamine (MCA), is a psychostimulant of the amphetamine family and a serotonergic neurotoxin related to para-chloroamphetamine (PCA; 4-chloroamphetamine).[1][2][3][4]

The drug is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA).[5][6][7] Its EC50 values for induction of monoamine release are 9.4 nM for norepinephrine, 11.8 nM for dopamine, and 120 nM for serotonin. Hence, 3-CA shows around 10-fold preference for induction of catecholamine release over induction of serotonin release.[5][6][8][9]

3-CA is closely related to the potent serotonergic neurotoxin PCA.[10][11][1] In contrast to PCA, 3-CA produced no serotonergic neurotoxicity in rodents.[10][11][1] However, this was found to be due to rapid metabolism via para-hydroxylation.[11][1] When the metabolism of 3-CA was inhibited, the drug produced approximately equivalent serotonergic neurotoxicity to PCA.[11][1]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 "Amphetamines: Structure-Activity Relationships". Stimulants. Boston, MA: Springer US. 1978. p. 1–39. doi:10.1007/978-1-4757-0510-2_1. ISBN 978-1-4757-0512-6. "The position of the chloro substituent also markedly affects the activity of the compounds (Table 6). The effect of the meta derivative was approximately equivalent to that of the para derivative but only after inhibition of para-hydroxylation, while the ortho-substituted compound actually slightly raised rather than lowered the serotonin levels (Fuller and Molloy, 1974)." 
  2. ↑ "4-methylamphetamine (4-MA): chemistry, pharmacology and toxicology of a new potential recreational drug". Mini Reviews in Medicinal Chemistry 13 (14): 2097–2101. December 2013. doi:10.2174/13895575113136660106. PMID 24195663. "[...] was less potent than amphetamine, 3-chloroamphetamine and 4-chloroamphetamine in inducing motor stimulation [31]. [...]". 
  3. ↑ "Synthetic amphetamine derivatives, benzofurans, and benzodifurans". Novel Psychoactive Substances. Elsevier. 2022. pp. 247–278. doi:10.1016/b978-0-12-818788-3.00007-3. ISBN 978-0-12-818788-3. "[...] amphetamine analogue required to increase motor activity by 200 percent was 38 μmol/kg for 4-MA, 16 μmol/kg for amphetamine and 24 μmol/kg for both 2- and 3-chloroamphetamine." 
  4. ↑ "Long-lasting reduction of brain 5-hydroxytryptamine concentration by 3-chloramphetamine and 4-chloroamphetamine in iprindole-treated rats". The Journal of Pharmacy and Pharmacology 26 (11): 912–914. November 1974. doi:10.1111/j.2042-7158.1974.tb09206.x. PMID 4156568. 
  5. ↑ 5.0 5.1 Forsyth, Andrea N (22 May 2012). "Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines". https://scholarworks.uno.edu/td/1436/. 
  6. ↑ 6.0 6.1 "Dopamine-releasing agents". Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. July 2008. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf. 
  7. ↑ "Substituted amphetamine derivatives. I. Effect on uptake and release of biogenic monoamines and on monoamine oxidase in the mouse brain". Acta Pharmacol Toxicol (Copenh) 41 (4): 337–352. October 1977. doi:10.1111/j.1600-0773.1977.tb02673.x. PMID 579062. 
  8. ↑ "Hybrid dopamine uptake blocker-serotonin releaser ligands: a new twist on transporter-focused therapeutics". ACS Med Chem Lett 5 (6): 623–627. June 2014. doi:10.1021/ml500113s. PMID 24944732. 
  9. ↑ "Norfenfluramine to treat dravet syndrome". 9 March 2023. https://patents.google.com/patent/US20230076320A1/en. 
  10. ↑ 10.0 10.1 "Effects of p-chloroamphetamine on brain serotonin neurons". Neurochem Res 17 (5): 449–456. May 1992. doi:10.1007/BF00969891. PMID 1528354. 
  11. ↑ 11.0 11.1 11.2 11.3 "Structure-activity relationships among the halogenated amphetamines". Ann N Y Acad Sci 305 (1): 147–159. June 1978. doi:10.1111/j.1749-6632.1978.tb31518.x. PMID 152079. Bibcode: 1978NYASA.305..147F. 



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