Chemistry:2-Chloroamphetamine
2-Chloroamphetamine (2-CA), also known as ortho-chloroamphetamine (OCA), is a monoamine releasing agent (MRA) of the amphetamine family related to 2-fluoroamphetamine (2-FA).[1]
Pharmacology
Pharmacodynamics
It has been found to induce the release of norepinephrine and dopamine in rat brain synaptosomes with EC50 values of 19.1 and 62.4 nM, respectively, whereas serotonin was not reported.[1] It has been found to also induce the release of serotonin in mouse brain slices to some degree,[2] whereas it did not induce the release of serotonin in the brain in rats in vivo.[3]
In contrast to amphetamine and para-chloroamphetamine (PCA; 4-chloroamphetamine), 2-CA does not appear to produce hyperlocomotion in mice, and instead has been found to decrease locomotor activity.[4] However, it did potentiate the effects of levodopa similarly to amphetamine and PCA.[4] On the other hand, like amphetamine but in contrast to PCA and 4-methylamphetamine (4-MA), 2-CA did not potentiate the effects of 5-hydroxytryptophan (5-HTP).[4] Unlike PCA, 2-CA did not produce the head-twitch response, a behavioral proxy of psychedelic-like effects, in mice.[4]
In contrast to PCA, but similarly to amphetamine, 2-CA does not appear to produce serotonergic neurotoxicity in rats or guinea pigs.[5][6][3][7] While this could be attributed to rapid metabolism in the case of 3-chloroamphetamine (3-CA), 2-CA continued to lack serotonergic neurotoxicity even when its metabolism was inhibited by desipramine.[6]
References
- ↑ 1.0 1.1 "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.
- ↑ "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.
- ↑ 3.0 3.1 "Drug disposition as a factor in the lowering of brain serotonin by chloroamphetamines in the rat". Biochem Pharmacol 21 (10): 1413–1417. May 1972. doi:10.1016/0006-2952(72)90365-6. PMID 5029422.
- ↑ 4.0 4.1 4.2 4.3 "Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones". Acta Pharmacol Toxicol (Copenh) 41 (4): 353–368. October 1977. doi:10.1111/j.1600-0773.1977.tb02674.x. PMID 303437.
- ↑ "Effects of p-chloroamphetamine on brain serotonin neurons". Neurochem Res 17 (5): 449–456. May 1992. doi:10.1007/BF00969891. PMID 1528354.
- ↑ 6.0 6.1 "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.
- ↑ "Further structure-activity studies on the lowering of brain 5-hydroxyindoles by 4-chloramphetamine". Neuropharmacology 12 (1): 33–42. January 1973. doi:10.1016/0028-3908(73)90129-9. PMID 4687274.
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