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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).

It has been found to induce the release of norepinephrine and dopamine in rat brain synaptosomes with EC₅₀Tooltip half-maximal effective concentration values of 19.1 and 62.4 nM, respectively, whereas serotonin was not reported. It has been found to also induce the release of serotonin in mouse brain slices to some degree, whereas it did not induce the release of serotonin in the brain in rats in vivo.

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. However, it did potentiate the effects of levodopa similarly to amphetamine and PCA. 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). Unlike PCA, 2-CA did not produce the head-twitch response, a behavioral proxy of psychedelic-like effects, in mice.

In contrast to PCA, but similarly to amphetamine, 2-CA does not appear to produce serotonergic neurotoxicity in rats or guinea pigs. 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.

References

1. ^ Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken : Wiley. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.
2. Ross SB, Ogren SO, Renyi AL (October 1977). "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. doi:10.1111/j.1600-0773.1977.tb02673.x. PMID 579062.
3. ^ Fuller RW, Schaffer RJ, Roush BW, Molloy BB (May 1972). "Drug disposition as a factor in the lowering of brain serotonin by chloroamphetamines in the rat". Biochem Pharmacol. 21 (10): 1413–1417. doi:10.1016/0006-2952(72)90365-6. PMID 5029422.
4. ^ Ogren SO, Ross SB (October 1977). "Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones". Acta Pharmacol Toxicol (Copenh). 41 (4): 353–368. doi:10.1111/j.1600-0773.1977.tb02674.x. PMID 303437.
5. Fuller RW (May 1992). "Effects of p-chloroamphetamine on brain serotonin neurons". Neurochem Res. 17 (5): 449–456. doi:10.1007/BF00969891. PMID 1528354.
6. ^ Fuller RW (June 1978). "Structure-activity relationships among the halogenated amphetamines". Ann N Y Acad Sci. 305 (1): 147–159. Bibcode:1978NYASA.305..147F. doi:10.1111/j.1749-6632.1978.tb31518.x. PMID 152079.
7. Fuller RW, Snoddy HD, Roush BW, Molloy BB (January 1973). "Further structure-activity studies on the lowering of brain 5-hydroxyindoles by 4-chloramphetamine". Neuropharmacology. 12 (1): 33–42. doi:10.1016/0028-3908(73)90129-9. PMID 4687274.

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