2-Chloroamphetamine

vanc 6 2-Chloroamphetamine structure.svg skin-invert-image 200px Monoamine releasing agent 21193-23-7 152331 134269 00Q9Z0HNOQ 180535 2-CA; ortho-Chloroamphetamine; o-Chloroamphetamine; OCA; o-CA 1-(2-chlorophenyl)propan-2-amine 9 12 1 1 CC(CC1=CC=CC=C1Cl)N 1S/C9H12ClN/c1-7(11)6-8-4-2-3-5-9(8)10/h2-5,7H,6,11H2,1H3 IQHHOHJDIZRBGM-UHFFFAOYSA-N 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). Blough B Dopamine-releasing agents Trudell ML, Izenwasser S Dopamine Transporters: Chemistry, Biology and Pharmacology 305–320 July 2008 978-0-470-11790-3 181862653 OL18589888W Wiley Hoboken [NJ] https://books.google.com/books?id=QCagLAAACAAJ https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf Pharmacology Pharmacodynamics It has been found to induce the release of norepinephrine and dopamine in rat brain synaptosomes with EC50 half-maximal effective concentration values of 19.1 and 62.4nM, respectively, whereas serotonin was not reported. It has been found to also induce the release of serotonin in mouse brain slices to some degree, Ross SB, Ogren SO, Renyi AL 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 579062 10.1111/j.1600-0773.1977.tb02673.x 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. Ogren SO, Ross SB Substituted amphetamine derivatives. II. Behavioural effects in mice related to monoaminergic neurones Acta Pharmacol Toxicol (Copenh) 41 4 353–368 October 1977 303437 10.1111/j.1600-0773.1977.tb02674.x 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. Fuller RW Effects of p-chloroamphetamine on brain serotonin neurons Neurochem Res 17 5 449–456 May 1992 1528354 10.1007/BF00969891 Fuller RW Structure-activity relationships among the halogenated amphetamines Ann N Y Acad Sci 305 1 147–159 June 1978 152079 10.1111/j.1749-6632.1978.tb31518.x 1978NYASA.305..147F Fuller RW, Schaffer RJ, Roush BW, Molloy BB Drug disposition as a factor in the lowering of brain serotonin by chloroamphetamines in the rat Biochem Pharmacol 21 10 1413–1417 May 1972 5029422 10.1016/0006-2952(72)90365-6 Fuller RW, Snoddy HD, Roush BW, Molloy BB Further structure-activity studies on the lowering of brain 5-hydroxyindoles by 4-chloramphetamine Neuropharmacology 12 1 33–42 January 1973 4687274 10.1016/0028-3908(73)90129-9 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 Category:2-Chlorophenyl compounds Category:Monoamine releasing agents Category:Substituted amphetamines