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Fuller RW, Perry KW, Wong DT, Molloy BB. 
“Effects of some homologues of 4-chloroamphetamine on brain serotonin metabolism”. 
Neuropharmacology. 1974 Jul 17;13(7):609-14.
Three homologues of 4-chloroamphetamine, with longer or shorter side chains, had different effects on rat brain serotonin (5-HT) and 5-hydroxyindoleacetic acid (5-HIAA) levels than did 4-chloroamphetamine itself. Shortening the side chain greatly diminished the activity of 4-chloroamphetamine on 5-hydroxyindole metabolism; 4-chloro-x-methylbenzylamine had little effect on 5-HT or 5-HIAA levels in vivo or on 5-HT uptake into synaptosomes or oxidation by monoamine oxidase in vitro. Lengthening the side chain abolished depletion of brain 5-HT by 4-chloroamphetamine but not the ability to affect 5-HT uptake and metabolism. 4-Chloro-x-methylphenylpropylamine increased 5-HT levels and decreased 5-HIAA levels in vivo and was as potent as 4-chloroamphetamine in vitro in blocking 5-HT uptake and 5-HT oxidation. 4-Chloro-x-methylphenylbutylamine did not change 5-HT levels but reduced 5-HIAA levels in vivo: it inhibited 5-HT uptake in vitro and apparently did so in vivo as well. Both of the longer homologues antagonized the depletion of brain 5-HT by 4-chloroamphetamine. a further indication that they block uptake by 5-HT neurones in vivo. These results indicate that the depleting action of 4-chloroamphetamine on brain 5-HT is lost by altering the side chain but that other actions of 4-chloroamphetamine on brain 5-HT metabolism are retained in the longer side-chain homologues.
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