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  • Title: Structure-activity relations for the inhibition of 5-hydroxytryptamine uptake by tricyclic antidepressants into synaptosomes from serotoninergic neurones in rat brain homogenates.
    Author: Horn AS, Trace RC.
    Journal: Br J Pharmacol; 1974 Jul; 51(3):399-403. PubMed ID: 4451753.
    Abstract:
    1 The inhibitory effects of various analogues of imipramine on [(3)H]-5-hydroxytryptamine (5-HT) uptake into homogenates of rat hypothalamus were examined.2 For structures with a three carbon side chain the tertiary amine derivative was more potent than the compound with a secondary amine function.3 Potency was reduced by increasing or decreasing the length of the three carbon side chain by one carbon atom.4 Substitution of a methyl group in the alpha or beta position in the side chain reduced potency.5 Replacement of the dimethylene bridge in imipramine by a sulphur atom or substitution of a C=C double bond for the exocyclic N-C bond of imipramine both led to a fall in potency.6 3-Chlorimipramine was the most potent inhibitor of [(3)H]-5-hydroxytryptamine uptake of the compounds tested.
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