(−)-5-Methyl-8-hydroxy-(di-n-propylamino)tetralin: A new 5-HT1A receptor antagonist

Add time:08/07/2019    Source:sciencedirect.com

− (±)-5-Me-8-OH-DPAT 4 was synthesized by a new synthetic pathway recently described by us. The (+)- and (−)-enantiomers 4 were prepared from the primary amine 8 by crystallisation of the (+)- and (−)-mandelic acid salts. The enantiomers reacted with propyl iodide and were demethylated by 48% HBr to the (+)- and (−)-4 compounds. These compounds had good affinity for 5-HT1A receptors (Ki = 32.9 ± 0.8 and 45.6 ± 2 nM, respectively) but lacked enantioselectivity. In contrast to 8-OH-DPAT, but similar to WAY 100635 and (+)-WAY 100135, the addition of GTP-γS did not decrease the affinity of these compounds for 5-HT1A receptors, suggesting a partial agonist or antagonist profile. Adenylyl cyclase assays with rat hippocampal membranes showed that (−)-4 was totally inactive as an agonist over a wide concentration range in contrast to (+)-4 which was a partial agonist. (−)-4 (1 and 10 μM) shifted the concentration—effect curve for the inhibition by 8-OH-DPAT of forskolin-stimulated cyclic AMP production to the right (pA2 = 7.6), demonstrating a competitive interaction between the two drugs.

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