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The enantiomers of the potent σ 1 receptor antagonist (±)- 1 were synthesized and evaluated for their affinity at σ 1 , σ 2 receptors and dopamine transporter (DAT). Analogously to (±)- 1 , both of the enantiomers showed very high affinity for the σ 1 receptor and unprecedented selectivity over both the σ 2 receptor and DAT. The lack of enantioselectivity between ( + )- 1 and (-)- 1 indicated that the center of chirality in the 2-position of the benzothiochromane nucleus does not play a crucial role in the interaction with any of the studied targets. Docking studies confirmed that the configuration of the enantiomers has only marginal effects on the molecular interactions with the σ 1 receptor. In in vivo studies in a female rat model of binge eating, (±)- 1 dose-dependently decreased the binge eating episode elicited by a history of intermittent food restriction and stress, confirming and strengthening the important role played by the σ 1 receptor in bingeing-related eating disorders.

acs chemical neuroscience

Investigation of the Role of Chirality in the Interaction with σ Receptors and Effect on Binge Eating Episode of a Potent σ<sub>1</sub> Antagonist Analogue of Spipethiane

Investigation of the Role of Chirality in the Interaction with σ Receptors and Effect on Binge Eating Episode of a Potent σ1 Antagonist Analogue of Spipethiane

Investigation of the Role of Chirality in the Interaction with σ Receptors and Effect on Binge Eating Episode of a Potent σ₁ Antagonist Analogue of Spipethiane