Synthesis and pharmacological characterization of A-80426: A putative novel antidepressant combining α-2 antagonism with 5-HT uptake inhibition

Bioorganic & Medicinal Chemistry Letters
1995.0

Abstract

A-80426, (N-[2-(Benzofuran-6-yl)ethyl]-N-[(R)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-ylmethyl]-N-methylamine) represents the first example of a new structural class of agents combining potent α-2 antagonist activity with equivalent 5-HT uptake inhibitory activity. This profile of combined activities may have utility in the treatment of depression.Modulation of biogenic amines, particularly serotonin and norepinephrine, is the principal pharmacological mechanism of action of all therapeutic agents currently in use for the treatment of depressive disorders. Inhibitors of norepinephrine (NE) or serotonin (5-HT) reuptake are currently among the most efficacious pharmacological treatments of depression. However, neurotransmitter release is under the control of inhibitory presynaptic auto and heteroreceptors. Several studies have indicated that there may be a correlation between desensitization of inhibitory presynaptic α-2 receptors and onset of antidepressant action. The presence of presynaptic α-2 heteroreceptors on 5-HT neurons, and their inhibitory effect on 5-HT release, suggest that antagonism of these sites may act to increase synaptic concentrations of 5-HT. Thus, a combined profile of α-2 antagonism and 5-HT uptake inhibition may more efficaciously increase synaptic 5-HT availability than either pharmacological action alone, and consequently result in an improved antidepressant profile. Herein, we describe the synthesis and pharmacological characterization of a novel agent, A-80426 (1) which combines high affinity at α-2 receptors with potent and selective inhibitory activity for the reuptake of 5-HT, and present preliminary evidence of activity in an animal model predictive of antidepressant efficacy.

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