Noxiptiline


Noxiptiline, also known as noxiptyline and dibenzoxine, is a tricyclic antidepressant that was introduced in Europe in the 1970s for the treatment of depression. It has imipramine-like effects, acting as a serotonin and norepinephrine reuptake inhibitor, among other properties. Of the TCAs, noxiptiline has been described as one of the most effective, rivaling amitriptyline in clinical efficacy.

Synthesis

The ketone dibenzosuberenone is treated with hydroxylamine to give its ketoxime. Base-catalyzed alkylation with yields noxiptiline.