Noxiptiline (brand names Agedal, Elronon, Nogedal), also known as noxiptyline and dibenzoxine, is a

tricyclic antidepressant Tricyclic antidepressants (TCAs) are a class of medications that are used primarily as antidepressants, which is important for the management of depression. They are second-line drugs next to SSRIs. TCAs were discovered in the early 1950s and wer ...

(TCA) that was introduced in

Europe Europe is a large peninsula conventionally considered a continent in its own right because of its great physical size and the weight of its history and traditions. Europe is also considered a subcontinent of Eurasia and it is located entirel ...

in the 1970s for the treatment of depression. It has

imipramine Imipramine, sold under the brand name Tofranil, among others, is a tricyclic antidepressant (TCA) mainly used in the treatment of depression. It is also effective in treating anxiety and panic disorder. The drug is also used to treat bedwetting. ...

-like effects, acting as a serotonin and

norepinephrine reuptake inhibitor A norepinephrine reuptake inhibitor (NRI, NERI) or noradrenaline reuptake inhibitor or adrenergic reuptake inhibitor (ARI), is a type of drug that acts as a reuptake inhibitor for the neurotransmitters norepinephrine (noradrenaline) and epin ...

, among other properties. Of the TCAs, noxiptiline has been described as one of the most effective, rivaling

amitriptyline Amitriptyline, sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat cyclic vomiting syndrome (CVS), major depressive disorder and a variety of pain syndromes from neuropathic pain to fibromyalgi ...

in clinical efficacy.

Synthesis

Ths synthesis is similar to that for

Demexiptiline Demexiptiline (brand names Deparon, Tinoran) is a tricyclic antidepressant (TCA) used in France for the treatment of depression. It acts primarily as a norepinephrine reuptake inhibitor similarly to desipramine. Synthesis The synthesis is simila ...

The condensation of dibenzosuberone (1) with

hydroxylamine Hydroxylamine is an inorganic compound with the formula . The material is a white crystalline, hygroscopic compound.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–43 ...

(2) gives the corresponding oxime 785-74-6(3). This is then reacted with 2-(dimethylamine)ethyl chloride 584-46-7(4).

References

Dibenzocycloheptenes Dimethylamino compounds Ketoximes Tricyclic antidepressants {{nervous-system-drug-stub