53179-07-0

Antidepressant.

ChEBI: Nisoxetine is a secondary amino compound that is N-methyl-3-phenylpropan-1-amine substituted at position 3 by a 2-methoxyphenoxy group. It has a role as an antidepressant and an adrenergic uptake inhibitor. It is an aromatic ether and a secondary amino compound.

Nisoxetine is a SNERI and is an antidepressant. Most activityresides in the β-isomer.

Nisoxetine was the initial phenoxyphenylpropylamine synthesized in the Lilly research laboratories during the early 1970s from the rearrangement of an oxygen atom in diphenyhydramine, a diphenylmethoxyethylamine, to a phenoxyphenylpropylamine. Nisoxetine was discovered to be a potent and very selective SNRI, with little affinity for other receptors. It underwent clinical studies as an alternative to Lilly's best-selling antidepressant, nortriptyline, but without the adverse effects associated with the tricyclic secondary amines. It was never marketed, however, because of a greater interest in developing its 4-trifluoromethyl analogue, fluoxetine, an SSRI.