Nisoxetine is a drug which inhibits the reuptake of norepinephrine

Norepinephrine

Norepinephrine is the US name for noradrenaline , a catecholamine with multiple roles including as a hormone and a neurotransmitter...

 (noradrenaline). It is a racemic

Racemic

In chemistry, a racemic mixture, or racemate , is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule. The first known racemic mixture was "racemic acid", which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid.- Nomenclature :A...

 compound with two isomer

Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...

s. Nisoxetine is not currently used in humans, but was originally researched as an antidepressant and is now widely used in scientific research as a standard selective noradrenaline reuptake inhibitor.

Synthesis

In the last step, an N-methyl group is cleaved by treatment of the intermediate with
cyanogen bromide

Cyanogen bromide

Cyanogen bromide is a pseudohalogen compound with the formula CNBr. It is a colorless solid that is widely used to modify biopolymers, fragment proteins and peptides, and synthesize other compounds.-Synthesis, basic properties, and structure:...

 followed by hydrolysis (von Braun reaction

Von Braun reaction

The Von Braun reaction is an organic reaction in which a tertiary amine reacts with cyanogen bromide to an organocyanamide. An example is the reaction of dimethyl-α-naphthylamine :...

). A recently developed modification that uses ethyl chloroformate

Ethyl chloroformate

Ethyl chloroformate is the ethyl ester of chloroformic acid. It is a reagent used in organic synthesis for the introduction of the ethyl carbamate protecting group and for the formation of carboxylic anhydrides....

 (see synthesis of atomoxetine for details).
See also the synthesis of fluoxetine

Fluoxetine

Fluoxetine is an antidepressant of the selective serotonin reuptake inhibitor class. It is manufactured and marketed by Eli Lilly and Company...

, atomoxetine and seproxetine since these are all chemically related (as well as duloxetine

Duloxetine

Duloxetine is a serotonin-norepinephrine reuptake inhibitor manufactured and marketed by Eli Lilly. It is effective for major depressive disorder and has been shown to be as effective as venlafaxine for generalized anxiety disorder...

).