Nisoxetine

Nisoxetine
Nisoxetine
Systematic (IUPAC) name
(RS)-3-(2-methoxyphenoxy)-N-methyl-3-phenylpropan-1-amine
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 57226-61-6 YesY
ATC code None
PubChem CID 4500
UNII 17NV064B2D N
KEGG D05173 YesY
ChEMBL CHEMBL295467 N
Chemical data
Formula C17H21NO2 
Mol. mass 271.354 g/mol
 N(what is this?)  (verify)

Nisoxetine (LY-94939) is a drug which inhibits the reuptake of norepinephrine (noradrenaline). It is a racemic compound with two isomers. Nisoxetine is not currently used in humans,[1] but was originally researched as an antidepressant and is now widely used in scientific research as a standard selective noradrenaline reuptake inhibitor.[2]

Synthesis

In the last step, an N-methyl group is cleaved by treatment of the intermediate with cyanogen bromide followed by hydrolysis (von Braun reaction).[3] A recently developed modification that uses ethyl chloroformate (see synthesis of atomoxetine for details).

Nisoxetine synthesis.png

See also the synthesis of fluoxetine, atomoxetine and seproxetine since these are all chemically related (as well as duloxetine).

References

  1. ^ Kelwala, S; Stanley, M; Gershon, S (1983). "History of antidepressants: Successes and failures". The Journal of clinical psychiatry 44 (5 Pt 2): 40–8. PMID 6222036. 
  2. ^ Graham, D; Langer, SZ (1992). "Advances in sodium-ion coupled biogenic amine transporters". Life sciences 51 (9): 631–45. PMID 1501510. 
  3. ^ Molloy, B. B.; Schmiegel, K. K.; German Patent, 1975, DE 2500110 

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