Nisoxetine

Not to be confused with Ansoxetine.
Nisoxetine
Clinical data
Other namesLY-94939,
(±)-γ-(2-Methoxyphenoxy)-N-methyl-benzenepropanamine hydrochloride
ATC code
  • None
Legal status
Legal status
  • Never marketed
Identifiers
  • (RS)-3-(2-methoxyphenoxy)-N-methyl-3-phenylpropan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H21NO2
Molar mass271.360 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • CNCCC(C1=CC=CC=C1)OC2=CC=CC=C2OC
  • InChI=1S/C17H21NO2/c1-18-13-12-15(14-8-4-3-5-9-14)20-17-11-7-6-10-16(17)19-2/h3-11,15,18H,12-13H2,1-2H3 checkY
  • Key:ITJNARMNRKSWTA-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Nisoxetine, originally synthesized in the Lilly research laboratories during the early 1970s, is a potent and selective inhibitor for the reuptake of norepinephrine (noradrenaline) into synapses. It currently has no clinical applications in humans,[1] although it was originally researched as an antidepressant. Nisoxetine is now widely used in scientific research as a standard selective norepinephrine reuptake inhibitor.[2] It has been used to research obesity and energy balance,[3] and exerts some local analgesia effects.[4]

Researchers have attempted to use a carbon-labeled form of nisoxetine for positron emission tomography (PET) imaging of the norepinephrine transporter (NET), with little success.[5] However, it seems that tritium labeled nisoxetine (3H-nisoxetine, 3H-NIS) is a useful radioligand for labeling norepinephrine uptake sites in vitro, which nisoxetine and other antagonists for NET are able to inhibit.[6]

  1. ^ Kelwala S, Stanley M, Gershon S (May 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. doi:10.1016/0024-3205(92)90236-I. PMID 1501510.
  3. ^ Billes SK, Cowley MA (April 2007). "Inhibition of dopamine and norepinephrine reuptake produces additive effects on energy balance in lean and obese mice". Neuropsychopharmacology. 32 (4): 822–34. doi:10.1038/sj.npp.1301155. PMID 16841072.
  4. ^ Chen YW, Chu CC, Chen YC, Wang JJ, Hung CH, Shao DZ (January 2012). "Nisoxetine produces local but not systemic analgesia against cutaneous nociceptive stimuli in the rat". European Journal of Pharmacology. 675 (1–3): 22–5. doi:10.1016/j.ejphar.2011.11.042. PMID 22166377.
  5. ^ Nguyen VL, Pichika R, Bhakta PH, Kant R, Mukherjee J (February 2010). "(R)-N-Methyl-3-(3'-[F]fluoropropyl)phenoxy)-3-phenylpropanamine (F-MFP3) as a potential PET imaging agent for norepinephrine transporter". Journal of Labelled Compounds & Radiopharmaceuticals. 53 (4): 172–177. doi:10.1002/jlcr.1744. PMC 2873203. PMID 20495670.
  6. ^ Tejani-Butt SM, Brunswick DJ, Frazer A (November 1990). "[3H]nisoxetine: a new radioligand for norepinephrine uptake sites in brain". European Journal of Pharmacology. 191 (2): 239–43. doi:10.1016/0014-2999(90)94155-Q. PMID 2086242.