Structure via PubChem · Public domain (PubChem)
nisoxetine
Sign in to saveAlso known as DL-N-Methyl-3-(o-methoxyphenoxy)-N-methyl-3-phenylpropylamine, N-Methyl-gamma-(2-methylphenoxy)phenylpropanolamine, 3-(o-Methoxyphenoxy)-N-methyl-3-phenylpropylamine, 3-(2-Methoxyphenoxy)-N-methyl-3-phenylpropylamine
Nisoxetine (developmental code name LY-94939), 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, although it was originally researched as an antidepressant. Nisoxetine is now widely used in scientific research as a standard selective norepinephrine reuptake inhibitor. It has been used to research obesity and energy balance, and exerts some local analgesia effects.
Chemical data
- Formula
- C17H21NO2
- Molecular weight
- 271.35 g/mol
- IUPAC name
- 3-(2-methoxyphenoxy)-N-methyl-3-phenylpropan-1-amine
- SMILES
- CNCCC(C1=CC=CC=C1)OC2=CC=CC=C2OC
- InChIKey
- ITJNARMNRKSWTA-UHFFFAOYSA-N
- XLogP
- 3.1
- Polar surface area
- 30.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 271.157229
Show 4 more facts
- chemical formula
- C₁₇H₂₁NO₂
- canonical SMILES
- CNCCC(C1=CC=CC=C1)OC2=CC=CC=C2OC
- World Health Organisation international non-proprietary name
- nisoxetine
- Commons category
- Nisoxetine
via Wikidata · CC0
~14 min read
Encyclopedic overview
11 sectionsContents
- History
- Research
- Obesity
- Analgesia effects
- <sup>3</sup>H-nisoxetine
- NET imaging using PET
- Pharmacological properties
- Adverse effects
- Chemical properties
- See also
- References
Nisoxetine (developmental code name LY-94939), 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, although it was originally researched as an antidepressant. Nisoxetine is now widely used in scientific research as a standard selective norepinephrine reuptake inhibitor. It has been used to research obesity and energy balance, and exerts some local analgesia effects.
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. 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.
Excerpted from Wikipedia’s “nisoxetine” article, available under the CC BY-SA 4.0 licence.