Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H15NO |
| Molecular Weight | 177.2429 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)[N+](\[O-])=C\C1=CC=CC=C1
InChI
InChIKey=IYSYLWYGCWTJSG-XFXZXTDPSA-N
InChI=1S/C11H15NO/c1-11(2,3)12(13)9-10-7-5-4-6-8-10/h4-9H,1-3H3/b12-9-
| Molecular Formula | C11H15NO |
| Molecular Weight | 177.2429 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
Phenyl N-tert-butylnitrone (also known as α-Phenyl-N-tert-butylnitrone or PBN), a free radical spin trap, protects retinas against light-induced neurodegeneration by means of inhibition of RPE65 catalytic action. In addition, in experiments on rodents was shown, that PBN reduces mechanical allodynia in chemotherapy-induced neuropathic pain.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Enhanced NADPH oxidases and reactive oxygen species in the mechanism of methanol-initiated protein oxidation and embryopathies in vivo and in embryo culture. | 2016-03 |
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| Deficient DNA repair exacerbates ethanol-initiated DNA oxidation and embryopathies in ogg1 knockout mice: gender risk and protection by a free radical spin trapping agent. | 2016-02 |
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| Complement component 3 inhibition by an antioxidant is neuroprotective after cerebral ischemia and reperfusion in mice. | 2013-02 |
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| Phenyl N-tert-butylnitrone, a free radical scavenger, reduces mechanical allodynia in chemotherapy-induced neuropathic pain in rats. | 2010-02 |
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| Protection of DFP-induced oxidative damage and neurodegeneration by antioxidants and NMDA receptor antagonist. | 2009-10-15 |
|
| Manganese inhibits the ability of astrocytes to promote neuronal differentiation. | 2009-10-15 |
|
| Reactive oxygen species mediate TNFR1 increase after TRPV1 activation in mouse DRG neurons. | 2009-06-17 |
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| Persistent pain is dependent on spinal mitochondrial antioxidant levels. | 2009-01-07 |
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| Oxidative stress in the spinal cord is an important contributor in capsaicin-induced mechanical secondary hyperalgesia in mice. | 2008-09-15 |
|
| 1Alpha,25-dihydroxyvitamin D3 attenuates cyanide-induced neurotoxicity by inhibiting uncoupling protein-2 up-regulation. | 2008-05-01 |
|
| Reactive oxygen species contribute to lipopolysaccharide-induced teratogenesis in mice. | 2008-05 |
|
| The role of reactive oxygen species in capsaicin-induced mechanical hyperalgesia and in the activities of dorsal horn neurons. | 2007-12-15 |
|
| Reactive oxygen species (ROS) are involved in enhancement of NMDA-receptor phosphorylation in animal models of pain. | 2007-10 |
|
| Perinatal lipopolysaccharide exposure downregulates pregnane X receptor and Cyp3a11 expression in fetal mouse liver. | 2005-09 |
|
| Nitric oxide produced by inducible nitric oxide synthase is associated with mammary tumorigenesis in irradiated rats. | 2005-02 |
|
| Vitamin E, aging and Leydig cell steroidogenesis. | 2005-01-27 |
|
| A novel hypothesis for thalidomide-induced limb teratogenesis: redox misregulation of the NF-kappaB pathway. | 2004-02 |
|
| An inducible nitric oxide synthase-luciferase reporter system for in vivo testing of anti-inflammatory compounds in transgenic mice. | 2003-06-15 |
|
| Misregulation of gene expression in the redox-sensitive NF-kappab-dependent limb outgrowth pathway by thalidomide. | 2002-10 |
|
| Embryonic arrhythmia by inhibition of HERG channels: a common hypoxia-related teratogenic mechanism for antiepileptic drugs? | 2002-05 |
|
| Nitric oxide modulates high-energy phosphates in brain regions of rats intoxicated with diisopropylphosphorofluoridate or carbofuran: prevention by N-tert-butyl-alpha-phenylnitrone or vitamin E. | 2001-08 |
|
| p38 activation is required upstream of potassium current enhancement and caspase cleavage in thiol oxidant-induced neuronal apoptosis. | 2001-05-15 |
|
| Evaluation of the effects of alpha-phenyl-N-tert-butyl nitrone pretreatment on the neurobehavioral effects of methamphetamine. | 2000-08-18 |
|
| Spin trapping agent phenyl-N-tert-butylnitrone prevents diisopropylphosphorofluoridate-induced excitotoxicity in skeletal muscle of the rat. | 2000-01-07 |
|
| Role of oxygen free radicals in cocaine-induced vascular disruption in mice. | 1994-03 |
|
| Protective effects of spin-trapping agents on adriamycin-induced cardiotoxicity in isolated rat atria. | 1991 |
|
| Halothane-induced liver injury as a consequence of enhanced microsomal lipid peroxidation in guinea pigs. | 1988-08 |
Sample Use Guides
in rats: dose of 50 mg/kg α-Phenyl-N-tert-butylnitrone (PBN) dissolved in saline was chosen for intraperitoneal injection in the rats in the treatment group. An equal volume of saline was injected into control rats
Route of Administration:
Intraperitoneal
It has been shown that conversion of all-trans-retinyl ester to 11-cis-retinol catalyzed by RPE65 is a rate-limiting step in the visual cycle. To determine the direct inhibition of α-Phenyl-N-tert-butylnitrone (PBN) on isomerohydrolase activity of RPE65, it was used an in vitro isomerohydrolase assay. Incubation of the rat RPE microsomes with all-trans-[3H]retinol resulted in formation of all-trans-retinyl esters and significant amounts of 11-cis-[3H]retinol, as shown by the HPLC elution. The addition of 1 mM PBN to the reaction resulted in almost complete inhibition of 11-cis-retinol generation, whereas the production of retinyl ester did not decrease, suggesting that LRAT was not inhibited by PBN. The PBN (range of concentration 0-6 mM) inhibition of isomerohydrolase activity was concentration-dependent with an apparent IC50 of 0.1 mM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:10:57 GMT 2025
by
admin
on
Mon Mar 31 19:10:57 GMT 2025
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| Record UNII |
3I91332OPG
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| Record Status |
Validated (UNII)
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3376-24-7
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NON-SPECIFIC STEREOCHEMISTRY | |||
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DTXSID8040648
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3I91332OPG
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m8432
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222-168-6
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C029217
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52392-70-8
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638877
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