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-
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 |
|---|---|---|
| Halothane-induced liver injury as a consequence of enhanced microsomal lipid peroxidation in guinea pigs. | 1988 Aug |
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| Role of oxygen free radicals in cocaine-induced vascular disruption in mice. | 1994 Mar |
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| Evaluation of the effects of alpha-phenyl-N-tert-butyl nitrone pretreatment on the neurobehavioral effects of methamphetamine. | 2000 Aug 18 |
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| 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 Aug |
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| Embryonic arrhythmia by inhibition of HERG channels: a common hypoxia-related teratogenic mechanism for antiepileptic drugs? | 2002 May |
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| Misregulation of gene expression in the redox-sensitive NF-kappab-dependent limb outgrowth pathway by thalidomide. | 2002 Oct |
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| An inducible nitric oxide synthase-luciferase reporter system for in vivo testing of anti-inflammatory compounds in transgenic mice. | 2003 Jun 15 |
|
| Reactive oxygen species contribute to lipopolysaccharide-induced teratogenesis in mice. | 2008 May |
|
| Persistent pain is dependent on spinal mitochondrial antioxidant levels. | 2009 Jan 7 |
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.
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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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admin on Fri Dec 15 18:20:33 GMT 2023 , Edited by admin on Fri Dec 15 18:20:33 GMT 2023
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SUBSTANCE RECORD
