PHENYL-N-TERT-BUTYLNITRONE

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

Structure Search

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-

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21785167 | https://www.ncbi.nlm.nih.gov/pubmed/20068451

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

Targets

Primary Target	Pharmacology	Condition	Potency
Retinoid isomerohydrolase 3 Target ID: Q16518 Gene ID: 6121.0 Gene Symbol: RPE65 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21785167	Inhibitor 8297		0.1 mM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chemotherapy-induced neuropathic pain 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068451	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Halothane-induced liver injury as a consequence of enhanced microsomal lipid peroxidation in guinea pigs.	1988 Aug	3187193
Role of oxygen free radicals in cocaine-induced vascular disruption in mice.	1994 Mar	8059426
Evaluation of the effects of alpha-phenyl-N-tert-butyl nitrone pretreatment on the neurobehavioral effects of methamphetamine.	2000 Aug 18	10983851
Spin trapping agent phenyl-N-tert-butylnitrone prevents diisopropylphosphorofluoridate-induced excitotoxicity in skeletal muscle of the rat.	2000 Jan 7	10643792
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	11570692
p38 activation is required upstream of potassium current enhancement and caspase cleavage in thiol oxidant-induced neuronal apoptosis.	2001 May 15	11331359
Embryonic arrhythmia by inhibition of HERG channels: a common hypoxia-related teratogenic mechanism for antiepileptic drugs?	2002 May	12027905
Misregulation of gene expression in the redox-sensitive NF-kappab-dependent limb outgrowth pathway by thalidomide.	2002 Oct	12242718
An inducible nitric oxide synthase-luciferase reporter system for in vivo testing of anti-inflammatory compounds in transgenic mice.	2003 Jun 15	12794164
Nitric oxide produced by inducible nitric oxide synthase is associated with mammary tumorigenesis in irradiated rats.	2005 Feb	15631943
The role of reactive oxygen species in capsaicin-induced mechanical hyperalgesia and in the activities of dorsal horn neurons.	2007 Dec 15	17379413
Reactive oxygen species contribute to lipopolysaccharide-induced teratogenesis in mice.	2008 May	18281254
1Alpha,25-dihydroxyvitamin D3 attenuates cyanide-induced neurotoxicity by inhibiting uncoupling protein-2 up-regulation.	2008 May 1	18183618
Persistent pain is dependent on spinal mitochondrial antioxidant levels.	2009 Jan 7	19129394
Reactive oxygen species mediate TNFR1 increase after TRPV1 activation in mouse DRG neurons.	2009 Jun 17	19531269
Protection of DFP-induced oxidative damage and neurodegeneration by antioxidants and NMDA receptor antagonist.	2009 Oct 15	19615394
Manganese inhibits the ability of astrocytes to promote neuronal differentiation.	2009 Oct 15	19524604
Complement component 3 inhibition by an antioxidant is neuroprotective after cerebral ischemia and reperfusion in mice.	2013 Feb	23199288
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 Feb	25354798
Enhanced NADPH oxidases and reactive oxygen species in the mechanism of methanol-initiated protein oxidation and embryopathies in vivo and in embryo culture.	2016 Mar	25726414

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Name

Type

Language

PHENYL-N-TERT-BUTYLNITRONE

Systematic Name

English

2-METHYL-N-(PHENYLMETHYLENE)-2-PROPANAMINE N-OXIDE

Systematic Name

English

PHENYL T-BUTYLNITRONE [INCI]

Common Name

English

BENZYLIDENE-TERT-BUTYLAMINE OXIDE

Systematic Name

English

N-TERT-BUTYL-.ALPHA.-PHENYLNITRONE

Common Name

English

2-PROPANAMINE, 2-METHYL-N-(PHENYLMETHYLENE)-, N-OXIDE, (N(Z))-

Common Name

English

PBN [MI]

Common Name

English

(Z)-N-(TERT-BUTYL)-1-PHENYLMETHANIMINE OXIDE

Common Name

English

PHENYL T-BUTYLNITRONE

Official Name

English

N-TERT-BUTYL PHENYL NITRONE

Systematic Name

English

Code System Code Type Description

CAS

3376-24-7