n-tert-butyl-n-[(e)-phenylmethylene]amine oxide

Names

[ Name ]:
n-tert-butyl-n-[(e)-phenylmethylene]amine oxide

[Synonym ]:
N-tert-Butyl-alpha-phenylnitrone
phenyl t-butyl nitrone
N-Benzylidene-tert-butylamine N-oxide,PBN,Phenyl N-t-butylnitrone
N-tert-Butyl-α-phenylnitrone
Styryl phenyl sulfone
2-Phenylethenyl phenyl sulfone
MFCD00008799
EINECS 222-168-6
N-Benzylidene-N-(2-methyl-2-propanyl)amine oxide
N-benzylidene-tert-butylamine N-oxide
n-tert-butyl-n-[(e)-phenylmethylene]amine oxide
N-benzylidene-t-butylamine N-oxide
PHENYL TRANS-STYRYL SULFONE 99
Azane, (1,1-dimethylethyl)(phenylmethylene)-, oxide

Biological Activity

[Description]:

N-tert-Butyl-α-phenylnitrone is a nitrone-based free radical scavenger that forms nitroxide spin adducts. N-tert-Butyl-α-phenylnitrone inhibits COX2 catalytic activity. N-tert-Butyl-α-phenylnitrone has potent ROS scavenging, anti-inflammatory, neuroprotective, anti-aging and anti-diabetic activities, and can penetrate the blood-brain barrier[1][2][3][4].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

[Target]

COX-2

Reactive oxygen species (ROS)

[In Vitro]

N-tert-Butyl-α-phenylnitrone (PBN) (25-100 µM) treatment leads to a significant decrease in 2,2'-azobis (2-amidinopropane) dihydrochloride (AAPH)-induced intracellular ROS accumulation. N-tert-Butyl-α-phenylnitrone also attenuates AAPH-induced cytotoxicity, matrix degradation, and apoptosis. N-tert-Butyl-α-phenylnitrone suppresses AAPH-induced activation of ERK/MAPK pathway. N-tert-Butyl-α-phenylnitrone has the potenial for intervertebral disc degeneration (IDD) research[1].

[In Vivo]

N-tert-Butyl-α-phenylnitrone (PBN; 100 mg/kg; intraperitoneal injection; twice a day; C57Bl/6 mice) treatment not only abolishes the LPS-induced lipid peroxidation, nitrotyrosine residue levels, and GSH depletion, but also decreases the incidence of external malformations[2]. Animal Model: C57Bl/6 mice induced by lipopolysaccharide (LPS)[2] Dosage: 100 mg/kg Administration: Intraperitoneal injection; twice a day (on gestational day 8) Result: Abolished LPS-induced lipid peroxidation, nitrotyrosine residues, and GSH depletion.

[References]

[1]. Zhenggang Zhou, et al. PBN Protects NP Cells From AAPH-induced Degenerative Changes by Inhibiting the ERK1/2 Pathway. Connect Tissue Res. 2020 Mar 30;1-10.

[2]. Lei Zhao, et al. Reactive Oxygen Species Contribute to Lipopolysaccharide-Induced Teratogenesis in Mice. Toxicol Sci. 2008 May;103(1):149-57.

[3]. Y Kotake, et al. Inhibition of NF-kappaB, iNOS mRNA, COX2 mRNA, and COX Catalytic Activity by phenyl-N-tert-butylnitrone (PBN). Biochim Biophys Acta. 1998 Nov 19;1448(1):77-84.

[4]. R A Floyd. Antioxidants, Oxidative Stress, and Degenerative Neurological Disorders. Proc Soc Exp Biol Med. 1999 Dec;222(3):236-45.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
283.3±23.0 °C at 760 mmHg

[ Melting Point ]:
71-75ºC

[ Molecular Formula ]:
C₁₁H₁₅NO

[ Molecular Weight ]:
177.243

[ Flash Point ]:
118.5±15.4 °C

[ Exact Mass ]:
177.115356

[ PSA ]:
28.75000

[ LogP ]:
1.25

[ Appearance of Characters ]:
powder | white

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.552

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: soluble

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
TX1760000

[ HS Code ]:
2925290090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2925290090

[ Summary ]:
2925290090 other imines and their derivatives; salts thereof。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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Related Compounds

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