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C5151

Sigma-Aldrich

3-Carbamoyl-PROXYL

Synonym(s):

3-Carbamoyl-2,2,5,5-tetramethyl-1-pyrrolidineoxy, 3-Carbamoyl-2,2,5,5-tetramethylpyrrolidin-1-yloxy, free radical

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About This Item

Empirical Formula (Hill Notation):
C9H17N2O2
CAS Number:
4399-80-8
Molecular Weight:
185.24
EC Number:
224-533-5
MDL number:
MFCD00003168
UNSPSC Code:
12352000
PubChem Substance ID:
24892761
NACRES:
NA.22

form

powder

Quality Level

100

mp

173-175 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)CC(C(N)=O)C(C)(C)N1[O]

InChI

1S/C9H17N2O2/c1-8(2)5-6(7(10)12)9(3,4)11(8)13/h6H,5H2,1-4H3,(H2,10,12)

InChI key

XNNPAWRINYCIHL-UHFFFAOYSA-N

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Application

A spin label useful for non-invasive detection of free radicals in vivo by electron spin resonance imaging.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ken-Ichiro Matsumoto et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 12(8), 2455-2462 (2006-04-28)
There is considerable research directed toward the identification and development of functional contrast agents for medical imaging that superimpose tissue biochemical/molecular information with anatomical structures. Nitroxide radicals were identified as in vivo radioprotectors. Being paramagnetic, they can provide image contrast
Guohan Hu et al.
Journal of neurosurgery, 98(2), 393-396 (2003-02-21)
Nitroxides mimic superoxide dismutase (SOD) biochemically and may prevent free radical oxidative injury in settings in which endogenous SOD is overwhelmed. The authors have previously shown the efficacy of a nitroxide, Tempol, in reducing stroke infarct size. Of the nitroxides
Th Herrling et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 63(4), 840-845 (2006-03-18)
Free radicals/reactive oxygen species (ROS) generated in skin by UV irradiation were measured by electron spin resonance (ESR). To increase the sensitivity of measurement the short life free radicals/ROS were scavenged and accumulated by using the nitroxyl probe 3-carboxy-2,2,5,5-tetrametylpyrrolidine-1-oxyl (PCA).
Tomiko Mikuni et al.
Cancer research, 64(18), 6495-6502 (2004-09-18)
Electron paramagnetic resonance imaging (EPRI) enables noninvasive spatial mapping of free radical metabolism and has recently been shown to provide in vivo physiologic information regarding alterations in the redox state of tumors and neoplastic tissues. With the use of nitroxide
Fuminori Hyodo et al.
Cancer research, 66(20), 9921-9928 (2006-10-19)
Nitroxide radicals are paramagnetic contrast agents, used in magnetic resonance imaging (MRI), that also exert antioxidant effects. Participating in cellular redox reactions, they lose their ability to provide contrast as a function of time after administration. In this study, the
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