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Merck
CN

155683

Sigma-Aldrich

3-Carbamoyl-2,2,5,5-tetramethyl-3-pyrrolin-1-oxyl

99%

Synonym(s):

2,2,5,5-Tetramethyl-3-carbamido-3-pyrroline-1-oxyl, 3-Carbamoyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy

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About This Item

Empirical Formula (Hill Notation):
C9H15N2O2
CAS Number:
Molecular Weight:
183.23
Beilstein:
4138020
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Assay

99%

form

solid

mp

197-200 °C (lit.)

functional group

amide

storage temp.

2-8°C

SMILES string

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

InChI

1S/C9H15N2O2/c1-8(2)5-6(7(10)12)9(3,4)11(8)13/h5H,1-4H3,(H2,10,12)

InChI key

RUEXQFPLRRIFTI-UHFFFAOYSA-N

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Application

3-Carbamoyl-2,2,5,5-tetramethyl-3-pyrrolin-1-oxyl is a nitroxide radical that can be used:
  • As a spin probe in the study of simulation of Overhauser dynamic nuclear polarization signal.
  • As a starting material in the synthesis of nitroxide based polyethers possessing charge transport properties.
  • As a nitroxide imaging probe applicable for EPR imaging of brain diseases in animal models.

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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F Gomi et al.
Life sciences, 52(25), 2027-2033 (1993-01-01)
After the nitroxyl radical 3-carbamoyl-2,2,5,5-tetramethyl-1-pyrrolidinyloxyl (carbamoylPROXYL) was intraperitoneally administered to mice, the time courses of changes in the intensity of signals in L-band electron spin resonance spectra from their brains were measured. The spin clearance rate of old, ad libitum-fed
Ichiro Koshiishi et al.
The Biochemical journal, 395(2), 303-309 (2006-01-07)
Lipoxygenases have been proposed to be a possible factor that is responsible for the pathology of certain diseases, including ischaemic injury. In the peroxidation process of linoleic acid by lipoxygenase, the E,Z-linoleate allyl radical-lipoxygenase complex seems to be generated as
B H Robinson et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 138(2), 210-219 (1999-05-26)
This work demonstrates that homogeneous linewidths can be extracted from continuous wave electron paramagnetic resonance spectra and that they quantitatively agree with the predictions of existing relaxation theory. We suggest that relaxation theory can be used to predict experimental lineshapes
Hiroshi Hirata et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 190(1), 124-134 (2007-11-17)
A loop resonator was developed for 300 MHz continuous-wave electron paramagnetic resonance (CW-EPR) spectroscopy and imaging in live rats. A single-turn loop (55 mm in diameter) was used to provide sufficient space for the rat body. Efficiency for generating a
Synthesis and charge transport properties of redox-active nitroxide polyethers with large site density
Oyaizu K, et al.
Macromolecules, 43(24), 10382-10389 (2010)

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