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163945

Sigma-Aldrich

4-Amino-TEMPO, free radical

97%

Synonym(s):

4-Amino-2,2,6,6-tetramethylpiperidine-1-oxyl, 4-Amino-2,2,6,6-tetramethylpiperidinyloxy, free radical, 4-Amino-TEMPO

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About This Item

Empirical Formula (Hill Notation):
C9H19N2O
CAS Number:
14691-88-4
Molecular Weight:
171.26
Beilstein:
3933966
EC Number:
238-738-2
MDL number:
MFCD00006479
UNSPSC Code:
12352000
PubChem Substance ID:
24850044
NACRES:
NA.22

Quality Level

200

Assay

97%

form

solid

mp

~0 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C9H19N2O/c1-8(2)5-7(10)6-9(3,4)11(8)12/h7H,5-6,10H2,1-4H3

InChI key

XUXUHDYTLNCYQQ-UHFFFAOYSA-N

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Application

Useful spin label for studying biological systems, polymers, and as a building block for more elaborate spin labels.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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N Naber et al.
Biochemistry, 33(13), 3855-3861 (1994-04-05)
Each actin molecule contains a nucleotide, tightly bound in a deep cleft that divides the molecule. To probe conformational changes within this region of the molecule, we have incorporated two spin label analogues of ATP into actin. In both analogs
Spin-Labeled Dendrimers in EPR Imaging with Low Molecular Weight Nitroxides.
Alexander T. Yordanov et al.
Angewandte Chemie (International ed. in English), 40(14), 2690-2692 (2001-07-18)
Jianfei Jiang et al.
The Journal of pharmacology and experimental therapeutics, 320(3), 1050-1060 (2006-12-21)
Suppression of mitochondrial production of reactive oxygen species is a promising strategy against intrinsic apoptosis typical of degenerative diseases. Stable nitroxide radicals such as 4-hydroxy-2,2,6,6-tetramethyl piperidine-1-oxyl (TEMPOL) and its analogs combine several important features, including recycleability, electron acceptance from respiratory
D A Hall et al.
Science (New York, N.Y.), 276(5314), 930-932 (1997-05-09)
Large dynamic nuclear polarization signal enhancements (up to a factor of 100) were obtained in the solid-state magic-angle spinning nuclear magnetic resonance (NMR) spectra of arginine and the protein T4 lysozyme in frozen glycerol-water solutions with the use of dynamic
Veronica Wasserman et al.
Langmuir : the ACS journal of surfaces and colloids, 23(4), 1937-1947 (2007-02-07)
The piperidine nitroxide tempamine (TMN) is a cell-permeable, stable radical having antioxidant, anticancer, and proapoptotic and/or pronecrotic activities, as was demonstrated by us in cell cultures. We also demonstrated synergism between TMN and doxorubicin in doxorubicin-sensitive and doxorubicin-resistant cell lines.
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