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B2050

Sigma-Aldrich

3-Bromo-7-nitroindazole

≥98% (TLC), powder

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About This Item

Empirical Formula (Hill Notation):
C7H4BrN3O2
CAS Number:
74209-34-0
Molecular Weight:
242.03
MDL number:
MFCD00159910
UNSPSC Code:
12352202
PubChem Substance ID:
24278258

Assay

≥98% (TLC)

form

powder

color

light yellow

solubility

ethanol: 25 mg/mL
DMSO: soluble

storage temp.

2-8°C

SMILES string

[O-][N+](=O)c1cccc2c(Br)n[nH]c12

InChI

1S/C7H4BrN3O2/c8-7-4-2-1-3-5(11(12)13)6(4)9-10-7/h1-3H,(H,9,10)

InChI key

NFSTZPMYAZRZPC-UHFFFAOYSA-N

Biochem/physiol Actions

A potent inhibitor of all nitric oxide synthase isoforms. Shows substantial neuroprotective effects against hypoxic damage (such as stroke) and animal models of Parkinson′s disease. Crystallographic studies show that inhibition of eNOS is due to an induced cascade of conformation changes that ultimately dissociates the tetrahydrobiopterin cofactor from the enzyme.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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N E Stagliano et al.
Brain research, 759(1), 32-40 (1997-06-06)
Although nitric oxide (NO) has been shown to play an important role in the pathophysiology of cerebral ischemia, its contribution to the pathogenesis of experimentally induced thromboembolic stroke is unknown. In this study, we pharmacologically manipulated NO levels in the
Saurav Bhowmick et al.
Free radical biology & medicine, 113, 203-211 (2017-10-01)
Cerebral ischemia-reperfusion (I/R) injury initiates a cascade of events, generating nitric oxide (NO) and superoxide(O
Carmen R Sunico et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(47), E7564-E7571 (2016-11-09)
Recent studies have pointed to protein S-nitrosylation as a critical regulator of cellular redox homeostasis. For example, S-nitrosylation of peroxiredoxin-2 (Prx2), a peroxidase widely expressed in mammalian neurons, inhibits both enzymatic activity and protective function against oxidative stress. Here, using
M J O'Neill et al.
Brain research, 760(1-2), 170-178 (1997-06-20)
Recent studies have shown that the novel antioxidant LY231617 protects against ischaemia-induced neuronal damage in rat models of global cerebral ischaemia. In the present studies we have examined the effects of LY231617 in the gerbil model of global cerebral ischaemia.
P A Bland-Ward et al.
Life sciences, 57(11), PL131-PL135 (1995-01-01)
The effect of 7-nitro indazole (7-NI) and a range of substituted indazole derivatives on nitric oxide synthase (NOS) enzyme activity in homogenates of rat cerebellum, bovine endothelial cells and lung from endotoxin-pretreated rats was investigated. 3-bromo 7-nitro indazole was either
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