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A5581

Sigma-Aldrich

3,3-Bis(aminoethyl)-1-hydroxy-2-oxo-1-triazene

≥95%

Synonym(s):

2,2′-(Hydroxynitrosohydrazino)bis-ethanamine, DETA NONOate, NOC-18

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About This Item

Empirical Formula (Hill Notation):
C4H13N5O2
CAS Number:
146724-94-9
Molecular Weight:
163.18
MDL number:
MFCD00278808
UNSPSC Code:
12352200
PubChem Substance ID:
24890998
NACRES:
NA.77

Assay

≥95%

form

powder

solubility

0.1 M NaOH: 10 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

NCCN(CCN)\[N+]([O-])=N/O

InChI

1S/C4H13N5O2/c5-1-3-8(4-2-6)9(11)7-10/h10H,1-6H2/b9-7+

InChI key

YNRCBOXEDICOIX-VQHVLOKHSA-N

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Application

3,3-Bis(aminoethyl)-1-hydroxy-2-oxo-1-triazene has been used as a nitric oxide donor supplement for neuronal culture. It has also been used as a nitric oxide donor to study the effects of protein S-nitrosation (SNO) after nitrite treatment.
3,3-Bis(aminoethyl)-1-hydroxy-2-oxo-1-triazene has been used to provide insight into the molecular pathways that may contribute to the beneficial effects of nicorandil in the cardiovascular system. 3,3-Bis(aminoethyl)-1-hydroxy-2-oxo-1-triazene causes the release of nitric oxide spontaneously in a rate-controlled manner.

Biochem/physiol Actions

3,3-Bis(aminoethyl)-1-hydroxy-2-oxo-1-triazene is a long-acting nitric oxide donor. It might exhibit nociceptive effects in rats.

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H242

Hazard Classifications

Self-react. C

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

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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Shumin Tan et al.
PLoS pathogens, 9(4), e1003282-e1003282 (2013-04-18)
The ability of Mycobacterium tuberculosis (Mtb) to thrive in its phagosomal niche is critical for its establishment of a chronic infection. This requires that Mtb senses and responds to intraphagosomal signals such as pH. We hypothesized that Mtb would respond
Iris C Vermeulen Windsant et al.
Critical care (London, England), 16(3), R95-R95 (2012-05-26)
The increasing number of reports on the relation between transfusion of stored red blood cells (RBCs) and adverse patient outcome has sparked an intense debate on the benefits and risks of blood transfusions. Meanwhile, the pathophysiological mechanisms underlying this postulated
Natalia Rios et al.
Free radical biology & medicine, 101, 284-295 (2016-09-20)
The specific and sensitive detection of peroxynitrite (ONOO-/ONOOH) in biological systems is a great challenge due to its high reactivity towards several biomolecules. Herein, we validated the advantages of using fluorescein-boronate (Fl-B) as a highly sensitive fluorescent probe for the
Keigo Ueno et al.
PloS one, 6(9), e24759-e24759 (2011-09-21)
The intestinal resident Candida glabrata opportunistically infects humans. However few genetic factors for adaptation in the intestine are identified in this fungus. Here we describe the C. glabrata CYB2 gene encoding lactate dehydrogenase as an adaptation factor for survival in
A new nitric oxide donor, NOC-18, exhibits a nociceptive effect in the rat formalin model
Shibuta S, et al.
Journal of the Neurological Sciences, 141(1), 1-5 (1996)
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