A5581

Sigma-Aldrich

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

≥95%

Synonym(s):
DETA NONOate, NOC-18, 2,2′-(Hydroxynitrosohydrazino)bis-ethanamine
Empirical Formula (Hill Notation):
C4H13N5O2
CAS Number:
Molecular Weight:
163.18
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

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.

Packaging

50 mg in poly bottle
10 mg in glass insert

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

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis
Certificate of Origin
Mitochondrial Complex I Reversible S-Nitrosation Improves Bioenergetics and Is Protective in Parkinson's Disease
Milanese C, et al.
Antioxidants & Redox Signaling, 28(1), 44-61 (2018)
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...
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...
Aizhou Wang et al.
Transfusion, 59(1), 359-370 (2018-11-18)
Hemoglobin-based oxygen carriers (HBOCs) are potential alternatives to red blood cells in transfusions. Clinical trials using early versions of HBOCs noted adverse effects that appeared to result from removal of the vasodilator nitric oxide (NO). Previous reports suggest that size-enlarged...
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...
Articles
Nitric oxide (NO) as a signal transporter in neurons, endothelial cells and in the immune system.
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