Page last updated: 2024-12-11

1,1-diethyl-2-hydroxy-2-nitrosohydrazine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

**1,1-Diethyl-2-hydroxy-2-nitrosohydrazine** (DEHNH) is a chemical compound with the molecular formula C6H15N3O2. It is a colorless to pale yellow liquid with a pungent odor.

**Importance for Research:**

DEHNH is a **potent spin trap** and has been extensively studied in research due to its ability to trap and identify free radicals.

**Spin Trapping:**

Spin trapping is a technique used in chemistry and biology to study short-lived free radicals. Free radicals are highly reactive species with unpaired electrons. Spin traps react with free radicals to form stable, detectable adducts.

**Mechanism of Action:**

DEHNH reacts with free radicals to form **nitroxyl radicals**. Nitroxyl radicals are stable and can be detected using electron paramagnetic resonance (EPR) spectroscopy.

**Applications in Research:**

* **Free Radical Detection and Identification:** DEHNH is used to detect and identify various free radicals in biological and chemical systems. This information can be used to study the role of free radicals in various processes, such as oxidative stress, inflammation, and aging.
* **Study of Reaction Mechanisms:** DEHNH can be used to study the mechanisms of reactions involving free radicals. By trapping the radicals, researchers can determine the intermediates and products of these reactions.
* **Development of Spin Trap-Based Therapies:** DEHNH and other spin traps have been investigated for their potential therapeutic applications, particularly in diseases involving oxidative stress.

**Other Uses:**

DEHNH has also been used in research related to:

* **Organic Synthesis:** As a reagent in various organic reactions.
* **Polymer Chemistry:** As a crosslinking agent for polymers.

**Safety Considerations:**

DEHNH is a toxic compound and should be handled with caution. It is a skin and eye irritant and may be carcinogenic. Proper safety measures should be taken when working with DEHNH.

**Conclusion:**

1,1-Diethyl-2-hydroxy-2-nitrosohydrazine (DEHNH) is a versatile spin trap that has played a significant role in research related to free radical chemistry. Its ability to trap and identify free radicals has enabled scientists to gain valuable insights into the role of free radicals in various biological and chemical processes.

1,1-diethyl-2-hydroxy-2-nitrosohydrazine: RN given in first source; RN refers to ion(1-); do not confuse with DEA-NO cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6331148
CHEBI ID77713
MeSH IDM0223368

Synonyms (16)

Synonym
d-nonoate
(c2h5)2n(n(o)no)-na+
diethylamine dinitric oxide
hydrazine, 1,1-diethyl-2-hydroxy-2-nitroso-, ion(1-)
1-(n,n-diethylamino)diazen-1-ium-1,2-diolate
dea-no
86831-65-4
1,1-diethyl-2-hydroxy-2-nitrosohydrazine
1,1-diethyl-3-oxotriazan-2-olate
n-(diethylamino)-n-oxidonitrous amide
k4gi9z98kv ,
ccris 8432
unii-k4gi9z98kv
CHEBI:77713
n-(diethylamino)-n-oxido-nitrous amide
DTXSID401007136

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Intracellular killing of Leishmania parasites within activated murine macrophages is thought to result from the toxic activities of nitrogen oxidation products (referred to as NO) released by the activated cells."( Leishmania spp.: mechanisms of toxicity of nitrogen oxidation products.
Mauël, J; Ransijn, A, 1997
)
0.3

Bioavailability

ExcerptReferenceRelevance
" Since nitric oxide bioavailability is decreased in sickle cell disease and nitric oxide may inhibit leukocyte adhesion, we investigated whether stimulation of NO-signaling pathways can reduce the adhesive properties of neutrophils from sickle cell disease individuals (sickle cell diseaseneu)."( Increased adhesive properties of neutrophils in sickle cell disease may be reversed by pharmacological nitric oxide donation.
Canalli, AA; Conran, N; Costa, FF; Franco-Penteado, CF; Saad, ST, 2008
)
0.35
" These results suggest that BAY 60-2770 would be effective in the treatment of erectile dysfunction when NO bioavailability is reduced, after pelvic nerve injury, and when sGC is oxidized."( The sGC activator BAY 60-2770 has potent erectile activity in the rat.
Frink, TJ; Kadowitz, PJ; Lasker, GF; Pankey, EA; Walter, KA; Zeitzer, JR, 2013
)
0.39
"Hemolysis and consequent release of cell-free hemoglobin (CFHb) impair vascular nitric oxide (NO) bioavailability and cause oxidative and inflammatory processes."( Acute hemolytic vascular inflammatory processes are prevented by nitric oxide replacement or a single dose of hydroxyurea.
Almeida, CB; Conran, N; Costa, FF; Costa, FT; Covas, DT; Leonardo, FC; Souza, LE; Werneck, CC, 2015
)
0.42
"There is increasing evidence that the permeability of the glomerular filtration barrier (GFB) is partly regulated by a balance between the bioavailability of nitric oxide (NO) and that of reactive oxygen species (ROS)."( Nitric oxide synthase inhibition causes acute increases in glomerular permeability in vivo, dependent upon reactive oxygen species.
Dolinina, J; Öberg, CM; Rippe, A; Rippe, B; Sverrisson, K, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" To obtain dose-response curves, single doses (as boluses) of acetylcholine were infused and the maximal A-V delay induced by each dose was determined."( Endothelium-mediated negative dromotropic effects of intravascular acetylcholine.
Ceballos, G; Rubio, R, 1998
)
0.3
" The dose-response for SNAP increases in cyclic GMP was shifted nearly two orders of magnitude lower in the presence of glutathione."( Comparative effects of several nitric oxide donors on intracellular cyclic GMP levels in bovine chromaffin cells: correlation with nitric oxide production.
Ferrero, R; Miras-Portugal, MT; Rodríguez-Pascual, F; Torres, M, 1999
)
0.3
" The 4 high-dose NTG pulse injections produced a marked shift in the dose-response curves for arterial pressure depression induced by intravenous injection of the challenge doses of NTG, but did not alter hypotensive responses to sodium nitroprusside."( Effects of nitric oxide and noradrenergic activation in the posterior hypothalamus on arterial pressure tolerance to nitroglycerin in rats.
Guettler, DL; Ma, SX, 2008
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
organic anionAny organic ion with a net negative charge.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (252)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's55 (21.83)18.2507
2000's140 (55.56)29.6817
2010's55 (21.83)24.3611
2020's2 (0.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.90

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index8.90 (24.57)
Research Supply Index5.56 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.90)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (0.39%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other257 (99.61%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]