Compounds > ethyl nitrite
Page last updated: 2024-11-05

ethyl nitrite

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

Ethyl nitrite is a volatile, yellowish liquid with a characteristic fruity odor. It is prepared by reacting ethanol with sodium nitrite in the presence of sulfuric acid. Ethyl nitrite is primarily known for its use as a vasodilator, meaning it widens blood vessels. This effect is due to the release of nitric oxide (NO) when ethyl nitrite is metabolized in the body. It is primarily used in the treatment of angina pectoris, a condition characterized by chest pain caused by reduced blood flow to the heart. Historically, ethyl nitrite was also used as an inhalant to treat asthma and as a diuretic. However, these uses have been largely discontinued due to the development of safer and more effective alternatives. Research on ethyl nitrite focuses on its potential applications in various medical fields, including cardiovascular disease treatment, anti-inflammatory therapies, and even anti-cancer research. For instance, studies explore its role in regulating blood pressure, improving blood flow, and its potential to induce apoptosis (programmed cell death) in cancer cells. The study of ethyl nitrite continues due to its unique properties and the potential for its use in developing novel therapies.'

Cross-References

ID SourceID
PubMed CID8026
CHEMBL ID1551365
CHEBI ID173313
MeSH IDM0101894

Synonyms (36)

Synonym
CHEBI:173313
nitrous ether
nitrous ethyl ether
ethyl nitrite
ethylester kyseliny dusite [czech]
einecs 203-722-6
fema no. 2446
un1194
ai3-25307
hyponitrous ether
hsdb 416
nitrosyl ethoxide
brn 1699562
nitrous acid, ethyl ester
ethyl-nitrite-
NCGC00166242-01
109-95-5
E0152
nitrous acid ethyl ester
A802116
ethylester kyseliny dusite
8c7cj279rv ,
unii-8c7cj279rv
cas-109-95-5
tox21_112368
dtxcid7026574
dtxsid9046574 ,
CHEMBL1551365
ethyl nitrite [mi]
ethyl nitrite [hsdb]
ethyl nitrite [fhfi]
ethyl nitrite [mart.]
ethylnitrite
fema 2446
Q3342209
ethyl nitrite (mart.)

Research Excerpts

Overview

Ethyl nitrite (ENO) is a gas with chemical properties favoring SNO formation. It is a new metabolite of ethanol in vivo.

ExcerptReferenceRelevance
"Ethyl nitrite (ENO) is a gas with chemical properties favoring SNO formation."( Protection from lipopolysaccharide-induced lung injury by augmentation of airway S-nitrosothiols.
Auten, RL; Foster, WM; Kelleher, ZT; Marshall, HE; Potts, EN; Stamler, JS, 2009)		1.07
"Ethyl nitrite is a new metabolite of ethanol in vivo."( Formation of ethyl nitrite in vivo after ethanol administration.
Bludeau, P; Deitrich, RA; Deng, XS, )		1.22

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51

Dosage Studied

ExcerptRelevanceReference
"A preliminary dosing study identified 20 ppm ethyl nitrite as a concentration that produced a 4-fold increase in S-nitrosylated hemoglobin concentration with no increase in methemoglobin."( Pharmacologically augmented S-nitrosylated hemoglobin improves recovery from murine subarachnoid hemorrhage.
Auten, RL; Demchenko, IT; Piantadosi, CA; Reynolds, JD; Sheng, H; Stamler, JS; Warner, DS, 2011)		0.63
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
nitroso compoundCompounds having the nitroso group, -NO, attached to carbon, or to another element, most commonly nitrogen or oxygen.
[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]

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency0.04990.000811.382244.6684AID686978; AID686979
estrogen nuclear receptor alphaHomo sapiens (human)Potency33.49150.000229.305416,493.5996AID743079
histone-lysine N-methyltransferase 2A isoform 2 precursorHomo sapiens (human)Potency35.48130.010323.856763.0957AID2662
gemininHomo sapiens (human)Potency0.94410.004611.374133.4983AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (8.70)18.7374
1990's0 (0.00)18.2507
2000's11 (47.83)29.6817
2010's8 (34.78)24.3611
2020's2 (8.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 41.71

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index41.71 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index4.27 (4.65)
Search Engine Demand Index61.55 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (41.71)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (8.00%)5.53%
Reviews1 (4.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (88.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetaldehyde
Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.		3.2310aldehydecarcinogenic agent;
EC 3.5.1.4 (amidase) inhibitor;
electron acceptor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
mutagen;
oxidising agent;
Saccharomyces cerevisiae metabolite;
teratogenic agent
nitrates
Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.		2.1110monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species
nitrites
Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)		9.82222monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species		human metabolite
diethyl sulfate
diethyl sulfate: RN given refers to parent cpd; structure. diethyl sulfate : The diethyl ester of sulfuric acid.		3.2310alkyl sulfatealkylating agent;
apoptosis inducer;
carcinogenic agent;
mutagen
caffeic acid
trans-caffeic acid : The trans-isomer of caffeic acid.		7.0510caffeic acidgeroprotector;
mouse metabolite
ethyl glucuronide
ethyl glucuronide: structure given in first source; RN given refers to (BETA-D)-isomer. ethyl glucuronide : A beta-D-glucosiduronic acid that is the ethyl derivative of beta-D-glucuronic acid.		3.2310beta-D-glucosiduronic acidhuman urinary metabolite
phosphatidylethanol
phosphatidylethanol: formed in rat brain by phospholipase D. phosphatidylethanol : A glycerophospholipid that is the monoethyl ester of any phosphatidic acid.		3.2310
cyclic gmp
Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.		2.31103',5'-cyclic purine nucleotide;
guanyl ribonucleotide		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
allopurinol
Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.		3.2310nucleobase analogue;
organic heterobicyclic compound		antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
ConditionIndicatedRelationship StrengthStudiesTrials
Anoxemia
[description not available]		07.79101
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		05.0631
Hypoxia
Sub-optimal OXYGEN levels in the ambient air of living organisms.		07.79101
Muscle Relaxation
That phase of a muscle twitch during which a muscle returns to a resting position.		02.1110
Pulmonary Hypertension
[description not available]		07.97111
Acute Disease
Disease having a short and relatively severe course.		02.0410
Hypertension, Pulmonary
Increased VASCULAR RESISTANCE in the PULMONARY CIRCULATION, usually secondary to HEART DISEASES or LUNG DISEASES.		07.97111
Lung Injury, Acute
[description not available]		02.9610
Acute Lung Injury
A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).		02.9610
Pneumoperitoneum
A condition with trapped gas or air in the PERITONEAL CAVITY, usually secondary to perforation of the internal organs such as the LUNG and the GASTROINTESTINAL TRACT, or to recent surgery. Pneumoperitoneum may be purposely introduced to aid radiological examination.		02.0510
Hemorrhage, Subarachnoid
[description not available]		02.0610
Subarachnoid Hemorrhage
Bleeding into the intracranial or spinal SUBARACHNOID SPACE, most resulting from INTRACRANIAL ANEURYSM rupture. It can occur after traumatic injuries (SUBARACHNOID HEMORRHAGE, TRAUMATIC). Clinical features include HEADACHE; NAUSEA; VOMITING, nuchal rigidity, variable neurological deficits and reduced mental status.		02.0610
Brain Dead
[description not available]		02.0810
Hyperoxia
An abnormal increase in the amount of oxygen in the tissues and organs.		07.9510
Innate Inflammatory Response
[description not available]		02.9510
Bronchopulmonary Dysplasia
A chronic lung disease developed after OXYGEN INHALATION THERAPY or mechanical ventilation (VENTILATION, MECHANICAL) usually occurring in certain premature infants (INFANT, PREMATURE) or newborn infants with respiratory distress syndrome (RESPIRATORY DISTRESS SYNDROME, NEWBORN). Histologically, it is characterized by the unusual abnormalities of the bronchioles, such as METAPLASIA, decrease in alveolar number, and formation of CYSTS.		02.9510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.9510
Vascular Diseases
Pathological processes involving any of the BLOOD VESSELS in the cardiac or peripheral circulation. They include diseases of ARTERIES; VEINS; and rest of the vasculature system in the body.		02.0310
Alcohol Drinking
Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.		01.9610