n-butyl nitrite profile

n-Butyl nitrite is an alkyl nitrite that is a clear, yellowish liquid at room temperature with a characteristic sweet, fruity odor. It is synthesized by reacting 1-butanol with sodium nitrite in the presence of a strong acid. n-Butyl nitrite is primarily known for its vasodilating properties, causing blood vessels to relax and widen. This effect is attributed to its ability to release nitric oxide (NO), a potent vasodilator. n-Butyl nitrite is primarily used in the treatment of angina pectoris, a condition characterized by chest pain due to reduced blood flow to the heart. It is also used in the treatment of certain types of heart failure. Due to its effects on smooth muscle, n-Butyl nitrite has been used recreationally as a euphoric inhalant. However, its use in this manner is considered dangerous due to the potential for serious adverse effects, including methemoglobinemia (a condition in which red blood cells lose their ability to carry oxygen) and death. Research on n-Butyl nitrite focuses on its potential therapeutic applications, particularly in the treatment of cardiovascular disorders. Additionally, researchers are investigating its effects on smooth muscle function, its role in the release of nitric oxide, and its potential toxicities.'

n-butyl nitrite: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1570 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	10996
CHEMBL ID	3181968
CHEBI ID	173360
SCHEMBL ID	166345
MeSH ID	M0082196

Synonym
1-butyl nitrite ,
LS-13006
CHEBI:173360
n-butyl nitrite
nsc8426
nsc-8426
544-16-1
nitrous acid, butyl ester
nitrous acid, n-butyl ester
butyl nitrite
ccris 838
nsc 8426
brn 1701036
ai3-15310
nci-c56553
einecs 208-862-1
NBN ,
butyl nitrite, 95%
inchi=1/c4h9no2/c1-2-3-4-7-5-6/h2-4h2,1h3
jqjpbyftqaanle-uhfffaoysa-
nitrous acid butyl ester
N0376
tox21_202927
cas-544-16-1
dtxcid7029378
NCGC00260473-01
n-butylnitrite
dtxsid8049418 ,
A830171
AKOS015995388
STL280334
44p8qg0f3t ,
unii-44p8qg0f3t
BP-20316
butylnitrite
butyl nitrite [mart.]
n-butyl nitrite [mi]
SCHEMBL166345
un 2351
n-c4h9ono
butyl ester of nitrous acid
CHEMBL3181968
J-519967
J-802250
t-butyl-2-bromobutanoate
mfcd00002058
Q3342208
AMY4016
butyl nitrite(technical)

Excerpt	Reference	Relevance
" The toxic effects of this substances, either by ingestion or inhalation, are described as well as risks of use in "everyday life"."	( [Toxicity and dangers of volatile nitrites sold in sex shops]. Arditti, J; Brun, A; David, JM; Fauchier, R; Jean, P; Jouglard, J; Malavaud, A, 1983)	0.27

Class	Description
nitroso compound	Compounds 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	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	49.7949	0.0015	30.6073	15,848.9004	AID1224841
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	17 (40.48)	18.7374
1990's	4 (9.52)	18.2507
2000's	3 (7.14)	29.6817
2010's	15 (35.71)	24.3611
2020's	3 (7.14)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (4.35%)	6.00%
Case Studies	6 (13.04%)	4.05%
Observational	0 (0.00%)	0.25%
Other	38 (82.61%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	1.96	1	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
indole [no description available]	2.11	1	indole; polycyclic heteroarene	Escherichia coli metabolite
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.67	3	monovalent 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)	6.68	42	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
pentamidine Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.	2	1	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.05	1	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	3.47	2	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	1.96	1	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
trimethylchlorosilane trimethylsilyl chloride: structure in first source. chlorotrimethylsilane : A silyl chloride consisting of a central silicon atom covalently bound to one chloro and three methyl groups. Chlorotrimethylsilane is a derivatisation agent used in gas chromatography/mass spectrometry applications.	2.1	1	silyl chloride	chromatographic reagent
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.31	1	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
isatin tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;	2.15	1	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
isoamyl nitrite isoamyl nitrite : A nitrite ester having isopentyl as the alkyl group.	2.53	2	nitrite esters	antihypertensive agent; vasodilator agent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.41	1	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	2.11	1	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.31	1	diazine; pyrazines	Daphnia magna metabolite
n-pentyl nitrite Amyl Nitrite: A vasodilator that is administered by inhalation. It is also used recreationally due to its supposed ability to induce euphoria and act as an aphrodisiac.. n-pentyl nitrite : A nitrite ester having n-pentyl as the alkyl group.	4.95	12	nitrite esters	vasodilator agent
isobutyl nitrite isobutyl nitrite: ''recreational'' drug of abuse, sniffed.	5.21	9	nitrite esters
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.1	1	metal allergen; nickel group element atom; platinum group metal atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	2.06	1	iron group element atom; platinum group metal atom
nitrous acid Nitrous Acid: Nitrous acid (HNO2). A weak acid that exists only in solution. It can form water-soluble nitrites and stable esters. (From Merck Index, 11th ed)	2.06	1	nitrogen oxoacid
mecysteine mecysteine: RN given refers to parent cpd(L)-isomer. methyl L-cysteinate : An L-cysteinyl ester resulting from the formal condensation of the carboxylic acid group of L-cysteine with methanol. It is used (as the hydrochloride salt) as a mucolytic for the treatment of respiratory disorders associated with productive cough.	2.06	1	L-cysteinyl ester; primary amino compound; thiol	mucolytic
alkenes [no description available]	2.82	3
amyl nitrate [no description available]	1.96	1
s-nitrosoglutathione [no description available]	2.39	2	glutathione derivative; nitrosothio compound	bronchodilator agent; nitric oxide donor; platelet aggregation inhibitor; signalling molecule
4-methoxyphenylboronic acid 4-methoxyphenylboronic acid: structure in first source	2.13	1
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	2.15	1	gamma-lactam; indolinone
thiohydantoins Thiohydantoins: Sulfur analogs of hydantoins with one or both carbonyl groups replaced by thiocarbonyl groups.	2.13	1
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	2.08	1	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.06	1	cysteinium	fundamental metabolite
sodium nitrite Sodium Nitrite: Nitrous acid sodium salt. Used in many industrial processes, in meat curing, coloring, and preserving, and as a reagent in ANALYTICAL CHEMISTRY TECHNIQUES. It is used therapeutically as an antidote in cyanide poisoning. The compound is toxic and mutagenic and will react in vivo with secondary or tertiary amines thereby producing highly carcinogenic nitrosamines.. sodium nitrite : An inorganic sodium salt having nitrite as the counterion. Used as a food preservative and antidote to cyanide poisoning.	1.96	1	inorganic sodium salt; nitrite salt	antidote to cyanide poisoning; antihypertensive agent; antimicrobial food preservative; food antioxidant; poison
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	1.96	1
didanosine Didanosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.. didanosine : A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.	2	1	purine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor; geroprotector; HIV-1 reverse transcriptase inhibitor

Condition	Relationship Strength	Studies
Retinal Diseases Diseases involving the RETINA.	2.15	1
Ataxia Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.	2.13	1
Chemical Dependence [description not available]	3.09	5
Substance-Related Disorders Disorders related to substance use or abuse.	3.09	5
Anemia, Hemolytic, Acquired [description not available]	2.38	2
Deficiency of Glucose-6-Phosphate Dehydrogenase [description not available]	2.02	1
Anemia, Hemolytic A condition of inadequate circulating red blood cells (ANEMIA) or insufficient HEMOGLOBIN due to premature destruction of red blood cells (ERYTHROCYTES).	2.38	2
Glucosephosphate Dehydrogenase Deficiency A disease-producing enzyme deficiency subject to many variants, some of which cause a deficiency of GLUCOSE-6-PHOSPHATE DEHYDROGENASE activity in erythrocytes, leading to hemolytic anemia.	2.02	1
Facial Dermatoses Skin diseases involving the FACE.	1.96	1
Sinus Infections [description not available]	1.96	1
Sinusitis Inflammation of the NASAL MUCOSA in one or more of the PARANASAL SINUSES.	1.96	1
Dermatitis Medicamentosa [description not available]	1.96	1
Cyanosis A bluish or purplish discoloration of the skin and mucous membranes due to an increase in the amount of deoxygenated hemoglobin in the blood or a structural defect in the hemoglobin molecule.	2.38	2
Methemoglobinemia The presence of methemoglobin in the blood, resulting in cyanosis. A small amount of methemoglobin is present in the blood normally, but injury or toxic agents convert a larger proportion of hemoglobin into methemoglobin, which does not function reversibly as an oxygen carrier. Methemoglobinemia may be due to a defect in the enzyme NADH methemoglobin reductase (an autosomal recessive trait) or to an abnormality in hemoglobin M (an autosomal dominant trait). (Dorland, 27th ed)	3.28	2
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	1.99	1
HIV Coinfection [description not available]	2	1
Nasal Diseases [description not available]	2	1
Acrodermatitis Inflammation involving the skin of the extremities, especially the hands and feet. Several forms are known, some idiopathic and some hereditary. The infantile form is called Gianotti-Crosti syndrome.	2	1
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	2	1
Acquired Immune Deficiency Syndrome [description not available]	3.29	2
Kaposi Sarcoma [description not available]	3.29	2
Acquired Immunodeficiency Syndrome An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.	3.29	2
Sarcoma, Kaposi A multicentric, malignant neoplastic vascular proliferation characterized by the development of bluish-red cutaneous nodules, usually on the lower extremities, most often on the toes or feet, and slowly increasing in size and number and spreading to more proximal areas. The tumors have endothelium-lined channels and vascular spaces admixed with variably sized aggregates of spindle-shaped cells, and often remain confined to the skin and subcutaneous tissue, but widespread visceral involvement may occur. Kaposi's sarcoma occurs spontaneously in Jewish and Italian males in Europe and the United States. An aggressive variant in young children is endemic in some areas of Africa. A third form occurs in about 0.04% of kidney transplant patients. There is also a high incidence in AIDS patients. (From Dorland, 27th ed & Holland et al., Cancer Medicine, 3d ed, pp2105-7) HHV-8 is the suspected cause.	3.29	2
Spider Veins [description not available]	1.97	1
Telangiectasis Permanent dilation of preexisting blood vessels (CAPILLARIES; ARTERIOLES; VENULES) creating small focal red lesions, most commonly in the skin or mucous membranes. It is characterized by the prominence of skin blood vessels, such as vascular spiders.	1.97	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	1.96	1

n-butyl nitrite

Description

Cross-References

Synonyms (49)

Research Excerpts

Toxicity

Drug Classes (1)

Protein Targets (1)

Potency Measurements

Research

Studies (42)

Study Types