Page last updated: 2024-11-05

isobutyl nitrite

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

Description

isobutyl nitrite: ''recreational'' drug of abuse, sniffed. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10958
CHEMBL ID1526886
CHEBI ID46643
SCHEMBL ID190439
MeSH IDM0069308

Synonyms (52)

Synonym
LS-13005
isobutyl nitrite
(ch3)2chch2ono
542-56-3
NCGC00091558-01
blackjack
einecs 208-819-7
nci-c61052
ccris 1099
hsdb 4368
brn 1699518
nitrous acid, 2-methylpropyl ester
nitrous acid, isobutyl ester
2-methylpropyl nitrite
IBN ,
CHEBI:46643 ,
isobutylnitrit
isobutyl nitrite, 95%
I0528
NCGC00091558-02
isobutylnitrite
cas-542-56-3
tox21_302863
dtxcid70750
dtxsid3020750 ,
NCGC00256551-01
NCGC00259960-01
tox21_202411
nitrous acid 2-methylpropyl ester
A830069
gw9wab6qom ,
4-01-00-01595 (beilstein handbook reference)
unii-gw9wab6qom
AKOS015915458
SCHEMBL190439
i-butylnitrite
iso-butyl nitrite
2-methyl-1-nitrosooxy-propane
isobutyl nitrite [hsdb]
isobutyl nitrite [mart.]
isobutyl nitrite [iarc]
isobutyl nitrite [mi]
isobutyl nitrite stab. with potassium carbonate
CHEMBL1526886
J-802227
mfcd00002056
EN300-120670
isobutyl nitrite (|a-methylpropyl nitrite)
isobutyl nitrile
Q1151479
AMY4012
?isobutylnitrite

Research Excerpts

Overview

Isobutyl nitrite is an effective nitrosating agent at acidic, neutral and basic pH in the presence of species arising from phosphate ion. It is a popular recreational drug among both homosexuals and heterosexuals as it is alleged to enhance sexual pleasure.

ExcerptReferenceRelevance
"Isobutyl nitrite is an effective nitrosating agent at acidic, neutral and basic pH in the presence of species arising from phosphate ion. "( Nitrosation by alkyl nitrites. Catalysis by inorganic salts.
Dabora, R; Molina, M; Ng, V; Tannenbaum, SR; Wishnok, JS, 1984
)
1.71
"Isobutyl nitrite is a popular recreational drug among both homosexuals and heterosexuals as it is alleged to enhance sexual pleasure and prolong orgasm. "( Fatal methemoglobinemia due to inhalation of isobutyl nitrite.
Bradberry, SM; Parry, DA; Vale, JA; Whittington, RM, 1994
)
1.99
"Isobutyl nitrite is an inhalant abused principally by male homosexuals. "( Acute exposure to the abused inhalant, isobutyl nitrite, reduced T cell responsiveness and spleen cellularity.
Barnett, JB; Flick, JT; Guo, GL; Rose, D; Soderberg, LS, 2000
)
2.02
"Isobutyl nitrite is a drug of abuse popular among male homosexuals and among adolescents. "( Exposure to inhaled isobutyl nitrite reduces T cell blastogenesis and antibody responsiveness.
Barnett, JB; Soderberg, LS, 1991
)
2.05
"Isobutyl nitrite is a volatile liquid sold without a prescription as a "room odorizer" but is widely used as an inhalant to produce feelings of euphoria. "( Abuse of isobutyl nitrite inhalation (Rush) by adolescents.
Peary, P; Schwartz, RH, 1986
)
2.13

Effects

ExcerptReferenceRelevance
"Isobutyl nitrite has recently become a popularly abused drug in the United States. "( Severe tracheobronchitis from inhalation of an isobutyl nitrite preparation.
Covalla, JR; Lech, JG; Strimlan, CV, 1981
)
1.96

Toxicity

ExcerptReferenceRelevance
" These data suggest that mild tissue injury, restricted to the lung, and methemoglobinemia are the major toxic effects observed following exposures of mice to IBN at concentrations up to 300 ppm for 18 wk."( Subchronic inhalation toxicity of isobutyl nitrite in BALB/c mice. I. Systemic toxicity.
Burg, JR; Chandler, FW; Khan, A; Kimbrough, RD; Lewis, DM; Lewis, TR; Lynch, DW; Moorman, WJ; Phipps, FC; Spira, TJ, 1985
)
0.55
" 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

Pharmacokinetics

ExcerptReferenceRelevance
" In this report, we applied the analytical method to obtain new pharmacokinetic information about ISBN."( Analysis of isobutyl nitrite inhalant in rat and human blood: application for pharmacokinetic investigations.
Bauer, JA; Fung, HL; Kielbasa, WB, 1999
)
0.68

Bioavailability

ExcerptReferenceRelevance
" Little is known regarding the bioavailability and disposition of volatile nitrites."( Pharmacokinetics of a model organic nitrite inhalant and its alcohol metabolite in rats.
Fung, HL; Kielbasa, W, 2000
)
0.31

Dosage Studied

ExcerptRelevanceReference
" The hepatic microsomal metabolizing activity for nitriles was at a maximum 13 h after ethanol dosing (4."( Influence of ethanol on the in vivo and in vitro metabolism of nitriles in mice.
Hashimoto, K; Tanii, H, 1986
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
nitrite esters
[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 (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency31.62280.011212.4002100.0000AID1030
estrogen nuclear receptor alphaHomo sapiens (human)Potency8.15700.000229.305416,493.5996AID743069; AID743075
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency20.97900.001024.504861.6448AID743212
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency44.66840.001019.414170.9645AID588537
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency37.57800.000627.21521,122.0200AID651741
Nuclear receptor ROR-gammaHomo sapiens (human)Potency33.49150.026622.448266.8242AID651802
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IINuclear receptor ROR-gammaHomo sapiens (human)
xenobiotic metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
regulation of glucose metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
regulation of steroid metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
intracellular receptor signaling pathwayNuclear receptor ROR-gammaHomo sapiens (human)
circadian regulation of gene expressionNuclear receptor ROR-gammaHomo sapiens (human)
cellular response to sterolNuclear receptor ROR-gammaHomo sapiens (human)
positive regulation of circadian rhythmNuclear receptor ROR-gammaHomo sapiens (human)
regulation of fat cell differentiationNuclear receptor ROR-gammaHomo sapiens (human)
positive regulation of DNA-templated transcriptionNuclear receptor ROR-gammaHomo sapiens (human)
adipose tissue developmentNuclear receptor ROR-gammaHomo sapiens (human)
T-helper 17 cell differentiationNuclear receptor ROR-gammaHomo sapiens (human)
regulation of transcription by RNA polymerase IINuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription factor activityNuclear receptor ROR-gammaHomo sapiens (human)
protein bindingNuclear receptor ROR-gammaHomo sapiens (human)
oxysterol bindingNuclear receptor ROR-gammaHomo sapiens (human)
zinc ion bindingNuclear receptor ROR-gammaHomo sapiens (human)
ligand-activated transcription factor activityNuclear receptor ROR-gammaHomo sapiens (human)
sequence-specific double-stranded DNA bindingNuclear receptor ROR-gammaHomo sapiens (human)
nuclear receptor activityNuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleusNuclear receptor ROR-gammaHomo sapiens (human)
nucleoplasmNuclear receptor ROR-gammaHomo sapiens (human)
nuclear bodyNuclear receptor ROR-gammaHomo sapiens (human)
chromatinNuclear receptor ROR-gammaHomo sapiens (human)
nucleusNuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Research

Studies (73)

TimeframeStudies, This Drug (%)All Drugs %
pre-199025 (34.25)18.7374
1990's22 (30.14)18.2507
2000's16 (21.92)29.6817
2010's8 (10.96)24.3611
2020's2 (2.74)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (5.19%)6.00%
Case Studies18 (23.38%)4.05%
Observational0 (0.00%)0.25%
Other55 (71.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]