Isobutyl nitrite

Isobutyl nitrite[1]
Names
Preferred IUPAC name
2-Methylpropyl nitrite
Other names
Isobutyl nitrite
Identifiers
CAS Number
  • 542-56-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:46643 checkY
ChemSpider
  • 10493 checkY
ECHA InfoCard 100.008.018 Edit this at Wikidata
PubChem CID
  • 10958
UNII
  • GW9WAB6QOM checkY
CompTox Dashboard (EPA)
  • DTXSID3020750 Edit this at Wikidata
InChI
  • InChI=1S/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3 checkY
    Key: APNSGVMLAYLYCT-UHFFFAOYSA-N checkY
  • InChI=1/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3
    Key: APNSGVMLAYLYCT-UHFFFAOYAF
  • O=NOCC(C)C
Properties
Chemical formula
C4H9NO2
Molar mass 103.11976
Appearance Colorless liquid
Odor Almond-like[2]
Density 0.87 g/mL
Boiling point 67 °C (153 °F; 340 K)
Solubility in water
Slightly soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly flammable
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references
Chemical compound

Isobutyl nitrite, C4H9NO2, is an alkyl nitrite, an ester of isobutanol and nitrous acid. Its chemical structure is (CH3)2CH-CH2-ONO.

Isobutyl nitrite is a pungent colorless liquid. It acts as a vasodilator, and is used as an inhalant recreational drug, poppers.

Applications

Isobutyl nitrite is one of the compounds used as poppers, an inhalant drug that induces a brief euphoria. Also, it is used as part of the antidote package for cyanide poisoning.[medical citation needed]

Safety

May cause headaches, dizziness and fainting. Isobutyl nitrite is poisonous to people with glucose-6-phosphate dehydrogenase deficiency.[4]

References

  1. ^ Merck Index, 11th Edition, 5032.
  2. ^ CDC - NIOSH Pocket Guide to Chemical Hazards
  3. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  4. ^ Bubp, Jeff; Jen, Marilyn; Matuszewski, Karl (September 2015). "Caring for Glucose-6-Phosphate Dehydrogenase (G6PD)–Deficient Patients: Implications for Pharmacy". Pharmacy and Therapeutics. 40 (9): 572–574. ISSN 1052-1372. PMC 4571844. PMID 26417175.
  • v
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Forms
  • Nitroxyl anion (NO; oxonitrate(1-), hyponitrite anion)
  • Nitric oxide (NO; nitrogen monoxide)
  • Nitrosonium (NO+; nitrosyl cation)
Targets
sGC
  • Inhibitors: ODQ
NO donors
(prodrugs)
  • NONOates (diazeniumdiolates): Diethylamine/NO (DEA/NO)
  • Diethylenetriamine/NO (DETA/NO)
  • GLO/NO
  • JS-K
  • Methylamine hexamethylene methylamine/NO (MAHMA/NO)
  • PROLI/NO
  • Spermine/NO (SPER/NO)
  • V-PYRRO/NO
  • Unsorted: Cimlanod
  • FK-409
  • FR144220
  • FR146881
  • N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
Enzyme
(inhibitors)
NOS
nNOS
iNOS
  • 1-Amino-2-hydroxyguanidine
  • 2-Ethylaminoguanidine
  • 2-Iminopiperidine
  • 1400W
  • AEITU
  • Aminoguanidine (pimagedine)
  • AMT
  • AR-C 102222
  • BYK-191023
  • Canavanine
  • Cindunistat (SD-6010)
  • EITU
  • IPTU
  • MITU
  • N5-(1-Iminoethyl)-L-ornithine (L-NIO)
  • N6-(1-Iminoethyl)-L-lysine (L-NIL)
  • Nω-Methyl-L-arginine (L-NMA)
  • Ronopterin (VAS-203)
  • TRIM
eNOS
Unsorted
Arginase
CAMK
  • Calmidazolium
  • W-7
Others
  • Precursors: L-Arginine
  • Nω-Hydroxy-L-arginine (NOHA)
See also: Receptor/signaling modulators


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