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Ethyl nitrite

From Wikipedia, the free encyclopedia
Ethyl nitrite
Names
Preferred IUPAC name
Ethyl nitrite
Other names
1-Nitrosooxyethane
Ethyl alcohol nitrite
Nitrous acid
Nitrous ether
Ethyl ester
Nitrethyl
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.003.385Edit this at Wikidata
UNII
  • InChI=1S/C2H5NO2/c1-2-5-3-4/h2H2,1H3 checkY
    Key: QQZWEECEMNQSTG-UHFFFAOYSA-N checkY
  • InChI=1/C2H5NO2/c1-2-5-3-4/h2H2,1H3
    Key: QQZWEECEMNQSTG-UHFFFAOYAU
  • O=NOCC
Properties
C2H5NO2
Molar mass75.067 g·mol−1
Boiling point17 °C (63 °F; 290 K)
5.07 g/100 ml
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
[1]
NFPA 704 (fire diamond)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Thechemical compoundethyl nitrite is analkyl nitrite with a chemical formula C2H5NO2. It may be prepared fromethanol.[2]

Uses

[edit]

It is used as a reagent withbutanone to yield thedimethylglyoxime end product.

Ethyl nitrite is the main ingredient in a traditional ethanol-based South African remedy for colds and flu known asWitdulsies, which is sold in pharmacies. It is known as a traditional Afrikaans remedy; the same remedy is apparently made by theAmish in the US. However, FDA has blocked over-the-counter sales of this same remedy, known in the US assweet nitrite orsweet spirit of nitre, since 1980.[3] Its use has been associated with fatalmethemoglobinemia.[4]

Methemoglobinemia is the primary toxic effect of ethyl nitrite.[5] Due to ethyl nitrite's high volatility and faint smell, in the presence of ethyl nitrite vapors, it is easy to breathe a high dose of it without realizing, resulting in methemoglobinemia,[6]which may or may not be severe, or even fatal.

References

[edit]
  1. ^"NFPA 704 Ratings for Common Chemicals".
  2. ^Semon, W. L.; Damerell, V. R. (1943)."Dimethylglyoxime".Organic Syntheses;Collected Volumes, vol. 2, p. 204.
  3. ^"Rulemaking History for OTC Sweet Spirits of Nitre Drug Products". fda.gov. Archived fromthe original on July 9, 2009. Retrieved2016-12-26.
  4. ^"ETHYL NITRITE - National Library of Medicine HSDB Database".toxnet.nlm.nih.gov. Retrieved2017-11-18."ETHYL NITRITE - National Library of Medicine HSDB Database". Archived from the original on 2017-12-01. Retrieved2017-11-18.{{cite web}}: CS1 maint: bot: original URL status unknown (link)
  5. ^"Ethyl nitrite". Haz-Map. Retrieved2020-08-08.
  6. ^Titov, V Yu; Petrenko, Yu M (2005). "Proposed mechanism of nitrite-induced methemoglobinemia".Biochemistry (Moscow).70 (4):473–83.doi:10.1007/s10541-005-0139-7.PMID 15892615.S2CID 22906218.

External links

[edit]
Forms
Targets
sGC
NO donors
(prodrugs)
Enzyme
(inhibitors)
NOS
nNOS
iNOS
eNOS
Unsorted
Arginase
CAMK
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