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Ethyl nitrite

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 InfoCard 100.003.385 Edit 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 mass 75.067 g·mol−1
Boiling point 17 °C (63 °F; 290 K)
5.07 g/100 ml
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 [1]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
2
4
4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

The chemical compound ethyl nitrite is an alkyl nitrite with a chemical formula C2H5NO2. It may be prepared from ethanol.[2]

Uses

It is used as a reagent with butanone to yield the dimethylglyoxime end product.

Ethyl nitrite is the main ingredient in a traditional ethanol-based South African remedy for colds and flu known as Witdulsies, which is sold in pharmacies. It is known as a traditional Afrikaans remedy; the same remedy is apparently made by the Amish in the US. However, FDA has blocked over-the-counter sales of this same remedy, known in the US as sweet nitrite or sweet spirit of nitre, since 1980.[3] Its use has been associated with fatal methemoglobinemia.[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 breath a high dose of it without realizing, resulting in methemoglobinemia,[6] which may or may not be severe, or even fatal.

References

  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. Retrieved 2016-12-26.
  4. ^ "ETHYL NITRITE - National Library of Medicine HSDB Database". toxnet.nlm.nih.gov. Retrieved 2017-11-18. "Archived copy". Archived from the original on 2017-12-01. Retrieved 2017-11-18.{{cite web}}: CS1 maint: archived copy as title (link) CS1 maint: bot: original URL status unknown (link)
  5. ^ "Ethyl nitrite". Haz-Map. Retrieved 2020-08-08.
  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.
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