Ethyl nitrite

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

Ethyl nitrite
Names
Preferred IUPAC name
Ethyl nitrite
Other names
1-Nitrosooxyethane
Ethyl alcohol nitrite
Nitrous acid
Nitrous ether
Ethyl ester
Nitrethyl
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.385
PubChem CID
UNII
InChI
  • InChI=1S/C2H5NO2/c1-2-5-3-4/h2H2,1H3 Y
    Key: QQZWEECEMNQSTG-UHFFFAOYSA-N Y
  • InChI=1/C2H5NO2/c1-2-5-3-4/h2H2,1H3
    Key: QQZWEECEMNQSTG-UHFFFAOYAU
SMILES
  • O=NOCC
Properties
Chemical formula
 C2H5NO2
Molar mass 75.067 g·mol−1
Boiling point 17 °C (63 °F; 290 K)
Solubility in water
 5.07 g/100 ml
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 [1]
NFPA 704 (fire diamond)
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 YN ?)
Infobox references

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.; Collective Volume, 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 2017-12-01 at the Wayback Machine
  5. "Ethyl nitrite". Haz-Map. Retrieved 2020-08-08.
  6. Titov, V Yu; Petrenko, Yu M (2005). "Proposed mechanism of nitrite-induced methemoglobinemia". Biochemistry (Mosc). 70 (4): 473–83. doi:10.1007/s10541-005-0139-7. PMID 15892615.
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