Ethyl nitrite
{{Chembox
| Verifiedfields = changed
| verifiedrevid = 399924589
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| Name =
| ImageFile =
| ImageFileL1 = Ethyl-nitrite-2D-skeletal.png
| ImageFileR1 = Ethyl_nitrite_3d_structure.png
| PIN = Ethyl nitrite
| OtherNames = 1-Nitrosooxyethane
Ethyl alcohol nitrite
Nitrous acid
Nitrous ether
Ethyl ester
Nitrethyl
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7735
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1551365
| InChI = 1/C2H5NO2/c1-2-5-3-4/h2H2,1H3
| InChIKey = QQZWEECEMNQSTG-UHFFFAOYAU
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H5NO2/c1-2-5-3-4/h2H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QQZWEECEMNQSTG-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 109-95-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8C7CJ279RV
| PubChem = 8026
| SMILES = O=NOCC
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| Section2 = {{Chembox Properties
| C=2|H=5|N=1|O=2
| Appearance =
| Density =
| MeltingPt =
| BoilingPtC = 17
| Solubility = 5.07 g/100 ml
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| Section3 = {{Chembox Hazards
| MainHazards = {{cite web|url=http://www.newenv.com/resources/nfpa_chemicals/|title=NFPA 704 Ratings for Common Chemicals}}
| FlashPt =
| AutoignitionPt =
| NFPA-H = 2
| NFPA-F = 4
| NFPA-R = 4
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The chemical compound ethyl nitrite is an alkyl nitrite with a chemical formula C2H5NO2. It may be prepared from ethanol.{{OrgSynth |author1=Semon, W. L.|author2=Damerell, V. R. | title = Dimethylglyoxime | collvol = 2 | collvolpages = 204 | year = 1943 | prep = cv2p0204}}
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.{{cite web|url=https://www.fda.gov/Drugs/DevelopmentApprovalProcess/DevelopmentResources/Over-the-CounterOTCDrugs/StatusofOTCRulemakings/ucm072140.htm|archive-url=https://web.archive.org/web/20090709213803/http://www.fda.gov/Drugs/DevelopmentApprovalProcess/DevelopmentResources/Over-the-CounterOTCDrugs/StatusofOTCRulemakings/ucm072140.htm|url-status=dead|archive-date=July 9, 2009|publisher=fda.gov|title=Rulemaking History for OTC Sweet Spirits of Nitre Drug Products|access-date=2016-12-26}} Its use has been associated with fatal methemoglobinemia.{{Cite web|url=https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+416|title=ETHYL NITRITE - National Library of Medicine HSDB Database|website=toxnet.nlm.nih.gov|access-date=2017-11-18}} {{Cite web |url=https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+416 |title=Archived copy |access-date=2017-11-18 |archive-date=2017-12-01 |archive-url=https://web.archive.org/web/20171201042855/https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+416 |url-status=bot: unknown }}
Methemoglobinemia is the primary toxic effect of ethyl nitrite.{{cite web|url=https://www.haz-map.com/Agents/1476|publisher=Haz-Map|title=Ethyl nitrite|access-date=2020-08-08}} 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,{{cite journal|doi=10.1007/s10541-005-0139-7|pmid=15892615|title=Proposed mechanism of nitrite-induced methemoglobinemia|journal= Biochemistry (Moscow)|volume=70|issue=4|pages=473–83|year=2005|last1=Titov|first1=V Yu|last2=Petrenko|first2=Yu M|s2cid=22906218 |url=https://pubmed.ncbi.nlm.nih.gov/15892615/}} which may or may not be severe, or even fatal.
References
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External links
- [http://webbook.nist.gov/cgi/cbook.cgi?ID=C109955&Units=SI WebBook page for ethyl nitrite]
{{Nitric oxide signaling}}