Ethyl nitrite: Difference between revisions

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| Name =

| ImageFile =

| ImageFileR1 = Ethyl_nitrite_3d_structure.png

| PIN = Ethyl nitrite

| OtherNames = 1-Nitrosooxyethane<br />Ethyl alcohol nitrite<br />Nitrous acid<br />Nitrous ether<br />Ethyl ester<br />Nitrethyl

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1551365

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 109-95-5

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| UNII = 8C7CJ279RV

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| Solubility = 5.07 g/100 ml

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| Section3 = {{Chembox Hazards

| MainHazards = <ref>{{cite web|url=http://www.newenv.com/resources/nfpa_chemicals/|title=NFPA 704 Ratings for Common Chemicals}}</ref>

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| NFPA-H = 2

| NFPA-F = 4

| NFPA-R = 4

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The [[chemical compound]] '''ethyl nitrite''' is an [[Alkyl nitrites|alkyl nitrite]] with a chemical formula C₂H₅NO₂. It may be prepared from [[ethanol]].<ref>{{OrgSynth |author1=Semon, W. L.|author2=Damerell, V. R. | title = Dimethylglyoxime | collvol = 2 | collvolpages = 204 | year = 1943 | prep = cv2p0204}}</ref>

== Uses ==

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

:[[File:Preparation_of_dimethylglyoxime.png|400px]]

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.<ref name="fda">{{cite web|url=https://www.fda.gov/Drugs/DevelopmentApprovalProcess/DevelopmentResources/Over-the-CounterOTCDrugs/StatusofOTCRulemakings/ucm072140.htm|publisher=fda.gov|title=Rulemaking History for OTC Sweet Spirits of Nitre Drug Products|access-date=2016-12-26}}</ref> Its use has been associated with fatal [[methemoglobinemia]].<ref>{{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 }}</ref>

[[Methemoglobinemia#Diagnosis|Methemoglobinemia]] is the primary toxic effect of ethyl nitrite.<ref name="hazmap">{{cite web|url=https://www.haz-map.com/Agents/1476|publisher=Haz-Map|title=Ethyl nitrite|access-date=2020-08-08}}</ref> 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,<ref>{{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/}}</ref> [[Methemoglobinemia#Signs_and_symptoms|which may or may not be severe, or even fatal]].

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{{Nitric oxide signaling}}

[[Category:Traditional medicine]]