Hexyl nitrite
{{Chembox
| ImageFile = Hexyl nitrite.svg
| ImageSize = 200px
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| IUPACName =
| OtherNames = n-Hexyl nitrite; Nitrous acid, hexyl ester
| Section1 = {{Chembox Identifiers
| CASNo = 638-51-7
| Beilstein = 1702621
| ChemSpiderID = 4895948
| EC_number = 680-102-5
| PubChem = 6365123
| StdInChI=1S/C6H13NO2/c1-2-3-4-5-6-9-7-8/h2-6H2,1H3
| StdInChIKey = SGRWGISGVDVSJV-UHFFFAOYSA-N
| SMILES = CCCCCCON=O
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| Section2 = {{Chembox Properties
| C = 6 | H = 13 | N = 1 | O = 2
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| Section3 = {{Chembox Hazards
| GHS_ref=[https://pubchem.ncbi.nlm.nih.gov/compound/6365123#section=Safety-and-Hazards]
| GHSPictograms = {{GHS02}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|302|312|332}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|280|301+317|302+352|303+361+353|304+340|317|321|330|362+364|370+378|403+235|501}}
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Hexyl nitrite has the formula C6H13NO2 and is a nitrite and more specifically, an alkyl nitrite. It is an ester of hexanol and nitrous acid. It has the structural formula of: CH3(CH2)5ONO The CAS Registry Number is 638-51-7 and the European Community number 680-102-5. It is REACH and TSCA registered. {{Cite web | work = PubChem |title=Hexyl nitrite |url=https://pubchem.ncbi.nlm.nih.gov/compound/6365123 |access-date=2023-05-18 |publisher = U.S. National Library of Medicine }}{{Cite web |title=Hexyl nitrite |url=https://webbook.nist.gov/cgi/inchi/InChI=1S/C6H13NO2/c1-2-3-4-5-6-9-7-8/h2-6H2,1H3 |access-date=2023-05-18 |website=webbook.nist.gov |language=en}} It is also known as nitrous acid, hexyl ester.{{Cite web |title=Hexyl nitrite | work = ChemSpider |url=http://www.chemspider.com/Chemical-Structure.4895948.html |access-date=2023-05-18 }} It is the aliphatic analogue of cyclohexyl nitrite.
Applications
Hexyl nitrite is one of the compounds used as poppers, an inhalant drug that induces a brief euphoria.{{Cite web |title=Poppers Guide |url=https://poppersguide.com/ |access-date=2023-05-18 |website=poppersguide.com}} It, along with other hexyl nitrites, was investigated in the 1930s for angiospastic conditions.{{Cite journal | vauthors = Krantz JC, Carr CJ, Forman SE |date= November 1938 |title=Alkyl Nitrites II. the Pharmacology of 2-Ethyl-N-Hexyl-1-Nitrite |url=https://jpet.aspetjournals.org/content/64/3/302 |journal=Journal of Pharmacology and Experimental Therapeutics |language=en |volume=64 |issue=3 |pages=302–313 |issn=0022-3565}} It has subsequently been used in treatment of various cardiovascular conditions.{{cite journal | vauthors = Nossaman VE, Nossaman BD, Kadowitz PJ | title = Nitrates and nitrites in the treatment of ischemic cardiac disease | language = en-US | journal = Cardiology in Review | volume = 18 | issue = 4 | pages = 190–197 | date = July 2010 | pmid = 20539102 | pmc = 2885014 | doi = 10.1097/CRD.0b013e3181c8e14a }}{{Cite journal | vauthors = Cohen S |date=1979-05-11 |title=The Volatile Nitrites |journal=JAMA: The Journal of the American Medical Association |language=en |volume=241 |issue=19 |pages=2077–2078 |doi=10.1001/jama.1979.03290450071034 |pmid=430807 |issn=0098-7484}} Its most popular use though is as a stimulant particularly popular in the gay community as a sex aid.{{Cite web | vauthors = Mack D |date=2021-07-27 |title=This Man Does Not Make Poppers |url=https://www.buzzfeednews.com/article/davidmack/poppers-factory |access-date=2023-05-18 |website=BuzzFeed News |language=en}}
Physiological effects
Hexyl nitrite like other alkyl nitrites,{{cite book | vauthors = Nickerson M, Parker JO, Lowry TP, Swenson EW | title = Isobutyl Nitrite and Related Compounds. | location = San Francisco California | publisher = PHARMEX | date = 1979 | url = http://www.virusmythpoppersmyth.org/isobutyl_nitrite_and_rela/files/IBNtextnpttypepad.pdf | archive-url = https://web.archive.org/web/20070927023207/http://www.virusmythpoppersmyth.org/isobutyl_nitrite_and_rela/files/IBNtextnpttypepad.pdf | archive-date=2007-09-27 | edition = 1st }} is a vasodilator resulting in the expansion of blood vessels, thus lowering blood pressure. Side effects can be headaches, flushing, heart rate increase, dizziness, and relaxation of involuntary muscles, such as the internal and external anal sphincter. Overdoses can cause nausea and fainting. It is extremely fast reacting, usually a few seconds, but the effects disappear after a few minutes.{{cite book | vauthors = Cytowic R | author-link1 = Richard Cytowic | title = The Man Who Tasted Shapes | date = 2003 | publisher = MIT Press | isbn = 978-0-262-53255-6 }}
Safety
Warnings have been issued by the FDA about its use.{{Cite journal | author = Office of th Commissioner |date=2023-03-07 |title=Ingesting or Inhaling Nitrite "Poppers" Can Cause Severe Injury or Death |url=https://www.fda.gov/consumers/consumer-updates/ingesting-or-inhaling-nitrite-poppers-can-cause-severe-injury-or-death |journal=FDA |language=en}} Some of the side effects include headaches, dizziness and fainting. As they are extensively used as a recreational stimulant, its use along with other alkyl nitrites has been extensively studied. In particular the potential for methemoglobinization of blood and thus loss of oxygen transport potential.{{Cite journal | vauthors = Oae S, Asai N, Fujimori K | date = January 1978 |title=Alkaline hydrolyses of alkyl nitrites and related carboxylic esters |journal=Journal of the Chemical Society, Perkin Transactions 2 |language=en |issue=6 |pages=571–577 |doi=10.1039/P29780000571 |issn=1364-5471}} Its possible implication in HIV/AIDS transmission has been discredited.{{cite journal | vauthors = Haverkos HW, Kopstein AN, Wilson H, Drotman P | title = Nitrite inhalants: history, epidemiology, and possible links to AIDS | journal = Environmental Health Perspectives | volume = 102 | issue = 10 | pages = 858–861 | date = October 1994 | pmid = 9644194 | pmc = 1567358 | doi = 10.1289/ehp.94102858 | bibcode = 1994EnvHP.102..858H }}