Chemistry:Hexyl nitrite

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Hexyl nitrite
Hexyl nitrite.svg
Names
Other names
n-Hexyl nitrite; Nitrous acid, hexyl ester
Identifiers
3D model (JSmol)
Properties
C6H13NO2
Molar mass 131.175 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

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. [1][2] It is also known as nitrous acid, hexyl ester.[3] 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.[4] It, along with other hexyl nitrites, was investigated in the 1930s for angiospastic conditions.[5] It has subsequently been used in treatment of various cardiovascular conditions.[6][7] Its most popular use though is as a stimulant particularly popular in the gay community as a sex aid.[8]

Physiological effects

Hexyl nitrite like other alkyl nitrites,[9] 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.[10]

Safety

Warnings have been issued by the FDA about its use.[11] 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.[12] Its possible implication in HIV/AIDS transmission has been discredited.[13]

References

  1. ↑ "Hexyl nitrite". PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/6365123. 
  2. ↑ "Hexyl nitrite" (in en). https://webbook.nist.gov/cgi/inchi/InChI=1S/C6H13NO2/c1-2-3-4-5-6-9-7-8/h2-6H2,1H3. 
  3. ↑ "Hexyl nitrite". ChemSpider. http://www.chemspider.com/Chemical-Structure.4895948.html. 
  4. ↑ "Poppers Guide". https://poppersguide.com/. 
  5. ↑ "Alkyl Nitrites II. the Pharmacology of 2-Ethyl-N-Hexyl-1-Nitrite" (in en). Journal of Pharmacology and Experimental Therapeutics 64 (3): 302–313. November 1938. ISSN 0022-3565. https://jpet.aspetjournals.org/content/64/3/302. 
  6. ↑ "Nitrates and nitrites in the treatment of ischemic cardiac disease" (in en-US). Cardiology in Review 18 (4): 190–197. July 2010. doi:10.1097/CRD.0b013e3181c8e14a. PMID 20539102. 
  7. ↑ "The Volatile Nitrites" (in en). JAMA: The Journal of the American Medical Association 241 (19): 2077–2078. 1979-05-11. doi:10.1001/jama.1979.03290450071034. ISSN 0098-7484. PMID 430807. 
  8. ↑ "This Man Does Not Make Poppers" (in en). 2021-07-27. https://www.buzzfeednews.com/article/davidmack/poppers-factory. 
  9. ↑ Isobutyl Nitrite and Related Compounds. (1st ed.). San Francisco California: PHARMEX. 1979. http://www.virusmythpoppersmyth.org/isobutyl_nitrite_and_rela/files/IBNtextnpttypepad.pdf. 
  10. ↑ The Man Who Tasted Shapes. MIT Press. 2003. ISBN 978-0-262-53255-6. 
  11. ↑ Office of th Commissioner (2023-03-07). "Ingesting or Inhaling Nitrite "Poppers" Can Cause Severe Injury or Death" (in en). FDA. https://www.fda.gov/consumers/consumer-updates/ingesting-or-inhaling-nitrite-poppers-can-cause-severe-injury-or-death. 
  12. ↑ "Alkaline hydrolyses of alkyl nitrites and related carboxylic esters" (in en). Journal of the Chemical Society, Perkin Transactions 2 (6): 571–577. January 1978. doi:10.1039/P29780000571. ISSN 1364-5471. 
  13. ↑ "Nitrite inhalants: history, epidemiology, and possible links to AIDS". Environmental Health Perspectives 102 (10): 858–861. October 1994. doi:10.1289/ehp.94102858. PMID 9644194. 



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