:Butyl nitrite
{{Short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 411437556
| IUPAC_name = 1-nitrosooxybutane
| image = Butyl-nitrite-3DV-vdW.svg
| width = 150
| image2 = Butyl_nitrite_3d_structure.png
| tradename =
| pregnancy_AU =
| pregnancy_US =
| legal_AU = S4
| legal_AU_comment = [https://www.legislation.gov.au/F2024L01228 Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024] (Cth)
| legal_CA =
| legal_UK = Controlled Drug (Medicines Act 1968)
| legal_US = Unscheduled (illegal under Anti-Drug Abuse Act of 1988)
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 544-16-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 44P8QG0F3T
| ATC_prefix = none
| PubChem = 10996
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10530
| C=4 | H=9 | N=1 | O=2
| smiles = CCCCON=O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H9NO2/c1-2-3-4-7-5-6/h2-4H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JQJPBYFTQAANLE-UHFFFAOYSA-N
| boiling_point=78.0
}}
Butyl nitrite is the organic compound with the formula CH3(CH2)3ONO. It is an alkyl nitrite made from n-butanol. Butyl nitrite is used recreationally as poppers. Synonyms include 1-butyl nitrite, n-butyl nitrite and nitrous acid butyl ester.
It can be prepared by treating nitrous acid (generated in situ) with n-butanol.{{cite journal |doi=10.15227/orgsyn.016.0007|title=N-Butyl Nitrite|journal=Organic Syntheses|year=1936|volume=16|page=7| vauthors = Noyes WA }}
Applications
Butyl nitrite is one of the compounds used as poppers, inhalant drugs that induce brief euphoria. It was developed by Clifford Hassing, a graduate student in Los Angeles, as a faster-acting analog of alkyl nitrite. Among the inhalants' trade names are Rush, Locker Room, and Bolt. They are sometimes marketed as "Cleaner", liquid incense, or room odorizer. It is used for its euphoric effect and for relaxing the smooth muscles during sexual intercourse.{{Cite web |title=Doctors Say It Can Kill You, but Butyl Nitrite Is a Legal High in Portland | vauthors = Orlean SC |work=Willamette Week |date=5 February 1980 |access-date=5 June 2022 |url= https://www.wweek.com/news/2022/06/04/doctors-say-it-can-kill-you-but-butyl-nitrite-is-a-legal-high-in-portland/}}{{Cite web |title=This Man Does Not Make Poppers | vauthors = Mack D |work=BuzzFeed News |date=27 July 2021 |access-date=5 June 2022 |url= https://www.buzzfeednews.com/article/davidmack/poppers-factory}}
Butyl nitrite is an important reagent in the synthesis of both organic and inorganic compounds and in the production of various other nitrites.Santa Cruz Biotechnology: [https://www.scbt.com/p/butyl-nitrite-544-16-1 Butyl nitrite | CAS 544-16-1 | SCBT - Santa Cruz Biotechnology], retrieved on 19 October 2024. It is often used as a nitrosating agent, particularly for the production of nitrosamines.{{citation|author=Nigel S. Simpkins |chapter=n -Butyl Nitrite |date=2001 |doi=10.1002/047084289x.rb404 |isbn=978-0-471-93623-7 |location=Chichester, UK |publisher=John Wiley & Sons, Ltd |title=Encyclopedia of Reagents for Organic Synthesis}}
See also
References
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