Butyl nitrite: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 411437556

| IUPAC_name = 1-nitrosooxybutane

| image = Butyl-nitrite-3DV-vdW.svg

<!--Clinical data-->

| tradename =

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->

| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = [[Medicines Act 1968|Controlled Drug (Medicines Act 1968)]]<!-- GSL / P / POM / CD / Class A, B, C -->

| legal_US = Unscheduled [[Anti-Drug Abuse Act of 1988|(illegal under Anti-Drug Abuse Act of 1988)]]<!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 544-16-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 44P8QG0F3T

| ATC_prefix = none

| PubChem = 10996

<!--Chemical data-->

| C=4 | H=9 | N=1 | O=2

| smiles = CCCCON=O

| 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|''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|''n''-butanol]].<ref>{{cite journal |doi=10.15227/orgsyn.016.0007|title=N-Butyl Nitrite|journal=Organic Syntheses|year=1936|volume=16|page=7| vauthors = Noyes WA }}</ref>

==Applications==

Butyl nitrite is one of the compounds used as [[poppers]], [[inhalant]] drugs that induce brief [[euphoria]]. It was developed by Clifford Hassing,<ref name="ww"/><ref name="buzz"/> 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 muscle|smooth muscles]] during sexual intercourse.<ref name="ww">{{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/}}</ref><ref name="buzz">{{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}}</ref>

Butyl nitrite is an important reagent in the synthesis of both organic and inorganic compounds and in the production of various other nitrites.<ref name="scbt.com">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.</ref> It is often used as a [[nitrosating agent]], particularly for the production of [[nitrosamines]].<ref name="EROS">{{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}}<!-- auto-translated from German by Module:CS1 translator --></ref>

==See also==

*[[tert-butyl nitrite]]

{{Nitric oxide signaling}}

[[Category:Butyl esters]]