Butyl nitrite

Butyl nitrite
Clinical data
ATC code	none;
Legal status
Legal status	UK: Controlled Drug (Medicines Act 1968); US: Unscheduled (illegal under Anti-Drug Abuse Act of 1988);
Identifiers
	IUPAC name 1-nitrosooxybutane;
CAS Number	544-16-1 ;
PubChem CID	10996;
ChemSpider	10530 ;
UNII	44P8QG0F3T;
CompTox Dashboard (EPA)	DTXSID8049418 ;
ECHA InfoCard	100.008.057
Chemical and physical data
Formula	C4H9NO2
Molar mass	103.121 g·mol−1
3D model (JSmol)	Interactive image;
Boiling point	78.0 °C (172.4 °F)
	SMILES CCCCON=O;
	InChI InChI=1S/C4H9NO2/c1-2-3-4-7-5-6/h2-4H2,1H3 ; Key:JQJPBYFTQAANLE-UHFFFAOYSA-N ;
	(verify)

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.^[1]

Applications

Butyl nitrite is one of the compounds used as poppers, inhalant drugs that induce brief euphoria. It was developed by Clifford Hassing,^[2]^[3] 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.^[2]^[3]

Butyl nitrite is an important reagent in the synthesis of both organic and inorganic compounds and in the production of various other nitrites.^[4] It is often used as a nitrosating agent, particularly for the production of nitrosamines.^[5]

References

^ Noyes WA (1936). "N-Butyl Nitrite". Organic Syntheses. 16: 7. doi:10.15227/orgsyn.016.0007.
^ ^a ^b Orlean SC (5 February 1980). "Doctors Say It Can Kill You, but Butyl Nitrite Is a Legal High in Portland". Willamette Week. Retrieved 5 June 2022.
^ ^a ^b Mack D (27 July 2021). "This Man Does Not Make Poppers". BuzzFeed News. Retrieved 5 June 2022.
^ Santa Cruz Biotechnology: Butyl nitrite | CAS 544-16-1 | SCBT - Santa Cruz Biotechnology, retrieved on 19 October 2024.
^ Nigel S. Simpkins (2001), "n -Butyl Nitrite", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289x.rb404, ISBN 978-0-471-93623-7

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[1] Noyes WA (1936). "N-Butyl Nitrite". Organic Syntheses. 16: 7. doi:10.15227/orgsyn.016.0007.

[ww-2] Orlean SC (5 February 1980). "Doctors Say It Can Kill You, but Butyl Nitrite Is a Legal High in Portland". Willamette Week. Retrieved 5 June 2022.

[buzz-3] Mack D (27 July 2021). "This Man Does Not Make Poppers". BuzzFeed News. Retrieved 5 June 2022.

[scbt.com-4] Santa Cruz Biotechnology: Butyl nitrite | CAS 544-16-1 | SCBT - Santa Cruz Biotechnology, retrieved on 19 October 2024.

[EROS-5] Nigel S. Simpkins (2001), "n -Butyl Nitrite", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289x.rb404, ISBN 978-0-471-93623-7

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Applications

See also

References