Amyl nitrite

Amyl nitrite
Clinical data
Other names	Isoamyl nitrite,; Isopentyl nitrite,; Nitramyl,; 3-methyl-1-nitrosooxybutane,; Pentyl alcohol nitrite (ambiguous),; poppers (ambiguous, colloquial, slang)
ATC code	V03AB22 (WHO) ;
Legal status
Legal status	AU: S3 (Pharmacist only) / S4 (Prescription only); BR: Class C1 (Other controlled substances); DE: Unscheduled (unauthorized sale and purchase illegal); UK: Controlled Drug (Medicines Act 1968); US: Unscheduled (illegal under Crime Control Act of 1990);
Identifiers
	IUPAC name (3-methylbutyl) nitrite;
CAS Number	110-46-3 ;
PubChem CID	8053;
DrugBank	DB01612 ;
ChemSpider	7762 ;
UNII	5N0U5TUC9Z;
KEGG	D00517 ;
ChEBI	CHEBI:2691 ;
CompTox Dashboard (EPA)	DTXSID9025455 ;
Chemical and physical data
Formula	C5H11NO2
Molar mass	117.148 g·mol−1
3D model (JSmol)	Interactive image;
Density	0.872 g/cm3
Boiling point	99 °C (210 °F)
Solubility in water	Slightly soluble mg/mL (20 °C)
	SMILES CC(C)CCON=O;
	InChI InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3 ; Key:OWFXIOWLTKNBAP-UHFFFAOYSA-N ;
	(verify)

Amyl nitrite is a chemical compound with the formula C₅H₁₁ONO. A variety of isomers are known, but they all feature an amyl group attached to the nitrite functional group. The alkyl group (the amyl in this case) is unreactive and the chemical and biological properties are mainly due to the nitrite group. Like other alkyl nitrites, amyl nitrite is bioactive in mammals, being a vasodilator, which is the basis of its use as a prescription medicine.^[3] As an inhalant, it also has a psychoactive effect, which has led to its recreational use, with its smell being described as that of old socks or dirty feet.^[4] It was first documented in 1844 and came into medical use in 1867.^[5]

^ Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024 (Cth). Schedule 3 "when in preparations for human therapeutic use and packaged in containers with child‑resistant closures"; schedule 4 otherwise.
^ Anvisa (2024-05-28). "RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived from the original on 2024-09-25. Retrieved 2024-09-25.
^ "Amyl Nitrite (Inhalation Route) Description and Brand Names - Mayo Clinic". www.mayoclinic.org. Retrieved 2023-12-05.
^ "Drugs - Amyl, Butyl or Isobutyl Nitrite, Nitrates, Poppers". urban75.com.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. XXX. ISBN 9783527607495.

[1] Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024 (Cth). Schedule 3 "when in preparations for human therapeutic use and packaged in containers with child‑resistant closures"; schedule 4 otherwise.

[2] Anvisa (2024-05-28). "RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived from the original on 2024-09-25. Retrieved 2024-09-25.

[3] "Amyl Nitrite (Inhalation Route) Description and Brand Names - Mayo Clinic". www.mayoclinic.org. Retrieved 2023-12-05.

[4] "Drugs - Amyl, Butyl or Isobutyl Nitrite, Nitrates, Poppers". urban75.com.

[5] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. XXX. ISBN 9783527607495.

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