Amyl nitrite

Amyl nitrite

Names
IUPAC name (3-methylbutyl) nitrite
Other names Isoamyl nitrite Nitramyl 3-methyl-1-nitrosooxybutane Pentyl alcohol nitrite(ambiguous) Nitrous acid, pentyl ester(ambiguous) poppers (colloquial, street slang)
Identifiers
CAS Number	110-46-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:55344 Y
ChemSpider	9632 Y
DrugBank	DB01612 Y
ECHA InfoCard	100.003.429
KEGG	D00517 Y
PubChem	10026
RTECS number	NT0187500
UNII	5N0U5TUC9Z Y
InChI InChI=1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3 Y Key: CSDTZUBPSYWZDX-UHFFFAOYSA-N Y InChI=1/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3 Key: CSDTZUBPSYWZDX-UHFFFAOYAT
SMILES O=NOCCCCC
Properties
Chemical formula	C5H11NO2
Molar mass	117.15 g·mol−1
Appearance	Colourless liquid
Density	0.872 g/cm3, liquid (25 °C)
Boiling point	99 °C (210 °F; 372 K)
Solubility in water	slightly soluble
Pharmacology
ATC code	V03AB22 (WHO)
Hazards
Main hazards	vasodilator
Flash point	21 °C (70 °F; 294 K)
Autoignition temperature	209 °C (408 °F; 482 K)
Related compounds
Related compounds	Nitroglycerine Isopentanol Butyl nitrite Isobutyl nitrite Ethyl nitrite Methyl nitrite Isopropyl nitrite Cyclohexyl nitrite
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

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 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. 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. It is also referred to as banapple gas.

The term "amyl nitrite" encompasses several isomers. For example, a common form of amyl nitrite with the formula (CH₃)₂CHCH₂CH₂ONO may be more specifically referred to as isoamyl nitrite. When the amyl group is a linear or normal (n) alkyl group, the resulting amyl nitrite would have the structural formula CH₃(CH₂)₄ONO.

Despite a very similar name to amyl nitrite, amyl nitrate has a different chemical composition and different properties. Vast numbers of people confuse the two drugs, especially those wishing to purchase "poppers" (amyl nitrite) for recreational purposes.

Alkyl nitrites are prepared by the reaction of alcohols with nitrous acid:

The reaction is called esterification. Synthesis of alkyl nitrites is, in general, straightforward and can be accomplished in home laboratories. A common procedure includes the dropwise addition of concentrated sulfuric acid to a cooled mixture of an aqueous sodium nitrite solution and an alcohol. The intermediately-formed stoichiometric mixture of nitrous and nitric oxide then converts the alcohol to the alkyl nitrite, which, due to its low density, will form an upper layer that can be easily decanted from the reaction mixture.