Isoamyl Nitrite
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| Synonyms | Isoamyl nitrite, Nitramyl, 3-methyl-1-nitrosooxybutane, Pentyl alcohol nitrite (ambiguous), poppers (colloquial, slang) |
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| ECHA InfoCard | 100.003.429 |
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| Formula | C5H11NO2 |
| Molar mass | 117.15 g·mol−1 |
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| Density | 0.872 g/cm3 |
| Boiling point | 99 °C (210 °F) |
| Solubility in water | slightly soluble mg/mL (20 °C) |
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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.
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