Amyl nitrite

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Amyl nitrite
Chemical structure of amyl nitrite
Ball-and-stick model of 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
110-46-3 YesY
ChEBI CHEBI:55344 YesY
ChemSpider 9632 YesY
DrugBank DB01612 YesY
Jmol 3D model Interactive image
KEGG D00517 YesY
PubChem 10026
RTECS number NT0187500
UNII 5N0U5TUC9Z YesY
  • InChI=1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3 YesY
    Key: CSDTZUBPSYWZDX-UHFFFAOYSA-N YesY
  • InChI=1/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3
    Key: CSDTZUBPSYWZDX-UHFFFAOYAT
  • O=NOCCCCC
Properties
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)
slightly soluble
Pharmacology
ATC code V03AB22
Vapor pressure {{{value}}}
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).
YesY verify (what is YesYN ?)
Infobox references

Amyl nitrite is the 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.

Nomenclature

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.

Synthesis and reactions

Alkyl nitrites are prepared by the reaction of alcohols with nitrous acid:[1]

C5H11OH + HONO → C5H11ONO + H2O

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.

Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the isoamyl alcohol:

C5H11ONO + NaOH → C5H11OH + NaNO2

Amyl nitrite, like other alkyl nitrites, reacts with carbanions to give oximes.[2]

Amyl nitrites are also useful as reagents in a modification of the Sandmeyer reaction. The reaction of the alkyl nitrite with an aromatic amine in a halogenated solvent produces a radical aromatic species, this then abstracts a halogen atom from the solvent. For the synthesis of aryl iodides diiodomethane is used,[3][4] whereas bromoform is the solvent of choice for the synthesis of aryl bromides.[5]

Physiological effects

Amyl nitrite, in common with other alkyl nitrites,[6] is a potent vasodilator; it expands blood vessels, resulting in lowering of the blood pressure. Alkyl nitrites are a source of nitric oxide, which signals for relaxation of the involuntary muscles. Physical effects include decrease in blood pressure, headache, flushing of the face, increased heart rate, dizziness, and relaxation of involuntary muscles, especially the blood vessel walls and the internal and external anal sphincter. There are no withdrawal symptoms. Overdose symptoms include nausea, vomiting, hypotension, hypoventilation, shortness of breath, and fainting. The effects set in very quickly, typically within a few seconds and disappear within a few minutes. Amyl nitrite may also intensify the experience of synesthesia.[7]

Applications

  • Amyl nitrite is employed medically to treat heart diseases such as angina. It is also used as an inhalant drug that induces a brief euphoric state, and when combined with other intoxicant stimulant drugs such as cocaine or ecstasy (see MDMA), the euphoric state intensifies and is prolonged. Once some stimulative drugs wear off, a common side effect is a period of depression or anxiety, colloquially called a "come down"; amyl nitrite is sometimes used to combat these negative after-effects. This effect, combined with its dissociative effects, has led to its use as a recreational drug (see poppers).[8]

References

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  6. Nickerson, Mark, John O Parker, Thomas P Lowry, and Edward W Swenson. Isobutyl Nitrite and Related Compounds, 1st ed. San Francisco: Pharmex, Ltd, 1979.
  7. Richard Cytowic, The Man Who Tasted Shapes, 2003.
  8. 8.0 8.1 AJ Giannini, AE Slaby, MC Giannini. The Handbook of Overdose and Detoxification Emergencies. New Hyde Park, NY. Medical Examination Publishing Co., 1982, pp.48-50.
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  12. amylnitrite.org Amyl

External links

  • Lua error in package.lua at line 80: module 'strict' not found. Editorial on the use of the word "amyl".