Amyl nitrite

Not to be confused with amyl nitrate.
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
3D model (Jmol) Interactive image
ChEBI CHEBI:55344 YesY
ChemSpider 9632 YesY
DrugBank DB01612 YesY
ECHA InfoCard 100.003.429
KEGG D00517 YesY
PubChem 10026
RTECS number NT0187500
UNII 5N0U5TUC9Z YesY
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
V03AB22 (WHO)
Hazards
Main hazards vasodilator
Flash point 21 °C (70 °F; 294 K)
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).
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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.

Uses

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:[6]

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.[7]

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 frees a halogen atom from the solvent. For the synthesis of aryl iodides diiodomethane is used,[8][9] whereas bromoform is the solvent of choice for the synthesis of aryl bromides.[10]

Physiological effects

Amyl nitrite, in common with other alkyl nitrites,[11] 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.[12]

References

  1. 1 2 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.
  2. Cheng, L.; Goodwin, C. A.; Schully, M. F.; Kakkar, V. V.; Claeson, G. (1965). "The Effects of Nitroglycerin and Amyl Nitrite on Arteriolar and Venous Tone in the Human Forearm". Circulation. 3 (2): 755–66. doi:10.1161/01.cir.32.5.755. PMID 4954412.
  3. Vale, J. A. (2001). "Cyanide Antidotes: from Amyl Nitrite to Hydroxocobalamin – Which Antidote is Best?". Toxicology. 168 (1): 37–38.
  4. "Dichlorodifluoromethane at LearnChemistry (Royal Society of Chemistry)".
  5. amylnitrite.org Amyl
  6. Noyes, W. A. (1943). "n-Butyl Nitrite". Org. Synth.; Coll. Vol., 2, p. 108
  7. Chen, Y. K.; Jeon, S.-J; Walsh, P. J.; Nugent, W. A. (2005). "(2S)-(−)-3-exo-(Morpholino)isoborneol ((−)-MIB)". Org. Synth. 82: 87.
  8. Smith, William B.; Ho, Oliver Chenpu (1990). "Application of the isoamyl nitrite-diiodomethane route to aryl iodides". The Journal of Organic Chemistry. 55 (8): 2543–2545. doi:10.1021/jo00295a056.
  9. Cornforth, John; Kumar, Ashok; Stuart, Alan S. (1987). "Synthesis of substituted dibenzophospholes. Part 6. Preparation of symmetrical and non-symmetrical quaterphenyl intermediates". Journal of the Chemical Society, Perkin Transactions 1: 859. doi:10.1039/P19870000859.
  10. Cadogan, J. I. G.; Roy, D. A.; Smith, D. M. (1966). "An alternative to the Sandmeyer reaction". Journal of the Chemical Society C: Organic: 1249. doi:10.1039/J39660001249.
  11. Nickerson, Mark, John O Parker, Thomas P Lowry, and Edward W Swenson. Isobutyl Nitrite and Related Compounds, 1st ed. San Francisco: Pharmex, Ltd, 1979.
  12. Richard Cytowic, The Man Who Tasted Shapes, 2003.

External links


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