Amyl nitrite
Amyl nitrite
Identifiers
CAS number 110-46-3 YesY
PubChem 10026
ChemSpider 9632 YesY
UNII 5N0U5TUC9Z YesY
DrugBank DB01612
KEGG D00517 YesY
ChEBI CHEBI:55344 YesY
RTECS number NT0187500
ATC code V03AB22
Jmol-3D images Image 1
Properties
Molecular formula C5H11NO2
Molar mass 117.15 g mol−1
Appearance Colourless liquid
Density 0.872 g/cm3, liquid (25 °C)
Boiling point

99 °C, 372 K, 210 °F

Solubility in water Low
Hazards
Main hazards vasodilator
Flash point 21 °C
Related compounds
Related compounds Nitroglycerine
Isopentanol
Butyl nitrite
Isobutyl nitrite
Ethyl nitrite
Methyl nitrite
Isopropyl nitrite
Cyclohexyl nitrite
 YesY nitrite (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 nitrito 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.

Contents

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 (i.e., it expands blood vessels, resulting in lowering of the blood pressure). Alkyl nitrites function as 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 anal sphincter. There are no withdrawal symptoms. Overdose symptoms include nausea, emesis (vomiting), hypotension, hypoventilation, dyspnea (shortness of breath), and syncope (fainting). The effects set in very quickly, typically within a few seconds and disappear soon after (within minutes).

It induces the formation of methemoglobin, which sequesters cyanide as nontoxic cyanomethemoglobin.[7]

Applications

Amyl nitrite is employed medically to treat heart diseases such as angina and also to treat cyanide poisoning.[8] It is also used as an inhalant drug that induces a brief euphoric state, and when combined with other intoxicatant 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, makes it an attractive but risky recreational drug (see poppers).[9]

References

  1. ^ Noyes, W. A. (1943), "n-Butyl Nitrite", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV2P0108 ; Coll. Vol. 2: 108 
  2. ^ Chen, Y. K.; Jeon, S.-J; Walsh, P. J.; Nugent, W. A. (2005), "(2S)-(-)-3-exo-(Morpholino)isoborneol ((-)-MIB)", Org. Synth. 82: 87, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v82p0087 
  3. ^ 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. doi:10.1021/jo00295a056. 
  4. ^ 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. 
  5. ^ 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. 
  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. ^ Vale, J. A. (2001). "Cyanide Antidotes: from Amyl Nitrite to Hydroxocobalamin - Which Antidote is Best?". Toxicology 168 (1): 37–38. 
  8. ^ 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. PMID 4954412. 
  9. ^ 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.

External links

  • Kjonaas, Richard A. (1996). "Amyl: A Misunderstood Word". Journal of Chemical Education 73 (12): 1127. doi:10.1021/ed073p1127.  Editorial on the use of the word "amyl".

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Look at other dictionaries:

  • amyl nitrite — n a pale yellow pungent flammable liquid ester C5H11NO2 of commercial amyl alcohol and nitrous acid that is used chiefly in medicine as a vasodilator esp. in treating angina pectoris and illicitly as an aphrodisiac called also isoamyl nitrite… …   Medical dictionary

  • Amyl nitrite — A yellowish oily volatile liquid, {C5H11NO2}, used in medicine as a heart stimulant and a vasodilator. The inhalation of its vapor instantly produces flushing of the face. [Webster 1913 Suppl.] …   The Collaborative International Dictionary of English

  • Amyl nitrite — Nitrite Ni trite, n. [Cf. F. nitrite. See {Niter}.] (Chem.) A salt or ester of nitrous acid; a compound bearing the { NO2} radical. [1913 Webster +PJC] {Amyl nitrite}, a yellow oily volatile liquid, used in medicine as a depressant and a vaso… …   The Collaborative International Dictionary of English

  • amyl nitrite — n. a volatile liquid, C5H11NO2, that is inhaled to dilate blood vessels, esp. in angina pectoris …   English World dictionary

  • amyl nitrite — Pharm. a yellowish, fragrant, flammable liquid, C5H11NO2, used in medicine chiefly as a vasodilator, esp. in the treatment of angina pectoris: misused by inhalation as a stimulant, esp. of sexual sensation. Also called isoamyl nitrite. * * * ▪… …   Universalium

  • amyl nitrite — noun a) The ester of amyl alcohol and nitrous acid. b) isoamyl nitrite …   Wiktionary

  • amyl nitrite — noun : a pale yellow pungent flammable liquid ester C5H11ONO of commercial amyl alcohol and nitrous acid that is used chiefly in medicine as a vasodilator especially in angina pectoris called also isoamyl nitrite …   Useful english dictionary

  • amyl nitrite — noun Date: circa 1881 a pale yellow pungent flammable liquid ester C5H11NO2 of commercial amyl alcohol and nitrous acid that is used in medicine as a vasodilator and inhaled illicitly especially as an aphrodisiac compare popper 2 …   New Collegiate Dictionary

  • amyl nitrite — /æməl ˈnaɪtraɪt/ (say amuhl nuytruyt) noun a yellowish volatile liquid ester, C5H11NO2, with a fragrant odour, used in medicine as a vasodilator especially in the treatment of angina pectoris, and to heighten pleasure during sexual orgasm. Also,… …   Australian English dictionary

  • amyl nitrite — n. (Chemistry) yellowish and oily liquid used in medicine to enlarge blood vessels, substance inhaled for its rousing stimulatory effects …   English contemporary dictionary

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