Amyl nitrite

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Not to be confused with amyl nitrate.
Amyl nitrite
Chemical structure of amyl nitrite
Ball-and-stick model of amyl nitrite
IUPAC name
(3-methylbutyl) nitrite
Other names
Isoamyl nitrite
Pentyl alcohol nitrite(ambiguous)
Nitrous acid, pentyl ester(ambiguous)
poppers (colloquial, street slang)
ATC code V03AB22
110-46-3 YesY
ChEBI CHEBI:55344 YesY
ChemSpider 9632 YesY
DrugBank DB01612 YesY
Jmol-3D images Image
KEGG D00517 YesY
PubChem 10026
RTECS number NT0187500
Molar mass 117.15 g·mol−1
Appearance Colourless liquid
Density 0.872 g/cm3, liquid (25 °C)
slightly soluble
Main hazards vasodilator
Flash point 21 °C (70 °F; 294 K)
209 °C (408 °F; 482 K)
Related compounds
Related compounds
Butyl nitrite
Isobutyl nitrite
Ethyl nitrite
Methyl nitrite
Isopropyl nitrite
Cyclohexyl nitrite
 YesY verify (what isYesY/N?)
Infobox references




Despite a very similar name to amyl nitrite, amyl nitrate has a different chemical composition and different properties.

Synthesis and reactions[edit]

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.


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[edit]

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 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 nitrate may also intensify the experience of synesthesia.[7]


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]

Amyl nitrite is also sometimes used as an antidote for cyanide poisoning.[9][8] It can act as an oxidant, to induce the formation of methemoglobin. Methemoglobin in turn can sequester cyanide as cyanomethemoglobin.[10]


  1. ^ Noyes, W. A. (1943). "n-Butyl Nitrite". Org. Synth. ; Coll. Vol. 2, p. 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. 
  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. ^ Richard Cytowic, The Man Who Tasted Shapes, 2003.
  8. ^ a b 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.
  9. ^ 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. 
  10. ^ Vale, J. A. (2001). "Cyanide Antidotes: from Amyl Nitrite to Hydroxocobalamin - Which Antidote is Best?". Toxicology 168 (1): 37–38. 

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