The Handbook of Overdose and Detoxification Emergencies. Isobutyl Nitrite and Related Compounds, 1st ed.
↑ Nickerson, Mark, John O Parker, Thomas P Lowry, and Edward W Swenson.Methemoglobin in turn can sequester cyanide as cyanomethemoglobin. It can act as an oxidant, to induce the formation of methemoglobin. Īmyl nitrite is also sometimes used as an antidote for cyanide poisoning. This effect, combined with its dissociative effects, has led to its use as a recreational drug (see poppers). 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. 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. The effects set in very quickly, typically within a few seconds and disappear soon after (within minutes).Īmyl nitrite is employed medically to treat heart diseases such as angina. Overdose symptoms include nausea, emesis (vomiting), hypotension, hypoventilation, dyspnea (shortness of breath), and syncope (fainting). 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. Alkyl nitrites function as a source of nitric oxide, which signals for relaxation of the involuntary muscles.
Physiological effectsĪmyl nitrite, in common with other alkyl nitrites, is a potent vasodilator ( i.e., it expands blood vessels, resulting in lowering of the blood pressure). For the synthesis of aryl iodides diiodomethane is used, whereas bromoform is the solvent of choice for the synthesis of aryl bromides. 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. Īmyl nitrites are also useful as reagents in a modification of the Sandmeyer reaction. Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the isoamyl alcohol:Īmyl nitrite, like other alkyl nitrites, reacts with carbanions to give oximes. 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. A common procedure includes the dropwise addition of concentrated sulfuric acid to a cooled mixture of an aqueous sodium nitrite solution and an alcohol. Synthesis of alkyl nitrites is, in general, straightforward and can be accomplished in home laboratories. When the amyl group is a linear or normal (n) alkyl group, the resulting amyl nitrite would have the structural formula CH 3(CH 2) 4ONO.ĭespite a very similar name to amyl nitrite, amyl nitrate has a different chemical composition and different properties.Īlkyl nitrites are prepared by the reaction of alcohols with nitrous acid: C 5H 11OH + HONO → C 5H 11ONO + H 2O For example, a common form of amyl nitrite with the formula (CH 3) 2CHCH 2CH 2ONO may be more specifically referred to as isoamyl nitrite. The term "amyl nitrite" encompasses several isomers.