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| Other names | Isoamyl nitrite, Isopentyl nitrite, Nitramyl, 3-methyl-1-nitrosooxybutane, Pentyl alcohol nitrite (ambiguous), poppers (ambiguous, colloquial, slang) |
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| Formula | C5H11NO2 |
| Molar mass | 117.148 g·mol−1 |
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| Density | 0.872 g/cm3 |
| Boiling point | 99 °C (210 °F) |
| Solubility in water | Slightly soluble mg/mL (20 °C) |
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Amyl nitrite is achemical compound with theformula C5H11NO2. A variety of isomers are known, but they all feature anamyl group attached to thenitrite functional group. The alkyl group (the amyl in this case) is unreactive and the chemical and biological properties are mainly due to the nitrite group. Like otheralkyl nitrites, amyl nitrite is bioactive in mammals, being avasodilator, which is the basis of its use as a prescription medicine.[3] As an inhalant, it also has apsychoactive effect, which has led to its recreational use, with its smell being described as that of old socks or dirty feet.[4] It was first documented in 1844 and came into medical use in 1867.[5]
The term "amyl nitrite" encompasses severalisomers. In older literature, the common non-systematic nameamyl was often used for thepentyl group, where the amyl group is alinear or normal (n)alkyl group, and the resulting amyl nitrite would have the structural formula CH3(CH2)3CH2ONO, also referred to as n-amyl nitrite.
A common form of amyl nitrite is the isomer with the formula (CH3)2CHCH2CH2ONO, which may be more specifically referred to as isoamyl nitrite.
The similarly namedamyl nitrate has very different properties. At the same time,isopropyl nitrite has a similar structure and similar uses (also called 'poppers') but with worse side-effects.[13]
Amyl nitrite is sometimes referred to colloquially asbanapple gas.[14]
Alkyl nitrites are prepared by the reaction ofalcohols withnitrous acid:[15]
The reaction is calledesterification. Synthesis of alkyl nitrites is, in general, straightforward and can be accomplished in home laboratories. A common procedure includes the dropwise addition of concentratedsulfuric acid to a cooled mixture of an aqueous sodium nitrite solution and an alcohol. The intermediately-formed stoichiometric mixture of nitrogen dioxide 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 easilydecanted from the reaction mixture.
Isoamyl nitrite decomposes in the presence of base to give nitrite salts and theisoamyl alcohol:
Amyl nitrite, like other alkyl nitrites, reacts withcarbanions to giveoximes.[16]
Amyl nitrites are also useful as reagents in a modification of theSandmeyer reaction. The reaction of the alkyl nitrite with an aromaticamine in a halogenated solvent produces aradical aromatic species, this then frees ahalogen atom from the solvent. For the synthesis ofaryl iodidesdiiodomethane is used,[17][18] whereasbromoform is the solvent of choice for the synthesis ofaryl bromides.[19]
Amyl nitrite, in common with otheralkyl nitrites,[20] is a potentvasodilator; it expandsblood vessels, resulting in lowering of theblood pressure. Amyl nitrite may be used during cardiovascular stress testing in patients with suspected hypertrophic cardiomyopathy to cause vasodilation and thereby reduceafterload and provoke obstruction of blood flow towards the aorta from the ventricle by increasing the pressure gradient, thereby causing left ventricular outflow obstruction. Alkyl nitrites are a source ofnitric oxide, which signals for relaxation of theinvoluntary muscles. Physical effects include decrease in blood pressure, headache, flushing of the face, increased heart rate, dizziness, and relaxation of involuntary muscles, especially theblood vessel walls and theinternal andexternal anal sphincter. There are nowithdrawal symptoms.Overdose symptoms includenausea,vomiting,hypotension,hypoventilation,shortness of breath, andfainting. The effects set in very quickly, typically within a few seconds and disappear within a few minutes. Amyl nitrite may also intensify the experience ofsynesthesia.[21] Amyl nitrite, when given as a medication for patients with angina, can also be administered as an ampule. The ampule is put in a gauze pad and then inhaled by the patient during an angina attack and repeated every fifteen minutes. However, oral dosing of amyl nitrite is ineffective due to poor absorption and extensive hepatic metabolism. Amyl nitrite has been widely replaced bynitroglycerin for the treatment of acute angina.[citation needed]
There are case reports of life-threatening toxicity involving unusually large amounts.[22] However, there is little evidence that typical inhaled doses of amyl nitrite pose a significant risk, except when combined with drugs used for erectile dysfunction.[23][24] One study found neurotoxic effects in rats injected with alkyl nitrites, including impairments to memory, learning, and motor coordination, hypothesized to be due to effects on the glutamergic pathway in the hippocampus.[25] Further, liquid amyl nitrite is highly toxic when ingested because of the dangerously high concentration it causes in the blood.[26] Regardless of the form or route of administration, toxicity principally results when the nitrite oxidizes a significant proportion of hemoglobin in the blood without oxygen, forming methemoglobin, which cannot carry oxygen. Severe poisoning cases will progress tomethemoglobinemia, characterized by a blue-brown discoloration under the skin which could be mistaken for cyanosis.[22][26] Treatment with oxygen and intravenous methylene blue frustrates visual confirmation further as methylene blue itself is, as its name suggests, a blue dye; the patient's changes in different shades of blue notwithstanding, it is an effective antidote by way of catalyzing the production of the enzyme responsible for reducing the methemoglobin in the blood back to hemoglobin.
The discoloration does mean that regular near-infrared–based pulse oximetry becomes useless. More fundamentally, blood gas analysis on the whole has limited effectiveness, as the increased methemoglobin level increases the oxygen binding affinity of regular hemoglobin.[22] Therefore, the measurement of actual ratios and levels of methemoglobin and hemoglobin must accompany any blood gas partial pressure sample in these cases.
TheColumbo episode titled "Troubled Waters" (1974–1975) features amyl nitrite inhaled by the antagonist Hayden Danziger – played byRobert Vaughn – to help him feign a heart attack for his alibi. However, the episode consistently refers to the substance incorrectly as amyl nitrate.[27]
The 1978Derek Jarman filmJubilee features a character credited as "Amyl Nitrite", although in the film itself the character is "Amyl Nitrate".
The title of the 1993 song "Animal Nitrate" by English bandSuede is a pun on amyl nitrite, referencing its recreational use, although singerBrett Anderson has said the song has more to do with other drugs likeecstasy and cocaine.[28]
In the 1999 filmFight Club, the character Chloe, a terminally ill woman, mentions having a collection of amyl nitrite while openly discussing her unfulfilled desires at a cancer support group.
The punk bandAmyl and the Sniffers reference recreational use of amyl nitrite in their name.[29]
TheHunter S. Thompson bookFear and Loathing in Las Vegas sees amyl nitrite as one of the many drugs Raoul Duke packs for the trip toLas Vegas, taking about two dozen ampules of it with him and usually justifying its usage by him andDr. Gonzo to other people around them by claiming it is forangina.
In Season 1, Episode 9 ofBob's Burgers, "Spaghetti Western and Meatballs", Gene guesses amyl nitrite for the A in the ABS program near the end of the episode.
