Amyl nitrite

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Amyl nitrite

Amyl nitrite is the chemical compound

Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
with the formula

Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
C₅H₁₁ONO. A variety of isomers are known, but they all feature an amyl

Amyl

The word or root amyl has two meanings, in organic chemistry and biochemistry....
group attached to the nitrito functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
. 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.

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Encyclopedia

Amyl nitrite is the chemical compound

Chemical compound

Chemical formula

Amyl

The word or root amyl has two meanings, in organic chemistry and biochemistry....
group attached to the nitrito functional group

Functional group

Psychoactive drug

A psychoactive drug or psychotropic substance is a chemical substance that acts primarily upon the central nervous system where it alters brain function, resulting in temporary changes in perception, mood , consciousness and behaviour....
effect which has led to its recreational use.

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)

Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
alkyl

Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
group, the resulting amyl nitrite would have the structural formula CH₃(CH₂)₄ONO.

Amyl nitrite is often confused with amyl nitrate

Amyl nitrate

Amyl nitrate is the chemical compound with the chemical formula CH34ONO2. This molecule consists of the 5-carbon amyl group attached to a nitrate functional group....
, a substance with a different chemical composition and different properties.

Synthesis and reactions

Alkyl nitrites are prepared by the reaction of alcohol

Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s with nitrous acid

Nitrous acid

Nitrous acid is a weak and monobasic acid known only in solution and in the form of nitrite salts.Nitrous acid is used to make diazo from amines; this occurs by nucleophilic attack of the amine onto the nitrite, reprotonation by the surrounding solvent, and double-elimination of water....
:

C₅H₁₁OH + HONO ? C₅H₁₁ONO + H₂O

The reaction is called esterification

Esterification

Esterification is the general name for a chemical reaction in which two reactants form an ester as the product . Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor....
. Synthesis of alkyl nitrites is generally 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

Decantation

Decantation is a process for the separation of mixtures, carefully pouring a solution from a container in order to leave the precipitate in the bottom of the original container....
from the reaction mixture.

Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the isoamyl alcohol

Amyl alcohol

Amyl alcohol is an organic compound with the formula C5H12O. All eight isomers of amyl alcohol are known:|+Isomers of amyl alcohol...
:

C₅H₁₁ONO + NaOH ? C₅H₁₁OH + NaNO₂

Sodium nitrite

Sodium nitrite, with chemical formula SodiumNitrogenOxygen2, is used as a colour retention agent and preservative in meats and fish....

Amyl nitrite, like other alkyl nitrites, reacts with carbanion

Carbanion

A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons ....
s to give oxime

Oxime

An oxime is one in a class of chemical compounds with the general formula R1R2carbonnitrogenoxygenhydrogen, where R1 is an organic compound side chain and R2 is either hydrogen, forming an aldoxime, or another organic group, forming a ketoxime....
s.

Physiological effects

Amyl nitrite, in common with other alkyl nitrites

Alkyl nitrites

Alkyl nitrites are chemical compounds of structure R-ONO. Formally they are alkyl esters of nitrous acid. They are distinct from nitro compounds ....
, is a potent vasodilator, i.e. it expands blood vessel

Blood vessel

The blood vessels are the part of the circulatory system that transport blood throughout the body. There are three major types of blood vessels: the artery, which carry the blood away from the heart, the capillary, which enable the actual exchange of water and chemicals between the blood and the tissues; and the veins, which carry blood from...
s, resulting in lowering of the blood pressure

Blood pressure

Blood pressure is the pressure exerted by circulating blood on the walls of blood vessels, and constitutes one of the principal vital signs. The pressure of the circulating blood decreases as it moves away from the heart through artery and capillary, and toward the heart through veins....
. Alkyl nitrites function as a source of nitric oxide

Nitric oxide

Nitric oxide or nitrogen monoxide is a chemical compound with chemical formula NitrogenOxygen. This gas is an important signaling molecule in the body of mammals, including humans, and is an extremely important intermediate in the chemical industry....
, 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

Blood vessel

Withdrawal

Withdrawal, also known as withdrawal/abstinence syndrome, refers to the characteristic signs and symptoms that appear when a drug that causes physical dependence is regularly used for a long time and then suddenly discontinued or decreased in dosage....
symptoms. Overdose symptoms include nausea

Nausea

Nausea is the sensation of unease and discomfort in the stomach with an urge to vomit....
, emesis (vomiting), hypotension

Hypotension

In physiology and medicine, hypotension refers to an abnormally low blood pressure. This is best understood as a physiologic state, rather than a disease....
, hypoventilation

Hypoventilation

In medicine, hypoventilation occurs when Ventilation is inadequate to perform needed gas exchange. By definition it causes an increased concentration of carbon dioxide and respiratory acidosis....
, dyspnea

Dyspnea

Dyspnea or dyspnoea , from Latin language dyspnoea, from Greek language dyspnoia from dyspnoos, shortness of breath) or shortness of breath is perceived to be difficulty of breathing or painful breathing that a patient is aware of....
(shortness of breath), and syncope (fainting). The effects set in very quickly, typically within a few seconds and disappearing soon after (within a minute).

It induces the formation of methemoglobin, which sequesters cyanide as non-toxic cyanomethemoglobin.

Applications

Amyl nitrite is employed medically to treat heart disease

Ischaemic heart disease

Ischaemic or ischemic heart disease , or myocardial ischaemia, is a disease characterized by reduced blood supply to the myocardium, usually due to Coronary heart disease ....
s such as angina and also to treat cyanide

Cyanide

A cyanide is any chemical compound that contains the nitrile , which consists of a carbon atom chemical bond to a nitrogen atom. Inorganic cyanides are hydrogen cyanide salts in which cyanide is generally the anion CN-....
poisoning. It is also used as an inhalant

Inhalant

Inhalants are a broad range of drugs in the forms of gases,aerosols, or solvents which are breathed in and absorbed through the lungs. While some inhalant drugs are used for List of medical inhalants, as in the case of nitrous oxide , this article focuses on the non-medical use of inhalants, as recreational drugs which are used for their int...
drug that induces a brief euphoria

Euphoria

Euphoria or euphoric may refer to:* Euphoria , an emotional and mental state Defined as a sense of great elation and wellbeing* 4-Methyl-aminorex , a stimulant drug with effects comparable to methamphetamine...
; whilst already intoxicated with stimulant drugs such as cocaine

Cocaine

Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine....
or ecstasy (see MDMA) the euphoric state intensifies and lasts for several minutes longer. Once some stimulative drugs wear off, a common side effect is a period of depression

Clinical depression

Major depressive disorder is a mental disorder characterized by a pervasive depression , low self-esteem, and anhedonia in normally enjoyable activities....
or anxiety

Anxiety

Anxiety is a psychological and physiological state characterized by cognitive, somatic, emotional, and behavioral components. These components combine to create an unpleasant feeling that is typically associated with uneasiness, fear, or worry....
, colloquially called a "come down"; amyl nitrite is sometimes used to "come up" again in order to stop these adverse effects. This drug is often used to obtain an erection with rather rapid onset. This effect, combined with its dissociative effects, makes it an attractive but risky recreational drug (see poppers

Poppers

Poppers is the street term for various alkyl nitrites taken for recreational purposes through direct inhalant, particularly amyl nitrite, butyl nitrite, isopropyl nitrite and isobutyl nitrite....
).

External links

for an article in the Journal of Chemical Education (1996, volume 73, page 1127) by Richard A. Kjonaas on the use of the word "amyl".