Amyl nitrite
IUPAC name	3-methyl-1-nitrosooxybutane
Other names	Isoamyl nitrite Nitramyl 3-methyl-1-nitrosooxybutane Pentyl alcohol nitrite(ambiguous) Nitrous acid, pentyl ester(ambiguous)
Identifiers
CAS number	110-46-3
RTECS number	NT0187500
SMILES	CC(C)CCON=O
Properties
Molecular formula	C5H11NO2
Molar mass	117.15 g/mol
Appearance	Colourless liquid
Density	0.872 g/cm³, liquid (25 °C)
Melting point	?? °C Image File history File links Amyl_nitrite. ... Image File history File links Size of this preview: 800 × 401 pixel Image in higher resolution (1100 × 551 pixel, file size: 119 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Amyl nitrite ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	99 °C Italic text This article is about the boiling point of liquids. ...
Solubility in water	Low
Hazards
Main hazards	vasodialator
Flash point	21 °C
Related Compounds
Related compounds	nitroglycerine isopentanol Butyl nitrite Isobutyl nitrite Ethyl nitrite Methyl nitrite Isopropyl nitrite Cyclohexyl nitrite Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... The examples and perspective in this article or section may not represent a worldwide view. ... For other uses, see Flash point (disambiguation). ... Nitroglycerin (also nitroglycerine, trinitroglycerin, or glyceryl trinitrate) is a chemical compound, a heavy, colorless, poisonous, oily, explosive liquid obtained by nitrating glycerol. ... This article is part of the Wikiproject on Drugs, which is an attempt to facilitate the categorization and creation of accurate and formal drug-related articles on Wikipedia. ... Isobutyl nitrite is an alkyl nitrite, an ester of isobutyl alcohol and nitrous acid. ... The chemical compound ethyl nitrite is an Alkyl nitrite. ... The chemical compound methyl nitrite is an Alkyl nitrite. ... The chemical compound isopropyl nitrite (or propyl nitrite) is an Alkyl nitrite. ... Cyclohexyl Nitrite is an Alkyl nitrite made from Cyclohexl alcohol. ...
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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 substituent is not reactive, but the ON=O group behaves as other nitrites. 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 illegal drug use. The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Amyl is a linguistic root word derived from the Latin amylum, from Greek αμυλον, meaning starch. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... Rush, and Rave; Marketed Brands of Alkyl Nitrites Alkyl nitrites or Poppers are a class of inhalant used for the treatment of angina. ... Rush, and Rave; Marketed Brands of Alkyl Nitrites Alkyl nitrites or Poppers are a class of inhalant used for the treatment of angina. ... Vasodilation is where blood vessels in the body become wider following the relaxation of the smooth muscle in the vessel wall. ...

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 chain consists of five carbon atoms in a row, the resulting "amyl nitrite" would be described with the structural formula CH₃(CH₂)₄ONO. Sometimes the latter isomer is called n-amyl nitrite, n denoting normal. Also, the five carbon chain is sometimes referred to as a straight chain, although chains of carbon atoms are usually zig-zag in conformation. In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of bonds between atoms, but in which the atoms are arranged differently. ... Conformational isomerism is the phenomenon of molecules with the same structural formula but different conformations (conformers) of atoms about a rotating bond. ...

Amyl nitrite is often confused with amyl nitrate, a substance with a different chemical composition and different properties. Amyl nitrate is used medically to treat psyhcos, and is sometimes used postoperatively in urologic procedures to rapidly abort unwanted erections (especially in the cases of Nesbitt procedures and complex urethroplasty). ...

Synthesis and reactions

Alkyl nitrites are prepared by the reaction of alcohols with nitrous acid:^[1] This article does not cite any references or sources. ... Nitrous acid (molecular formula HNO2) is a weak monobasic acid known only in solution and in the form of nitrite salts. ...

C₅H₁₁OH + HONO →→ C₅H₁₁ONO + H₂O

The reaction is called esterification. 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 from the reaction mixture. Esterification is the general name for a chemical reaction in which two chemicals (typically an alcohol and an acid) form an ester as the reaction product. ...

Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the isoamyl alcohol: There are eight isomers of amyl alcohol (C5H11OH): Three of these alcohols, active amyl alcohol, methyl (n) propyl carbinol, and methyl isopropyl carbinol, contain an asymmetric carbon atom and can consequently each exist in two optically active, and one optically inactive form. ...

C₅H₁₁ONO + NaOH → C₅H₁₁OH + NaNO₂

Amyl nitrite, like other alkyl nitrites, reacts with carbanions to give oximes.^[2] Sodium nitrite, with chemical formula NaNO2, is used as a color fixative and preservative in meats and fish. ... 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. ... An oxime is one in a class of chemical compounds with the general formula R1R2 C N O H, where R1 is an organic side chain and R2 is either hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. ...

Physiological effects

Amyl nitrite, in common with other alkyl nitrites,^[3] 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. Alkyl nitrites are a group of organic compounds with the general formula R-O-N=O, where R is any organic group. ... Vasodilation is where blood vessels in the body become wider following the relaxation of the smooth muscle in the vessel wall. ... f you all The blood vessels are part of the circulatory system and function to transport blood throughout the body. ... A sphygmomanometer, a device used for measuring arterial pressure. ... R-phrases , , , , S-phrases , , , Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Nitric oxide or Nitrogen monoxide is a chemical compound with chemical formula NO. This gas is an important signaling molecule in the body of... Involuntary muscles are smooth, uninucleated, non-branching muscles that are not directly controllable at will. ... f you all The blood vessels are part of the circulatory system and function to transport blood throughout the body. ... Male Anatomy The anus, in anatomy, is the external opening of the rectum. ... Withdrawal, also known as withdrawal 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. ... A drug overdose occurs when a chemical substance (i. ... For other uses, see Nausea (disambiguation). ... Vomiting (or emesis) is the forceful expulsion of the contents of ones stomach through the mouth. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... In medicine, hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (hypo means below) to perform needed gas exchange. ... Dyspnea (R06. ... It has been suggested that Central Ischaemic Response be merged into this article or section. ...

It induces the formation of methemoglobin, which sequesters cyanide as non-toxic cyanomethemoglobin.^[4] Methemoglobin (also hemiglobin) is a type of hemoglobin that is produced by the oxidation of the ferrous iron contained in hemoglobin to ferric iron which doesnt have the capacity for carrying oxygen. ...

Applications

Amyl nitrite is employed medically to treat heart diseases such as angina and to treat cyanide poisoning.^[5] It is also used as an illegal inhalant drug that induces a brief euphoria. See Poppers. Ischaemic (or ischemic) heart disease is a disease characterized by reduced blood supply to the heart. ... angina tonsillaris see tonsillitis. ... This article is about the chemical compound. ... An aerosol metered-dose inhaler (MDI) used for administration of asthma medication. ... Variety of popper brands Poppers is the street term for various alkyl nitrites taken for recreational purposes through direct inhalation, particularly amyl nitrite, butyl nitrite and isobutyl nitrite. ...

References

William A. Noyes (1857-1941) was an American analytical and organic chemist. ... Toxicology (from the Greek words toxicos and logos [1]) is the study of the adverse effects of chemicals on living organisms [2]. It is the study of symptoms, mechanisms, treatments and detection of poisoning, especially the poisoning of people. ... The word circulation can mean the following: The transport of blood through the circulatory system. ...

External links

• Abstract 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".