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| {{Chembox new
| | #REDIRECT [[Amyl nitrite#Pharmacology]] |
| | Name = Amyl nitrite
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| | ImageFile = Amyl nitrite.svg
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| | ImageSize = 160px
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| | ImageName = Chemical structure of amyl nitrite
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| | ImageFile1 = Amyl-nitrite-3D-balls.png
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| | ImageSize1 = 200px
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| | ImageName1 = Ball-and-stick model of amyl nitrite
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| | IUPACName = 3-methyl-1-nitrosooxybutane
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| | OtherNames = Isoamyl nitrite<br/>Nitramyl<br/>3-methyl-1-nitrosooxybutane<br/>Pentyl alcohol nitrite(ambiguous)<br/>Nitrous acid, pentyl ester(ambiguous)
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| | Section1 = {{Chembox Identifiers
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| | SMILES = CC(C)CCON=O
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| | CASNo = 110-46-3
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| | RTECS = NT0187500
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| }}
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| | Section2 = {{Chembox Properties
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| | Formula = C<sub>5</sub>H<sub>11</sub>NO<sub>2</sub>
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| | MolarMass = 117.15 g/mol
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| | Appearance = Colourless liquid
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| | Density = 0.872 g/cm³, liquid (25 °C)
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| | Solubility = Low
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| | MeltingPt = ?? °C
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| | BoilingPt = 99 °C
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| }}
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| | Section7 = {{Chembox Hazards
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| | MainHazards = vasodialator
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| | FlashPt = 21 °C
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| }}
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| | Section8 = {{Chembox Related
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| | OtherCpds = [[nitroglycerine]]<br/>[[isopentanol]]<br/>[[Butyl nitrite]]<br/>[[Isobutyl nitrite]]<br/> [[Ethyl nitrite]]
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| <br/> [[Methyl nitrite]]<br/> [[Isopropyl nitrite]]<br/> [[Cyclohexyl nitrite]]
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| }}
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| }}
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| {{EH}}
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| ==Overview==
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| '''Amyl nitrite''' is the [[chemical compound]] with the [[chemical formula|formula]] C<sub>5</sub>H<sub>11</sub>ONO. 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 [[alkyl nitrite|nitrite]]s. Like other [[alkyl nitrite]]s, 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 psychoactive effect which has led to illegal drug use.
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| ==Nomenclature==
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| The term "amyl nitrite" encompasses several [[isomers]]. For example, a common form of amyl nitrite with the formula (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>ONO 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 CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>ONO. 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 [[Conformational isomerism|conformation]].
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| Amyl nitrite is often confused with [[amyl nitrate]], a substance with a different chemical composition and different properties.
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| ==Synthesis and reactions==
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| Alkyl nitrites are prepared by the reaction of [[alcohol]]s with [[nitrous acid]]:<ref>[[William A. Noyes|Noyes, W. A.]] “n-Butyl Nitrite” Organic Syntheses, Collected Volume 2, p.108 (1943). [http://www.orgsyn.org/orgsyn/pdfs/CV2P0108.pdf] (PDF)</ref>
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| :C<sub>5</sub>H<sub>11</sub>OH + HONO →→ C<sub>5</sub>H<sub>11</sub>ONO + H<sub>2</sub>O
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| 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.
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| Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the [[Amyl alcohol|isoamyl alcohol]]:
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| :C<sub>5</sub>H<sub>11</sub>ONO + NaOH → C<sub>5</sub>H<sub>11</sub>OH + [[sodium nitrite|NaNO<sub>2</sub>]]
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| Amyl nitrite, like other alkyl nitrites, reacts with [[carbanion]]s to give [[oxime]]s.<ref>Chen, Y. K.; Jeon, S.-J; Walsh, P. J.; Nugent, W. A. “(2S)-(-)-3-exo-(Morpholino)isoborneol ((-)-MIB)” Organic Syntheses, Volume 82, pp. 87 (2005). [http://www.orgsyn.org/orgsyn/pdfs/v82p0087.pdf] (PDF)</ref>
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| ==Physiological effects==
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| Amyl nitrite, in common with other [[alkyl nitrites]]<ref>Nickerson, Mark, John O Parker, Thomas P Lowry, and Edward W Swenson. Isobutyl Nitrite and Related Compounds. 1st ed. San Francisco: Pharmex, Ltd, 1979. [http://www.virusmythpoppersmyth.org/isobutyl_nitrite_and_rela/files/IBNtextnpttypepad.pdf]PDF</ref>, is a potent [[vasodilator]], i.e. it expands [[blood vessel]]s, resulting in lowering of the [[blood pressure]]. Alkyl nitrites function as a source of [[nitric oxide]], which signals for relaxation of the [[involuntary muscle]]s. 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 [[fainting|syncope]] (fainting). The effects set in very quickly, typically within a few seconds.
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| It induces the formation of [[methemoglobin]], which sequesters cyanide as non-toxic cyanomethemoglobin.<ref>{{cite journal| title = Cyanide Antidotes: from Amyl Nitrite to Hydroxocobalamin - Which Antidote is Best?| author = Vale, J. A.| journal = [[Toxicology]]| year = 2001| volume = 168| issue = 1| pages = 37-38}}</ref>
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| ==Applications==
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| Amyl nitrite is employed medically to treat [[ischaemic heart disease|heart disease]]s such as [[Angina pectoris|angina]] and to treat [[cyanide]] poisoning.<ref>{{cite journal| title = The Effects of Nitroglycerin and Amyl Nitrite on Arteriolar and Venous Tone in the Human Forearm| author = Cheng, L.; Goodwin, C. A.; Schully, M. F.; Kakkar, V. V.; Claeson, G.| journal = [[Circulation]]| year = 1965| volume = 3| issue = 2| pages = 755}}</ref> It is also used as an illegal [[inhalant]] drug that induces a brief euphoria. See [[Poppers]].
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| ==References==
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| <div class="references-small"><references/></div>
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| ==External links==
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| * [http://www.jce.divched.org/Journal/Issues/1996/Dec/abs1127.html 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".
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| {{Alkyl nitrites}}
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| {{Antidotes}}
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| [[Category:Antianginals]]
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| [[Category:Antidotes]]
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| [[Category:Alkyl nitrites]]
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| [[Category:Muscle relaxants]]
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| [[cs:Dusitan amylnatý]]
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| [[de:Amylnitrit]]
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| [[fr:Nitrite amylique]]
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| [[ja:亜硝酸アミル]]
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| [[pl:Azotyn amylu]]
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| [[ru:Изоамилнитрит]]
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| [[fi:Isoamyylinitriitti]]
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| [[sv:Amylnitrit]]
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