Amyl nitrite detailed information
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| Amyl nitrite | |
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| 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 | |
| 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 |
| Boiling point |
99 °C |
| Solubility in water | Low |
| Hazards | |
| Main hazards | vasodialator |
| Flash point | 21 °C |
| Related Compounds | |
| Related compounds | nitroglycerine isopentanol Butyl nitrite Isobutyl nitrite Ethyl nitrite |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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Overview
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 psychoactive effect which has led to illegal drug 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 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.
Amyl nitrite is often confused with amyl nitrate, a substance with a different chemical composition and different properties.
Synthesis and reactions
Alkyl nitrites are prepared by the reaction of alcohols with nitrous acid:[1]
- 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.
Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the isoamyl alcohol:
- C5H11ONO + NaOH → C5H11OH + NaNO2
Amyl nitrite, like other alkyl nitrites, reacts with carbanions to give oximes.[1]
Physiological effects
Amyl nitrite, in common with other alkyl nitrites[1], 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.
It induces the formation of methemoglobin, which sequesters cyanide as non-toxic cyanomethemoglobin.[1]
Applications
Amyl nitrite is employed medically to treat heart diseases such as angina and to treat cyanide poisoning.[1] It is also used as an illegal inhalant drug that induces a brief euphoria. See Poppers.
References
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".
Alkyl nitrites |
|---|
| Amyl nitrite | Butyl nitrite | Ethyl nitrite | Methyl nitrite | Isopropyl nitrite | Isobutyl nitrite | Cyclohexyl nitrite | "Poppers" (used as a recreational drug) |
Antidotes (V03AB) | |
|---|---|
| Methanol / Ethylene glycol | Ethanol - Fomepizole |
| Paracetamol (Acetaminophen) | Acetylcysteine - Glutathione - Methionine |
| Arsenic | Dimercaprol - Succimer |
| Cyanide | 4-Dimethylaminophenol - Amyl nitrite - Hydroxocobalamin - Sodium nitrite - Sodium thiosulfate |
| Heparin | Protamine |
| Nerve agent / Organophosphate pesticide | Atropine - Biperiden - Diazepam - Oximes (Pralidoxime, Obidoxime) - see also Cholinesterase |
| Opioid | Diprenorphine - Nalorphine - Naloxone - Naltrexone - Nalmefene |
| Benzodiazepine | Flumazenil |
| Toxic metals (Cadmium, Mercury, Lead etc) | Edetates - Dimercaprol |
| Other | Ipecacuanha - Prednisolone/promethazine - Methylthioninium chloride - Potassium permanganate - Physostigmine - Copper sulfate - Potassium iodide - Digoxin Immune Fab - Prussian blue |
de:Amylnitrit fr:Nitrite amylique ja:亜硝酸アミルfi:Isoamyylinitriitti sv:Amylnitrit
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
