Amyl nitrite
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| IUPAC name: 3-methyl-1-nitrosooxybutane | |
| CAS number 463-04-7 | ATC code V03AB22 |
| Chemical formula | C5H11NO2 |
| Molecular weight | 117.15 g/mol |
| Bioavailability | ? |
| Metabolism | ? |
| Elimination half life | ? |
| Excretion | ? |
| Pregnancy category | ? |
| Legal status | Schedule VI |
| Delivery | ? |
The chemical compound amyl nitrite (here referring to isoamyl nitrite) is an alkyl nitrite. It has a characteristic penetrating odour, and produces marked effects on the human body when its vapour is inhaled. It acts as a vasodilator (expanding blood vessels and thus lowering blood pressure) and finds applications in medicine in the treatment of heart disease such as angina. Amyl nitrite is also used to treat cyanide poisoning. It induces the formation methemoglobin which binds cyanide into non-toxic cyanomethemoglobin. When used recreationally, doses of it are often called poppers. See the article alkyl nitrites for more information on its recreational use as an inhalant. The effects of amyl nitrite are thought to be due to the action of nitric oxide in the body.
Physical effects include headache, flushing of the face, decrease in blood pressure, increase in pulse, dizziness and relaxation of involuntary muscles, especially the blood vessel walls and the anal sphincter. There are no withdrawal symptoms. Overdose symptoms include nausea, vomiting, badly decreased blood pressure and respiration, fainting, cold skin and possible circulatory collapse and death. If one inhales deeply more than eight times in any 72 hour period they can overdose and die of the above symptoms.
Nitramyl is another name for isoamyl nitrite. The name "amyl nitrite" is actually ambiguous as it can refer not only to 3-methyl-1-nitrosooxybutane, but also its isomers 2-methyl-1-nitrosooxybutane, 3-nitrosooxypentane, 2-nitrosooxypentane, and most commonly 1-nitrosooxypentane - n-amyl nitrite. Other synonyms for amyl nitrite, which may refer to any isomer, include Pentyl Alcohol Nitrite and Nitrous acid, pentyl ester. The name "amyl nitrate" is commonly mistaken for amyl nitrite; they are two different chemicals.
Chemistry
Isoamyl nitrite is a clear liquid of specific gravity 0.872, boiling at about 95 to 96 degrees Celsius. It has a solubility in water of about .01 g/100 mL, but dissolves readily in alcohol, ether, glacial acetic acid, chloroform, and benzene. It is prepared by passing nitrous fumes (from starch and concentrated nitric acid) into warm isoamyl alcohol, or by distilling a mixture of 26 parts of potassium nitrite in 15 parts of water with 30 parts of isoamyl alcohol in 30 parts of sulfuric acid. On heating with methanol, it is converted into isoamyl alcohol and methyl nitrite; a similar reaction takes place with ethanol, but the change is less complete. It is readily decomposed by nascent hydrogen, with the formation of ammonia and isoamyl alcohol; and in alkaline hydrolysis it forms isoamyl alcohol.
n-amyl nitrite is a yellow-coloured liquid of specific gravity 0.853, boiling at 104 degrees Celsius. It decomposes in water. When the liquid is dropped onto fused caustic potash (liquid KOH), it forms potassium valerate.