N-Amyl nitrite

Equip a 1-litre three-necked flask with a powerful mechanical stirrer, a separatory funnel with stem extending to the bottom of the flask, and a thermometer. Cool the flask in a mixture of ice and salt. Place a solution of 95 g. of A.R. sodium nitrite in 375 ml. of water in the flask and stir. When the temperature has fallen to 0° (or slightly below) introduce slowly from the separatory funnel a mixture of 25 ml. of water, 62 5 g. (34 ml.) of concentrated sulphuric acid and 110 g. (135 ml.) of n-amyl alcohol, which has previously been cooled to 0°. The rate of addition must be controlled so that the temperature is maintained at 1° the addition takes 45-60 minutes. AUow the mixture to stand for 1 5 hours and then filter from the precipitated sodium sulphate (1). Separate the upper yellow n-amyl nitrite layer, wash it with a solution containing 1 g. of sodium bicarbonate and 12 5 g. of sodium chloride in 50 ml. of water, and dry it with 5-7 g. of anhydrous magnesium sulphate. The resulting crude n-amyl nitrite (107 g.) is satisfactory for many purposes (2). Upon distillation, it passes over largely at 104° with negligible decomposition. The b.p. under reduced pressure is 29°/40 mm. 

Ammonolysis, 401 Ampoules, glass. 205 n-Amylamine, 413, 417 n-Amyl acetate, 383 -Amyl alcohol, 247, 249 n-Amylbenzene, 511, 517 n-Amyl borate, 305 n-Amyl bromide, 279 tao-Amyl bromide, 279 n-Amyl chloride, 273 tao-Amyl chloride, 273 tert.-Amyl chloride, 275 n-Amyl cyanide, 407, 408 Amylene, 239 n-Amyl fluoride, 272, 289 n-Amyl iodide, 288 n-Amyl nitrite, 302, 306... 

DOT CLASSIFICATION Forbidden SAFETY PROFILE Moderately toxic by inhalation. Mutation data reported. Narcotic in high concentration. A very dangerous fire and explosion hazard when exposed to heat or flame. A heat-sensitive explosive more powerful than ethyl nitrite. When heated to decomposition it emits toxic fumes of NO. See also NITRITES and n-AMYL NITRITE. 

Amyl nitrite ( -mil NYE-trite) commonly occurs in two isomeric forms n-amyl nitrite and isoamyl nitrite (3-methy-lamyl nitrite or 3-methylpentyl nitrite). In common usage, the term amyl nitrite most commonly refers to the isoamyl form. Both isomers occur as yellowish liquids with a distinctive sweet odor and a pungent taste. They are unstable and break down when exposed to air, light, or water. Both isomers are probably best known as vasodilators, substances that cause blood vessels to relax and expand, allowing an increased flow of blood through the body. Because of its widespread use as a hazardous recreational drug, isoamyl nitrite has been banned, except for specified medical uses. 

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