1911 Encyclopædia Britannica/Amyl Nitrite

AMYL NITRITE (isoamyl nitrite), C₅H₁₁·ONO, a liquid 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 sulphuric acid (Renard, Jahresb., 1874, p. 352). It is a yellow-coloured liquid of specific gravity 0·877, boiling at about 95°–96° C. It has a characteristic penetrating odour, and produces marked effects on the system when its vapour is inhaled. It is insoluble in water, but dissolves readily in alcohol, ether, glacial acetic acid, chloroform and benzene. On heating with methyl alcohol it is converted into isoamyl alcohol, methyl nitrite being produced at the same time; a similar reaction takes place with ethyl alcohol, but the change is less complete. It is readily decomposed by nascent hydrogen, with the formation of ammonia and isoamyl alcohol; and on hydrolysis with caustic potash it forms potassium nitrite and isoamyl alcohol. When the liquid is dropped on to fused caustic potash, it forms potassium valerate. Amyl nitrite finds application in medicine, and in the preparation of anhydrous diazonium salts (E. Knoevenagel, Berichte, 1890, 23, p. 2094).