Alkyl nitrite

Alkyl nitrites were initially, and largely still are, used as medications and chemical reagents, a practice which began in the late 19th century.

In their use as medicine, they are often inhaled for relief of angina and other heart-related symptoms of disease.

However, when referred to as "poppers", alkyl nitrites represent recreational drugs.

[1] They are also prone to undergo homolytic cleavage to form alkyl radicals, the nitrite C–O bond being very weak (on the order of 40–50 kcal ⋅ mol−1).

[2] An isolated but classic example of the use of alkyl nitrites can be found in Woodward and Doering's quinine total synthesis:[10] for which they proposed this reaction mechanism: