The first few members of the series are
volatile liquids;
methyl nitrite and
ethyl nitrite are gaseous at room temperature and pressure. The compounds have a distinctive fruity odor. Another frequently encountered nitrite is
amyl nitrite (3-methylbutyl 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.
Synthesis and properties
Organic nitrites are prepared from
alcohols and
sodium nitrite in
sulfuric acidsolution. They decompose slowly on standing, the decomposition products being
oxides of
nitrogen,
water, the alcohol, and
polymerization products of the
aldehyde.[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).