Thiuram disulfide

These compounds are used in sulfur vulcanization of rubber as well as in the manufacture of pesticides and drugs.

They are typically white or pale yellow solids that are soluble in organic solvents.

[1] Thiuram disulfides are prepared by oxidizing the salts of the corresponding dithiocarbamates (e.g. sodium diethyldithiocarbamate).

Typical oxidants employed include chlorine and hydrogen peroxide: Thiuram disulfides react with Grignard reagents to give esters of dithiocarbamic acid, as in the preparation of methyl dimethyldithiocarbamate:[2] The compounds feature planar dithiocarbamate subunits and are linked by an S−S bond of 2.00 Å.

It produces an acute sensitivity to alcohol ingestion by blocking metabolism of acetaldehyde by acetaldehyde dehydrogenase, leading to a higher concentration of the aldehyde in the blood, which in turn produces symptoms of a severe hangover.