Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH3)2SO. This colorless liquid is the most widely used sulfoxide commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. DMSO has a relatively high boiling point and the unusual property that many individuals perceive a garlic-like taste in the mouth after DMSO makes contact with their skin.

In terms of chemical structure, the DMSO molecule has idealized Cs symmetry. It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds, with a nonbonded electron pair on the approximately tetrahedral sulfur atom.

DMSO was first synthesized in 1866 by Russian scientist Alexander Zaytsev, who reported his findings in 1867. Today, DMSO is produced industrially from dimethyl sulfide, a by-product of the Kraft process, by oxidation with oxygen or nitrogen dioxide.

DMSO is a versatile solvent with many applications. As a polar aprotic solvent, it is less toxic than other members of this class such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, and hexamethylphosphoramide (HMPA). DMSO is frequently used as a solvent for chemical reactions involving salts, most notably Finkelstein reactions and other nucleophilic substitutions. It is also extensively used as an extractant in biochemistry and cell biology.

In addition to its use as a solvent, DMSO has also been used for its anti-inflammatory properties and as a cryoprotectant in cell culture and tissue preservation. It has also been investigated for its potential use in treating various medical conditions such as interstitial cystitis and scleroderma.

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