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Mesylate
  In organosulfur chemistry, a mesylate is any salt or ester of methanesulfonic acid (CH3SO3H). In salts, the mesylate is present as the CH3SO−3 anion. When modifying the international nonproprietary name of a pharmaceutical substance containing the group or anion, the spelling used is sometimes mesilate (as in imatinib mesilate, the mesylate salt of imatinib).[1] Mesylate esters are a group of organic compounds that share a common functional group with the general structure CH3SO2O−R, abbreviated MsO−R, where R is an organic substituent. Mesylate is considered a leaving group in nucleophilic substitution reactions.[2] PreparationMesylate esters are generally prepared by treating an alcohol and methanesulfonyl chloride in the presence of a base, such as triethylamine.[3] MesylRelated to mesylate is the mesyl (Ms) or methanesulfonyl (CH3SO2) functional group. The shortened term itself was coined by Helferich et al. in 1938 similarly to tosyl adopted earlier.[4] Methanesulfonyl chloride is often referred to as mesyl chloride. Whereas mesylates are often hydrolytically labile, mesyl groups, when attached to nitrogen, are resistant to hydrolysis.[5] This functional group appears in a variety of medications, particularly cardiac (antiarrhythmic) drugs, as a sulfonamide moiety. Examples include sotalol, ibutilide, sematilide, dronedarone, dofetilide, E-4031, and bitopertin.[citation needed] Natural occurrenceIce core samples from a single spot in Antarctica were found to have tiny inclusions of magnesium methanesulfonate dodecahydrate. This natural phase is recognized as the mineral ernstburkeite. It is extremely rare.[6][7] See alsoReferences
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