In
organosulfur chemistry, a mesylate is any
salt or
ester of
methanesulfonic acid
Methanesulfonic acid (MsOH) or methanesulphonic acid (in British English) is an organosulfuric, colorless liquid with the chemical formula and structure . It is the simplest of the alkylsulfonic acids (). Salts and esters of methanesulfonic aci ...
(). In salts, the mesylate is present as the
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
Imatinib, sold under the brand names Gleevec and Glivec (both marketed worldwide by Novartis) among others, is an oral chemotherapy medication used to treat cancer. Imatinib is a small molecule inhibitor targeting multiple receptor tyrosine kin ...
).
Mesylate esters are a group of
organic compounds that share a common
functional group with the general structure , abbreviated , where R is an organic
substituent
A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...
. Mesylate is considered a
leaving group in
nucleophilic substitution reactions.
Preparation
Mesylates are generally prepared by treating an alcohol and
methanesulfonyl chloride in the presence of a
base, such as
triethylamine.
Mesyl
Related to mesylate is the mesyl (Ms) or methanesulfonyl (CH
3SO
2) functional group.
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. This
functional group appears in a variety of medications, particularly
cardiac (
antiarrhythmic) drugs, as a
sulfonamide
In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the structure . It consists of a sulfonyl group () connected to an amine group (). Relatively speaking this group is unreactive. ...
moiety. Examples include
sotalol
Sotalol, sold under the brand name Betapace among others, is a medication used to treat and prevent abnormal heart rhythms. It is only recommended in those with significant abnormal heart rhythms due to potentially serious side effects. Evidence ...
,
ibutilide
Ibutilide is a Class III antiarrhythmic agent that is indicated for acute cardioconversion of atrial fibrillation and atrial flutter of a recent onset to sinus rhythm. It exerts its antiarrhythmic effect by induction of slow inward sodium current ...
,
sematilide
Sematilide is an antiarrhythmic agent
Antiarrhythmic agents, also known as cardiac dysrhythmia medications, are a group of pharmaceuticals that are used to suppress abnormally fast rhythms ( tachycardias), such as atrial fibrillation, suprave ...
,
dronedarone,
dofetilide
Dofetilide is a class III antiarrhythmic agent. It is marketed under the trade name Tikosyn by Pfizer, and is available in the United States in capsules containing 125, 250, and 500 µg of dofetilide. It is not available in Europe or Australia. I ...
,
E-4031
E-4031 is an experimental class III antiarrhythmic drug that blocks potassium channels of the hERG-type.
Chemistry
E-4031 is a synthetized toxin that is a methanesulfonanilide class III antiarrhythmic drug.
Target
E-4031 acts on a specif ...
, and
bitopertin.
Natural occurrence
Ice 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.
Ernstburkeite
Mindat
See also
* Tosylate
References
{{Reflist
Leaving groups
Sulfonates