chemistry

Mesylate

Mesylate is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Mesylate rather than just read about it. In short: 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.

Key takeaways

Mesylate belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Mesylate to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Mesylate from memory before moving on to harder problems.

Reference excerpt

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). 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.

Preparation Mesylate esters 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 (CH3SO2) functional group. The shortened term itself was coined by Helferich et al. in 1938 similarly to tosyl adopted earlier. 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 moiety. Examples include sotalol, ibutilide, sematilide, dronedarone, dofetilide, E-4031, and bitopertin.

Pharmaceutical preparations Mesylate salts are often used in preparing the dosage forms of basic drugs. Mesylate salts often yield a higher solubility, and may also excel in other pharmaceutically-relevant factors such as hygroscopicity, clean polymorphic profile, particle size, and flow properties.

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.

See also Tosylate Triflate, the fluorinated analog of mesylate.

References

Illustrations

Worked examples

Example 1 — a first encounter with Mesylate

Start with the simplest possible case. Write down what Mesylate claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Mesylate before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Mesylate ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Mesylate

In research: Mesylate appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Mesylate in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Mesylate is common in secondary-school and first-year university syllabi. It links to neighbouring topics Leaving groups, Mesyl compounds, so understanding it makes those chapters shorter.
In everyday life: Look for Mesylate outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Mesylate in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Mesylate means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Mesylate out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Mesylate in simple terms?

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.

Why does Mesylate matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Mesylate?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Mesylate.