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Mesylate
 
 
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In chemistry
Chemistry

Chemistry is the science concerned with the composition, structure, and properties of matter, as well as the changes it undergoes during chemical reactions....
, a mesylate is any salt
Salt

A salt, in chemistry, is defined as the product formed from the neutralisation reaction of acids and base . Salts are ionic compounds composed of cations and anions so that the product is electrically electric charge ....
 or ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
 of methanesulfonic acid
Methanesulfonic acid

Methanesulfonic acid is a colorless liquid with the chemical formula CH3SO3H. It is the simplest of the alkylsulfonic acids....
 (C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
3S
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
O
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
3H). In salts, the mesylate is present as the CH3SO3- anion. When modifying the International Nonproprietary Name
International Nonproprietary Name

An International Nonproprietary Name is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization ....
 of a pharmaceutical substance
Medication

A pharmaceutical drug, also referred to as medicine or medicament, can be loosely defined as any substance intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease....
 containing the group or anion, the correct spelling is mesilate (as in imatinib mesilate, the mesylate salt of imatinib
Imatinib

Imatinib is a medication used to treat certain types of cancer. It is currently marketed by Novartis as Gleevec or Glivec as its mesylate salt, imatinib mesilate ....
).

Mesylate esters are a group of organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s that share a common functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
 with the general structure CH3SO2O-R , abbreviated MsO-R, where R is an organic substituent.






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In chemistry
Chemistry

Chemistry is the science concerned with the composition, structure, and properties of matter, as well as the changes it undergoes during chemical reactions....
, a mesylate is any salt
Salt

A salt, in chemistry, is defined as the product formed from the neutralisation reaction of acids and base . Salts are ionic compounds composed of cations and anions so that the product is electrically electric charge ....
 or ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
 of methanesulfonic acid
Methanesulfonic acid

Methanesulfonic acid is a colorless liquid with the chemical formula CH3SO3H. It is the simplest of the alkylsulfonic acids....
 (C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
3S
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
O
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
3H). In salts, the mesylate is present as the CH3SO3- anion. When modifying the International Nonproprietary Name
International Nonproprietary Name

An International Nonproprietary Name is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization ....
 of a pharmaceutical substance
Medication

A pharmaceutical drug, also referred to as medicine or medicament, can be loosely defined as any substance intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease....
 containing the group or anion, the correct spelling is mesilate (as in imatinib mesilate, the mesylate salt of imatinib
Imatinib

Imatinib is a medication used to treat certain types of cancer. It is currently marketed by Novartis as Gleevec or Glivec as its mesylate salt, imatinib mesilate ....
).

Mesylate esters are a group of organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s that share a common functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
 with the general structure CH3SO2O-R , abbreviated MsO-R, where R is an organic substituent. Mesylate is considered excellent leaving group
Leaving group

A leaving group in chemistry is an ion or substituent with the ability to detach itself from a molecule. The remaining molecule or fragment remaining is known as the residual or main part....
s in nucleophilic substitution
Nucleophilic substitution

In organic chemistry and inorganic chemistry, nucleophilic substitution is a fundamental class of substitution reaction in which an "electron rich" nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom attached to a group or atom called the leaving group; the positive or partially positive atom...
 reactions.

Mesyl is the term for the methylsulfonyl or CH3SO2- (Ms-) functional group. For example, methanesulfonyl chloride
Methanesulfonyl chloride

Methanesulfonyl chloride is a compound containing a sulfonyl chloride used to make methanesulfonates and to generate sulfene....
 is often referred to as mesyl chloride.

Preparation

Mesylates may be prepared using an alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 and methanesulfonyl chloride
Methanesulfonyl chloride

Methanesulfonyl chloride is a compound containing a sulfonyl chloride used to make methanesulfonates and to generate sulfene....
 in the presence of a base
Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
, often amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
 bases such as triethylamine
Triethylamine

Triethylamine is the chemical compound with the chemical formula N3, commonly abbreviated ethyl group3N or TEA. It is a commonly encountered in organic synthesis probably because it is the simplest symmetrically trisubstituted amine, i.e....
. In principle, mesylates could be prepared by combining an alcohol, methanesulfonic anhydride
Methanesulfonic anhydride

Methanesulfonic anhydride is an is the acid anhydride of methanesulfonic acid. Like methanesulfonyl chloride, it may be used to generate mesylates ....
 and base, although this route is rarely employed.

See also

  • Tosylate