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Hydrochloride

From Wikipedia, the free encyclopedia
Any salt of an organic base and hydrochloric acid
Not to be confused withHydrochloric acid.
Sample of a hydrochloride salt,triethylammonium chloride

In chemistry, ahydrochloride is anacid salt resulting, or regarded as resulting, from the reaction ofhydrochloric acid with an organicbase (e.g. anamine). An alternative name ischlorhydrate, which comes from French. An archaic alternative name ismuriate, derived from hydrochloric acid's ancient name: muriatic acid.

Uses

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Convertingamines into their hydrochlorides is a common way to improve theirwater solubility, which can be desirable for substances used in medications.[1] TheEuropean Pharmacopoeia lists more than 200 hydrochlorides as active ingredients in medications.[2] These hydrochlorides, compared tofree bases, may more readily dissolve in the gastrointestinal tract and be absorbed into the bloodstream more quickly. Additionally, many hydrochlorides of amines have a longer shelf-life than their respective free bases.

Amine hydrochlorides represent latent forms of a more reactive free base. In this regard, formation of an amine hydrochloride confersprotection. This effect is illustrated by the hydrochlorides of the amino acids.Glycine methyl ester hydrochloride is a shelf-stable salt that can be readily converted to a reactive glycine methyl ester, a compound that is not shelf-stable.[3][4]

See also

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References

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  1. ^Stahl, P. Heinrich;Wermuth, Camille G., eds. (2011).Pharmaceutical Salts: Properties, Selection, and Use (2nd ed.).John Wiley & Sons.ISBN 978-3-90639-051-2.
  2. ^European Pharmacopoeia 7th Edition 2011, EDQM.
  3. ^Myers, Andrew G.; Gleason, James L. (1999). "Asymmetric Synthesis of α-Amino Acids by the Alkylation of Pseudoephedrine Glycinamide: L-Allylglycine and N-BOC-l-Allylglycine".Organic Syntheses.76: 57.doi:10.15227/orgsyn.076.0057.
  4. ^White, James D.; Kranemann, Christian L.; Kuntiyong, Punlop (2002). "4-Methoxycarbonyl-2-methyl-1,3-oxazole".Org. Synth.79: 244.doi:10.15227/orgsyn.079.0244.
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