Phenothiazine

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Phenothiazine is an organic compound that occurs in various antipsychotic and antihistaminic drugs. It has the formula S(C6H4)2NH. This yellow tricyclic compound is soluble in acetic acid, benzene, and ether. The compound is related to the thiazine-class of heterocyclic compounds. Derivatives of the parent compound find wide use as drugs.

Contents

Synthesis

The compound was originally prepared by Bernthsen in 1883 via the reaction of diphenylamine with sulfur, but more recent syntheses rely on the cyclization of 2-substituted diphenylsulfide. The pharmaceutically significant derivatives of phenothiazine are not prepared from phenothiazine.[2]

Non-drug applications

The synthetic dye methylene blue, containing the structure, was described in 1876. Phenothiazine itself was introduced by DuPont as an insecticide in 1935.[3] It is sometimes used as an antihelminthic in livestock.

Phenothiazine-derived drugs

The phenothiazine structure occurs in various neuroleptic drugs, e.g. chlorpromazine, and antihistaminic drugs, e.g. promethazine. The term "phenothiazines" describes the largest of the five main classes of neuroleptic antipsychotic drugs. These drugs have antipsychotic and, often, antiemetic properties, although they may also cause severe side effects such as extrapyramidal symptoms (including akathisia and tardive dyskinesia), hyperprolactinaemia, and the rare but potentially fatal neuroleptic malignant syndrome as well as substantial weight gain.

Phenothiazines are used as inodilators in congestive heart failure, acting upon the type I calcium/calmodulin dependent phosphodiesterase.[4][citation needed]

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