Chlorproethazine, sold under the brand name Neuriplege, is a

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...

of the

phenothiazine Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history. T ...

group described as a muscle relaxant or tranquilizer which is or has been marketed in

Europe Europe is a large peninsula conventionally considered a continent in its own right because of its great physical size and the weight of its history and traditions. Europe is also considered a Continent#Subcontinents, subcontinent of Eurasia ...

as a

topical A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes ...

cream Cream is a dairy product composed of the higher-fat layer skimmed from the top of milk before homogenization. In un-homogenized milk, the fat, which is less dense, eventually rises to the top. In the industrial production of cream, this process ...

for the treatment of muscle pain. It has been associated with photoallergic contact dermatitis.

Synthesis

Chlorproethazine can be synthesized from a diphenylsulfide

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...

. The general scheme is sufficiently flexible to permit the interchange of the order of some of the steps. Chlorproethazine synthesis

Thus alkylation of 2-(2-bromo-phenylsulfanyl)-5-chloro-aniline 05790-02-1(1) with 3-chloro-1-diethylaminopropane 04-77-8(2) leads to the intermediate (3). Ring closure as above by nucleophilic aromatic displacement leads to the antipsychotic drug chlorproethazine (4). The last step uses copper powder and is a form of the

Ullmann condensation The Ullmann condensation or Ullmann-type reaction is the copper-promoted conversion of aryl halides to aryl ethers, aryl thioethers, aryl nitriles, and aryl amines. These reactions are examples of cross-coupling reactions. Ullmann-type reactions ...

(i.e. the

Goldberg reaction Goldberg or Goldberger may refer to: Arts and entertainment * Goldberg Ensemble, a British string ensemble * ''Goldberg Variations'', a set of 30 keyboard variations by Johann Sebastian Bach * ''The Goldbergs (broadcast series)'', American radio ...

References

Analgesics Chloroarenes Phenothiazines Diethylamino compounds {{analgesic-stub