Dimethoxanate (trade names Cothera, Cotrane, Atuss, Perlatoss, Tossizid) is a

cough suppressant Cold medicines are a group of medicinal, medications taken individually or in Combination drug, combination as a Symptomatic treatment, treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The t ...

of the phenothiazine class.

Side effects

Dimethoxanate may have

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

, local anesthetic, and central nervous system depressant effects, but it may also produce nausea and vomiting.

Pharmacology

It binds to the sigma-1 receptor in the brain with an IC₅₀ of 41 nM.

Society and culture

Dimethoxanate was introduced in Austria, Belgium, and France in 1911, and in Italy and Spain in 1963. Approval for marketing in the US was withdrawn by the

FDA The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food s ...

in 1975 due to lack of evidence of efficacy.

Synthesis

Phenothiazine (1) is reacted with

phosgene Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, espe ...

to give Phenothiazine-10-carbonyl chloride 8956-87-1(2). Further reaction with 2-(2-(dimethylamino)ethoxy)ethanol 704-62-7(3) completed the synthesis of Dimethoxanate (4).

References

Phenothiazines Antitussives Sigma agonists Carbamates Ethers Dimethylamino compounds Ethanolamines Abandoned drugs Withdrawn drugs {{respiratory-system-drug-stub