Dimethoxanate (trade names Cothera, Cotrane, Atuss, Perlatoss, Tossizid)[1] is a cough suppressant of the phenothiazine class.[2]
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Trade names | Atuss, Cothera, Cotrane, Perlatos, Pulmoll, Tussizid |
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ECHA InfoCard | 100.006.838 |
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Formula | C19H22N2O3S |
Molar mass | 358.46 g·mol−1 |
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Dimethoxanate may have analgesic, local anesthetic, and central nervous system depressant effects, but it may also produce nausea and vomiting.[3]
It binds to the sigma-1 receptor in the brain with an IC50 of 41 nM.[4]
Dimethoxanate was introduced in Austria, Belgium, and France in 1911, and in Italy and Spain in 1963.[5] Approval for marketing in the US was withdrawn by the FDA in 1975 due to lack of evidence of efficacy.[6]
Phenothiazine (1) is reacted with phosgene to give Phenothiazine-10-carbonyl chloride [18956-87-1] (2). Further reaction with 2-(2-(dimethylamino)ethoxy)ethanol [1704-62-7] (3) completed the synthesis of Dimethoxanate (4).