dimethoxanate dimethoxanate dimethoxanate (trade names cothera, cotrane, atuss, perlatoss, tossizid) is a cough suppressant of the phenothiazine class. dimethoxanateclinical datatrade namesatuss, cothera, cotrane, perlatos, pulmoll, tussizidahfs/drugs.cominternational drug namesatc coder05db28 (who) identifiers iupac name 2-(2-dimethylaminoethoxy)ethyl phenothiazine-10-carboxylate cas number477-93-0pubchem cid10610chemspider10165 yunii1e3kg5fwdbkeggd07397 ycomptox dashboard (epa)dtxsid50197257 echa infocard100.006.838 chemical and physical dataformulac19h22n2o3smolar mass358.46 g·mol−13d model (jsmol)interactive image smiles o=c(occoccn(c)c)n1c3c(sc2c1cccc2)cccc3 inchi inchi=1s/c19h22n2o3s/c1-20(2)11-12-23-13-14-24-19(22)21-15-7-3-5-9-17(15)25-18-10-6-4-8-16(18)21/h3-10h,11-14h2,1-2h3 ykey:oovjcspcmcaxex-uhfffaoysa-n y (verify) side effects dimethoxanate may have analgesic, 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 approval for marketing in the us was withdrawn by the fda in 1975 due to lack of evidence of efficacy. synthesis synthesis: patent: phenothiazine (1) is reacted with phosgene to give phenothiazine-10-carbonyl chloride (2). further reaction with 2-(2-(dimethylamino)ethoxy)ethanol (3) completed the synthesis of dimethoxanate (4).