Dimethoxanate
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| Trade names | Atuss, Cothera, Cotrane, Perlatos, Pulmoll, Tussizid |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.006.838 |
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| Formula | C19H22N2O3S |
| Molar mass | 358.46 g·mol−1 |
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Dimethoxanate (trade names Cothera, Cotrane, Atuss, Perlatoss, Tossizid)[1] is a cough suppressant of the phenothiazine class.[2]
Side effects[edit]
Dimethoxanate may have analgesic, local anesthetic, and central nervous system depressant effects, but it may also produce nausea and vomiting.[3]
Pharmacology[edit]
It binds to the sigma-1 receptor in the brain with an IC50 of 41 nM.[4]
Society and culture[edit]
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in Austria, Belgium, and France in 1911, and in Italy and Spain in 1963.[5] Approval for marketing in the US was withdrawn by the FDA in 1975 due to lack of evidence of efficacy.[6]
Synthesis[edit]
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).
References[edit]
- ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1332–3. ISBN 978-0-8155-1856-3.
- ^ Parish FA (November 1959). "Clinical evaluation of the antitussive, dimethoxanate". Medical Times. 87: 1488–90. PMID 14430450.
- ^ Martín AV (2004). "Tratamiento sintomático de la tos y del resfriado común". Farmacología clínica y terapéutica médica. McGraw-Hill/Interamericana. p. 260. ISBN 9788448604271.
- ^ Klein M, Musacchio JM (October 10, 1988). "Dextromethorphan binding sites in the guinea pig brain". Cellular and Molecular Neurobiology. 8 (2): 149–156. doi:10.1007/BF00711241. PMID 3044591. S2CID 33844132.
- ^ Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 67. ISBN 0-8103-7177-4.
- ^ Cough Preparation Containing Dimethoxanate Hydrochloride (PDF). Federal Register (Report). Vol. 40. December 18, 1975. 75N–0321.
- ^ Weston, Arthur W.; DeNet, Robert W.; Michaels, R. J. (1953). "Antispasmodics. Basic Esters and Amides of Some Heterocyclic N-Carboxylic Acids". Journal of the American Chemical Society. 75 (16): 4006–4008. doi:10.1021/ja01112a038.
- ^ Seemann Carl Von, U.S. patent 2,778,824 (1957 to American Home Prod).
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