Dimethoxanate

Dimethoxanate (trade names Cothera, Cotrane, Atuss, Perlatoss, Tossizid)[1] is a cough suppressant of the phenothiazine class.[2]

Dimethoxanate
Clinical data
Trade namesAtuss, Cothera, Cotrane, Perlatos, Pulmoll, Tussizid
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 2-(2-dimethylaminoethoxy)ethyl phenothiazine-10-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.006.838
Chemical and physical data
FormulaC19H22N2O3S
Molar mass358.46 g·mol−1
3D model (JSmol)
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 Y
  • Key: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.[3]

Pharmacology

It binds to the sigma-1 receptor in the brain with an IC50 of 41 nM.[4]

Society and culture

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in Austria, Belgium, and France in 1911, and in Italy and Spain in 1963.[5] Approval for marketing in the US was withdrawn by the FDA in 1975 due to lack of evidence of efficacy.[6]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
Synthesis:[7] Patent:[8]

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
  1. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1332–3. ISBN 978-0-8155-1856-3.
  2. Parish FA (November 1959). "Clinical evaluation of the antitussive, dimethoxanate". Medical Times. 87: 1488–90. PMID 14430450.
  3. Martín, Alfonso Velasco (2004). "Tratamiento sintomático de la tos y del resfriado común". Farmacología clínica y terapéutica médica. p. 260. ISBN 9788448604271.
  4. Klein M, Musacchio JM (October 10, 1988). "Dextromethorphan binding sites in the guinea pig brain". Cellular and Molecular Neurobiology. 8 (2): 149–156.
  5. Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 67. ISBN 0-8103-7177-4.
  6. Cough Preparation Containing Dimethoxanate Hydrochloride (PDF). Federal Register (Report). Vol. 40. December 18, 1975. 75N–0321.
  7. 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.
  8. Seemann Carl Von, U.S. Patent 2,778,824 (1957 to American Home Prod).
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