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Dimethoxanate
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Dimethoxanate

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Dimethoxanate
Dimethoxanate.png
Clinical data
Trade names Atuss, Cothera, Cotrane, Perlatos, Pulmoll, Tussizid
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
  • 2-(2-dimethylaminoethoxy)ethyl phenothiazine-10-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.838
Chemical and physical data
Formula C19H22N2O3S
Molar mass 358.46 g·mol−1
3D model (JSmol)
  • O=C(OCCOCCN(C)C)N1c3c(Sc2c1cccc2)cccc3
  • 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 checkY
  • Key:OOVJCSPCMCAXEX-UHFFFAOYSA-N checkY
  (verify)

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

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 Approval for marketing in the US was withdrawn by the FDA in 1975 due to lack of evidence of efficacy.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 [18956-87-1] (2). Further reaction with 2-(2-(dimethylamino)ethoxy)ethanol [1704-62-7] (3) completed the synthesis of Dimethoxanate (4).


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