Dacemazine

Chemical compound From Wikipedia, the free encyclopedia

Dacemazine (INN, also known as Ahistan and Histantine)[1] is a phenothiazine derivative which acts as a histamine antagonist at the H1 subtype. First described in 1951, it was never marketed as a drug on its own, although a combination of dacemazine and di-tert-butylnaphthalenesulfonate was sold as an antispasmodic and antitussive under the trade name Codopectyl.[1] It was also assessed as a possible anticancer drug.[2]

ATC code
  • none
Quick facts Clinical data, ATC code ...
Dacemazine
Clinical data
ATC code
  • none
Identifiers
  • 2-dimethylamino-1-phenothiazin-10-ylethanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H16N2OS
Molar mass284.38 g·mol−1
3D model (JSmol)
  • O=C(N1c3c(Sc2c1cccc2)cccc3)CN(C)C
  • InChI=1S/C16H16N2OS/c1-17(2)11-16(19)18-12-7-3-5-9-14(12)20-15-10-6-4-8-13(15)18/h3-10H,11H2,1-2H3 checkY
  • Key:HKUCYAHWPVLPFN-UHFFFAOYSA-N checkY
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Synthesis

Synthesis:[3][4][5] Patent (Example 8):[6]

Amide formation between phenothiazine (1) and chloroacetyl chloride (2) gives 10-(chloroacetyl)-phenothiazine (3). The subsequent displacement of the remaining halogen with dimethylamine (4) completes the synthesis of dacemazine (5).

References

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