Chemistry:Dacemazine
From HandWiki
Short description: Chemical compound
 | |
| Clinical data | |
|---|---|
| ATC code |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C16H16N2OS |
| Molar mass | 284.38 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (what is this?) (verify) | |
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]
Synthesis
Amide formation between phenothiazine (1) and chloroacetyl chloride (2) gives 10-(Chloroacetyl)-phenothiazine [786-50-5] (3). The subsequent displacement of the remaining halogen with dimethylamine (4) completes the synthesis of dacemazine (5).
References
- ↑ 1.0 1.1 Dictionary of Pharmacological Agents. 1. Boca Raton: Chapman & Hall/CRC. 1996. pp. 711. ISBN 0-412-46630-9. https://books.google.com/books?id=DeX7jgInYFMC. Retrieved on August 2, 2008 through Google Book Search.
- ↑ "[The anticarcinogenic effect of dimethylaminoacetyl-phentiazide (ahistan)]" (in ro). Kiserletes Orvostudomany 4 (4): 260–2. August 1952. PMID 13023855.
- ↑ Dahlbom, Richard; Ekstrand, Torsten; Rubin, Inger; Saluste, E.; Stjernholm, R.; Ehrensvärd, G. (1951). "10-Aminoacylphenothiazines. I. Aminoacetyl and Aminopropionyl Derivatives." Acta Chemica Scandinavica. 5: 102–114. doi:10.3891/acta.chem.scand.05-0102.
- ↑ Wassermann, N. et al, Rev. Chim., 1959, 10, 81 (synth) (only until 1991)
- ↑ Kano; Makisumi Shionogi Kenkyusho Nenpo, 1957 , # 7 p. 511,514 Chem.Abstr., 1958 , p. 10094.
- ↑ John W. Cusic, U.S. Patent 2,694,705 (1954 to G. D. Searle & Co.).
 |  |
