Dacemazine

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]

Dacemazine
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 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)
SMILES
  • O=C(N1c3c(Sc2c1cccc2)cccc3)CN(C)C
InChI
  • 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 Y
  • Key:HKUCYAHWPVLPFN-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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

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. Triggle DJ, Ganellin CR, MacDonald F (1996). Dictionary of Pharmacological Agents. Vol. 1. Boca Raton: Chapman & Hall/CRC. p. 711. ISBN 0-412-46630-9. Retrieved on August 2, 2008 through Google Book Search.
  2. Karolyhazy G, Havas I, Jansco G, Kapas L, Sellei C (August 1952). "[The anticarcinogenic effect of dimethylaminoacetyl-phentiazide (ahistan)]". Kiserletes Orvostudomany (in Romanian). 4 (4): 260–2. PMID 13023855.
  3. 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.
  4. Wassermann, N. et al, Rev. Chim., 1959, 10, 81 (synth) (only until 1991)
  5. Kano; Makisumi Shionogi Kenkyusho Nenpo, 1957 , # 7 p. 511,514 Chem.Abstr., 1958 , p. 10094.
  6. John W. Cusic, U.S. Patent 2,694,705 (1954 to G. D. Searle & Co.).


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