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Chemical compound
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
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
^
a
b 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 .
^ 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 .
^ 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.).
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