Dacemazine

Dacemazine

Clinical data
ATC code	none
Identifiers
IUPAC name 2-dimethylamino-1-phenothiazin-10-ylethanone
CAS Number	518-61-6  N
PubChem CID	68846
ChemSpider	62079  Y
UNII	88D34UY0QI
ChEMBL	ChEMBL2107547  N
CompTox Dashboard (EPA)	DTXSID70199733
Chemical and physical data
Formula	C16H16N2OS
Molar mass	284.38 g·mol−1
3D model (JSmol)	Interactive image
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)

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: Patent (Ex 8):

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

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.).