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 (Example 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   978-0-412-46630-4.
2. Karolyhazy G, Havas I, Jancso G, Kapas L, Sellei C (August 1952). "[The anticarcinogenic effect of dimethylaminoacetyl-phentiazide (ahistan)]". Kiserletes Orvostudomany (in Romanian). 4 (4): 260–262. PMID   13023855.
3. Dahlbom R, Ekstrand T, Rubin I, 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, Ionescu M, Cuiban L, Panaiteslu T, Gheorghiu M, Arhip C (1959). "Syntheses of phenothiazine drugs". Revistade Chimie. 10. Bucharest, Romania: 81–85.
5. Kano H, Makisumi Y (1957). "Phenothiazine derivatives. II. Synthesis of 10-(alkylaminoacetyl)phenothiazines". Shionogi Kenkyusho Nempo[Annual Report of Shionogi Research Laboratory] (in Japanese). 7: 511–516. Abstract in: Chem Abstr. 1958;52:10094.
6. US 2694705,Cusic JW,"N-(Hydroxyalkylaminoalkanoyl)phenothiazines",issued 16 Novmember 1954, assigned to G.D. Searle & Co.