9306. Thiazinamium Methylsulfate

Nomenclature

CAS number: 58-34-4
N,N,N,α-Tetramethyl-10H-phenothiazine-10-ethanaminium methyl sulfate; trimethyl(1-methyl-2-phenothiazin-10-ylethyl)ammonium methyl sulfate; trimethyl[1-methyl-2-(10-phenothiazinyl)ethyl]ammonium methyl sulfate; N-[β-(10-phenothiazinyl)propyl]trimethylammonium methyl sulfate; RP-3554; Multergan (Specia); Padisal (Bayer).
C19H26N2O4S2; mol wt 410.55.
C 55.58%, H 6.38%, N 6.82%, O 15.59%, S 15.62%.

Description and references

Prepd by treating promethazine with dimethyl sulfate: GB 641452 (1950 to Rh^one-Poulenc). Crystal structure: P. Marsau, Y. Cam, Acta Crystallogr. B29, 980 (1973). Determn in body fluids: J. H. G. Jonkman et al., J. Pharm. Pharmacol. 27, 849 (1975). Bioavailability: idem et al., Clin. Pharmacol. Ther. 21, 457 (1977). Pharmacokinetics: idem et al., Arzneim.-Forsch. 23, 223 (1983); idem et al., Int. J. Clin. Pharmacol. Ther. Toxicol. 21, 454 (1983).

Chemical structure

Properties

Crystals, mp 206-210° (some dec). Discolors on exposure to light. Soly in water (25°): ≈10%. Freely sol in abs ethanol; sparingly sol in acetone. Practically insol in ether, benzene.

Therapeutic Category

Antihistaminic.

Keywords

Antihistaminic; Tricyclics; Phenothiazines