9457. Tipepidine

Nomenclature

CAS number: 5169-78-8
3-(Di-2-thienylmethylene)-1-methylpiperidine; 1-methyl-3-piperidylidenedi(2-thienyl)methane; tipedine; AT-327; CR-662.
C15H17NS2; mol wt 275.43.
C 65.41%, H 6.22%, N 5.09%, S 23.28%.

Description and references

Prepn: Okumura et al., Tanabe Seiyaku Kenkyu Nempo 3, 30 (1958), C.A. 53, 10214 (1959); Ponomarev, Martem'yanova, SU 176903 (1965), C.A. 64, 12648b (1966). Synthesis: eidem, Khim. Geterotsikl. Soedin. 1967, 174, C.A. 67, 73501g (1967). Prepn of hibenzate: M. Yamamoto, H. Yoshikawa, JP 62 17988 C.A. 59, 11446a (1963); GB 924544 (1962, 1963 both to Tanabe Seiyaku). Pharmacology and clinical efficacy: Higaki et al., Tanabe Seiyaku Kenkyu Nempo 4, 35 (1959), C.A. 54, 3725h (1960); Kase et al., Chem. Pharm. Bull. 7, 372 (1959). Metabolism: Watanabe et al., Yakugaku Zasshi 89, 29 (1969); Sasaki et al., ibid. 345.

Chemical structure

Properties

Yellow crystals from petr ether, mp 64-65°. bp4-5 178-184°. LD50 in mice (mg/kg): 294 i.p.; 308 i.m.; 867 orally (Higaki).

Derivative

Citrate monohydrate.

Nomenclature

Bithiodine.
C15H17NS2.C6H8O7.H2O; mol wt 485.57.
C 51.94%, H 5.60%, N 2.88%, S 13.21%, O 26.36%.

Properties

Yellow crystals, mp 138-139°. Sol in water, ethanol, propylene glycol.

Derivative

Hibenzate.

Nomenclature

CAS number: 31139-87-4
Asverin (Tanabe Seiyaku); Sotal (Gramon).
C29H27NO4S2; mol wt 517.66.
C 67.29%, H 5.26%, N 2.71%, O 12.36%, S 12.39%.

Properties

Crystals from acetone, mp 187-190°. Sparingly sol in water.

Therapeutic Category

Antitussive.

Keywords

Antitussive