3311. Diphenidol

Nomenclature

CAS number: 972-02-1
α,α-Diphenyl-1-piperidinebutanol; 1,1-diphenyl-4-piperidino-1-butanol; diphenyl-[3-(1-piperidyl)propyl]carbinol; defenidol; SKF-478.
C21H27NO; mol wt 309.45.
C 81.51%, H 8.79%, N 4.53%, O 5.17%.

Description and references

Prepn: Miescher, Marxer, US 2411664 (1946 to Ciba); Barrett, Wilkinson, GB 683950 (1952 to Wellcome Foundation), C.A. 48, 2112e (1954). Structure-activity studies: Gautier et al., Med. Pharmacol. Exp. 13, 325 (1965). Clinical studies: Cutt et al., Aerosp. Med. 39, 682 (1968); Benson, ibid. 40, 589 (1969). Acute toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).

Chemical structure

Properties

Needles from petr ether, mp 104-105°. LD50 s.c. in rats: 50 mg/kg (Goldenthal).

Derivative

Hydrochloride.

Nomenclature

CAS number: 3254-89-5
SKF-478-A; Ansmin (SS Pharm.); Cefadol (Nippon Shinyaku); Celmidol (Tobishi); Difenidolin (Taiyo); Maniol (Morishita); Mecalmin (Yoshitomi); Pineroro (Maruko); Satanolon (Tatsumi); Tenesdol (Hishiyama); Vontrol (SK & F); Wansar (Hoei).
C21H27NO.HCl; mol wt 345.91.
C 72.92%, H 8.16%, N 4.05%, O 4.63%, Cl 10.25%.

Properties

Crystals from chloroform + ethyl acetate, mp 212-214°. Freely sol in methanol; sol in water, chloroform. Practically insol in ether, benzene, petr ether.

Therapeutic Category

Antiemetic.

Keywords

Antiemetic