1075. Benzetimide

Nomenclature

CAS number: 14051-33-3
3-Phenyl-1′-(phenylmethyl)-[3,4′-bipiperidine]-2,6-dione; 2-(1-benzyl-4-piperidyl)-2-phenylglutarimide; 1-benzyl-4-(2,6-dioxo-3-phenyl-3-piperidyl)piperidine.
C23H26N2O2; mol wt 362.46.
C 76.21%, H 7.23%, N 7.73%, O 8.83%.

Description and references

Anticholinergic. Prepn: Janssen, US 3125578 (1964 to Janssen); Hermans et al., J. Med. Chem. 11, 797 (1968). Synthesis of labelled compound: van Wijngaarden, Soudijn, J. Labelled Compd. 1, 207 (1965). Resolution of isomers and pharmacology: van Wijngaarden, Life Sci. 8, 517 (1969); ibid. 9, part 1, 489 (1970); Janssen et al., Arzneim.-Forsch. 21, 1365 (1971). Metabolism: van Wijngaarden, Soudijn, Life Sci. 7, 225 (1968).

Chemical structure

Properties

Crystals, mp 156-159°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 5633-14-7
R-4929; Dioxatrine (Janssen); Spasmentral (Janssen).
C23H26N2O2.HCl; mol wt 398.93.
C 69.25%, H 6.82%, N 7.02%, O 8.02%, Cl 8.89%.

Properties

Crystals, mp 299-301.5°. LD50 in rats, mice (mg/kg): 37.6, 46.0 i.v. (Janssen).

Derivative

l-Form.

Properties

mp 180.5-182° (from toluene). [α]D20 124° (chloroform). LD50 i.v. in mice: 38.5 mg/kg (Janssen).

Derivative

d-Form see Dexetimide.

Therapeutic Category

Antiparkinsonian.

Therapeutic Category (Veterinary)

Antidiarrheal.

Keywords

Antiparkinsonian; Antimuscarinic