7501. Pirmenol

Nomenclature

CAS number: 68252-19-7
cis-(±)-α-[3-(2,6-Dimethyl-1-piperidinyl)propyl]-α-phenyl-2-pyridinemethanol; (±)-cis-2,6-dimethyl-α-phenyl-α-2-pyridyl-1-piperidinebutanol; (±)-1-phenyl-1-(2-pyridyl)-4-(cis-2,6-dimethyl-1-piperidyl)butanol.
C22H30N2O; mol wt 338.49.
C 78.06%, H 8.93%, N 8.28%, O 4.73%.

Description and references

Prepn: R. W. Fleming, DE 2806654; idem, US 4112103 (both 1978 to Parke, Davis). Anti-arrhythmic profile in dogs: T. E. Mertz, T. J. Steffe, J. Cardiovasc. Pharmacol. 2, 527 (1980). Toxicology study: J. L. Schardein et al., Toxicol. Appl. Pharmacol. 56, 294 (1980). HPLC determn in biological fluids: E. L. Johnson, L. A. Pachla, J. Pharm. Sci. 73, 754 (1984). Pharmacokinetics in humans: S. C. Hammill et al., Circulation 65, 369 (1982); S. W. Sanders et al., J. Clin. Pharmacol. 23, 113 (1983). Hemodynamic effects in cardiac patients: M. S. Nieminen et al., Eur. Heart J. 7, 150 (1986). Clinical evaluations in ventricular arrhythmias: L. K. Toivonen et al., J. Cardiovasc. Pharmacol. 8, 156 (1986); E. M. Hampton et al., Eur. J. Clin. Pharmacol. 31, 15 (1986). Chronic toxicity study: J. R. Watkins et al., Drug Invest. 3, 141 (1991). Evaluation of carcinogenicity: G. E. Macallum et al., ibid. 278. Symposium on pharmacology and clinical efficacy: Am. J. Cardiol. 59, Suppl., 1H-57H (1987).

Chemical structure

Properties

Crystals from petroleum ether, mp 70-71°.

Derivative

Monohydrochloride.

Nomenclature

CI-845.
C22H30N2O.HCl; mol wt 374.95.
C 70.47%, H 8.33%, N 7.47%, O 4.27%, Cl 9.46%.

Properties

mp 171-172°. LD50 in mice, rats, dogs (mg/kg): 20.8, 23.6, >7.0 i.v.; 215.5, 359.9, >40.0 orally (Schardein).

Therapeutic Category

Antiarrhythmic (class IA).

Keywords

Antiarrhythmic