13-01524. Butobendine [Archived]
Nomenclature
CAS number: 55769-65-8
3,4,5-Trimethoxybenzoic acid 1,2-ethanediylbis[(methylimino)[(2S)-2-ethyl-2,1-ethanediyl]] ester; (2S,2′S)-N,N′-dimethyl-N,N′-bis-1-(3′,4′,5′-trimethoxybenzoyloxy)butyl-2-ethylenediamine; (+)-(S,S)-ethylenebis[(methylimino)(2-ethylethylene)]bis(3,4,5-trimethoxybenzoate). C32H48N2O10; mol wt 620.73.
C 61.92%, H 7.79%, N 4.51%, O 25.78%.
Description and references
Antiarrhythmic agent which increases cardiac blood flow. Prepn: M. Eckstein et al., DE 2435380; eidem, US 4021473 (1975, 1977 both to Polfa). Series of articles on pharmacology, pharmacokinetics, toxicology: Pol. J. Pharmacol. Pharm. 32, 817-953 (1980). Physical properties: L. Krowczynski et al., ibid. 909. Toxicity data: J. Maj et al., ibid. 823.
Properties
Crystals, mp 60-62°. Also reported as mp 64-65° (Krowczynski). [α]D20 +2.4° (c = 5 in ethanol). Partition coefficient (n-octanol/water) at 20°: 31.49.Derivative
Dihydrochloride.Nomenclature
CAS number: 55769-64-7
M-71; Craviten (Polfa). C32H48N2O10.2HCl; mol wt 693.65.
C 55.41%, H 7.27%, N 4.04%, O 23.07%, Cl 10.22%.
Properties
White crystalline powder. Forms mono-, di- and trihydrates, melting range 83-113°. Also reported as crystals from isopropanol, mp 81-83° (Krowczynski). [α]D20 6.4° (c = 2.5 in ethanol). [α]D20 7.5° (c = 5 in H2O). [α]D20 5.5° (c = 5 in pyridine). pH (8% aq soln): 2.20. Partition coefficient (n-octanol/water) at 20°: 4.49. Sol in water, chloroform, ethanol. Slightly sol in methanol. Practically insol in benzene, CCl4, ether. LD50 in rats (mg/kg): 142.0 i.p., 15.8 i.v.; in mice (mg/kg): 550.0 i.p.; in rabbits (mg/kg): 5.1 i.v. (Maj).Therapeutic Category
Antiarrhythmic.
Keywords
Antiarrhythmic
Status
This monograph has been retired and is no longer subject to revision or update.