Butobendine

Title: Butobendine
CAS Registry Number: 55769-65-8
CAS Name: 3,4,5-Trimethoxybenzoic acid 1,2-ethanediylbis[(methylimino)[(2S)-2-ethyl-2,1-ethanediyl]] ester
Additional Names: (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)
Molecular Formula: C32H48N2O10
Molecular Weight: 620.73
Percent Composition: C 61.92%, H 7.79%, N 4.51%, O 25.78%
Literature 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). [a]D20 +2.4° (c = 5 in ethanol). Partition coefficient (n-octanol/water) at 20°: 31.49.
Melting point: mp 60-62°; mp 64-65° (Krowczynski)
Optical Rotation: [a]D20 +2.4° (c = 5 in ethanol)
Log P: Partition coefficient (n-octanol/water) at 20°: 31.49
Derivative Type: Dihydrochloride
CAS Registry Number: 55769-64-7
Manufacturers' Codes: M-71
Trademarks: Craviten (Polfa)
Molecular Formula: C32H48N2O10.2HCl
Molecular Weight: 693.65
Percent Composition: 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). [a]D20 -6.4° (c = 2.5 in ethanol). [a]D20 -7.5° (c = 5 in H2O). [a]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).
Melting point: mp 81-83° (Krowczynski)
Optical Rotation: [a]D20 -6.4° (c = 2.5 in ethanol); [a]D20 -7.5° (c = 5 in H2O); [a]D20 -5.5° (c = 5 in pyridine)
Log P: Partition coefficient (n-octanol/water) at 20°: 4.49
Toxicity data: 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)
Therap-Cat: Antiarrhythmic.
Keywords: Antiarrhythmic.
Status: This monograph has been retired and is no longer subject to revision or update.
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