Butropium Bromide

Title: Butropium Bromide
CAS Registry Number: 29025-14-7
CAS Name: [3(S)-endo]-8-[(4-Butoxyphenyl)methyl]-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-azoniabicyclo[3.2.1]octane bromide
Additional Names: 8-(p-butoxybenzyl)-3a-hydroxy-1aH,5aH-tropanium bromide (-)-tropate; l-[1-(p-n-butoxybenzyl)hyoscyaminium] bromide; BHB
Trademarks: Coliopan (Eisai)
Molecular Formula: C28H38BrNO4
Molecular Weight: 532.51
Percent Composition: C 63.15%, H 7.19%, Br 15.01%, N 2.63%, O 12.02%
Literature References: Anticholinergic. Prepn: S. Tanaka, K. Hashimoto, DE 1950378; eidem, US 3696110 (1970, 1972 both to Eisai); Tanaka et al., J. Pharm. Soc. Jpn. 92, 510 (1972). Prepn of the labelled compound: Fujita et al., J. Labelled Compd. 9, 149, 555 (1972). Activity: Akutsu, Ichikawa, Showa Igakkai Zasshi 32, 494 (1972), C.A. 78, 119243g (1973).
Properties: Crystals from ethanol-acetone, mp 166-168°; also reported as white needles from isopropanol, mp 158-160° (Tanaka, Hashimoto). [a]D20 -21.7° (c = 0.5 in water). Freely sol in glacial acetic acid; sol in chloroform, DMF. Sparingly sol in ethanol; slightly sol in water, 0.1N HCl, 0.1N NaOH. Practically insol in acetone, ether, benzene. LD50 in male mice (mg/kg): 1500 orally; 660 s.c.; 12.0 i.v. (Tanaka, Hashimoto, 1972).
Melting point: mp 166-168°; mp 158-160° (Tanaka, Hashimoto)
Optical Rotation: [a]D20 -21.7° (c = 0.5 in water)
Toxicity data: LD50 in male mice (mg/kg): 1500 orally; 660 s.c.; 12.0 i.v. (Tanaka, Hashimoto, 1972)
Therap-Cat: Antispasmodic.
Keywords: Antispasmodic; Antimuscarinic.
Butyl Carbitol? Butyl Cellosolve? Butyl Citrate Butyl Isocyanate Butyl Stearate