Methantheline Bromide
Title: Methantheline Bromide
CAS Registry Number: 53-46-3
CAS Name: N,N-Diethyl-N-methyl-2-[(9H-xanthen-9-ylcarbonyl)oxy]ethanaminium bromide
Additional Names: diethyl(2-hydroxyethyl)methylammonium bromide xanthene-9-carboxylate; b-diethylaminoethyl 9-xanthenecarboxylate methobromide
Manufacturers' Codes: MTB-51; SC-2910
Trademarks: Banthine Bromide (Searle); Avagal; Uldumont; Vagantin; Metaxan; Methanide; Xanteline; Gastron (Winthrop); Gastrosedan; Methanthine Bromide; Vagamin; Metanyl; Doladene; Asabaine
Molecular Formula: C21H26BrNO3
Molecular Weight: 420.34
Percent Composition: C 60.00%, H 6.23%, Br 19.01%, N 3.33%, O 11.42%
Literature References: Anticholinergic. Prepn from 9-xanthenecarboxylic acid and 2-diethylaminoethanol: J. W. Cusic, R. A. Robinson, J. Org. Chem. 16, 1921 (1951); eidem, US 2659732 (1952 to Searle). Pharmacology: W. E. Hambourger et al., J. Pharmacol. Exp. Ther. 99, 245 (1950).
Properties: Crystals from isopropanol, mp 175-176°. Bitter taste. Very slightly hygroscopic. Freely sol in water, alcohol. Practically insol in ether. pH (2% aq soln): 5.0-5.5. Aq solns tend to hydrolyze after a few days. The corresponding chloride is very hygroscopic. uv max (alc): 246, 282 nm (E1%1cm 135, 69). LD50 i.p. in mice: 76 mg/kg (Hambourger).
Melting point: mp 175-176°
Absorption maximum: uv max (alc): 246, 282 nm (E1%1cm 135, 69)
Toxicity data: LD50 i.p. in mice: 76 mg/kg (Hambourger)
Therap-Cat: Antispasmodic. In treatment of urinary incontinence.
Keywords: Antispasmodic; Antimuscarinic.

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