5958. Methantheline Bromide

Nomenclature

CAS number: 53-46-3
N,N-Diethyl-N-methyl-2-[(9H-xanthen-9-ylcarbonyl)oxy]ethanaminium bromide; diethyl(2-hydroxyethyl)methylammonium bromide xanthene-9-carboxylate; β-diethylaminoethyl 9-xanthenecarboxylate methobromide; MTB-51; SC-2910; Banthine Bromide (Searle); Avagal; Uldumont; Vagantin; Metaxan; Methanide; Xanteline; Gastron (Winthrop); Gastrosedan; Methanthine Bromide; Vagamin; Metanyl; Doladene; Asabaine.
C21H26BrNO3; mol wt 420.34.
C 60.00%, H 6.23%, Br 19.01%, N 3.33%, O 11.42%.

Description and 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).

Chemical structure

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).

Therapeutic Category

Antispasmodic. In treatment of urinary incontinence.

Keywords

Antispasmodic; Antimuscarinic