12-04709. Heteronium Bromide [Archived]

Nomenclature

CAS number: 7247-57-6
3-[(Hydroxyphenyl-2-thienylacetyl)oxy]-1,1-dimethylpyrrolidinium bromide; 3-hydroxy-1,1-dimethylpyrrolidinium bromide α-phenyl-2-thiopheneglycolate; 3-hydroxy-1,1-dimethylpyrrolidinium bromide α-phenyl-α-(2-thienyl)glycolate; 1-methyl-3-pyrrolidyl phenyl-2-thienylglycolate methobromide.
C18H22BrNO3S; mol wt 412.34.
C 52.43%, H 5.38%, Br 19.38%, N 3.40%, O 11.64%, S 7.78%.

Description and references

Anticholinergic. Prepn: Ryan, Ainsworth, J. Org. Chem. 27, 2901 (1962); of α- and β-diastereoisomers, Ainsworth, Ryan, US 3138614 (1964 to Lilly). Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).

Chemical structure

Properties

Crystals from abs ethanol; α- and β-diastereoisomers, separated by fractional crystn, have different crystal forms and different infrared absorption spectra. LD50 in female, male rats (mg/kg): 3399±624, 3576±954 orally (Goldenthal).

Derivative

α-Diastereoisomer.

Properties

Crystals from methanol + ethyl acetate, mp 210-211°.

Derivative

β-Diastereoisomer.

Properties

Crystals from methanol + ethyl acetate, mp 182-184°.

Status

This monograph has been retired and is no longer subject to revision or update.