12-05491. Levomepate [Archived]

Nomenclature

CAS number: 428-07-9
[3(S)-endo]-α-(Hydroxymethyl)-α-methylbenzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester; 1αH,5αH-tropan-3α-ol ()-2-methyl-2-phenylhydracrylate (ester); ()-2-methyl-2-phenylhydracrylic acid 3α-tropanyl ester; ()-α-methylhyoscyamine; 3α-tropanyl ()-2-methyl-2-phenylhydracrylate; tropine ()-α-methyltropate.
C18H25NO3; mol wt 303.40.
C 71.26%, H 8.31%, N 4.62%, O 15.82%.

Description and references

Prepd from tropine and ()-β-acetoxy-α-methyl-α-phenylpropionyl chloride: Vecchi et al., GB 874015 (1959 to Lepetit); Melone et al., J. Org. Chem. 25, 859 (1960). Pharmacology: Bianchi et al., Toxicol. Appl. Pharmacol. 10, 424 (1967).

Chemical structure

Derivative

Hydrochloride.
C18H25NO3.HCl; mol wt 339.86.
C 63.61%, H 7.71%, N 4.12%, O 14.12%, Cl 10.43%.

Properties

Crystals from ethyl acetate, mp 210-212°. [α]D20 6.8°.

Therapeutic Category

Antispasmodic.

Status

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