739. Apoatropine

Nomenclature

CAS number: 500-55-0
α-Methylenebenzeneacetic acid (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester; 1αH,5αH-tropan-3α-ol atropate; atropamine; atropyltropeine.
C17H21NO2; mol wt 271.35.
C 75.25%, H 7.80%, N 5.16%, O 11.79%.

Description and references

Anticholinergic. Occurs in root of Atropa belladonna L., Solanaceae. Also obtained from atropine by splitting off water or by total synthesis: Ladenburg, Ann. 217, 102 (1883); Merck, Arch. Pharm. 230, 134 (1892); 231, 110 (1893); Hesse, Ann. 261, 87 (1891); 271, 124 (1892); 277, 290 (1893). Isoln by chromatography: Steinegger, Phokas, Pharm. Acta Helv. 31, 284 (1956).

Chemical structure

Properties

Prisms from chloroform, mp 62°. Absorption spectrum: Gompel, Henri, Compt. Rend. 156, 1543 (1913). Freely sol in alcohol, ether, chloroform, benzene, carbon disulfide; slightly in petr ether, isoamyl alcohol. Almost insol in water.

Derivative

Hydrochloride.
C17H21NO2.HCl; mol wt 307.82.
C 66.33%, H 7.20%, N 4.55%, O 10.40%, Cl 11.52%.

Properties

Scales, mp 239°. Sol in hot water; sparingly sol in alc, acetone. Nearly insol in ether.

Derivative

Sulfate pentahydrate.
(C17H21NO2)2.H2SO4.5H2O; mol wt 730.86.
C 55.87%, H 7.45%, N 3.83%, O 28.46%, S 4.39%.

Properties

Crystals, sparingly sol in water.