12-01053. Belladonnine [Archived]

Nomenclature

CAS number: 510-25-8
1,2,3,4-Tetrahydro-1-phenyl-1,4-naphthalenedicarboxylic acid bis(8-methyl-8-azabicyclo[3.2.1]oct-3-yl) ester; isatropylditropeine; tropyl isatropate; ditropyl isatropate.
C34H42N2O4; mol wt 542.71.
C 75.25%, H 7.80%, N 5.16%, O 11.79%.

Description and references

From Atropa belladonna L. and allied Solanaceae. Probably formed during the process of extraction. Upon hydrolysis the substance extracted from plants yields β-isatropic acid and tropine: Küssner, Arch. Pharm. 276, 617 (1938); Hotovy et al., US 2734062 (1956 to E. Merck).

Chemical structure

Properties

Crystals from ethyl acetate, mp 129°. Sparingly sol in water, petr ether. Sol in alcohol, benzene, chloroform, ethyl acetate.

Derivative

Bisulfate monohydrate.

Nomenclature

CAS number: 5908-89-4
Bellacristin.
C34H42N2O4.H2SO4.H2O; mol wt 658.80.
C 61.99%, H 7.04%, N 4.25%, O 21.86%, S 4.87%.

Properties

Crystals, sol in water.

Derivative

Bis[ethobromide] tetrahydrate.

Nomenclature

Belladonnine bis[bromoethylate] tetrahydrate; C-100.
C38H52Br2N2O4.4H2O; mol wt 832.70.
C 54.81%, H 7.26%, Br 19.19%, N 3.36%, O 15.37%.

Properties

A quaternary tetrahydrate salt, crystals from water + acetone, mp 98-101°. uv max: 258, 261 nm. E1%1cm 4.8. Sol in water, methanol, ethanol. Practically insol in ether, petr ether, benzene, ethyl acetate.

Status

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