8407. Scopolamine N-Oxide

Nomenclature

CAS number: 97-75-6
(αS)-α-(Hydroxymethyl)benzeneacetic acid (1α,2β,4β,5α,7β)-9-methyl-9-oxido-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester N-oxide; 6β,7β-epoxy-1αH,5αH-tropan-3α-ol (-)-tropate 8-oxide; scopolamine aminoxide.
C17H21NO5; mol wt 319.35.
C 63.94%, H 6.63%, N 4.39%, O 25.05%.

Description and references

Anticholinergic. Prepn: Polonovski, Polonovski, Compt. Rend. 180, 1755 (1925). Absolute configuration: Huber et al., Can. J. Chem. 49, 3258 (1971).

Chemical structure

Properties

White powder, mp ≈80°. [α]D20 -14° in water.

Derivative

Hydrobromide.

Nomenclature

CAS number: 6106-81-6
Genoscopolamine (Amido).
C17H22BrNO5; mol wt 400.26.
C 51.01%, H 5.54%, Br 19.96%, N 3.50%, O 19.99%.

Properties

Prisms from water, mp 135-138°. [α]D25 -25° (c = 2). Soly in water about 10 g/100 ml. Slightly sol in alcohol, acetone. pH of 3% aq soln about 3.2.

Therapeutic Category

Antiparkinsonian.

Keywords

Antiparkinsonian; Antimuscarinic