12-06799. Norhyoscyamine [Archived]

Nomenclature

CAS number: 537-29-1
[3(S)-endo]-α-(Hydroxymethyl)benzeneacetic acid 8-azabicyclo[3.2.1]oct-3-yl ester; 1αH,5αH-nortropan-3α-ol (-)-tropate; 1-tropic acid 3α-nortropanyl ester; pseudohyoscyamine; solandrine.
C16H21NO3; mol wt 275.34.
C 69.79%, H 7.69%, N 5.09%, O 17.43%.

Description and references

Isoln from Solanaceae and structure: Carr, Reynolds, J. Chem. Soc. 101, 946 (1912). Synthesis: Fodor et al., Ber. 93, 2681 (1960). Identity with pseudohyoscyamine: Carr, Reynolds, loc. cit.; with solandrine: Petrie, C.A. 12, 23457 (1918).

Chemical structure

Properties

Crystals, mp 140.5°. Strongly basic. [α]D -23° (alcohol). Slightly sol in water, ether; sol in alcohol, chloroform.

Status

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