Nomenclature
CAS number: 23255-54-1
(3β)-1,6-Didehydro-14,17-dihydro-3-methoxy-16(15
H)-oxaerythrinan-15-one; 12,13-didehydro-2,7,13,14-tetrahydro-α-erythroidine.
C
16H
21NO
3; mol wt 275.34.
C 69.79%, H 7.69%, N 5.09%, O 17.43%.
Description and references
The more active of the two isomers that constitute
the principal alkaloidal fraction of seeds from several Erythrina spp. In contrast to curare, q.v., it retains its ability to block neuromuscular transmission
even when administered orally: K. Unna, J. G. Greslin, J. Pharmacol. 80, 53 (1944); K.
Unna et al., ibid. 39. Prepd by catalytic hydrogenation
of β-erythroidine or a salt of β-erythroidine: Folkers, Koniuszy, US 2370651 (1945 to Merck &
Co.). Structure: Boekelheide et al., J. Am. Chem. Soc. 75, 2550 (1953). Configuration: Hanson, Proc.
Chem. Soc. London 1963, 52.
Properties
Crystals from anhydr ethyl ether, dec 85-86°.
[α]D25 +102.5°. Soluble in ethanol. Alkaline hydrolysis
yields sodium dihydro-β-erythroidinate.Derivative
Hydrochloride.
Properties
Crystals from abs ethanol, mp 238°. [α]D25 +124.7°.Derivative
Hydrobromide.
Properties
Crystals from abs ethanol or abs ethanol + abs
ether, dec 242°. Bitter taste. [α]D25 +106-107.5°. Soly
in water 0.8 g/ml; in ethanol 0.5 g/100 ml.