3175. Dihydro-β-erythroidine

Nomenclature

CAS number: 23255-54-1
(3β)-1,6-Didehydro-14,17-dihydro-3-methoxy-16(15H)-oxaerythrinan-15-one; 12,13-didehydro-2,7,13,14-tetrahydro-α-erythroidine.
C16H21NO3; 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.

Chemical structure

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.