Dihydro-beta-erythroidine

Title: Dihydro-b-erythroidine
CAS Registry Number: 23255-54-1
CAS Name: (3b)-1,6-Didehydro-14,17-dihydro-3-methoxy-16(15H)-oxaerythrinan-15-one
Additional Names: 12,13-didehydro-2,7,13,14-tetrahydro-a-erythroidine
Molecular Formula: C16H21NO3
Molecular Weight: 275.34
Percent Composition: C 69.79%, H 7.69%, N 5.09%, O 17.43%
Literature 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 b-erythroidine or a salt of b-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°. [a]D25 +102.5°. Soluble in ethanol. Alkaline hydrolysis yields sodium dihydro-b-erythroidinate.
Optical Rotation: [a]D25 +102.5°
Derivative Type: Hydrochloride
Properties: Crystals from abs ethanol, mp 238°. [a]D25 +124.7°.
Melting point: mp 238°
Optical Rotation: [a]D25 +124.7°
Derivative Type: Hydrobromide
Properties: Crystals from abs ethanol or abs ethanol + abs ether, dec 242°. Bitter taste. [a]D25 +106-107.5°. Soly in water 0.8 g/ml; in ethanol 0.5 g/100 ml.
Optical Rotation: [a]D25 +106-107.5°
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