3680. β-Erythroidine
Nomenclature
CAS number: 466-81-9
(3β)-1,2,6,7-Tetradehydro-14,17-dihydro-3-methoxy-16(15H)-oxaerythrinan-15-one; 12,13-didehydro-13,14-dihydro-α-erythroidine. C16H19NO3; mol wt 273.33.
C 70.31%, H 7.01%, N 5.12%, O 17.56%.
Description and references
Skeletal muscle relaxant. Isolated from the seeds and other plant parts of Erythrina spp., Leguminosae: Folkers, Major, J. Am. Chem. Soc. 59, 1580 (1937); eidem, US 2373952; US 2385266; US 2407713 (1945 and 1946 to Merck & Co.). Structural studies: Koniuszy, Folkers, J. Am. Chem. Soc. 72, 5519 (1950); Boekelheide et al., ibid. 75, 2550 (1953). Absolute configuration: Wenzinger, Boekelheide, Proc. Chem. Soc. London 1963, 53; eidem, J. Org. Chem. 29, 1307 (1964). Toxicity data: F. M. Berger, R. P. Schwartz, J. Pharmacol. Exp. Ther. 93, 362 (1948). Review: Boekelheide, Rec. Chem. Prog. 16, 227-239 (1955).
Properties
Crystals from abs ethanol, mp 99.5-100°. [α]D25 +88.8°. Sol in water, benzene, chloroform, methanol, ethanol; moderately sol in diethyl ether. Reacts with NaOH to form sodium erythroidinate. LD50 i.p. in mice: 24.0 mg/kg (Berger, Schwartz).Derivative
Hydrochloride.C16H19NO3.HCl; mol wt 309.79.
C 62.03%, H 6.51%, N 4.52%, O 15.49%, Cl 11.44%.
Properties
Small needles from abs ethanol, mp 232° (dec). [α]D25 +10°. Unstable in air and light. Bitter taste. Sol in water, benzene, chloroform, methanol, ethanol; moderately sol in diethyl ether. Incompat. with oxidizing agents, alkaline solns, and akaloidal reagents.Derivative
Hydrochloride hemihydrate.C16H19NO3.HCl. 1/2 H2O; mol wt 318.80.
C 60.28%, H 6.64%, N 4.39%, O 17.57%, Cl 11.12%.
Properties
Small needles from abs ethanol, mp 229.5-230° (dec). [α]D +95°. Has curare-like action which is antagonized by prostigmine.Derivative
Hydrobromide.C16H19NO3.HBr; mol wt 354.24.
C 54.25%, H 5.69%, N 3.95%, O 13.55%, Br 22.56%.
Properties
Crystals from abs ethanol, mp 222.5°. [α]D25 +111.2°.Derivative
Hydriodide.C16H19NO3.HI; mol wt 401.24.
C 47.89%, H 5.02%, N 3.49%, O 11.96%, I 31.63%.
Properties
Crystals from abs ethanol, mp 206°. [α]D25 +108.1°.Derivative
Methiodide.C16H19NO3.CH3I; mol wt 415.27.
C 49.17%, H 5.34%, N 3.37%, O 11.56%, I 30.56%.