beta-Erythroidine

Title: b-Erythroidine
CAS Registry Number: 466-81-9
CAS Name: (3b)-1,2,6,7-Tetradehydro-14,17-dihydro-3-methoxy-16(15H)-oxaerythrinan-15-one
Additional Names: 12,13-didehydro-13,14-dihydro-a-erythroidine
Molecular Formula: C16H19NO3
Molecular Weight: 273.33
Percent Composition: C 70.31%, H 7.01%, N 5.12%, O 17.56%
Literature 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°. [a]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).
Melting point: mp 99.5-100°
Optical Rotation: [a]D25 +88.8°
Toxicity data: LD50 i.p. in mice: 24.0 mg/kg (Berger, Schwartz)
Derivative Type: Hydrochloride
Molecular Formula: C16H19NO3.HCl
Molecular Weight: 309.79
Percent Composition: C 62.03%, H 6.51%, N 4.52%, O 15.49%, Cl 11.44%
Properties: Small needles from abs ethanol, mp 232° (dec). [a]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.
Melting point: mp 232° (dec)
Optical Rotation: [a]D25 +10°
Derivative Type: Hydrochloride hemihydrate
Molecular Formula: C16H19NO3.HCl.½H2O
Molecular Weight: 318.80
Percent Composition: 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). [a]D +95°. Has curare-like action which is antagonized by prostigmine.
Melting point: mp 229.5-230° (dec)
Optical Rotation: [a]D +95°
Derivative Type: Hydrobromide
Molecular Formula: C16H19NO3.HBr
Molecular Weight: 354.24
Percent Composition: C 54.25%, H 5.69%, N 3.95%, O 13.55%, Br 22.56%
Properties: Crystals from abs ethanol, mp 222.5°. [a]D25 +111.2°.
Melting point: mp 222.5°
Optical Rotation: [a]D25 +111.2°
Derivative Type: Hydriodide
Molecular Formula: C16H19NO3.HI
Molecular Weight: 401.24
Percent Composition: C 47.89%, H 5.02%, N 3.49%, O 11.96%, I 31.63%
Properties: Crystals from abs ethanol, mp 206°. [a]D25 +108.1°.
Melting point: mp 206°
Optical Rotation: [a]D25 +108.1°
Derivative Type: Methiodide
Molecular Formula: C16H19NO3.CH3I
Molecular Weight: 415.27
Percent Composition: C 49.17%, H 5.34%, N 3.37%, O 11.56%, I 30.56%
Properties: White prisms from alcohol, mp 211°.
Melting point: mp 211°
beta-Eucaine beta-Farnesene beta-Glucogallin beta-Glucuronidase beta-Hydroxybutyric Acid