Ergocryptinine

Title: Ergocryptinine
CAS Registry Number: 511-10-4
Additional Names: Ergokryptinine
Molecular Formula: C32H41N5O5
Molecular Weight: 575.70
Percent Composition: C 66.76%, H 7.18%, N 12.16%, O 13.90%
Literature References: Alkaloid pair isomeric with a- and b-ergocryptine, resp., but differing by an a-configuration at C-8. The literature prior to 1967 refers to a-ergocryptinine as ergocryptinine. Isolation, structure, separation and purification see ergocryptine. Production: Abe et al., US 2835675 (1958). Prepn of b-ergocryptinine from b-ergocryptine: Schlientz et al., Experientia 23, 991 (1967). Synthesis of a- and b-ergocryptinin: Stadler et al., Helv. Chim. Acta 52, 1549 (1969).
Derivative Type: a-Ergocryptinine
Additional Names: 12¢-Hydroxy-2¢-(1-methylethyl)-5¢a-(2-methylpropyl)-8a-ergotaman-3¢,6¢,18-trione
Properties: Crystallizes solvent-free, unlike ergocryptine which tends to retain the solvent of crystn. Fine needles from methanol, dec 240-242°. [a]D20 +408° (chloroform); +485° (c = 0.5 in pyridine). uv max (methanol): 241.5, 312.5 nm (log e 4.30, 3.94). Sol in 20 parts boiling ethanol, 50 parts boiling methanol; freely sol in acetone, chloroform; almost insol in water. Does not seem to form salts.
Optical Rotation: [a]D20 +408° (chloroform); +485° (c = 0.5 in pyridine)
Absorption maximum: uv max (methanol): 241.5, 312.5 nm (log e 4.30, 3.94)
Derivative Type: b-Ergocryptinine
Properties: Colorless needles from methylene chloride-methanol, mp 217-218° (dec). [a]D20 +421° (chloroform); +497° (pyridine). uv max (methanol): 240.5, 312 nm (log e 4.31, 3.94). Differs from the a-isomer by the 1-methylpropyl group at the 5¢-position.
Melting point: mp 217-218° (dec)
Optical Rotation: [a]D20 +421° (chloroform); +497° (pyridine)
Absorption maximum: uv max (methanol): 240.5, 312 nm (log e 4.31, 3.94)
Ergoflavin Ergoloid Mesylates Ergometrinine Ergonovine Ergosine