Title: Ergocryptine
Additional Names: Ergokryptine
Molecular Formula: C32H41N5O5
Molecular Weight: 575.70
Percent Composition: C 66.76%, H 7.18%, N 12.16%, O 13.90%
Literature References: Two closely related isomers of the ergotoxine group which differ in the peptide portion of the molecule; a-ergocryptine yielding L-leucine upon hydrolysis, b-ergocryptine yielding L-isoleucine. The ergocryptine discussed in the literature prior to 1967 is now referred to as a-ergocryptine. Isoln from ergot: Stoll, Hofmann, Helv. Chim. Acta 26, 1570 (1943). Structure: Stoll et al., ibid. 34, 1544 (1951). Separation and purification: Stoll, Hofmann, US 2447214 (1948 to Sandoz). Separation of b-ergocryptine from a-ergocryptine: Schlientz et al., Experientia 23, 991 (1967); see also eidem, Pharm. Acta Helv. 43, 497 (1968). Synthesis of a- and b-ergocryptine: Stadler et al., Helv. Chim. Acta 52, 1549 (1969).
Derivative Type: a-Ergocryptine
CAS Registry Number: 511-09-1
CAS Name: (5¢a)-12¢-Hydroxy-2¢-(1-methylethyl)-5¢-(2-methylpropyl)ergotaman-3¢,6¢,18-trione
Properties: Solvated prisms from acetone, benzene, methanol. With MeOH of crystn, mp 212° (dec). [a]D20 -120° (pyridine); -198° (chloroform). uv max (methanol): 241, 312.5 nm (log e 4.31, 3.95). Freely sol in alcohol, chlorofom. Almost insol in water.
Melting point: mp 212° (dec)
Optical Rotation: [a]D20 -120° (pyridine); -198° (chloroform)
Absorption maximum: uv max (methanol): 241, 312.5 nm (log e 4.31, 3.95)
Derivative Type: b-Ergocryptine
CAS Registry Number: 20315-46-2
CAS Name: [5¢a(S)]-12¢-Hydroxy-2¢-(1-methylethyl)-5¢-(1-methylpropyl)ergotaman-3¢,6¢,18-trione
Properties: Rectangular plates from benzene, mp 173° (dec). [a]D20 -98° (c = 0.5 in pyridine); -179° (c = 0.5 in chloroform). uv max (methanol): 312 (log e 3.93).
Melting point: mp 173° (dec)
Optical Rotation: [a]D20 -98° (c = 0.5 in pyridine); -179° (c = 0.5 in chloroform)
Absorption maximum: uv max (methanol): 312 (log e 3.93)
Therap-Cat: See Ergot.
Keywords: Antimigraine. |