Ergocristine
Title: Ergocristine
CAS Registry Number: 511-08-0
CAS Name: (5¢a)-12¢-Hydroxy-2¢-(1-methylethyl)-5¢-(phenylmethyl)ergotaman-3¢,6¢,18-trione
Molecular Formula: C35H39N5O5
Molecular Weight: 609.71
Percent Composition: C 68.95%, H 6.45%, N 11.49%, O 13.12%
Literature References: Natural ergot alkaloid derived from lysergic acid; a member of the ergotoxine group. Isoln from ergot: Stoll, Burckhardt, Z. Physiol. Chem. 250, 1 (1937); 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). Synthesis: Stadler et al., Helv. Chim. Acta 52, 1549 (1969).
Properties: Orthorhombic crystals with 2C6H6 from benzene. mp 155-157° (dec) (solvent-free base). [a]D20 -183° (chloroform). Very sol in ethyl and methyl alcohol, acetone, chloroform, ethyl acetate. Slightly sol in ether. Practically insol in water, petr ether.
Melting point: mp 155-157° (dec) (solvent-free base)
Optical Rotation: [a]D20 -183° (chloroform)
 
Derivative Type: Phosphate
CAS Registry Number: 6424-36-8
Properties: Crystals, dec 195°.
 
Derivative Type: Ethanesulfonate
CAS Registry Number: 6055-56-7
Properties: Crystals, dec 207°.
 
Derivative Type: 8a-isomer
CAS Registry Number: 511-07-9
Additional Names: Ergocristinine
Properties: Crystallizes solvent-free, unlike ergocristine which tends to retain the solvent of crystn. Long prisms from abs alc, mp 226° (dec). [a]D20 +366° (c = 0.68 in chloroform); +471° (c = 0.35 in pyridine). uv max (methanol/methylene chloride): 313 nm (log e 3.96). Much less sol than ergocristine. Does not seem to form salts.
Melting point: mp 226° (dec)
Optical Rotation: [a]D20 +366° (c = 0.68 in chloroform); +471° (c = 0.35 in pyridine)
Absorption maximum: uv max (methanol/methylene chloride): 313 nm (log e 3.96)

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