3649. Ergocristine

Nomenclature

CAS number: 511-08-0
(5′α)-12′-Hydroxy-2′-(1-methylethyl)-5′-(phenylmethyl)ergotaman-3′,6′,18-trione.
C35H39N5O5; mol wt 609.71.
C 68.95%, H 6.45%, N 11.49%, O 13.12%.

Description and 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).

Chemical structure

Properties

Orthorhombic crystals with 2C6H6 from benzene. mp 155-157° (dec) (solvent-free base). [α]D20 -183° (chloroform). Very sol in ethyl and methyl alcohol, acetone, chloroform, ethyl acetate. Slightly sol in ether. Practically insol in water, petr ether.

Derivative

Phosphate.

Nomenclature

CAS number: 6424-36-8

Properties

Crystals, dec 195°.

Derivative

Ethanesulfonate.

Nomenclature

CAS number: 6055-56-7

Properties

Crystals, dec 207°.

Derivative

8α-isomer.

Nomenclature

CAS number: 511-07-9
Ergocristinine.

Properties

Crystallizes solvent-free, unlike ergocristine which tends to retain the solvent of crystn. Long prisms from abs alc, mp 226° (dec). [α]D20 +366° (c = 0.68 in chloroform); +471° (c = 0.35 in pyridine). uv max (methanol/methylene chloride): 313 nm (log ε 3.96). Much less sol than ergocristine. Does not seem to form salts.