5180. Isolysergic Acid

Nomenclature

CAS number: 478-95-5
(8α)-9,10-Didehydro-6-methylergoline-8-carboxylic acid.
C16H16N2O2; mol wt 268.31.
C 71.62%, H 6.01%, N 10.44%, O 11.93%.

Description and references

Parent compd of the ergotinine group of alkaloids from ergot. Prepn: Smith, Timmis, J. Chem. Soc. 1936, 1440; Craig et al., J. Biol. Chem. 125, 289 (1938). Differs from lysergic acid by the α-configuration at C-8. Stereochemical studies: Stenlake, J. Chem. Soc. 1955, 1626; Leemann, Fabbri, Helv. Chim. Acta 42, 2696 (1959).

Chemical structure

Properties

Dihydrate from water, mp 218° (dec). [α]D20 +281° (pyridine). pKa 3.44, pKb 8.61. More sol in water and pyridine than lysergic acid.

Derivative

Methyl ester.

Properties

Rods from benzene, mp 170-174°. [α]D20 +179° (c = 0.5 in chloroform).