Title: Isolysergic Acid
CAS Registry Number: 478-95-5
CAS Name: (8a)-9,10-Didehydro-6-methylergoline-8-carboxylic acid
Molecular Formula: C16H16N2O2
Molecular Weight: 268.31
Percent Composition: C 71.62%, H 6.01%, N 10.44%, O 11.93%
Literature 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 a-configuration at C-8. Stereochemical studies: Stenlake, J. Chem. Soc. 1955, 1626; Leemann, Fabbri, Helv. Chim. Acta 42, 2696 (1959).
Properties: Dihydrate from water, mp 218° (dec). [a]D20 +281° (pyridine). pKa 3.44, pKb 8.61. More sol in water and pyridine than lysergic acid.
Melting point: mp 218° (dec)
pKa: pKa 3.44, pKb 8.61
Optical Rotation: [a]D20 +281° (pyridine)
Derivative Type: Methyl ester
Properties: Rods from benzene, mp 170-174°. [a]D20 +179° (c = 0.5 in chloroform).
Melting point: mp 170-174°
Optical Rotation: [a]D20 +179° (c = 0.5 in chloroform)
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