Lysergic Acid
Title: Lysergic Acid
CAS Registry Number: 82-58-6
CAS Name: 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: Lysergic acid and isolysergic acid are the main cleavage products formed on alkaline hydrolysis of the alkaloids which are characteristic of ergot. Jacobs, Craig et al., J. Biol. Chem. 104, 547 (1934); 125, 289 (1938); 130, 399 (1939); 145, 487 (1942); J. Org. Chem. 10, 76 (1945). High-yield production by Claviceps paspali: Arcamone et al., Proc. R. Soc. London Ser. B 155, 26 (1961). Total synthesis: Kornfeld et al., J. Am. Chem. Soc. 76, 5256 (1954); 78, 3087 (1956); M. Julia et al., Tetrahedron Lett. 1969, 1569; V. W. Armstrong et al., ibid. 1976, 4311; W. Oppolzer et al., Helv. Chim. Acta 64, 478 (1981); R. Ramage et al., Tetrahedron 37, Suppl. 9, 157 (1981); J. Rebek, D. F. Tai, Tetrahedron Lett. 24, 859 (1983). Stereochemistry: Stoll et al., Helv. Chim. Acta 37, 2039 (1954); Stenlake, J. Chem. Soc. 1955, 1626; Leeman, Fabbri, Helv. Chim. Acta 42, 2696 (1959). Absolute configuration: Stadler, Hofmann, ibid. 45, 2005 (1962).
Properties: Hexagonal scales, plates with one or two moles H2O from water, mp 240° (dec). [a]D20 +40° (c = 0.5 in pyridine). Behaves as an acid and base, pKa 3.44, pKb 7.68. Moderately sol in pyridine. Sparingly sol in water and in neutral organic solvents; sol in NaOH, NH4OH, Na2CO3, and HCl solns. Slightly sol in dil H2SO4.
Melting point: mp 240° (dec)
pKa: pKa 3.44, pKb 7.68
Optical Rotation: [a]D20 +40° (c = 0.5 in pyridine)
 
Derivative Type: Methyl ester
Properties: Thin leaflets from benzene, mp 168°.
Melting point: mp 168°
 
NOTE: This is a controlled substance (depressant): 21 CFR, 1308.13.

Others monographs:
Hydroorotic Acid8-HydroxyquinolineCaptanHemisulfur Mustard
ThymostatinEinsteiniumSodium HydrideCetraric Acid
PyranineXanthinol NiacinateCefoxitinDiazolidinyl Urea
Bromphenol Blue3-DehydroretinolVelnacrineNilutamide
©2016 DrugLead US FDA&EMEA