Lysergic acid

  • D-( )-6 -methyl- 9 ,10- didehydro -ergoline -8 -carboxylic acid
  • (5R, 8R )-6 -methyl- 9 ,10- didehydro -ergoline -8 -carboxylic acid

Lamellar crystals

Fixed

240 ° C ( decomposition)

3.3

  • Moderately in pyridine
  • Little in water and organic solvents
  • Soluble in acidic and alkaline solution

Template: Infobox chemical / molecular formula search available

The lysergic acid is a tetracyclic ( structure with four rings ) β -amino acid. The D-( )- lysergic acid is the precursor for a variety of ergoline alkaloids from the ergot fungus Claviceps purpurea, other filamentous fungi and a few higher plants from the group of wind plants ( Convolvulaceae ) are produced. The name is derived from ergot, the French word for ' mother grain ' and lysis (Greek for ' resolution ').

The first correct structure proposal comes from WA Jacobs and was the synthesis of Dehydrolysergsäure by A. Stoll, A. Hofmann and F. Troxler confirmed .. The molecule has two stereocenters. There are four stereoisomers ( D- lysergic acid, lysergic acid L-, D -iso- lysergic acid and L -iso- lysergic acid ). The relative configuration of the two stereocenters in 1954 by Stoll et al. derived, the absolute configuration of 1959 determined by blank man and Fabbri by ORD measurements. The total synthesis of racemic lysergic acid succeeded in 1956, Woodward et al.

The biosynthesis of lysergic acid is - as with all ergot alkaloids - from tryptophan from.

Occurrence

Ergot ( Claviceps purpurea), morning glory (Ipomoea violacea ) and Ololiuqui ( Rivea corymbosa ) (producer are endophytes ).

Use

Lysergic acid and its amides have a significant therapeutic index. Lysergic acid in their basic form was first used in the early modern period to trigger contractions.

However, it is known as the base of the hallucinogen lysergic acid diethylamide (LSD ).

CAS registry number Walter Abraham Jacobs Arthur Stoll Albert Hofmann Optical rotatory dispersion Robert Burns Woodward
536713
de