The Structure of LSD – Part of 75th Anniversary: Synthesis of Lysergic Acid Diethylamide (LSD)

  • Author: ChemViews
  • Published Date: 08 November 2013
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

LSD contains stereogenic centers at the C5- and C8-positions
that are susceptible to epimerization and the active form, (+)-LSD, has the absolute configuration 5R, 8R.

The C5 isomers of lysergamides do not exist in nature and are not formed during the synthesis of (+)-LSD. However, the C8 center rapidly interconverts in the presence of base. The C8 isomer, (+)-iso-LSD, is not active and can be separated by chromatography and isomerized to give (+)-LSD.

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Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH