Lysergic acid
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| Surname | Lysergic acid | ||||||||||||||||||
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| Molecular formula | C 16 H 16 N 2 O 2 | ||||||||||||||||||
| Brief description |
lamellar crystals |
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| Molar mass | 268.31 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
240 ° C (decomposition) |
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| pK s value |
3.3 |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
The lysergic acid is a tetracyclic (structure with four rings) β-amino acid . The D is lysergic acid, the precursor for a plurality of - - (+) ergoline alkaloids derived from the ergot fungus Claviceps purpurea , other filamentous fungi and a few higher plants of the group of wind plants ( Convolvulaceae be produced). The name is derived from Ergot , the French word for ' ergot ' and lysis (Greek for 'dissolution').
The first correct structure proposal comes from WA Jacobs and was confirmed by the synthesis of dehydrolysergic acid by Arthur Stoll , Albert Hofmann and Franz Troxler . The molecule has two stereocenters . There are four stereoisomers : D -Lysergsäure, L -Lysergsäure, D iso-lysergic acid and L iso-lysergic acid. The relative configuration of the two stereocenters was determined in 1954 by Stoll et al. derived, the absolute configuration determined in 1959 by Leermann and Fabbri using ORD measurements . The total synthesis of racemic lysergic acid was achieved in 1956 by Woodward et al.
The biosynthesis of lysergic acid is - as with all ergot alkaloids - from tryptophan from.
Occurrence
Ergot ( Claviceps purpurea ), funnel vines (e.g. Ipomoea tricolor or Turbina corymbosa ) (producers of the winds are epibiotic fungi of the Clavicipitaceae family that are transmitted through the seeds ).
use
Lysergic acid and its amides have considerable therapeutic potential. Lysergic acid in its basic form was used for the first time to induce labor in the early modern times .
However, it is better known as the basis of the hallucinogen lysergic acid diethylamide (LSD).
Individual evidence
- ↑ a b c d e f Entry on lysergic acid. In: Römpp Online . Georg Thieme Verlag, accessed on April 22, 2020.
- ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition. 2006, ISBN 0-911910-00-X , p. 977.
- ↑ pKa Data , Compiled by R. Williams, chem.wisc.edu (PDF; 78 kB).
- ↑ a b Registration dossier on Lysergic acid ( GHS section ) at the European Chemicals Agency (ECHA), accessed on March 13, 2019.
- ↑ LC Craig, T. Shedlovsky, RG Gould, WA Jacobs in: . J. Biol. Chem . Vol 125, 1938, S. 289th
- ↑ A. Stoll, A. Hofmann, F. Troxler: About the isomerism of lysergic acid and isolysergic acid. 14. Communication on ergot alkaloids. In: Helvetica Chimica Acta. 32, 1949, pp. 506-521, doi: 10.1002 / hlca.19490320219 .
- ↑ M. Volkan Kisakürek, Edgar Heilbronner: Highlights of chemistry . Wiley-VCH-Verlag, Weinheim 1994, p. 164 ( limited preview in the Google book search).
- ↑ A. Stoll, T. Petrzilka, L. Rutschmann, A. Hofmann, HH Günthard in: Helv. Cim. Acta. Vol. 37, 1954, p. 2039.
- ↑ HG empty man, S. Fabbri in: Helv Cim.. Acta. Vol. 42, 1954, p. 2696.
- ^ EC Kornfeld, EJ Fornefeld, GB Kline, MJ Mann, DE Morrison, RG Jones, RB Woodward in: J. Am. Chem. Soc. Vol. 78, 1956, p. 3087.
- ↑ U Steiner, MA Ahimsa-Müller, A Markert, S Kucht, J Gross, N Kauf, M Kuzma, M Zych, M Lamshöft, Miroslawa Furmanowa, Volker Knoop, Christel Drewke, Eckhard Leistner: Molecular characterization of a seed transmitted clavicipitaceous fungus occurring on dicotyledoneous plants (Convolvulaceae) . In: Planta . 224, No. 3, 2006, pp. 533-544. doi : 10.1007 / s00425-006-0241-0 . PMID 16525783 .