Lysergic acid, also known as -lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline that are produced by the ergot fungus and found in the seeds of Argyreia nervosa (Hawaiian baby woodrose), and Ipomoea species (morning glories, ololiuhqui, tlitliltzin).
of lysergic acid, lysergamides, are widely used as and as , e.g. lysergic acid diethylamide (LSD). Lysergic acid is listed as a Table I precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.
The name "lysergic acid" comes from the fact that it is a carboxylic acid, and it was first made by hydrolysis of various ergot alkaloids.
Pharmacology
Lysergic acid failed to produce
LSD-like electroencephalogram (EEG) changes in rabbits.
Chemistry
Synthesis
Laboratory
Lysergic acid is generally produced by
hydrolysis of natural lysergamides, but can also be synthesized in the laboratory by a complex
total synthesis, for example by Robert Burns Woodward's team in 1956.
An
enantioselective total synthesis based on a
palladium-catalyzed domino cyclization reaction has been described in 2011 by Fujii and Ohno.
Lysergic acid monohydrate crystallizes in very thin hexagonal leaflets when recrystallized from water. Lysergic acid monohydrate, when dried (140 °C at ) forms anhydrous lysergic acid.
Biosynthesis
The biosynthetic route is based on the
alkylation of the amino acid
tryptophan with dimethylallyl diphosphate (
isoprene derived from 3
R-
mevalonic acid) giving 4-dimethylallyl--tryptophan which is
N-methylated with
S-adenosyl--methionine. Oxidative ring closure followed by decarboxylation, reduction, cyclization, oxidation, and allylic
isomerization yields -(+)-lysergic acid.
The biosynthetic pathway has been reconsituted in transgenic baker's yeast.
Isomers
Lysergic acid is a chiral compound with two
. The
isomer with inverted configuration at carbon atom 8 close to the
carboxyl group is called
isolysergic acid. Inversion at carbon 5 close to the
nitrogen atom leads to
-lysergic acid and
-isolysergic acid, respectively.
Society and culture
Legal status
See also
