Lysergic acid – The Well Known Psychedelic Drug
Lysergic acid, otherwise known as (+) – lysergic acid and D-lysergic acid acts as precursor for various ergoline alkaloids which are synthesized by ergot fungus species and are also traced in seeds of tlitliltzin, morning glories (Ipomoea tricolor), Hawaiian Baby Woodrose (Argyreia nervosa) and Ololiuhqui (Turbina corymbosa). The amide form of the lysergic acid, the lysergamides is widely employed as psychedelic drugs and for other pharmaceutical purposes. The lysergic acid got its name as it was obtained as the product of lysis reaction of several ergot alkaloids.
The IUPAC name of the lysergic acid is 7 – Methyl – 4 ,6,6a,7,8,9-hexahydroindolo [ 4,3-fg ] quinoline – 9 – carboxylic acid. The other names of the lysergic acid are 6 – Methyl – 9, 10 – didehydroergoline – 8 – carboxylic acid. The chemical formula for lysergic acid is C16H16N2O2. This lysergic acid belongs to the category of chiral compounds with two types of stereocenters. It is an isomer carrying an inverted configuration structure at its 8 th carbon atom near to carboxy group and is referred as isolysergic acid.
The inversion process carried out at the 5th carbon atom close to the presence of nitrogen atom results in the synthesis of L-isolysergic acid and L – lysergic acid. The lysergic acid is classified as Table I precursor as per United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.
The hydrolysis process carried out on natural lysergamides results in the synthesis of lysergic acid. It can also be chemically synthesized in laboratory conditions using complex reaction of total synthesis. This procedure was put forth in the year 1956 by a team led by Woodward. Fujii along with Ohno described an enantioselective process of total synthesis depending on a domino cyclization process catalyzed by palladium.
The monohydrate form of lysergic acid can be crystallized into very thin layers of hexagonal leaflets upon recrystallized from molecules of water. This monohydrate form of lysergic acid upon drying at 270 Pa or 140 degree centigrade at the 2 mm Hg may result in anhydrous form of lysergic acid. The complete biosynthetic process depends on alkylation process of tryptophan amino acid in the presence of dimethyl diphosphate (it an isoprene obtained from the 3R-mevalonic acid) producing 4 – dimethylallyl-L-tryptophan.
This form of 4 – dimethylallyl – L- tryptophan is N – methylated in the presence of S- adenosyl – L – methionine. The closure of oxidative ring is then followed by various processes including oxidation, cyclization, reduction, decarboxylation and finally allylic isomerization process yielding D – (+) – lysergic acid.