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Niwaguchi T, Inoue T, Sakai T. 
“Studies on the in vitro metabolism of compounds related to lysergic acid diethylamide (LSD)”. 
Biochem Pharmacol. 1974 Nov;23:3063-3066.
In a previous paper it was shown that D-lysergic acid diethylamide (LSD) was transformed to D-lysergic acid monoethyiamide (LAE) and D-N-demethyl-lysergic acid dicthylamide (norLSD) by an enzyme in liver microsomes supplemented with NADPH and oxygen.

Many LSD-related compounds are now available which show a variety of physiological actions. In most of these compounds, the side chain at position 8 of lysergic acid, the hydrogen at position 1 or the hydrogen at position 2 are substituted by an alkyl or alcohol amide group, a methyl group, or a bromine group, respectively. In order to find some clues to the mechanism of the hallucinogenic action of LSD. the metabolic pathways of these derivatives were investigated. The present paper described the metabolism of several lysergic acid derivatives by rat liver 9000 g supernatant.


From the above results, it was found that the enzymatic demethylation of lysergic acid derivatives at position 6 to form nor-derivatives was independent of their physiological actions, and that a side chain at position 8 of normal lysergic acid derivatives was enzymatically attacked to form monoalkylamides or hydroxyalkylamides. However, an exception occurs when the compound possesses a methyl group at position 1 for then demethylation occurs at position 1 instead of 6.
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