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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 Pharmaol. 1974;23:3063-3066.
In a previous paper it was shown that D-lysergic acid diethylamide (LSD) was transformed to -lysergic acid monoethylalllide (LAE) and D-lysergic acid diethylamide (norLSD) by an enzyme in liver microsomes supplemented wit NADPYH 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 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. The substrates used hl these experiments were as follows: D-2-bromolysergic acid diethylamide (BOL.) which has a strong antagonistic action to 5-hydroxytryptamine (5HT) in peripheral organs but no effect on the central nervous systems; 1-methyl-D-lysergic acid ( + butanolamide (2) (methysergide) which has an antagonistic action to 5HT in both the peripherals and central organs but no hallucinogenic action; D-lysergic acid (+ )-butanolamide - (2)(methergine) which has an antagonistic action to 5HT in peripheral organs but no action in the central nervous systems; D-lysergic acid dimethylamide (LDM) and lycergic acid amide (LAA) which have hallucinogenic actions about one tenth that of LSD6; and isomers such as isoLSD, isoLDM. isomethergine and isoLAA. LSD, LAM, I.AA, and methergin were prepared from D-lysergic acid by Garbrecht's method,7 their isomers being obtained as by-products. and BOL was prepared from LSD by the method of Trosler et al. Methysergide was supplied by Sandoz L'd., Basel, Switzerland. NADP and 'ADPH were obtained from Sigma Chemical Co Ltd., St. Louis, U.S.A. SKF 525-A was kindly supplied by Professor Kitagawa, University of Chiba, Japan. All other chemicals were special grade and purchased from Wako Pure Chemical Industries. Ltd., Tokyo, Japan......
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