Xenobiotica
January 1, 1980
T. Inoue, T. Niwaguchi, T. Murata
7 citations
Rat liver microsomes metabolize LSD into several products. Two previously reported metabolites, lysergic acid ethylamide and nor-LSD, were found alongside two newly identified ones: lysergic acid ethylvinylamide, formed by dehydrogenation of the side chain, and 13-hydroxy-LSD, a phenol. Pretreatment of rats with phenobarbitone sodium induced formation of lysergic acid ethylamide, lysergic acid ethylvinylamide, and nor-LSD, while 3-methylcholanthrene induced lysergic acid ethylamide, lysergic acid ethylvinylamide, and 13-hydroxy-LSD. Nor-LSD formation was induced only by phenobarbitone, and 13-hydroxy-LSD only by methylcholanthrene.
Xenobiotica
January 1, 1980
T. Inoue, T. Niwaguchi, Toshiro Murata
3 citations
LSD metabolism in rat liver microsomes involves at least three separate enzyme systems. In untreated rats, the inhibitor SKF 525-A most potently blocked hydroxylation at the 13-position, moderately blocked N-demethylation at the 6-position, and least affected side-chain metabolism at the 8-position. A carbon monoxide/oxygen atmosphere (80% CO, 20% O2) caused maximum inhibition of N-demethylation, moderate inhibition of 13-hydroxylation, and minimum inhibition of side-chain metabolism. In microsomes from rats pretreated with 3-methylcholanthrene, 13-hydroxylation was not inhibited by CO but still required NADPH and oxygen, suggesting catalysis by an unusual cytochrome P-448 enzyme system.
Chemischer Informationsdienst
January 10, 1978
Y. Nakahara, T. Niwaguchi, H. Ishii
Hydrogenation of LSD (I) with hydrogen over palladium on carbon yields dihydrolysergic acid diethylamide (II), whereas hydrogenation of iso-LSD (III) gives a mixture of the dihydro compounds (IV) and (V).
Chemischer Informationsdienst
October 26, 1976
T. Niwaguchi, Y. Nakahara, H. Ishii
No Summary
Chemischer Informationsdienst
August 20, 1974
Y. Nakahara, T. Niwaguchi
Amidation of lysergic acid (I) using triphenyl phosphite/imidazole/phosphoric acid tris-(dimethylamide) or phosphoric acid tris-(dimethylamide)/tosyl chloride yields compounds (II) and (III). With the latter reagent, compounds (II) are obtained in 68-75% yield and compounds (III) in up to 3-8% yield.