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Hashimoto H, Hayashi M, Nakahara Y, Niwaguchi T, Ishii H. 
“Actions Of D-lysergic Acid Diethylamide (LSD) And Its Derivatives On 5-hydroxytryptamine Receptors In The Isolated Uterine Smooth Muscle Of The Rat”. 
European Journal of Pharmacology. 1977;45:341-348.
Several metabolites of D-lysergic acid diethylamide (LSD) such as D-lysergic acid ethyl, 2'-hydroxyethylamide (LEO), D-lysergic acid ethyl,vinylamide (LEV), D-lysergic acid ethylamide (LAE) and D-norlysergic acid diethylamide (norLSD) are formed by liver tissue and by Streptomyces. These metabolites and synthetic N6-alkyl substituted derivatives such as N6-ethyl-, N6-propyl, N6-allyl and N6-hexyl-D-norLDS (ethyl-, propyl-, allyl- and hexyl-norLSD, respectively) were studied for their anti-5-hydroxytryptamine (anti-5-HT) and oxytoxic activities on isolated rat uteri. The LSD derivatives had less anti-5-HT activity than LSD. Except for hexyl-norLSD, N6alkyl substituted derivatives of LSD had higher oxytocic activities than LSD, LEO or LAE. Minimum effective concentrations as well as ED50 values for oxytocic activities of ethyl-norLSD, propyl-norLSD and allyl-norLSD were lower than that of LSD whereas those of the metabolites (LEO, LAE and norLSD) were higher than that of LSD. The oxytocic activity of allyl-norLSD was effectively antagonized by LSD and cyproheptadine, suggesting that this activity was due to its 5HT-like action. These results suggest that N6-alkyl substituted derivatives (ethyl-, propyl-, allyl-norLSD) have higher, but' the metabolites of LSD have lower affinity for 5-HT receptors than LSD, and that N6-substituted derivatives except for hexyl-norLSD have higher intrinsic activity than LSD.
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