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6-羟基化:对色胺类精神活性效力的影响

6-hydroxylation: effect on the psychotropic potency of tryptamines.

作者信息

Taborsky R G, Delvigs P, Page I H

出版信息

Science. 1966 Aug 26;153(3739):1018-20. doi: 10.1126/science.153.3739.1018.

DOI:10.1126/science.153.3739.1018
PMID:5917552
Abstract

6-Hydroxy-5-methoxy-N,N dimethyltryptamine and 5-methoxy-N, N-dimnethyltryptamine were synthesized and their psychotropic effects compared on trained rats in a Skinner box. The nonhydroxylated form was the more po tent. The metabolism of 5-methoxytryp tophol acetate ester was also studied to determine whether hydroxylation might occur in other than the six position with exogenous indoles. One metabolite was formed, with properties of a hydroxy-5-methoxyindole-3-acetic acid, which proved on chromatography not to be the 6-hydroxy structural isomer. Phar macologic and metabolic studies suggest that psychotropic activity of trypt amines may result from metabolites other than the 6-hydroxylated forms.

摘要

合成了6-羟基-5-甲氧基-N,N-二甲基色胺和5-甲氧基-N,N-二甲基色胺,并在斯金纳箱中对训练过的大鼠比较了它们的精神作用。未羟基化的形式活性更强。还研究了5-甲氧基色醇乙酸酯的代谢,以确定在外源性吲哚的情况下,羟基化是否可能发生在除6位以外的其他位置。形成了一种代谢产物,具有羟基-5-甲氧基吲哚-3-乙酸的性质,色谱分析证明它不是6-羟基结构异构体。药理和代谢研究表明,色胺的精神活性可能来自于除6-羟基化形式以外的代谢产物。

相似文献

1
6-hydroxylation: effect on the psychotropic potency of tryptamines.6-羟基化:对色胺类精神活性效力的影响
Science. 1966 Aug 26;153(3739):1018-20. doi: 10.1126/science.153.3739.1018.
2
Synthesis of some substituted tryptophols of possible physiological importance and a study with 3-(2-acetoxyethyl)-5-methoxyindole (5-methoxytryptophol O-acetate) on sexual maturation.
J Med Chem. 1966 Mar;9(2):251-4. doi: 10.1021/jm00320a028.
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Synthesis and biological activity of some ring-substituted tryptamines.一些环取代色胺的合成与生物活性
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Evidence from behavioural reactions to fenfluramine, 5-hydroxytryptophan, and 5-methoxy-N,N-dimethyltryptamine for differential effects of short-term and long-term lithium on indoleaminergic mechanisms in rats [proceedings].关于氟苯丙胺、5-羟色氨酸和5-甲氧基-N,N-二甲基色胺行为反应的证据,用于证明短期和长期锂对大鼠吲哚胺能机制的不同影响[会议论文集]
Br J Pharmacol. 1979 May;66(1):144P-145P.
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An investigation of demethylation in the metabolism of methoxytryptamine and methoxytryptophol.对甲氧基色胺和甲氧基色醇代谢中去甲基化作用的研究。
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Structure-activity relationships among 5-methoxy-n:n-dimethyltryptamine, 4-hydroxy-n:n-dimethyltryptamine (psilocin) and other substituted tryptamines.5-甲氧基-N,N-二甲基色胺、4-羟基-N,N-二甲基色胺(裸盖菇素)及其他取代色胺之间的构效关系。
Life Sci. 1968 Mar 1;7(5):267-77. doi: 10.1016/0024-3205(68)90200-2.
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5-Methoxy-N,N-dimethyltryptamine: behavioral and toxicological effects in animals.5-甲氧基-N,N-二甲基色胺:对动物的行为和毒理学影响
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Adv Biochem Psychopharmacol. 1974;11(0):299-313.

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Relative potency of amphetamine derivatives and N,N-dimethyltryptamines.苯丙胺衍生物和N,N-二甲基色胺的相对效价。
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