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伯脂肪胺代谢:稳定亚胺代谢物的形成。

Primary aliphatic amine metabolism: the formation of a stable imine metabolite.

作者信息

Raman A, Christou M, Gorrod J W

机构信息

Chelsea Department of Pharmacy, King's College London, University of London, UK.

出版信息

Eur J Drug Metab Pharmacokinet. 1987 Oct-Dec;12(4):279-83. doi: 10.1007/BF03189913.

DOI:10.1007/BF03189913
PMID:3449386
Abstract

The possible role of hydroxylamine and imine intermediates in the metabolism of amphetamine and related primary amines is discussed. The inherent instability of imines, has hitherto precluded the recognition of these compounds as metabolites of primary amines. During studies on the metabolism of o-methylbenzhydrylamine using washed hepatic microsomes from a number of mammalian species, the formation of o-methylbenzophenoneimine as a metabolite was observed. This metabolite was identified by preparative thin layer chromatography followed by gas-chromatography combined with mass spectrometry.

摘要

本文讨论了羟胺和亚胺中间体在苯丙胺及相关伯胺代谢过程中可能发挥的作用。亚胺固有的不稳定性,使得这些化合物迄今未被视作伯胺的代谢产物。在利用多种哺乳动物的洗涤肝微粒体对邻甲基二苯甲胺代谢进行研究的过程中,观察到了作为代谢产物的邻甲基二苯甲酮亚胺的形成。该代谢产物通过制备型薄层色谱法,随后结合气相色谱-质谱联用技术进行鉴定。

相似文献

1
Primary aliphatic amine metabolism: the formation of a stable imine metabolite.伯脂肪胺代谢:稳定亚胺代谢物的形成。
Eur J Drug Metab Pharmacokinet. 1987 Oct-Dec;12(4):279-83. doi: 10.1007/BF03189913.
2
Imines as intermediates in oxidative aralkylamine metabolism.亚胺作为氧化芳烷基胺代谢的中间体。
Drug Metab Rev. 1989;20(2-4):307-39. doi: 10.3109/03602538909103545.
3
In vitro microsomal metabolism of nuclear chloro substituted secondary amines and imines.
Eur J Drug Metab Pharmacokinet. 1997 Oct-Dec;22(4):351-8. doi: 10.1007/BF03190970.
4
Metabolic N-hydroxylation of substituted acetophenone imines. I. Evidence for formation of isomeric oximes.
Xenobiotica. 1986 Jun;16(6):575-85. doi: 10.3109/00498258609043546.
5
Meta-hydroxymexiletine, a new metabolite of mexiletine. Isolation, characterization, and species differences in its formation.美西律的新代谢产物间羟基美西律:分离、表征及其形成的种属差异
Drug Metab Dispos. 1991 Mar-Apr;19(2):458-61.
6
Metabolism of procainamide to a hydroxylamine by rat and human hepatic microsomes.大鼠和人肝微粒体将普鲁卡因胺代谢为羟胺。
Drug Metab Dispos. 1984 Jan-Feb;12(1):77-81.
7
Formation of imine derivatives between biologically occurring amines and oxo-steroids.生物胺与氧代甾体之间亚胺衍生物的形成。
J Steroid Biochem. 1984 Dec;21(6):643-51. doi: 10.1016/0022-4731(84)90025-6.
8
Glucuronide formation in the metabolism of N-substituted aryl compounds.N-取代芳基化合物代谢中的葡萄糖醛酸苷形成。
Natl Cancer Inst Monogr. 1981 Dec(58):109-11.
9
Gas chromatographic/mass spectrometric determination of alicyclic primary hydroxylamines in metabolic studies in vitro.体外代谢研究中脂环族伯羟胺的气相色谱/质谱测定
Biomed Environ Mass Spectrom. 1989 Sep;18(9):724-6. doi: 10.1002/bms.1200180913.
10
Metabolism of 4-substituted-N-ethyl-N-methylanilines: chromatographic and mass spectrometric identification of N-oxidation metabolic products formed in vitro.
Biomed Mass Spectrom. 1982 Jun;9(6):233-40. doi: 10.1002/bms.1200090603.

本文引用的文献

1
The enzymatic deamination of amphetamine (benzedrine).苯丙胺(安非他明)的酶促脱氨基作用。
J Biol Chem. 1955 Jun;214(2):753-63.
2
Conversion of N-hydroxyamphetamine to phenylacetone oxime by rat liver microsomes.大鼠肝脏微粒体将N-羟基苯丙胺转化为苯丙酮肟。
Biochem Pharmacol. 1982 Jan 1;31(1):105-8. doi: 10.1016/0006-2952(82)90244-1.
3
Phenylacetone oxime--an intermediate in the oxidative deamination of amphetamine.
Biochem Pharmacol. 1971 Aug;20(8):2123-8. doi: 10.1016/0006-2952(71)90425-4.
4
The enzymatic N-hydroxylation of an imine. A new cytochrome P-450-dependent reaction catalyzed by hepatic microsomal monooxygenases.亚胺的酶促N-羟基化。一种由肝微粒体单加氧酶催化的新的细胞色素P-450依赖性反应。
J Biol Chem. 1971 Nov 25;246(22):6953-5.
5
The mechanism of oxidation of amphetamine enantiomorphs by liver microsomal preparations from different species.不同物种肝脏微粒体制剂对苯丙胺对映体的氧化机制。
J Pharm Pharmacol. 1972 Feb;24(2):174-6. doi: 10.1111/j.2042-7158.1972.tb08959.x.
6
The mechanism of microsomal deamination: heavy isotope studies.微粒体脱氨基作用机制:重同位素研究
Drug Metab Dispos. 1973 Jan-Feb;1(1):337-41.
7
The identification, properties and analysis of N-hydroxyamphetamine--a metabolite of amphetamine.N-羟基苯丙胺的鉴定、性质及分析——苯丙胺的一种代谢物
J Pharm Pharmacol. 1973 Apr;25(4):329-34.
8
The metabolism of amphetamines in mammals.安非他命在哺乳动物体内的代谢。
Drug Metab Rev. 1976;5(2):219-80. doi: 10.3109/03602537609029979.