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N-甲基咔唑在体内和体外进行N-去甲基化反应时N-羟甲基中间体的形成。

The formation of an N-hydroxymethyl intermediate in the N-demethylation of N-methylcarbazole in vivo and in vitro.

作者信息

Gorrod J W, Temple D J

出版信息

Xenobiotica. 1976 May;6(5):265-74. doi: 10.3109/00498257609151638.

DOI:10.3109/00498257609151638
PMID:936646
Abstract
  1. The metabolism of N-methylcarbazole has been studied in several mammalian species, both in vivo and in vitro. 2. An important metabolite after incubation of N-methylcarbazole with liver microsomes in vitro was identified as N-hydroxymethylcarbazole. 3. This metabolite was also found as a conjugate (probably the O-glucuronide) in the urine of some species. 4. N-Hydroxymethylcarbazole decomposed spontaneously in solution at pH 7-4 to formaldehyde and carbazole; this breakdown was enhanced by incubation with liver microsomes from several species, especially the guinea-pig. 5. The role of N-methyl hydroxylation, compared with N-oxidation, in the mechanism of N-dealkylation of non-basic N-methyl compounds is discussed.
摘要
  1. 已在多种哺乳动物体内和体外研究了N-甲基咔唑的代谢情况。2. 体外将N-甲基咔唑与肝微粒体孵育后,一种重要的代谢产物被鉴定为N-羟甲基咔唑。3. 在某些物种的尿液中也发现这种代谢产物是以结合物形式(可能是O-葡萄糖醛酸苷)存在。4. N-羟甲基咔唑在pH 7 - 4的溶液中会自发分解为甲醛和咔唑;与几种物种(尤其是豚鼠)的肝微粒体一起孵育可增强这种分解。5. 讨论了与N-氧化相比,N-甲基羟基化在非碱性N-甲基化合物N-脱烷基化机制中的作用。

相似文献

1
The formation of an N-hydroxymethyl intermediate in the N-demethylation of N-methylcarbazole in vivo and in vitro.N-甲基咔唑在体内和体外进行N-去甲基化反应时N-羟甲基中间体的形成。
Xenobiotica. 1976 May;6(5):265-74. doi: 10.3109/00498257609151638.
2
Source of the oxygen atom in the product of cytochrome P-450-catalyzed N-demethylation reactions.细胞色素P-450催化的N-去甲基化反应产物中氧原子的来源。
Mol Pharmacol. 1983 May;23(3):758-60.
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Studies on N-demethylation of methamphetamine by liver microsomes of guinea-pigs and rats: the role of flavin-containing mono-oxygenase and cytochrome P-450 systems.豚鼠和大鼠肝脏微粒体对甲基苯丙胺N-去甲基化的研究:含黄素单加氧酶和细胞色素P-450系统的作用。
Xenobiotica. 1984 Nov;14(11):861-6. doi: 10.3109/00498258409151484.
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The formation of N-hydroxymethylcarbazole as a metabolite of N-methylcarbazole.N-羟甲基咔唑作为N-甲基咔唑代谢产物的形成。
Biochem J. 1970 Apr;117(2):40P. doi: 10.1042/bj1170040p.
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Xenobiotica. 1971 Jul-Oct;1(4):365-83. doi: 10.3109/00498257109041503.
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Mol Pharmacol. 1979 Mar;15(2):396-409.

引用本文的文献

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Studies on the in vitro hepatic microsomal formation of amides during the metabolism of certain secondary and tertiary benzylic amines.
Eur J Drug Metab Pharmacokinet. 2000 Apr-Jun;25(2):145-50. doi: 10.1007/BF03190081.
2
Characterization of N-benzylcarbazole and its metabolites from microsomal mixtures by tandem mass spectrometry.通过串联质谱法对微粒体混合物中的N-苄基咔唑及其代谢物进行表征。
Eur J Drug Metab Pharmacokinet. 1994 Oct-Dec;19(4):343-8. doi: 10.1007/BF03188861.
3
Microsomal N-oxidation of long chain N,N-dimethylalkylamines: quantitative structure-activity relationships.
Eur J Drug Metab Pharmacokinet. 1987 Oct-Dec;12(4):267-73. doi: 10.1007/BF03189911.
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Pathway of degradation of nitrilotriacetate by a Pseudomonas species.一种假单胞菌属物种降解次氮基三乙酸的途径。
Appl Environ Microbiol. 1978 May;35(5):955-61. doi: 10.1128/aem.35.5.955-961.1978.