Liver microsomal metabolism of N-methylcarbazole

Structural identification of the four major metabolites of N-methylcarbazole using 1H Fourier transform NMR spectroscopy

R. F. Novak, Dennis Koop, P. F. Hollenberg

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19 Citations (Scopus)

Abstract

1H Fourier transform NMR spectroscopy, in conjunction with mass spectrometry, was employed for the identification of the four major metabolites formed from N-methylcarbazole, a cocarcinogen present in tobacco smoke, after incubation in vitro with rabbit liver microsomes. The four metabolites were separated by high pressure liquid chromatography and characterized by ultraviolet spectroscopy, mass spectrometry, and 1H Fourier transform NMR spectroscopy. Mass spectrometry established that each of the metabolites contained an oxygen atom and 1H Fourier transform NMR spectroscopy was used to identify the positional isomers of the hydroxylated N-methylcarbazole. It was used to identify the positional isomers of the hydroxylated N-methylcarbazole. It was established from comparison of the 1H Fourier transform NMR spectra of the isolated metabolites of N-methylcarbazole with those of the corresponding spectra for known synthetic compounds that the four major metabolites formed in vitro were: 1-hydroxy-N-methylcarbazole, 2-hydroxy-N-methylcarbazole, 3-hydroxy-N-methylcarbazole, and N-hydroxymethylcarbazole.

Original languageEnglish (US)
Pages (from-to)128-136
Number of pages9
JournalMolecular Pharmacology
Volume17
Issue number1
StatePublished - 1980
Externally publishedYes

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Fourier Analysis
Magnetic Resonance Spectroscopy
Liver
Mass Spectrometry
Liver Microsomes
Smoke
Tobacco
N-methylcarbazole
Spectrum Analysis
High Pressure Liquid Chromatography
Oxygen
Rabbits

ASJC Scopus subject areas

  • Pharmacology

Cite this

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abstract = "1H Fourier transform NMR spectroscopy, in conjunction with mass spectrometry, was employed for the identification of the four major metabolites formed from N-methylcarbazole, a cocarcinogen present in tobacco smoke, after incubation in vitro with rabbit liver microsomes. The four metabolites were separated by high pressure liquid chromatography and characterized by ultraviolet spectroscopy, mass spectrometry, and 1H Fourier transform NMR spectroscopy. Mass spectrometry established that each of the metabolites contained an oxygen atom and 1H Fourier transform NMR spectroscopy was used to identify the positional isomers of the hydroxylated N-methylcarbazole. It was used to identify the positional isomers of the hydroxylated N-methylcarbazole. It was established from comparison of the 1H Fourier transform NMR spectra of the isolated metabolites of N-methylcarbazole with those of the corresponding spectra for known synthetic compounds that the four major metabolites formed in vitro were: 1-hydroxy-N-methylcarbazole, 2-hydroxy-N-methylcarbazole, 3-hydroxy-N-methylcarbazole, and N-hydroxymethylcarbazole.",
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N2 - 1H Fourier transform NMR spectroscopy, in conjunction with mass spectrometry, was employed for the identification of the four major metabolites formed from N-methylcarbazole, a cocarcinogen present in tobacco smoke, after incubation in vitro with rabbit liver microsomes. The four metabolites were separated by high pressure liquid chromatography and characterized by ultraviolet spectroscopy, mass spectrometry, and 1H Fourier transform NMR spectroscopy. Mass spectrometry established that each of the metabolites contained an oxygen atom and 1H Fourier transform NMR spectroscopy was used to identify the positional isomers of the hydroxylated N-methylcarbazole. It was used to identify the positional isomers of the hydroxylated N-methylcarbazole. It was established from comparison of the 1H Fourier transform NMR spectra of the isolated metabolites of N-methylcarbazole with those of the corresponding spectra for known synthetic compounds that the four major metabolites formed in vitro were: 1-hydroxy-N-methylcarbazole, 2-hydroxy-N-methylcarbazole, 3-hydroxy-N-methylcarbazole, and N-hydroxymethylcarbazole.

AB - 1H Fourier transform NMR spectroscopy, in conjunction with mass spectrometry, was employed for the identification of the four major metabolites formed from N-methylcarbazole, a cocarcinogen present in tobacco smoke, after incubation in vitro with rabbit liver microsomes. The four metabolites were separated by high pressure liquid chromatography and characterized by ultraviolet spectroscopy, mass spectrometry, and 1H Fourier transform NMR spectroscopy. Mass spectrometry established that each of the metabolites contained an oxygen atom and 1H Fourier transform NMR spectroscopy was used to identify the positional isomers of the hydroxylated N-methylcarbazole. It was used to identify the positional isomers of the hydroxylated N-methylcarbazole. It was established from comparison of the 1H Fourier transform NMR spectra of the isolated metabolites of N-methylcarbazole with those of the corresponding spectra for known synthetic compounds that the four major metabolites formed in vitro were: 1-hydroxy-N-methylcarbazole, 2-hydroxy-N-methylcarbazole, 3-hydroxy-N-methylcarbazole, and N-hydroxymethylcarbazole.

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