Two metabolic pathways of tetrahydronorharmane (Tetrahydro-?-carboline) in rats
- 1 April 1984
- journal article
- research article
- Published by Springer Nature in Naunyn-Schmiedebergs Archiv für experimentelle Pathologie und Pharmakologie
- Vol. 325 (4) , 349-355
- https://doi.org/10.1007/bf00504380
Abstract
Metabolites of (14C)tetrahydronorharmane (THN, tetrahydro-β-carboline) have been identified by mass spectrometry and nuclear magnetic resonance spectroscopy. Two metabolic pathways are suggested: Hydroxylation of the benzene ring — most probably with an epoxide as intermediate — though no hydroxylated THN could be detected in the urine samples of male and female rats but conjugated compounds as the main metabolites. The intermediary epoxide is supported by the fact, that the hydroxy substituent of THN is positioned on C-6 or C-7 with a ratio of 55:45 in female rats and of 45:55 in male rats. Dehydrogenation yielding norharmane. This substance possibly gives rise to another metabolite — 1,2-dihydro-β-carboline-1-one. The pharmacological and toxicological implications of these findings are discussed.This publication has 21 references indexed in Scilit:
- In VitroStudies on the Effect of β-Carbolines on the Activities of Acetylcholinesterase and Choline Acetyltransferase and on the Muscarinic Receptor Binding of the Rat BrainJournal of Neurochemistry, 1983
- New heterocyclic stimulators of hepatic epoxide hydrolaseBiochemical Pharmacology, 1981
- Benzodiazepine antagonism by harmane and other β-carbolines in vitro and in vivoEuropean Journal of Pharmacology, 1981
- Identification and quantification of 1,2,3,4-tetrahydro-β-carboline, 2-methyl-1,2,3,4-tetrahydro-β-carboline, and 6-methoxy-1,2,3,4-tetrahydro-β-carboline as in vivo constituents of rat brain and adrenal glandBiochemical Pharmacology, 1981
- The effect of norharman on the metabolism of benzo[a]pyrene by rat-liver microsomes in vitro in relation to its enhancement of the mutagenicity of benzo[a]pyreneMutation Research/Genetic Toxicology, 1978
- Metabolic transformation of clinically used drugs to epoxides: New perspectives in drug-drug interactionsBiochemical Pharmacology, 1976
- A FURTHER INSIGHT INTO THE METABOLISM OF CERTAIN βCARBOLINESAnnals of the New York Academy of Sciences, 1973
- Mass spectra of selected beta-carbolines [β-9H-pyrido(3,4-b)indoles]Journal of Mass Spectrometry, 1970
- Mass spectra of indazolones and pyrazolones—I: IndazolonesJournal of Mass Spectrometry, 1969
- Studies in Mass Spectrometry. I. Structures and Reactions of Ions from Benzyl Alcohol, ortho-, meta-, and para-Hydroxybenzyl Alcohols, and their 0-Deuterated DerivativesAustralian Journal of Chemistry, 1962