Gas chromatographic-mass spectrometric characterization of thebaol,an opium constituent, and its structural analogs

Published: August 05, 2018

Author(s)

Anzor I. Mikaia, Levan Megutnishvili, Nino G. Todua, Stephen E. Stein

Abstract

A GC–MS method is described for the characterization of thebaol, a component of opium poppy. Themethod includes preliminary sample derivatization to TMS, TBDMS, TFA, PFP and HFB substitutedproducts. Fragmentation of resulting derivatives is unique under electron ionization, and proceeds viaconsecutive loss of two radicals that violate the “even-electron rule”. Peaks of [M-2CH3]+.and [M-C4H9-CH3]+.ions show maximum intensities in the spectra of trimethyl- and tert-butyldimethylsilyl-thebaols.Elimination of perfluoroalkyl and methyl radicals from M+.is characteristic for TFA, PFP and HFB the-baols. The same fragmentation peculiarity is characteristic for derivatives prepared from related naturalcompounds containing vicinal 2-methoxyphenol moieties. The unique fragmentation of trialkylsilyl andperfluoroacyl derivatives of thebaol can be successfully used for thebaol determination within complexmixtures. This is part 4 from the series “Analytical derivatives in mass spectrometry”, parts 1, 2 and 3 see[1–3].
Citation: Journal of Pharmaceutical and Biomedical Analysis
Volume: 157
Pub Type: Journals

Keywords

Thebaol, Phenols, GC–MS, Derivatization, Trialkylsilylation, Perfluoroacylation, Alkoxycarbonylation
Created August 05, 2018, Updated November 10, 2018