Structural modification of fentanyls for their retrospective identification by gas chromatographic analysis using chloroformate chemistry

Abstract The one-step breakdown and derivatization of a panel of nine fentanyls to yield uniquely tagged products that can be detected by Electron Ionization Gas Chromatography-Mass Spectrometry (EI-GC-MS) is presented. The method involves the treatment of the synthetic opioids with 2,2,2-trichloroe...

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Main Authors:	Carlos A. Valdez, Roald N. Leif, Robert D. Sanner, Todd H. Corzett, Mark L. Dreyer, Katelyn E. Mason
Format:	article
Language:	EN
Published:	Nature Portfolio 2021
Subjects:	Medicine R Science Q
Online Access:	https://doaj.org/article/19febadc72b24bd0b62e76ca5ee23c3c
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spelling	oai:doaj.org-article:19febadc72b24bd0b62e76ca5ee23c3c2021-11-21T12:17:49ZStructural modification of fentanyls for their retrospective identification by gas chromatographic analysis using chloroformate chemistry10.1038/s41598-021-01896-x2045-2322https://doaj.org/article/19febadc72b24bd0b62e76ca5ee23c3c2021-11-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-01896-xhttps://doaj.org/toc/2045-2322Abstract The one-step breakdown and derivatization of a panel of nine fentanyls to yield uniquely tagged products that can be detected by Electron Ionization Gas Chromatography-Mass Spectrometry (EI-GC-MS) is presented. The method involves the treatment of the synthetic opioids with 2,2,2-trichloroethoxycarbonyl chloride (TrocCl) at 60 °C for 3 h in dichloromethane and furnishes two products from one fentanyl molecule that can be used to retrospectively identify the original opioid. Parameters that were studied and fully optimized for the method included temperature, solvent, nature of scavenging base and reaction time. One of the two resulting products from the reaction bears the trichloroethoxycarbonyl (Troc) tag attached to the norfentanyl portion of the original opioid and greatly aids in the opioid detection and identification process. The methodology has been applied to the chemical modification of a panel of nine fentanyls and in all cases the molecular ion peak for the Troc-norfentanyl product bearing the distinctive trichloroethyl isotopic signature can be clearly observed. The method’s LLOD was determined to be 10 ng/mL while its LLOQ was found to be 20 ng/mL. This methodology represents the first application of chloroformates in the chemical modification of this class of synthetic opioids that are notoriously inert to common derivatization strategies available for GC–MS analysis.Carlos A. ValdezRoald N. LeifRobert D. SannerTodd H. CorzettMark L. DreyerKatelyn E. MasonNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-9 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Carlos A. Valdez Roald N. Leif Robert D. Sanner Todd H. Corzett Mark L. Dreyer Katelyn E. Mason Structural modification of fentanyls for their retrospective identification by gas chromatographic analysis using chloroformate chemistry
description	Abstract The one-step breakdown and derivatization of a panel of nine fentanyls to yield uniquely tagged products that can be detected by Electron Ionization Gas Chromatography-Mass Spectrometry (EI-GC-MS) is presented. The method involves the treatment of the synthetic opioids with 2,2,2-trichloroethoxycarbonyl chloride (TrocCl) at 60 °C for 3 h in dichloromethane and furnishes two products from one fentanyl molecule that can be used to retrospectively identify the original opioid. Parameters that were studied and fully optimized for the method included temperature, solvent, nature of scavenging base and reaction time. One of the two resulting products from the reaction bears the trichloroethoxycarbonyl (Troc) tag attached to the norfentanyl portion of the original opioid and greatly aids in the opioid detection and identification process. The methodology has been applied to the chemical modification of a panel of nine fentanyls and in all cases the molecular ion peak for the Troc-norfentanyl product bearing the distinctive trichloroethyl isotopic signature can be clearly observed. The method’s LLOD was determined to be 10 ng/mL while its LLOQ was found to be 20 ng/mL. This methodology represents the first application of chloroformates in the chemical modification of this class of synthetic opioids that are notoriously inert to common derivatization strategies available for GC–MS analysis.
format	article
author	Carlos A. Valdez Roald N. Leif Robert D. Sanner Todd H. Corzett Mark L. Dreyer Katelyn E. Mason
author_facet	Carlos A. Valdez Roald N. Leif Robert D. Sanner Todd H. Corzett Mark L. Dreyer Katelyn E. Mason
author_sort	Carlos A. Valdez
title	Structural modification of fentanyls for their retrospective identification by gas chromatographic analysis using chloroformate chemistry
title_short	Structural modification of fentanyls for their retrospective identification by gas chromatographic analysis using chloroformate chemistry
title_full	Structural modification of fentanyls for their retrospective identification by gas chromatographic analysis using chloroformate chemistry
title_fullStr	Structural modification of fentanyls for their retrospective identification by gas chromatographic analysis using chloroformate chemistry
title_full_unstemmed	Structural modification of fentanyls for their retrospective identification by gas chromatographic analysis using chloroformate chemistry
title_sort	structural modification of fentanyls for their retrospective identification by gas chromatographic analysis using chloroformate chemistry
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/19febadc72b24bd0b62e76ca5ee23c3c
work_keys_str_mv	AT carlosavaldez structuralmodificationoffentanylsfortheirretrospectiveidentificationbygaschromatographicanalysisusingchloroformatechemistry AT roaldnleif structuralmodificationoffentanylsfortheirretrospectiveidentificationbygaschromatographicanalysisusingchloroformatechemistry AT robertdsanner structuralmodificationoffentanylsfortheirretrospectiveidentificationbygaschromatographicanalysisusingchloroformatechemistry AT toddhcorzett structuralmodificationoffentanylsfortheirretrospectiveidentificationbygaschromatographicanalysisusingchloroformatechemistry AT markldreyer structuralmodificationoffentanylsfortheirretrospectiveidentificationbygaschromatographicanalysisusingchloroformatechemistry AT katelynemason structuralmodificationoffentanylsfortheirretrospectiveidentificationbygaschromatographicanalysisusingchloroformatechemistry
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Structural modification of fentanyls for their retrospective identification by gas chromatographic analysis using chloroformate chemistry

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