Willi Schirmer, Isabelle Mösch, Stefan Schürch, Wolfgang Weinmann
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引用次数: 0
Abstract
Tetrahydrocannabidiol (H4CBD) is an emerging semisynthetic cannabinoid, which has been known since 1940. Like hexahydrocannabinol (HHC), it is easily obtained by hydrogenation of available phytocannabinoids, in the case of H4CBD by hydrogenation of cannabidiol (CBD). H4CBD shows a weak affinity for the CB1 receptor, but it is unclear if H4CBD shows psychoactive properties, as reports from users are divided. Only a few countries have placed H4CBD under their narcotic substance law, for example, France and Switzerland. The aim of this study was to identify human Phase I and II metabolites in urine as potential forensic targets. The H4CBD used for this study was bought from an online store and analyzed beforehand using GC-MS. The Phase I and II metabolites were identified using LC-HR-MS/MS and GC-MS after trimethylsilylation. The found H4CBD metabolites were carboxylated, hydroxylated, and bishydroxylated species and their glucuronides with hydroxylation and carboxylation positions on the alicyclic moiety and on the side chain. The tentatively identified metabolites were the carboxylic acids 5″-COOH-H4CBD and 7-COOH-H4CBD, the hydroxylated metabolites (1R,6R)-OH-H4CBD, (1R,6S)-OH-H4CBD, two epimers of 2″-OH-H4CBD, and both epimers of 7-OH-H4CBD. The identified bishydroxylated metabolites were side-chain hydroxylated derivatives of 7-OH-H4CBD. Various other hydroxylated metabolites were found, but their exact hydroxylation positions could not be determined. Some ESI+ spectra of the metabolites showed very unusual fragmentation patterns, like the loss of both oxygens from the resorcinol moiety with subsequent ring contraction and the appearance of radical cations for Phase II metabolites. These unusual patterns were noticed for H4CBD and its side-chain-altered metabolites.
期刊介绍:
As the incidence of drugs escalates in 21st century living, their detection and analysis have become increasingly important. Sport, the workplace, crime investigation, homeland security, the pharmaceutical industry and the environment are just some of the high profile arenas in which analytical testing has provided an important investigative tool for uncovering the presence of extraneous substances.
In addition to the usual publishing fare of primary research articles, case reports and letters, Drug Testing and Analysis offers a unique combination of; ‘How to’ material such as ‘Tutorials’ and ‘Reviews’, Speculative pieces (‘Commentaries’ and ‘Perspectives'', providing a broader scientific and social context to the aspects of analytical testing), ‘Annual banned substance reviews’ (delivering a critical evaluation of the methods used in the characterization of established and newly outlawed compounds).
Rather than focus on the application of a single technique, Drug Testing and Analysis employs a unique multidisciplinary approach to the field of controversial compound determination. Papers discussing chromatography, mass spectrometry, immunological approaches, 1D/2D gel electrophoresis, to name just a few select methods, are welcomed where their application is related to any of the six key topics listed below.