Simultaneous quantification of THC‐COOH, OH‐THC, and further cannabinoids in human hair by gas chromatography–tandem mass spectrometry with electron ionization applying automated sample preparation

Kieliba, Tobias; Lerch, Oliver; Andresen‐Streichert, Hilke; Rothschild, Markus A.; Beike, Justus

doi:10.1002/dta.2490

Cited by 20 publications

(13 citation statements)

References 56 publications

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“…The hair drug analysis has become widespread in recent years and thus has become increasingly important [272,290,291,292]. The analysis provides long-term information on drug use over a time period as long as the length of the hair allows (weeks, months, or even years), something that does not occur with other biological matrices [290,292,293]. However, this specimen also presents its pitfalls.…”

Section: Challenges In the Determination Of Secondary Metabolites mentioning

confidence: 99%

“…This may be a problem, since the detection of this metabolite in hair is mandatory to distinguish active consumption from external contamination. In this sense, only sophisticated analytical methods are capable of THC–COOH determination, such as: GC-MS with negative chemical ionisation (NCI) after derivatization with fluorinated reagents; special GC techniques (large injection volume or bi-dimensional-GC); GC-MS/MS; LC-MS, and MS 2 [290]. In addition, external contamination of THCA has been reported, due to manipulation of cannabis material and side stream smoke [290].…”

Section: Challenges In the Determination Of Secondary Metabolites mentioning

confidence: 99%

“…In this sense, only sophisticated analytical methods are capable of THC–COOH determination, such as: GC-MS with negative chemical ionisation (NCI) after derivatization with fluorinated reagents; special GC techniques (large injection volume or bi-dimensional-GC); GC-MS/MS; LC-MS, and MS 2 [290]. In addition, external contamination of THCA has been reported, due to manipulation of cannabis material and side stream smoke [290]. Also, there is evidence of formation of THC resulting from decarboxylation of THCA when alkaline hair digestion at elevated temperatures was applied in sample preparation [290].…”

Section: Challenges In the Determination Of Secondary Metabolites mentioning

confidence: 99%

“…In addition, external contamination of THCA has been reported, due to manipulation of cannabis material and side stream smoke [290]. Also, there is evidence of formation of THC resulting from decarboxylation of THCA when alkaline hair digestion at elevated temperatures was applied in sample preparation [290]. Furthermore, the phase I metabolites of THC undergo phase II, forming corresponding glucuronides, and although THC–COOH-glucuronide has been already characterised in hair, the same has not been reported for 11–OH–THC glucuronide [290].…”

Section: Challenges In the Determination Of Secondary Metabolites mentioning

confidence: 99%

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Cannabis and Its Secondary Metabolites: Their Use as Therapeutic Drugs, Toxicological Aspects, and Analytical Determination

et al. 2019

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Although the medicinal properties of Cannabis species have been known for centuries, the interest on its main active secondary metabolites as therapeutic alternatives for several pathologies has grown in recent years. This potential use has been a revolution worldwide concerning public health, production, use and sale of cannabis, and has led inclusively to legislation changes in some countries. The scientific advances and concerns of the scientific community have allowed a better understanding of cannabis derivatives as pharmacological options in several conditions, such as appetite stimulation, pain treatment, skin pathologies, anticonvulsant therapy, neurodegenerative diseases, and infectious diseases. However, there is some controversy regarding the legal and ethical implications of their use and routes of administration, also concerning the adverse health consequences and deaths attributed to marijuana consumption, and these represent some of the complexities associated with the use of these compounds as therapeutic drugs. This review comprehends the main secondary metabolites of Cannabis, approaching their therapeutic potential and applications, as well as their potential risks, in order to differentiate the consumption as recreational drugs. There will be also a focus on the analytical methodologies for their analysis, in order to aid health professionals and toxicologists in cases where these compounds are present.

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Section: Challenges In the Determination Of Secondary Metabolites mentioning

confidence: 99%

Section: Challenges In the Determination Of Secondary Metabolites mentioning

confidence: 99%

Section: Challenges In the Determination Of Secondary Metabolites mentioning

confidence: 99%

Section: Challenges In the Determination Of Secondary Metabolites mentioning

confidence: 99%

See 2 more Smart Citations

Cannabis and Its Secondary Metabolites: Their Use as Therapeutic Drugs, Toxicological Aspects, and Analytical Determination

et al. 2019

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“…Similarly, the analytical recovery was also good and was within the range 68-97%. A simple SPE coupled with GC-MS/MS method for the determination of THC (10), CBD (3) and CBN(7) in hair samples from consumers of CBD rich cannabis extracts has been reported by Rodrigues et al36 Another similar GC-MS/MS method using EI mode of ionisation for simultaneous quantification of THC (10), CBD (3), CBN(7), THCA (11), 11-OH-THC (8) in human hair samples has also been described, where SPE was chosen for sample clean-up, applying a mixed-mode anion exchange sorbent,37 and the limit of detection was 0.2 pg/mg for THCA (11) and 11-OH-THC (8), and 2 pg/mg for THC (10), CBD (3) and CBN(7), respectively, which fulfils the Society of Hair Testing recommendations. It can be noted that although GC-MS/MS with NCI is still considered as the gold standard for achieving the highest sensitivity for the analysis of THCA (11) in human hair samples, it suffers from lack of flexibility in the chemical ionisation mode, when compared to EI ionisation mode.…”

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confidence: 92%

Gas chromatographic analysis of naturally occurring cannabinoids: A review of literature published during the past decade

Nahar

Chen

Sarker

2019

Phytochemical Analysis

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Introduction Cannabinoids are organic compounds, natural or synthetic, that bind to the cannabinoid receptors and have similar pharmacological properties as produced by the cannabis plant, Cannabis sativa. Gas chromatography (GC), e.g. gas chromatography mass spectrometry (GC–MS), is a popular analytical tool that has been used extensively to analyse cannabinoids in various matrices. Objective To review published literature on the use of various GC‐based analytical methods for the analysis of naturally occurring cannabinoids published during the past decade. Methodology A comprehensive literature search was performed utilising several databases, like Web of Knowledge, PubMed and Google Scholar, and other relevant published materials including published books. The keywords used, in various combinations, with cannabinoids being present in all combinations, in the search were cannabinoids, Cannabis sativa, marijuana, analysis, GC, quantitative, qualitative and quality control. Results During the past decade, several GC‐based methods for the analysis of cannabinoids have been reported. While simple one‐dimensional (1D) GC–MS and GC‐FID (flame ionisation detector) methods were found to be quite common in cannabinoids analysis, two‐dimensional (2D) GC–MS as well as GC–MS/MS also were popular because of their ability to provide more useful data for identification and quantification of cannabinoids in various matrices. Some degree of automation in sample preparation, and applications of mathematical and computational models for optimisation of different protocols were observed, and pre‐analyses included various derivatisation techniques, and environmentally friendly extraction protocols. Conclusions GC‐based analysis of naturally occurring cannabinoids, especially using GC–MS, has dominated the cannabinoids analysis in the last decade; new derivatisation methods, new ionisation methods, and mathematical models for method optimisation have been introduced.

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Quantification of cannabinoids in human hair using a modified derivatization procedure and liquid chromatography–tandem mass spectrometry

Alzahrani

Al-Asmari

Al-Zahrani

et al. 2021

Drug Testing and Analysis

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The aim of this work was to develop and validate a liquid chromatography-tandem mass spectrometry method for detecting of the main cannabinoids, cannabinol (CBN) and tetrahydrocannabinol (THC) and the primary metabolite 11-nor-9-carboxy-Δ 9tetrahydrocannabinol (THC-COOH) in hair samples. Extraction of the cannabinoids was carried out by a polymeric strong anion mixed-mode solid-phase extraction cartridge and then employing methanolic HCl followed by 2-fluoro-1-methylpyridinium-p-toluenesulfonate (FMP-TS) as a derivatization procedure of carboxyl and phenolic groups, respectively, offering enhanced sensitivity for the detection of THC-COOH in hair matrices. Formation of a methyl ester increased its lipophilicity and removed the negative charge on the carboxyl group. Calibration curves were prepared over the range of 0.02-4 pg/mg of hair for THC and CBN and 0.2-12 pg/mg of hair for THC-COOH. The extraction recovery was between 81% and 105% for all compounds. The limit of detection (LOD) and limit of quantification (LOQ) were 2 and 20 pg/mg, respectively, for both CBN and THC and 0.1 and 0.2 pg/mg, respectively, for THC-COOH, which met the society of hair testing recommendation. Intra-assay and interassay precision were always lower than 4% and 11%, respectively for these cannabinoids, whereas intra-assay and interassay bias were between +14% and −18% and +15% and −12%, respectively. Twenty-seven hair specimens from cannabis users were investigated. The concentrations of CBN, THC and THC-COOH gave ranges of (0.022-2.562 ng/mg), (0.049-0.431 ng/mg) and (0.222-4.867 pg/mg), respectively. This new method of derivatization improves the LOD to ensure detection of the metabolite.

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Simultaneous quantification of THC‐COOH, OH‐THC, and further cannabinoids in human hair by gas chromatography–tandem mass spectrometry with electron ionization applying automated sample preparation

Cited by 20 publications

References 56 publications

Cannabis and Its Secondary Metabolites: Their Use as Therapeutic Drugs, Toxicological Aspects, and Analytical Determination

Cannabis and Its Secondary Metabolites: Their Use as Therapeutic Drugs, Toxicological Aspects, and Analytical Determination

Gas chromatographic analysis of naturally occurring cannabinoids: A review of literature published during the past decade

Quantification of cannabinoids in human hair using a modified derivatization procedure and liquid chromatography–tandem mass spectrometry

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