Detection and quantification of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid in hair by GC/MS/MS in Negative Chemical Ionization mode (NCI) with a simple and rapid liquid/liquid extraction

Minoli, Mauro; Angeli, I; Ravelli, Alessandro; Gigli, F.; Lodi, F

doi:10.1016/j.forsciint.2011.10.014

Cited by 41 publications

(29 citation statements)

References 9 publications

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“…The general method used to quantify THC‐COOH in hair is as follows: a hair sample is digested with an alkaline solution. Next, THC‐COOH is extracted with an organic solvent under acidic conditions, and perfluoroalkyl‐derivatized THC‐COOH is quantified by gas chromatography/tandem mass spectrometry (GC/MS/MS) with negative ion chemical ionization (NICI) . However, GC/MS/MS with NICI requires time‐consuming and labor‐intensive replacement of the ion source for CI followed by stabilization of the instrument.…”

mentioning

confidence: 99%

Micro-pulverized extraction pretreatment for highly sensitive analysis of 11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol in hair by liquid chromatography/tandem mass spectrometry

Kuwayama

Miyaguchi

Yamamuro

et al. 2015

Rapid Commun. Mass Spectrom.

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confidence: 99%

Micro-pulverized extraction pretreatment for highly sensitive analysis of 11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol in hair by liquid chromatography/tandem mass spectrometry

Kuwayama

Miyaguchi

Yamamuro

et al. 2015

Rapid Commun. Mass Spectrom.

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“…The publication is accompanied by substantial data from 578 hair samples, among them 56.9% positive on OH‐THC. Recently, Angeli et al also combined an LLE method in a similar manner to that of Franz et al The aqueous phase extract was used for determination of THC‐COOH by GC–NCI–MS/MS, after derivatization. The organic supernatant was utilized for detection of OH‐THC (in addition to THC, CBD, CBN), after silylation by GC–EI–MS/MS.…”

Section: Resultsmentioning

confidence: 99%

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

Lerch

Andresen‐Streichert

et al. 2018

Drug Testing and Analysis

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The detection of Δ -tetrahydrocannabinol (THC), cannabidiol (CBD) and cannabinol (CBN) in hair, for the purpose of identifying cannabis consumption, is conducted in many forensic laboratories. Since external contamination of hair with these cannabis components cannot be excluded, even after hair decontamination, only the detection of THC metabolites such as 11-nor-9-carboxy-Δ -tetrahydrocannabinol (THC-COOH) or 11-hydroxy-Δ -tetrahydrocannabinol (OH-THC), is considered to prove cannabis consumption. At present, testing for THC metabolites is not standard practice due to its analytical complexity. For these reasons, we developed a novel method for the detection of THC-COOH and OH-THC as well as THC, CBD, and CBN in one single analytical run using gas chromatography-tandem mass spectrometry (GC-MS/MS) with electron ionization. After manual hair washing and grinding, sample preparation was fully automated, by means of a robotic autosampler. The hair extraction took place by digestion with sodium hydroxide. A solid-phase extraction (SPE) was chosen for sample clean-up, using a mixed-mode anion exchange sorbent. Derivatization of all analytes was by silylation. The method has been fully validated according to guidelines of the Society of Toxicological and Forensic Chemistry (GTFCh), with a limit of detection (LOD) of 0.2 pg/mg for THC-COOH and OH-THC and 2 pg/mg for THC, CBD and CBN, respectively, thus fulfilling the Society of Hair Testing (SoHT) recommendations. The validated method has been successfully applied to our routine forensic case work and a summary of data from authentic hair samples is given, as well as data from proficiency tests.

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“…Hair matrix is often used in forensic laboratories because it offers wider time window, non-invasive sampling and good stability of the analytes over time. Moreover, On the basis of literature data, hair sample is quite more challenging than urine in terms of complexity, especially in synthetic cannabinoids detection [12,[40][41][42].…”

Section: Experimental Testingmentioning

confidence: 99%

Selective solid phase extraction of JWH synthetic cannabinoids by using computationally designed peptides

Mascini

Montesano

Pérez

et al. 2017

Talanta

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A B S T R A C TThe objective of the present work is to demonstrate a rational way to prepare selective sorbents able to extract simultaneously several structural analogs. For this purpose the binding specificity of two hexapeptides computationally designed (VYWLVW and YYIGGF) versus four synthetic cannabinoids Naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH 018), naphthalen-1-yl-(1-butylindol-3-yl)methanone (JWH 073), (R)-(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone (AM 1220) and (R)-(+)-[2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-napthalenylmethanone (WIN 55) was computationally studied and then experimentally tested by solid-phase extraction (SPE) clean-up and ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) analysis. The two peptides were chosen using a semi combinatorial virtual technique by generating 4 cycles of peptide libraries (around 2.3×10 4 elements). To select the two peptides, the simulated binding scores between synthetic cannabinoids and peptides was used by maximizing the recognition properties of amino acid motif between the two JWH and the other synthetic cannabinoids. In particular, the peptide YYIGGF, having also affinity for AM 120, was selected as control because it was the only one without tryptophan residues within the best peptides obtained from simulation. Experimentally, the two hexapeptides were tested as SPE sorbent using nanomolar solutions of the four drugs. After optimization of best retentions the binding constants were calculated by loading synthetic cannabinoids solutions at different concentrations. The results indicated a strong interaction between hexapeptide VYWLVW and JWH 018 (15.58 ± 2.03×10 6 M -1 ), 3-fold and 40-fold larger compared to the analog JWH 073 and both AM 1220 and the WIN 55. Similar trend was observed for the hexapeptide YYIGGF but the binding constants were at least three times lower highlighting the key role of the tryptophan. To demonstrate the hexapeptides specific interaction with only synthetic cannabinoids, a cross-reactivity study was carried out using other drugs (cocaine, morphine, phencyclidine and methamphetamine) in the same SPE condition. Finally the practical utility of these peptide modified sorbent materials was further demonstrated by detecting the synthetic cannabinoids in real samples using hair matrix.

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Detection and quantification of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid in hair by GC/MS/MS in Negative Chemical Ionization mode (NCI) with a simple and rapid liquid/liquid extraction

Cited by 41 publications

References 9 publications

Micro-pulverized extraction pretreatment for highly sensitive analysis of 11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol in hair by liquid chromatography/tandem mass spectrometry

Micro-pulverized extraction pretreatment for highly sensitive analysis of 11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol in hair by liquid chromatography/tandem mass spectrometry

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

Selective solid phase extraction of JWH synthetic cannabinoids by using computationally designed peptides

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Detection and quantification of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid in hair by GC/MS/MS in Negative Chemical Ionization mode (NCI) with a simple and rapid liquid/liquid extraction

Cited by 41 publications

References 9 publications

Micro-pulverized extraction pretreatment for highly sensitive analysis of 11-nor-9-carboxy-Δ9-tetrahydrocannabinol in hair by liquid chromatography/tandem mass spectrometry

Micro-pulverized extraction pretreatment for highly sensitive analysis of 11-nor-9-carboxy-Δ9-tetrahydrocannabinol in hair by liquid chromatography/tandem mass spectrometry

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

Selective solid phase extraction of JWH synthetic cannabinoids by using computationally designed peptides

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Micro-pulverized extraction pretreatment for highly sensitive analysis of 11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol in hair by liquid chromatography/tandem mass spectrometry

Micro-pulverized extraction pretreatment for highly sensitive analysis of 11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol in hair by liquid chromatography/tandem mass spectrometry