Volume 13 Issue 10
Oct.  2023
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Katarzyna Woźniczka, Paweł Konieczyński, Alina Plenis, Tomasz Bączek, Anna Roszkowska. SPME as a green sample-preparation technique for the monitoring of phytocannabinoids and endocannabinoids in complex matrices[J]. Journal of Pharmaceutical Analysis, 2023, 13(10): 1117-1134. doi: 10.1016/j.jpha.2023.06.014
Citation: Katarzyna Woźniczka, Paweł Konieczyński, Alina Plenis, Tomasz Bączek, Anna Roszkowska. SPME as a green sample-preparation technique for the monitoring of phytocannabinoids and endocannabinoids in complex matrices[J]. Journal of Pharmaceutical Analysis, 2023, 13(10): 1117-1134. doi: 10.1016/j.jpha.2023.06.014

SPME as a green sample-preparation technique for the monitoring of phytocannabinoids and endocannabinoids in complex matrices

doi: 10.1016/j.jpha.2023.06.014
  • Received Date: Apr. 23, 2023
  • Accepted Date: Jun. 27, 2023
  • Rev Recd Date: Jun. 10, 2023
  • Publish Date: Oct. 30, 2023
  • The endocannabinoid system (ECS), particularly its signaling pathways and ligands, has garnered considerable interest in recent years. Along with clinical work investigating the ECS’ functions, including its role in the development of neurological and inflammatory conditions, much research has focused on developing analytical protocols enabling the precise monitoring of the levels and metabolism of the most potent ECS ligands: exogenous phytocannabinoids (PCs) and endogenous cannabinoids (endocannabinoids, ECs). Solid-phase microextraction (SPME) is an advanced, non-exhaustive sample-preparation technique that facilitates the precise and efficient isolation of trace amounts of analytes, thus making it appealing for the analysis of PCs and ECs in complex matrices of plant and animal/human origin. In this paper, we review recent forensic medicine and toxicological studies wherein SPME has been applied to monitor levels of PCs and ECs in complex matrices, determine their effects on organism physiology, and assess their role in the development of several diseases.
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  • E.F. Coccaro, M.N. Hill, L. Robinson, et al., Circulating endocannabinoids and affect regulation in human subjects, Psychoneuroendocrinology 92 (2018) 66-71.
    M.R. Jacobson, J.J. Watts, I. Boileau, et al., A systematic review of phytocannabinoid exposure on the endocannabinoid system: implications for psychosis, Eur. Neuropsychopharmacol. 29 (2019) 330-348.
    W.A. Devane, L. Hanus, A. Breuer, et al., Isolation and structure of a brain constituent that binds to the cannabinoid receptor, Science 258 (1992) 1946-1949.
    R. Mechoulam, S. Ben-Shabat, L. Hanus, et al., Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors, Biochem. Pharmacol. 50 (1995) 83-90.
    M. Maccarrone, Phytocannabinoids and endocannabinoids: different in nature, Rend. Lincei Sci. Fisiche E Nat. 31 (2020) 931-938.
    M.M. Almeida, C.P. Dias-Rocha, C. Calvino, et al., Lipid endocannabinoids in energy metabolism, stress and developmental programming, Mol. Cell. Endocrinol. 542 (2022), 111522.
    M. Maccarrone, S. Rossi, M. Bari, et al., Anandamide inhibits metabolism and physiological actions of 2-arachidonoylglycerol in the striatum, Nat. Neurosci. 11 (2008) 152-159.
    C. Silvestri, V. Di Marzo, The endocannabinoid system in energy homeostasis and the etiopathology of metabolic disorders, Cell Metab. 17 (2013) 475-490.
    C. Marchioni, I.D. de Souza, V.R.A. Junior, et al., Recent advances in LC-MS/MS methods to determine endocannabinoids in biological samples: application in neurodegenerative diseases, Anal. Chim. Acta 1044 (2018) 12-28.
    I. Smaga, J. Jastrzebska, M. Zaniewska, et al., Changes in the brain endocannabinoid system in rat models of depression, Neurotox. Res. 31 (2017) 421-435.
    H. Lu, K. Mackie, An introduction to the endogenous cannabinoid system, Biol. Psychiatry 79 (2016) 516-525.
    S.M. Nugent, B.J. Morasco, M.E. O'Neil, et al., The effects of Cannabis among adults with chronic pain and an overview of general harms, Ann. Intern. Med. 167 (2017), 319.
    L. Landa, J. Jurica, J. Sliva, et al., Medical cannabis in the treatment of cancer pain and spastic conditions and options of drug delivery in clinical practice, Biomed. Pap. 162 (2018) 18-25.
    R. de Carvalho Reis, K.J. Almeida, L. da Silva Lopes, et al., Efficacy and adverse event profile of cannabidiol and medicinal cannabis for treatment-resistant epilepsy: systematic review and meta-analysis, Epilepsy Behav. 102 (2020), 106635.
    B. Vinette, J. Cote, A. El-Akhras, et al., Routes of administration, reasons for use, and approved indications of medical cannabis in oncology: a scoping review, BMC Cancer 22 (2022), 319.
    K. Lim, Y.M. See, J. Lee, A systematic review of the effectiveness of medical Cannabis for psychiatric, movement and neurodegenerative disorders, Clin. Psychopharmacol. Neurosci. 15 (2017) 301-312.
    N. Montero-Oleas, I. Arevalo-Rodriguez, S. Nunez-Gonzalez, et al., Therapeutic use of cannabis and cannabinoids: an evidence mapping and appraisal of systematic reviews, BMC Complementary Med. Ther. 20 (2020), 12.
    P. Berman, K. Futoran, G.M. Lewitus, et al., A new ESI-LC/MS approach for comprehensive metabolic profiling of phytocannabinoids in Cannabis, Sci. Rep. 8 (2018), 14280.
    P.G. Vasquez-Ocmin, G. Marti, M. Bonhomme, et al., Cannabinoids vs. whole metabolome: relevance of cannabinomics in analyzing Cannabis varieties, Anal. Chim. Acta 1184 (2021), 339020.
    P. Berman, L. Sulimani, A. Gelfand, et al., Cannabinoidomics - an analytical approach to understand the effect of medical Cannabis treatment on the endocannabinoid metabolome, Talanta 219 (2020), 121336.
    A. Ligresti, L. De Petrocellis, V. Di Marzo, From phytocannabinoids to cannabinoid receptors and endocannabinoids: pleiotropic physiological and pathological roles through complex pharmacology, Physiol. Rev. 96 (2016) 1593-1659.
    P. Morales, D.P. Hurst, P.H. Reggio, Molecular targets of the phytocannabinoids: A complex picture. Phytocannabinoids. Cham: Springer, 2017: 103-131.
    C. Citti, F. Russo, S. Sgro, et al., Pitfalls in the analysis of phytocannabinoids in cannabis inflorescence, Anal. Bioanal. Chem. 412 (2020) 4009-4022.
    C. Citti, D. Braghiroli, M.A. Vandelli, et al., Pharmaceutical and biomedical analysis of cannabinoids: a critical review, J. Pharm. Biomed. Anal. 147 (2018) 565-579.
    E. Karschner, M. Swortwood, M. Huestis, Identifying and quantifying cannabinoids in biological matrices in the medical and legal Cannabis era, Clin. Chem. 66 (2020) 888-914.
    D. Kratz, A. Sens, S.M.G. Schafer, et al., Pre-analytical challenges for the quantification of endocannabinoids in human serum, J. Chromatogr. B 1190 (2022), 123102.
    V.R. Acquaro Jr, G.A. Gomez-Rios, M. Tascon, et al., Analysis of endocannabinoids in plasma samples by biocompatible solid-phase microextraction devices coupled to mass spectrometry, Anal. Chim. Acta 1091 (2019) 135-145.
    L. Chu, N. Li, J. Deng, et al., LC-APCI+-MS/MS method for the analysis of ten hormones and two endocannabinoids in plasma and hair from the mice with different gut microbiota, J. Pharm. Biomed. Anal. 185 (2020), 113223.
    Y. Gong, X. Li, L. Kang, et al., Simultaneous determination of endocannabinoids in murine plasma and brain substructures by surrogate-based LC-MS/MS: application in tumor-bearing mice, J. Pharm. Biomed. Anal. 111 (2015) 57-63.
    L.J. Ney, K.L. Felmingham, R. Bruno, et al., Simultaneous quantification of endocannabinoids, oleoylethanolamide and steroid hormones in human plasma and saliva, J. Chromatogr. B 1152 (2020), 122252.
    M. Yu, A. Roszkowska, J. Pawliszyn, In vivo solid-phase microextraction and applications in environmental sciences, ACS Environ. Au 2 (2022) 30-41.
    A. Roszkowska, N. Miekus, T. Baczek, Application of solid-phase microextraction in current biomedical research, J. Sep. Sci. 42 (2019) 285-302.
    L. Anzillotti, E. Castrignano, S.S. Rossi, et al., Cannabinoids determination in oral fluid by SPME-GC/MS and UHPLC-MS/MS and its application on suspected drivers, Sci. Justice 54 (2014) 421-426.
    L. Anzillotti, F. Marezza, L. Calo, et al., Determination of synthetic and natural cannabinoids in oral fluid by solid-phase microextraction coupled to gas chromatography/mass spectrometry: a pilot study, Talanta 201 (2019) 335-341.
    S. Gentili, C. Mortali, L. Mastrobattista, et al., Determination of different recreational drugs in sweat by headspace solid-phase microextraction gas chromatography mass spectrometry (HS-SPME GC/MS): application to drugged drivers, J. Pharm. Biomed. Anal. 129 (2016) 282-287.
    E. Boyaci, E. Gionfriddo, A. Roszkowska, et al., Advances in solid phase microextraction (SPME) for metabolomics. Advanced Mass Spectrometry-based Analytical Separation Techniques for Probing the Polar Metabolome. The Royal Society of Chemistry, (2021) 91-124.
    W. Filipiak, B. Bojko, SPME in clinical, pharmaceutical, and biotechnological research - how far are we from daily practice? Trac Trends Anal. Chem. 115 (2019) 203-213.
    J. Pawliszyn, Handbook of solid phase microextraction, first ed., Chemical Industry Press, Beijing, 2009.
    O.J. Portillo-Castillo, R. Castro-Rios, A. Chavez-Montes, et al., Developments of solid-phase microextraction fiber coatings for environmental pharmaceutical and personal care products analysis, Rev. Anal. Chem. 37 (2018), 20170018.
    C. Marchioni, T.M. Vieira, A.E. Miller Crotti, et al., In-tube solid-phase microextraction with a dummy molecularly imprinted monolithic capillary coupled to ultra-performance liquid chromatography-tandem mass spectrometry to determine cannabinoids in plasma samples, Anal. Chim. Acta 1099 (2020) 145-154.
    D. Morisue Sartore, J.L. Costa, F.M. Lancas, et al., Packed in-tube SPME-LC-MS/MS for fast and straightforward analysis of cannabinoids and metabolites in human urine, Electrophoresis 43 (2022) 1555-1566.
    V. Bessonneau, E. Boyaci, M. Maciazek-Jurczyk, et al., In vivo solid phase microextraction sampling of human saliva for non-invasive and on-site monitoring, Anal. Chim. Acta 856 (2015) 35-45.
    E. Boyaci, K. Gorynski, A. Rodriguez-Lafuente, et al., Introduction of solid-phase microextraction as a high-throughput sample preparation tool in laboratory analysis of prohibited substances, Anal. Chim. Acta 809 (2014) 69-81.
    N. Reyes-Garces, B. Bojko, J. Pawliszyn, High throughput quantification of prohibited substances in plasma using thin film solid phase microextraction, J. Chromatogr. A 1374 (2014) 40-49.
    B. Bojko, N. Looby, M. Olkowicz, et al., Solid phase microextraction chemical biopsy tool for monitoring of doxorubicin residue during in vivo lung chemo-perfusion, J. Pharm. Anal. 11 (2021) 37-47.
    M. Yu, S. Lendor, A. Roszkowska, et al., Metabolic profile of fish muscle tissue changes with sampling method, storage strategy and time, Anal. Chim. Acta 1136 (2020) 42-50.
    F.M. Musteata, M. Sandoval, J.C. Ruiz-Macedo, et al., Evaluation of in vivo solid phase microextraction for minimally invasive analysis of nonvolatile phytochemicals in Amazonian plants, Anal. Chim. Acta 933 (2016) 124-133.
    J. Pawliszyn, Evolution of Solid-Phase Microextaction Technology, first ed., Royal Society of Chemistry, 2023.
    F. Capetti, P. Rubiolo, G. Mastellone, et al., A sustainable approach for the reliable and simultaneous determination of terpenoids and cannabinoids in hemp inflorescences by vacuum assisted headspace solid-phase microextraction, Adv. Sample Prep. 2 (2022), 100014.
    N. Jornet-Martinez, A. Ortega-Sierra, J. Verdu-Andres, et al., Analysis of contact traces of Cannabis by In-tube solid-phase microextraction coupled to nanoliquid chromatography, Molecules 23 (2018), 2359.
    A. McDaniel, L. Perry, Q. Liu, et al., Toward the identification of marijuana varieties by headspace chemical forensics, Forensic Chem. 11 (2018) 23-31.
    M. Aslam, C. Feleder, R.J. Newsom, et al., In vivo monitoring of rat brain endocannabinoids using solid-phase microextraction, Bioanalysis 11 (2019) 1523-1534.
    I.D. Souza, L.W. Hantao, M.E.C. Queiroz, Polymeric ionic liquid open tubular capillary column for on-line in-tube SPME coupled with UHPLC-MS/MS to determine endocannabinoids in plasma samples, Anal. Chim. Acta 1045 (2019) 108-116.
    J.C. Cruz, M.A. Rosa, L. Mores, et al., Magnetic restricted-access carbon nanotubes for SPME to determine cannabinoids in plasma samples by UHPLC-MS/MS, Anal. Chim. Acta 1226 (2022), 340160.
    L.O. Hanus, Pharmacological and therapeutic secrets of plant and brain (endo)cannabinoids, Med. Res. Rev. 29 (2009) 213-271.
    D.A. Reason, M.N.C. Grainger, J.R. Lane, Optimization of the decarboxylation of Cannabis for commercial applications, Ind. Eng. Chem. Res. 61 (2022) 7823-7832.
    C.A.S. Tanney, R. Backer, A. Geitmann, et al., Cannabis glandular trichomes: a cellular metabolite factory, Front. Plant Sci. 12 (2021), 721986.
    L.L. Anderson, I.K. Low, S.D. Banister, et al., Pharmacokinetics of phytocannabinoid acids and anticonvulsant effect of cannabidiolic acid in a mouse model of dravet syndrome, J. Nat. Prod. 82 (2019) 3047-3055.
    V. Desaulniers Brousseau, B.S. Wu, S. MacPherson, et al., Cannabinoids and terpenes: How production of photo-protectants can be manipulated to enhance Cannabis sativa L. phytochemistry, Front. Plant Sci. 12 (2021), 620021.
    E.B. Russo, The case for the entourage effect and conventional breeding of clinical Cannabis: No “strain,” No gain, Front. Plant Sci. 9 (2019), 1969.
    A. Sulcova, Pharmacodynamics of cannabinoids, Arch. Pharm. Pharm. Sci. 3 (2019) 11-18.
    I. Ujvary, L.Hanus, Human metabolites of cannabidiol: a review on their formation, biological activity, and relevance in therapy, Cannabis Cannabinoid Res. 1 (2016) 90-101.
    R. Deidda, A. Dispas, C. De Bleye, et al., Critical review on recent trends in cannabinoid determination on cannabis herbal samples: from chromatographic to vibrational spectroscopic techniques, Anal. Chim. Acta 1209 (2022), 339184.
    G. Micalizzi, F. Vento, F. Alibrando, et al., Cannabis Sativa L.: a comprehensive review on the analytical methodologies for cannabinoids and terpenes characterization, J. Chromatogr. A 1637 (2021), 461864.
    W.H. Abd-Elsalam, M.A. Alsherbiny, J.Y. Kung, et al., LC-MS/MS quantitation of phytocannabinoids and their metabolites in biological matrices, Talanta 204 (2019) 846-867.
    F. Institute, for D. and M. (BfArM), Cannabis flos Monograph, Deutsches Arzneibuch, Bonn, 2018.
    F. Institute, for D. and M. (BfArM), Cannabis extractum normatum Monograph, Deutsches Arzneibuch, Bonn, 2020.
    V. Brighenti, F. Pellati, M. Steinbach, et al., Development of a new extraction technique and HPLC method for the analysis of non-psychoactive cannabinoids in fibre-type Cannabis sativa L. (hemp), J. Pharm. Biomed. Anal. 143 (2017) 228-236.
    A.J. Ocque, C.E. Hagler, R. DiFrancesco, et al., Development and validation of an assay to measure cannabidiol and Δ9-tetrahydrocannabinol in human EDTA plasma by UHPLC-MS/MS, J. Chromatogr. B 1112 (2019) 56-60.
    X. Dong, L. Li, Y. Ye, et al., Simultaneous determination of major phytocannabinoids, their main metabolites, and common synthetic cannabinoids in urine samples by LC-MS/MS, J. Chromatogr. B 1033-1034 (2016) 55-64.
    S. Pichini, S. Malaca, M. Gottardi, et al., UHPLC-MS/MS analysis of cannabidiol metabolites in serum and urine samples. application to an individual treated with medical cannabis, Talanta 223 (2021), 121772.
    R.C. Kevin, R. Vogel, P. Doohan, et al., A validated method for the simultaneous quantification of cannabidiol, Δ9-tetrahydrocannabinol, and their metabolites in human plasma and application to plasma samples from an oral cannabidiol open-label trial, Drug Test. Anal. 13 (2021) 614-627.
    A. Scheunemann, K. Elsner, T. Germerott, et al., Simultaneous quantification of 18 different phytocannabinoids in serum using a highly sensitive liquid chromatography-tandem mass spectrometry (LC-MS/MS) method, J. Chromatogr. B 1173 (2021), 122685.
    J.C. Cruz, L.F.C. Miranda, M.E.C. Queiroz, Pipette tip micro-solid phase extraction (octyl-functionalized hybrid silica monolith) and ultra-high-performance liquid chromatography-tandem mass spectrometry to determine cannabidiol and tetrahydrocannabinol in plasma samples, J. Sep. Sci. 44 (2021) 1621-1632.
    J.D. Reber, E.L. Karschner, J.Z. Seither, et al., Screening and confirmation methods for the qualitative identification of nine phytocannabinoids in urine by LC-MS/MS, Clin. Biochem. 98 (2021) 54-62.
    L. Mores, G.R. Borges, R.O. Saga Kitamura, et al., Assessment of a natural extraction phase in disposable pipette extraction coupled with the sub-minute determination of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid in human urine by fast-GC-FID, Sustain. Chem. Pharm. 20 (2021), 100390.
    R. Jain, R. Singh, Microextraction techniques for analysis of cannabinoids, Trac Trends Anal. Chem. 80 (2016) 156-166.
    M. Sergi, C. Montesano, S. Odoardi, et al., Micro extraction by packed sorbent coupled to liquid chromatography tandem mass spectrometry for the rapid and sensitive determination of cannabinoids in oral fluids, J. Chromatogr. A 1301 (2013) 139-146.
    L.M. Rosendo, T. Rosado, P. Oliveira, et al., The determination of cannabinoids in urine samples using microextraction by packed sorbent and gas chromatography-mass spectrometry, Molecules 27 (2022), 5503.
    L. Calvi, D. Pentimalli, S. Panseri, et al., Comprehensive quality evaluation of medical Cannabis sativa L. inflorescence and macerated oils based on HS-SPME coupled to GC-MS and LC-HRMS (q-exactive orbitrap®) approach, J. Pharm. Biomed. Anal. 150 (2018) 208-219.
    M. Ternelli, V. Brighenti, L. Anceschi, et al., Innovative methods for the preparation of medical Cannabis oils with a high content of both cannabinoids and terpenes, J. Pharm. Biomed. Anal. 186 (2020), 113296.
    M. Huestis, Human cannabinoid pharmacokinetics, Chem. Biodivers. 4 (2007) 1770-1804.
    J.C. Cruz, M.A. Rosa, L. Mores, et al., Magnetic restricted-access carbon nanotubes for SPME to determine cannabinoids in plasma samples by UHPLC-MS/MS, Anal. Chim. Acta 1226 (2022), 340160.
    N. Reyes-Garces, E. Gionfriddo, G.A. Gomez-Rios, et al., Advances in solid phase microextraction and perspective on future directions, Anal. Chem. 90 (2018) 302-360.
    O.H. Drummer, Drug testing in oral fluid, Clin. Biochem. Rev. 27 (2006) 147-159.
    T. Franklin, L. Perry, W.C. Shih, et al., Detection of phytocannabinoids from buccal swabs by headspace solid phase microextraction-gas chromatography/mass spectrometry, Anal. Methods 10 (2018) 942-946.
    B. Moosmann, N. Roth, M. Hastedt, et al., Cannabinoid findings in children hair - what do they really tell us? an assessment in the light of three different analytical methods with focus on interpretation of Δ9-tetrahydrocannabinolic acid A concentrations, Drug Test. Anal. 7 (2015) 349-357.
    E.M. Wymore, C. Palmer, G.S. Wang, et al., Persistence of Δ-9-tetrahydrocannabinol in human breast milk, JAMA Pediatr. 175 (2021), 632.
    G. de Oliveira Silveira, S. Loddi, C.D.R. de Oliveira, et al., Headspace solid-phase microextraction and gas chromatography-mass spectrometry for determination of cannabinoids in human breast milk, Forensic Toxicol. 35 (2017) 125-132.
    R. Cooray, V. Gupta, C. Suphioglu, Current aspects of the endocannabinoid system and targeted THC and CBD phytocannabinoids as potential therapeutics for Parkinson's and Alzheimer's diseases: a review, Mol. Neurobiol. 57 (2020) 4878-4890.
    K.R. Kozak, B.C. Crews, J.D. Morrow, et al., Metabolism of the endocannabinoids, 2-arachidonylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides, J. Biol. Chem. 277 (2002) 44877-44885.
    P. Urquhart, A. Nicolaou, D.F. Woodward, Endocannabinoids and their oxygenation by cyclo-oxygenases, lipoxygenases and other oxygenases, Biochim. Biophys. Acta BBA Mol. Cell Biol. Lipids 1851 (2015) 366-376.
    D. Luque-Cordoba, M. Calderon-Santiago, M.D. Luque de Castro, et al., Study of sample preparation for determination of endocannabinoids and analogous compounds in human serum by LC-MS/MS in MRM mode, Talanta 185 (2018) 602-610.
    T.A. de Roon-Cassini, C.L. Bergner, S.A. Chesney, et al., Circulating endocannabinoids and genetic polymorphisms as predictors of posttraumatic stress disorder symptom severity: Heterogeneity in a community-based cohort, Transl. Psychiatry 12 (2022), 48.
    V. Kantae, S. Ogino, M. Noga, et al., Quantitative profiling of endocannabinoids and related N-acylethanolamines in human CSF using nano LC-MS/MS, J. Lipid Res. 58 (2017) 615-624.
    M. Bobrich, R. Schwarz, R. Ramer, et al., A simple LC-MS/MS method for the simultaneous quantification of endocannabinoids in biological samples, J. Chromatogr. B 1161 (2020), 122371.
    C.D. Voegel, M.R. Baumgartner, T. Kraemer, et al., Simultaneous quantification of steroid hormones and endocannabinoids (ECs) in human hair using an automated supported liquid extraction (SLE) and LC-MS/MS - insights into EC baseline values and correlation to steroid concentrations, Talanta 222 (2021), 121499.
    A. Behnke, A.M. Gumpp, A. Krumbholz, et al., Hair-based biomarkers in women with major depressive disorder: glucocorticoids, endocannabinoids, N-acylethanolamines, and testosterone, Compr. Psychoneuroendocrinol. 7 (2021), 100068.
    W. Gao, A. Walther, M. Wekenborg, et al., Determination of endocannabinoids and N-acylethanolamines in human hair with LC-MS/MS and their relation to symptoms of depression, burnout, and anxiety, Talanta 217 (2020), 121006.
    S. Pati, S. Krishna, J.H. Lee, et al., Effects of high-fat diet and age on the blood lipidome and circulating endocannabinoids of female C57BL/6 mice, Biochim. Biophys. Acta BBA Mol. Cell Biol. Lipds. 1863 (2018) 26-39.
    D. Kratz, D. Thomas, R. Gurke, Endocannabinoids as potential biomarkers: It‘s all about pre-analytics, J. Mass Spectrom. Adv. Clin. Lab 22 (2021) 56-63.
    A.M. Dickens, F. Borgan, H. Laurikainen, et al., Links between central CB1-receptor availability and peripheral endocannabinoids in patients with first episode psychosis, NPJ Schizophr. 6 (2020), 21.
    I.G.C. Oliveira, I.D. de Souza, G.C. do Nascimento, et al., In-tube solid-phase microextraction directly coupled to tandem mass spectrometry for anandamide and 2-arachidonoylglycerol determination in rat brain samples from an animal model of Parkinson's disease, J. Chromatogr. A 1636 (2021), 461766.
    A. Roszkowska, I. Klejbor, J. Bogusiewicz, et al., Monitoring of age- and gender-related alterations of endocannabinoid levels in selected brain regions with the use of SPME probes, Metabolomics 19 (2023), 40.
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