Analytical approaches for the determination of phytocannabinoids and endocannabinoids in human matrices

Drug Testing and Analysis

Volumn 6, Issue 1-2, 2014, Pages 7-16

  Battista, Natalia ^a,b   Sergi, Manuel ^a   Montesano, Camilla ^c   Napoletano, Sabino ^c,d   Compagnone, Dario ^a   Maccarrone, Mauro ^b,e  

^a UNIVERSITY OF TERAMO   (Italy)

^b IRCCS FONDAZIONE SANTA LUCIA   (Italy)

^c SAPIENZA UNIVERSITY OF ROME   (Italy)

^d Ministry of Interior   (Italy)

^e UNIVERSITY CAMPUS BIO MEDICO   (Italy)

Author keywords

Anandamide; Liquid chromatography; Mass spectrometry

Indexed keywords

LIQUID CHROMATOGRAPHY;

ANALYTICAL APPROACH; ANALYTICAL METHOD; ANANDAMIDE; ENDOCANNABINOID; ENDOGENOUS SUBSTANCES; HUMAN MATRIX; INNOVATIVE TECHNIQUES; METHODOLOGICAL APPROACH; PLANT COMPOUNDS; SCIENTIFIC COMMUNITY;

MASS SPECTROMETRY;

CANNABINOID; ENDOCANNABINOID; PHYTOCANNABINOID; UNCLASSIFIED DRUG;

ANALYTIC METHOD; BODY FLUIDS AND SECRETIONS; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG DETERMINATION; DRUG FECES LEVEL; DRUG HAIR LEVEL; DRUG MILK LEVEL; DRUG URINE LEVEL; FLUID INTAKE; HUMAN; PRIORITY JOURNAL; REVIEW;

ANANDAMIDE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; Δ9-TETRAHYDROCANNABINOL;

ANIMALS; ARACHIDONIC ACIDS; BRAIN CHEMISTRY; CANNABINOID RECEPTOR AGONISTS; CHROMATOGRAPHY, LIQUID; DRONABINOL; ENDOCANNABINOIDS; HAIR; HUMANS; MASS SPECTROMETRY; MECONIUM; MILK; POLYUNSATURATED ALKAMIDES;

EID: 84892453118     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1574     Document Type: Review

References (165)

1. A.A. Izzo, F. Borrelli, R. Capasso, V. Di Marzo, R. Mechoulam. Non-psychotropic plant cannabinoids: New therapeutic opportunities from an ancient herb. Trends Pharmacol. Sci. 2009, 30, 515.
2. M.A. Elsohly, D. Slade. Chemical constituents of marijuana: The complex mixture of natural cannabinoids. Life Sci. 2005, 78, 539.
3. L.A. Matsuda, S.J. Lolait, M.J. Brownstein, A.C. Young, T.I. Bonner. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 1990, 346, 561.
4. S. Munro, K.L. Thomas, M. Abu-Shaar. Molecular characterization of a peripheral receptor for cannabinoids. Nature 1993, 365, 61.
5. W.A. Devane, L. Hanus, A. Breuer, R.G. Pertwee, L.A. Stevenson, G. Griffin, D. Gibson, A. Mandelbaum, A. Etinger, R. Mechoulam. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 1992, 258, 1946.
6. P.H. Reggio. Endocannabinoid structure-activity relationships for interaction at the cannabinoid receptors. Prostaglandins Leukot. Essent. Fatty Acids 2002, 66, 143.
7. V. Di Marzo, L. De Petrocellis. Why do cannabinoid receptors have more than one endogenous ligand? Philos. T. R. Soc. B. 2012, 367, 3216.
8. C.J.A. Morgan, E. Page, C. Schaefer, K. Chatten, A. Manocha, S. Gulati, H.V. Curran, B. Brandner, F.M. Leweke. Cerebrospinal fluid anandamide levels, cannabis use and psychotic-like symptoms. Brit. J. Psychiat. 2013, 202, 381.
9. V. Di Marzo, F. Berrendero, T. Bisogno, S. Gonzalez, P. Cavaliere, J. Romero, M. Cebeira, J.A. Ramos, J.J. Fernandez-Ruiz. Enhancement of anandamide formation in the limbic forebrain and reduction of endocannabinoid contents in the striatum of delta9-tetrahydrocannabinol-tolerant rats. J. Neurochem. 2000, 74, 1627.
10. E. Krämer, K.-A. Kovar. On-line coupling of automated solid-phase extraction with high-performance liquid chromatography and electrochemical detection: Quantitation of oxidizable drugs of abuse and their metabolites in plasma and urine. J. Chromatogr. B Biomed. Sci. Appl. 1999, 731, 167.
11. U. Backofen, F.-M. Matysik, C.E. Lunte. Determination of cannabinoids in hair using high-pH* non-aqueous electrolytes and electrochemical detection: Some aspects of sensitivity and selectivity. J. Chromatogr. A 2002, 942, 259.
12. L. Mercolini, A. Musenga, I. Comin, C. Baccini, M. Conti, M.A. Raggi. Determination of plasma and urine levels of Delta9-tetrahydrocannabinol and its main metabolite by liquid chromatography after solid-phase extraction. J. Pharm. Biomed. Anal. 2008, 47, 156.
13. C. Abbara, R. Galy, A. Benyamina, M. Reynaud, L. Bonhomme-Faivre. Development and validation of a method for the quantitation of Delta9 tetrahydrocannabinol in human plasma by high performance liquid chromatography after solid-phase extraction. J. Pharm. Biomed. Anal. 2006, 41, 1011.
14. A. Verstraete, A.S. Goessaert, J. Veramme. Comparison of the drug concentrations in oral fluid collected by two sampling methods (Varian OraLab and Statsure Saliva•Sampler). Ann. Toxicol. Anal. 2011, 23, 131.
15. O. Quintela, D.M. Andrenyak, A.M. Hoggan, D.J. Crouch. A validated method for the detection of Delta 9-tetrahydrocannabinol and 11-nor-9-carboxy- Delta 9-tetrahydrocannabinol in oral fluid samples by liquid chromatography coupled with quadrupole-time-of-flight mass spectrometry. J. Anal. Toxicol. 2007, 31, 157.
16. F. Peters, D. Remane. Aspects of matrix effects in applications of liquid chromatography-mass spectrometry to forensic and clinical toxicology-a review. Anal. Bioanal. Chem. 2012, 403, 2155.
17. A.A. Zoerner, F.M. Gutzki, S. Batkai, M. May, C. Rakers, S. Engeli, J. Jordan, D. Tsikas. Quantification of endocannabinoids in biological systems by chromatography and mass spectrometry: A comprehensive review from an analytical and biological perspective. Biochim. Biophys. Acta 2011, 1811, 706.
18. P.C. Schmid, R.J. Krebsbach, S.R. Perry, T.M. Dettmer, J.L. Maasson, H.H. Schmid. Occurrence and postmortem generation of anandamide and other long-chain N-acylethanolamines in mammalian brain. FEBS Lett. 1995, 375, 117.
19. T. Sugiura, N. Yoshinaga, K. Waku. Rapid generation of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand, in rat brain after decapitation. Neurosci. Lett. 2001, 297, 175.
20. M.N. Hill, B.S. McEwen. Involvement of the endocannabinoid system in the neurobehavioural effects of stress and glucocorticoids. Prog. Neuropsychopharmacol. Biol. Psychiat. 2010, 34, 791.
21. C.A. Rouzer, K. Ghebreselasie, L.J. Marnett. Chemical stability of 2-arachidonylglycerol under biological conditions. Chem. Phys. Lipids 2002, 119, 69.
22. S.P. Markey, T. Dudding, T.C. Wang. Base- and acid-catalyzed interconversions of O-acyl- and N-acyl-ethanolamines: A cautionary note for lipid analyses. J. Lipid Res. 2000, 41, 657.
23. F. Fanelli, V.D. Di Lallo, I. Belluomo, R. De Iasio, M. Baccini, E. Casadio, D.I. Gasparini, M. Colavita, A. Gambineri, G. Grossi, V. Vicennati, R. Pasquali, U. Pagotto. Estimation of reference intervals of five endocannabinoids and endocannabinoid related compounds in human plasma by two dimensional-LC/MS/MS. J. Lipid Res. 2012, 53, 481.
24. A.A. Zoerner, S. Batkai, M.T. Suchy, F.M. Gutzki, S. Engeli, J. Jordan, D. Tsikas. Simultaneous UPLC-MS/MS quantification of the endocannabinoids 2-arachidonoyl glycerol (2AG), 1-arachidonoyl glycerol (1AG), and anandamide in human plasma: minimization of matrix-effects, 2AG/1AG isomerization and degradation by toluene solvent extraction. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2012, 883/884, 161.
25. D. Richardson, C.A. Ortori, V. Chapman, D.A. Kendall, D.A. Barrett. Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry. Anal. Biochem. 2007, 360, 216.
26. B. Tan, Y.W. Yu, M.F. Monn, H.V. Hughes, D.K. O'Dell, J.M. Walker. Targeted lipidomics approach for endogenous N-acyl amino acids in rat brain tissue. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2009, 877, 2890.
27. O.A. Ismaiel, M.S. Halquist, M.Y. Elmamly, A. Shalaby, H.T. Karnes. Monitoring phospholipids for assessment of matrix effects in a liquid chromatography-tandem mass spectrometry method for hydrocodone and pseudoephedrine in human plasma. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2007, 859, 84.
28. P.J. Kingsley, L.J. Marnett. LC-MS-MS analysis of neutral eicosanoids. Methods Enzymol. 2007, 433, 91.
29. A. Thomas, G. Hopfgartner, C. Giroud, C. Staub. Quantitative and qualitative profiling of endocannabinoids in human plasma using a triple quadrupole linear ion trap mass spectrometer with liquid chromatography. Rapid Commun. Mass Spectrom. 2009, 23, 629.
30. M. Sergi, N. Battista, C. Montesano, R. Curini, M. Maccarrone, D. Compagnone. Determination of the two major endocannabinoids in human plasma by mu-SPE followed by HPLC-MS/MS. Anal. Bioanal. Chem. 2013, 405, 785.
31. H. Teixeira, A. Verstraete, P. Proenca, F. Corte-Real, P. Monsanto, D.N. Vieira. Validated method for the simultaneous determination of Delta9-THC and Delta9-THC-COOH in oral fluid, urine and whole blood using solid-phase extraction and liquid chromatography-mass spectrometry with electrospray ionization. Forensic Sci. Int. 2007, 170, 148.
32. C. Lacroix, E. Saussereau. Fast liquid chromatography/tandem mass spectrometry determination of cannabinoids in micro volume blood samples after dabsyl derivatization. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2012, 905, 85.
33. R. Andrews, S. Paterson. A validated method for the analysis of cannabinoids in post-mortem blood using liquid-liquid extraction and two-dimensional gas chromatography-mass spectrometry. Forensic Sci. Int. 2012, 222, 111.
34. C. Jamey, E. Szwarc, A. Tracqui, B. Ludes. Determination of cannabinoids in whole blood by UPLC-MS-MS. J. Anal. Toxicol. 2008, 32, 349.
35. A. Thomas, C. Widmer, G. Hopfgartner, C. Staub. Fast gas chromatography and negative-ion chemical ionization tandem mass spectrometry for forensic analysis of cannabinoids in whole blood. J. Pharmaceut. Biomed. 2007, 45, 495.
36. C. Coulter, E. Miller, K. Crompton, C. Moore. Tetrahydrocannabinol and two of its metabolites in whole blood using liquid chromatography-tandem mass spectrometry. J. Anal. Toxicol. 2008, 32, 653.
37. M. Del Mar Ramirez Fernandez, G. De Boeck, M. Wood, M. Lopez-Rivadulla, N. Samyn. Simultaneous analysis of THC and its metabolites in blood using liquid chromatography-tandem mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2008, 875, 465.
38. A.A. Elian, J. Hackett. Solid-phase extraction and analysis of THC and carboxy-THC from whole blood using a novel fluorinated solid-phase extraction sorbent and fast liquid chromatography-tandem mass spectrometry. J. Anal. Toxicol. 2009, 33, 461.
39. S. Konig, B. Aebi, S. Lanz, M. Gasser, W. Weinmann. On-line SPE LC-MS/MS for the quantification of Delta9-tetrahydrocannabinol (THC) and its two major metabolites in human peripheral blood by liquid chromatography tandem mass spectrometry. Anal. Bioanal. Chem. 2011, 400, 9.
40. S.B. Grauwiler, A. Scholer, J. Drewe. Development of a LC/MS/MS method for the analysis of cannabinoids in human EDTA-plasma and urine after small doses of Cannabis sativa extracts. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2007, 850, 515.
41. G. Skopp, L. Potsch. Stability of 11-nor-delta(9)-carboxy-tetrahydrocannabinol glucuronide in plasma and urine assessed by liquid chromatography-tandem mass spectrometry. Clin. Chem. 2002, 48, 301.
42. B. Maralikova, W. Weinmann. Confirmatory analysis for drugs of abuse in plasma and urine by high-performance liquid chromatography-tandem mass spectrometry with respect to criteria for compound identification. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2004, 811, 21.
43. B. Maralikova, W. Weinmann. Simultaneous determination of Delta9-tetrahydrocannabinol, 11-hydroxy-Delta9-tetrahydrocannabinol and 11-nor-9-carboxy- Delta9-tetrahydrocannabinol in human plasma by high-performance liquid chromatography/tandem mass spectrometry. J. Mass Spectrom. 2004, 39, 526.
44. S. Valiveti, A.L. Stinchcomb. Liquid chromatographic-mass spectrometric quantitation of Delta9-tetrahydrocannabinol and two metabolites in pharmacokinetic study plasma samples. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2004, 803, 243.
45. M. Laloup, M. Del Mar Ramirez Fernandez, M. Wood, G. De Boeck, V. Maes, N. Samyn. Correlation of Delta9-tetrahydrocannabinol concentrations determined by LC-MS-MS in oral fluid and plasma from impaired drivers and evaluation of the on-site Drager DrugTest. Forensic Sci. Int. 2006, 161, 175.
46. R.H. Lowe, E.L. Karschner, E.W. Schwilke, A.J. Barnes, M.A. Huestis. Simultaneous quantification of Delta9-tetrahydrocannabinol, 11-hydroxy-Delta9-tetrahydrocannabinol, and 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid in human plasma using two-dimensional gas chromatography, cryofocusing, and electron impact-mass spectrometry. J. Chromatogr. A 2007, 1163, 318.
47. J. Jung, J. Kempf, H. Mahler, W. Weinmann. Detection of Delta9-tetrahydrocannabinolic acid A in human urine and blood serum by LC-MS/MS. J. Mass Spectrom. 2007, 42, 354.
48. D.M. Schwope, E.L. Karschner, D.A. Gorelick, M.A. Huestis. Identification of recent cannabis use: Whole-blood and plasma free and glucuronidated cannabinoid pharmacokinetics following controlled smoked cannabis administration. Clin. Chem. 2011, 57, 1406.
49. E.L. Karschner, D.M. Schwope, E.W. Schwilke, R.S. Goodwin, D.L. Kelly, D.A. Gorelick, M.A. Huestis. Predictive model accuracy in estimating last Delta9-tetrahydrocannabinol (THC) intake from plasma and whole blood cannabinoid concentrations in chronic, daily cannabis smokers administered subchronic oral THC. Drug Alcohol Depend. 2012, 125, 313.
50. U. Mareck, N. Haenelt, H. Geyer, S. Guddat, M. Kamber, R. Brenneisen, M. Thevis, W. Schanzer. Temporal indication of cannabis use by means of THC glucuronide determination. Drug Test. Anal. 2009, 1, 505.
51. E.W. Schwilke, D.M. Schwope, E.L. Karschner, R.H. Lowe, W.D. Darwin, D.L. Kelly, R.S. Goodwin, D.A. Gorelick, M.A. Huestis. Delta9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC plasma pharmacokinetics during and after continuous high-dose oral THC. Clin. Chem. 2009, 55, 2180.
52. M. Maccarrone, H. Valensise, M. Bari, N. Lazzarin, C. Romanini, A. Finazzi-Agro. Relation between decreased anandamide hydrolase concentrations in human lymphocytes and miscarriage. Lancet 2000, 355, 1326.
53. J.C. Sipe, T.M. Scott, S. Murray, O. Harismendy, G.M. Simon, B.F. Cravatt, J. Waalen. Biomarkers of endocannabinoid system activation in severe obesity. PLoS One 2010, 5, e8792.
54. D. Grapov, S.H. Adams, T.L. Pedersen, W.T. Garvey, J.W. Newman. Type 2 diabetes associated changes in the plasma non-esterified fatty acids, oxylipins and endocannabinoids. PLoS One 2012, 7, e48852.
55. L. Jean-Gilles, S. Feng, C.R. Tench, V. Chapman, D.A. Kendall, D.A. Barrett, C.S. Constantinescu. Plasma endocannabinoid levels in multiple sclerosis. J. Neurol. Sci. 2009, 287, 212.
56. A. Gronewold, G. Skopp. A preliminary investigation on the distribution of cannabinoids in man. Forensic Sci. Int. 2011, 210, e7.
57. B. Brunet, C. Doucet, N. Venisse, T. Hauet, W. Hebrard, Y. Papet, G. Mauco, P. Mura. Validation of Large White Pig as an animal model for the study of cannabinoids metabolism: Application to the study of THC distribution in tissues. Forensic Sci. Int. 2006, 161, 169.
58. G. Nahas, C. Leger, B. Tocque, H. Hoellinger. The kinetics of cannabinoid distribution and storage with special reference to the brain and testis. J. Clin. Pharmacol. 1981, 21, 208S.
59. J.L. Poklis, C.C. Thompson, K.A. Long, A.H. Lichtman, A. Poklis. Disposition of cannabichromene, cannabidiol, and Delta(9)-tetrahydrocannabinol and its metabolites in mouse brain following marijuana inhalation determined by high-performance liquid chromatography-tandem mass spectrometry. J. Anal. Toxicol. 2010, 34, 516.
60. E.C. Nyoni, B.R. Sitaram, D.A. Taylor. Determination of delta 9-tetrahydrocannabinol levels in brain tissue using high-performance liquid chromatography with electrochemical detection. J. Chromatogr. B Biomed. Appl. 1996, 679, 79.
61. C.C. Felder, A. Nielsen, E.M. Briley, M. Palkovits, J. Priller, J. Axelrod, D.N. Nguyen, J.M. Richardson, R.M. Riggin, G.A. Koppel, S.M. Paul, G.W. Becker. Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. FEBS Lett. 1996, 393, 231.
62. M. Palkovits, J. Harvey-White, J. Liu, Z.S. Kovacs, M. Bobest, G. Lovas, A.G. Bago, G. Kunos. Regional distribution and effects of postmortal delay on endocannabinoid content of the human brain. Neuroscience 2008, 152, 1032.
63. M. Maccarrone, M. Attina, A. Cartoni, M. Bari, A. Finazzi-Agro. Gas chromatography-mass spectrometry analysis of endogenous cannabinoids in healthy and tumoral human brain and human cells in culture. J. Neurochem. 2001, 76, 594.
64. M. Steffens, T.J. Feuerstein, V. van Velthoven, P. Schnierle, R. Knorle. Quantitative measurement of depolarization-induced anandamide release in human and rat neocortex. Naunyn Schmiedebergs Arch. Pharmacol. 2003, 368, 432.
65. K.Y. Vinod, V. Arango, S. Xie, S.A. Kassir, J.J. Mann, T.B. Cooper, B.L. Hungund. Elevated levels of endocannabinoids and CB1 receptor-mediated G-protein signaling in the prefrontal cortex of alcoholic suicide victims. Biol. Psychiat. 2005, 57, 480.
66. M. Lehtonen, M. Storvik, E. Tupala, P. Hyytia, J. Tiihonen, J.C. Callaway. Endogenous cannabinoids in post-mortem brains of Cloninger type 1 and 2 alcoholics. Eur. Neuropsychopharmacol. 2010, 20, 245.
67. C. Muguruza, M. Lehtonen, N. Aaltonen, B. Morentin, J.J. Meana, L.F. Callado. Quantification of endocannabinoids in postmortem brain of schizophrenic subjects. Schizophr. Res. 2013, 148, 145.
68. N. Battista, M. Bari, A. Tarditi, C. Mariotti, A.C. Bachoud-Levi, C. Zuccato, A. Finazzi-Agro, S. Genitrini, M. Peschanski, S. Di Donato, E. Cattaneo, M. Maccarrone. Severe deficiency of the fatty acid amide hydrolase (FAAH) activity segregates with the Huntington's disease mutation in peripheral lymphocytes. Neurobiol. Dis. 2007, 27, 108.
69. E. Marchei, D. Escuder, C.R. Pallas, O. Garcia-Algar, A. Gomez, B. Friguls, M. Pellegrini, S. Pichini. Simultaneous analysis of frequently used licit and illicit psychoactive drugs in breast milk by liquid chromatography tandem mass spectrometry. J. Pharm. Biomed. Anal. 2011, 55, 309.
70. E. Fride, Y. Ginzburg, A. Breuer, T. Bisogno, V. Di Marzo, R. Mechoulam. Critical role of the endogenous cannabinoid system in mouse pup suckling and growth. Eur. J. Pharmacol. 2001, 419, 207.
71. H. Schuel, L.J. Burkman, J. Lippes, K. Crickard, E. Forester, D. Piomelli, A. Giuffrida. N-Acylethanolamines in human reproductive fluids. Chem. Phys. Lipids 2002, 121, 211.
72. P.M. Lam, T.H. Marczylo, J.C. Konje. Simultaneous measurement of three N-acylethanolamides in human bio-matrices using ultra performance liquid chromatography-tandem mass spectrometry. Anal. Bioanal. Chem. 2010, 398, 2089.
73. J. Ristimaa, M. Gergov, A. Pelander, E. Halmesmäki, I. Ojanperä. Broad-spectrum drug screening of meconium by liquid chromatography with tandem mass spectrometry and time-of-flight mass spectrometry. Anal. Bioanal. Chem. 2010, 398, 925.
74. C. Moore, A. Negrusz, D. Lewis. Determination of drugs of abuse in meconium. J. Chromatogr. B Biomed. Sci. Appl. 1998, 713, 137.
75. S. Narkowicz, J. Płotka, Ż. Polkowska, M. Biziuk, J. Namieśnik. Prenatal exposure to substance of abuse: A worldwide problem. Environ. Int. 2013, 54, 141.
76. T.R. Gray, R.D. Eiden, K.E. Leonard, G.J. Connors, S. Shisler, M.A. Huestis. Identifying prenatal cannabis exposure and effects of concurrent tobacco exposure on neonatal growth. Clin. Chem. 2010, 56, 1442.
77. S.J. Marin, R. Coles, F.M. Urry, G.A. McMillin. Confirmation of cannabinoids in meconium using two-dimensional gas chromatography with mass spectrometry detection. J. Chromatogr. B 2007, 858, 59.
78. C. Moore, D. Lewis, J. Becker, J. Leikin. The Determination of 11-Nor-Δ9-Tetrahydrocannabinol-9-Carboxylic acid (THCCOOH) in meconium. J. Anal. Toxicol. 1996, 20, 50.
79. R. Coles, T.T. Clements, G.J. Nelson, G.A. McMillin, F.M. Urry. Simultaneous analysis of the Δ9-THC Metabolites 11-nor-9-Carboxy-Δ9-THC and 11-Hydroxy-Δ9-THC in meconium by GC-MS. J. Anal. Toxicol. 2005, 29, 522.
80. S. Feng, M.A. ElSohly, S. Salamone, M.Y. Salem. Simultaneous analysis of Δ9-THC and its major metabolites in urine, plasma, and meconium by GC-MS using an immunoaffinity extraction procedure. J. Anal. Toxicol. 2000, 24, 395.
81. M.A. ElSohly, S. Feng. Δ9-THC metabolites in meconium: Identification of 11-OH-Δ9-THC, 8β, 11-diOH-Δ9-THC, and 11-nor-Δ9-THC-9-COOH as major metabolites of Δ9-THC. J. Anal. Toxicol. 1998, 22, 329.
82. T. Gray, A. Barnes, M. Huestis. Effect of hydrolysis on identifying prenatal cannabis exposure. Anal. Bioanal. Chem. 2010, 397, 2335.
83. N. Battista, R. Meccariello, G. Cobellis, S. Fasano, M. Di Tommaso, V. Pirazzi, J.C. Konje, R. Pierantoni, M. Maccarrone. The role of endocannabinoids in gonadal function and fertility along the evolutionary axis. Mol. Cell. Endocrinol. 2012, 355, 1.
84. X. Sun, S.K. Dey. Endocannabinoid signaling in female reproduction. ACS Chem. Neurosci. 2012, 3, 349.
85. M.R. El-Talatini, A.H. Taylor, J.C. Konje. Fluctuation in anandamide levels from ovulation to early pregnancy in in-vitro fertilization-embryo transfer women, and its hormonal regulation. Hum. Reprod. 2009, 24, 1989.
86. B.M. Fonseca, G. Correia-da-Silva, A.H. Taylor, P.M. Lam, T.H. Marczylo, J.C. Konje, N.A. Teixeira. Characterisation of the endocannabinoid system in rat haemochorial placenta. Reprod. Toxicol. 2012, 34, 347.
87. R.D. Harbison, B. Mantilla-Plata. Prenatal toxicity, maternal distribution and placental transfer of tetrahydrocannabinol. J. Pharmacol. Exp. Ther. 1972, 180, 446.
88. A.A. Amoako, T.H. Marczylo, P.M. Lam, J.M. Willets, A. Derry, J. Elson, J.C. Konje. Quantitative analysis of anandamide and related acylethanolamides in human seminal plasma by ultra performance liquid chromatography tandem mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2010, 878, 3231.
89. S.E. Lewis, C. Rapino, M. Di Tommaso, M. Pucci, N. Battista, R. Paro, L. Simon, D. Lutton, M. Maccarrone. Differences in the endocannabinoid system of sperm from fertile and infertile men. PLoS One 2012, 7, e47704.
90. M. Minoli, I. Angeli, A. Ravelli, F. Gigli, F. Lodi. Detection and quantification of 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid in hair by GC/MS/MS in Negative Chemical Ionization mode (NCI) with a simple and rapid liquid/liquid extraction. Forensic Sci. Int. 2012, 218, 49.
91. E. Han, Y. Park, E. Kim, S. In, W. Yang, S. Lee, H. Choi, H. Chung, J.M. Song. Simultaneous analysis of Delta(9)-tetrahydrocannabinol and 11-nor-9-carboxy-tetrahydrocannabinol in hair without different sample preparation and derivatization by gas chromatography-tandem mass spectrometry. J. Pharmaceut. Biomed. 2011, 55, 1096.
92. J.Y. Kim, J.C. Cheong, J.I. Lee, M.K. In. Improved gas chromatography-negative ion chemical ionization tandem mass spectrometric method for determination of 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid in hair using mechanical pulverization and bead-assisted liquid-liquid extraction. Forensic Sci. Int. 2011, 206, e99.
93. G. Skopp, P. Strohbeck-Kuehner, K. Mann, D. Hermann. Deposition of cannabinoids in hair after long-term use of cannabis. Forensic Sci. Int. 2007, 170, 46.
94. V. Auwarter, A. Wohlfarth, J. Traber, D. Thieme, W. Weinmann. Hair analysis for Delta9-tetrahydrocannabinolic acid A--new insights into the mechanism of drug incorporation of cannabinoids into hair. Forensic Sci. Int. 2010, 196, 10.
95. S. Strano-Rossi, M. Chiarotti. Solid-phase microextraction for cannabinoids analysis in hair and its possible application to other drugs. J. Anal. Toxicol. 1999, 23, 7.
96. N. Roth, B. Moosmann, V. Auwarter. Development and validation of an LC-MS/MS method for quantification of Delta9-tetrahydrocannabinolic acid A (THCA-A), THC, CBN and CBD in hair. J. Mass Spectrom. 2013, 48, 227.
97. M.A. Huestis, R.A. Gustafson, E.T. Moolchan, A. Barnes, J.A. Bourland, S.A. Sweeney, E.F. Hayes, P.M. Carpenter, M.L. Smith. Cannabinoid concentrations in hair from documented cannabis users. Forensic Sci. Int. 2007, 169, 129.
98. M. Uhl, H. Sachs. Cannabinoids in hair: strategy to prove marijuana/hashish consumption. Forensic Sci. Int. 2004, 145, 143.
99. C. Moore, C. Coulter, S. Rana, M. Vincent, J. Soares. Analytical procedure for the determination of the marijuana metabolite 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid in oral fluid specimens. J. Anal. Toxicol. 2006, 30, 409.
100. D. Di Corcia, F. D'Urso, E. Gerace, A. Salomone, M. Vincenti. Simultaneous determination in hair of multiclass drugs of abuse (including THC) by ultra-high performance liquid chromatography-tandem mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2012, 899, 154.
101. A. Salomone, E. Gerace, F. D'Urso, D. Di Corcia, M. Vincenti. Simultaneous analysis of several synthetic cannabinoids, THC, CBD and CBN, in hair by ultra-high performance liquid chromatography tandem mass spectrometry. Method validation and application to real samples. J. Mass Spectrom. 2012, 47, 604.
102. E. Lendoiro, O. Quintela, A. de Castro, A. Cruz, M. Lopez-Rivadulla, M. Concheiro. Target screening and confirmation of 35 licit and illicit drugs and metabolites in hair by LC-MSMS. Forensic Sci. Int. 2012, 217, 207.
103. L. Mercolini, R. Mandrioli, M. Protti, M. Conti, G. Serpelloni, M.A. Raggi. Monitoring of chronic Cannabis abuse: An LC-MS/MS method for hair analysis. J. Pharm. Biomed. Anal. 2013, 76, 119.
104. V. Cirimele, P. Kintz, P. Mangin. Testing human hair for cannabis. Forensic Sci. Int. 1995, 70, 175.
105. J. Thorspecken, G. Skopp, L. Potsch. In vitro contamination of hair by marijuana smoke. Clin. Chem. 2004, 50, 596.
106. J.Y. Kim, S.I. Suh, M.K. In, K.J. Paeng, B.C. Chung. Simultaneous determination of cannabidiol, cannabinol, and delta9-tetrahydrocannabinol in human hair by gas chromatography-mass spectrometry. Arch. Pharm. Res. 2005, 28, 1086.
107. C. Gambelunghe, R. Rossi, C. Ferranti, M. Bacci. Hair analysis by GC/MS/MS to verify abuse of drugs. J. Appl. Toxicol. 2005, 25, 205.
108. F. Musshoff, H.P. Junker, D.W. Lachenmeier, L. Kroener, B. Madea. Fully automated determination of cannabinoids in hair samples using headspace solid-phase microextraction and gas chromatography-mass spectrometry. J. Anal. Toxicol. 2002, 26, 554.
109. T. Nadulski, F. Pragst. Simple and sensitive determination of Delta(9)-tetrahydrocannabinol, cannabidiol and cannabinol in hair by combined silylation, headspace solid phase microextraction and gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2007, 846, 78.
110. C. Dizioli Rodrigues de Oliveira, M. Yonamine, R.L. de Moraes Moreau. Headspace solid-phase microextraction of cannabinoids in human head hair samples. J. Separate Sci. 2007, 30, 128.
111. E.S. Emidio, M. Prata Vde, H.S. Dorea. Validation of an analytical method for analysis of cannabinoids in hair by headspace solid-phase microextraction and gas chromatography-ion trap tandem mass spectrometry. Anal. Chim. Acta 2010, 670, 63.
112. D.W. Lachenmeier, L. Kroener, F. Musshoff, B. Madea. Application of tandem mass spectrometry combined with gas chromatography and headspace solid-phase dynamic extraction for the determination of drugs of abuse in hair samples. Rapid Commun. Mass Spectrom. 2003, 17, 472.
113. F. Musshoff, D.W. Lachenmeier, L. Kroener, B. Madea. Automated headspace solid-phase dynamic extraction for the determination of cannabinoids in hair samples. Forensic Sci. Int. 2003, 133, 32.
114. M.J. Baptista, P.V. Monsanto, E.G. Pinho Marques, A. Bermejo, S. Avila, A.M. Castanheira, C. Margalho, M. Barroso, D.N. Vieira. Hair analysis for delta(9)-THC, delta(9)-THC-COOH, CBN and CBD, by GC/MS-EI. Comparison with GC/MS-NCI for delta(9)-THC-COOH. Forensic Sci. Int. 2002, 128, 66.
115. G. Kauert, J. Rohrich. Concentrations of delta 9-tetrahydrocannabinol, cocaine and 6-monoacetylmorphine in hair of drug abusers. Int. J. Legal Med. 1996, 108, 294.
116. T.M. Pizzolato, M.J. de Alda, D. Barcelo. LC-based analysis of drugs of abuse and their metabolites in urine. Trends Anal. Chem. 2007, 26, 609.
117. M. Felli, S. Martello, M. Chiarotti. LC-MS-MS method for simultaneous determination of THCCOOH and THCCOOH-glucuronide in urine: Application to workplace confirmation tests. Forensic Sci. Int. 2011, 204, 67.
118. J.E. Manno, B.R. Manno, P.M. Kemp, D.D. Alford, I.K. Abukhalaf, M.E. McWilliams, F.N. Hagaman, M.J. Fitzgerald. Temporal indication of marijuana use can be estimated from plasma and urine concentrations of Δ9-Tetrahydrocannabinol, 11-Hydroxy-Δ9-Tetrahydrocannabinol, and 11-Nor-Δ9-Tetrahydrocannabinol-9-Carboxylic acid. J. Anal. Toxicol. 2001, 25, 538.
119. T.T. Abraham, R.H. Lowe, S.O. Pirnay, W.D. Darwin, M.A. Huestis. Simultaneous GC-EI-MS determination of Delta9-tetrahydrocannabinol, 11-hydroxy-Delta9-tetrahydrocannabinol, and 11-nor-9-carboxy-Delta9-tetrahydrocannabinol in human urine following tandem enzyme-alkaline hydrolysis. J. Anal. Toxicol. 2007, 31, 477.
120. R.H. Lowe, T.T. Abraham, W.D. Darwin, R. Herning, J.L. Cadet, M.A. Huestis. Extended urinary Delta9-tetrahydrocannabinol excretion in chronic cannabis users precludes use as a biomarker of new drug exposure. Drug Alcohol Depend. 2009, 105, 24.
121. K.B. Scheidweiler, N.A. Desrosiers, M.A. Huestis. Simultaneous quantification of free and glucuronidated cannabinoids in human urine by liquid chromatography tandem mass spectrometry. Clin. Chim. Acta 2012, 413, 1839.
122. E. Jagerdeo, M.A. Montgomery, R.P. Karas, M. Sibum. A fast method for screening and/or quantitation of tetrahydrocannabinol and metabolites in urine by automated SPE/LC/MS/MS. Anal. Bioanal. Chem. 2010, 398, 329.
123. W. Weinmann, M. Goerner, S. Vogt, R. Goerke, S. Pollak. Fast confirmation of 11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol (THC-COOH) in urine by LC/MS/MS using negative atmospheric-pressure chemical ionisation (APCI). Forensic Sci. Int. 2001, 121, 103.
124. R. Franski, A. Tezyk, R. Wachowiak, G. Schroeder. Influence of mobile phase composition on the high-performance liquid chromatographic/electrospray ionization mass spectrometric analysis of 11-nor-9-carboxy-delta9-tetrahydrocannabinol (THC-COOH) and its glucuronide in urine. J. Mass Spectrom. 2004, 39, 458.
125. C. Chebbah, O.J. Pozo, K. Deventer, P. Van Eenoo, F.T. Delbeke. Direct quantification of 11-nor-Delta(9)-tetrahydrocannabinol-9-carboxylic acid in urine by liquid chromatography/tandem mass spectrometry in relation to doping control analysis. Rapid Commun. Mass Spectrom. 2010, 24, 1133.
126. R.S. Niedbala, K.W. Kardos, D.F. Fritch, S. Kardos, T. Fries, J. Waga, J. Robb, E.J. Cone. Detection of marijuana use by oral fluid and urine analysis following single-dose administration of smoked and oral marijuana. J. Anal. Toxicol. 2001, 25, 289.
127. T. Breindahl, K. Andreasen. Determination of 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid in urine using high-performance liquid chromatography and electrospray ionization mass spectrometry. J. Chromatogr. B Biomed. Sci. Appl. 1999, 732, 155.
128. S. Huq, A. Dixon, K. Kelly, K.M. Kallury. Novel solid-phase extraction protocol for 11-nor-9-carboxy-delta9-tetrahydrocannabinol from urine samples employing a polymeric mixed-mode cation-exchange resin, Strata-X-C, suitable for gas chromatography-mass spectrometry or liquid chromatography-mass spectrometry analysis. J. Chromatogr. A 2005, 1073, 355.
129. P.V. Robandt, K.L. Klette, M. Sibum. Automated solid-phase extraction-liquid chromatography-tandem mass spectrometry analysis of 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid in human urine specimens: application to a high-throughput urine analysis laboratory. J. Anal. Toxicol. 2009, 33, 456.
130. M. Fernandez Mdel, S.M. Wille, N. Samyn, M. Wood, M. Lopez-Rivadulla, G. De Boeck. On-line solid-phase extraction combined with liquid chromatography-tandem mass spectrometry for high throughput analysis of 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid in urine. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2009, 877, 2153.
131. N. Stephanson, M. Josefsson, R. Kronstrand, O. Beck. Accurate identification and quantification of 11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid in urine drug testing: evaluation of a direct high efficiency liquid chromatographic-mass spectrometric method. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2008, 871, 101.
132. P.M. Kemp, I.K. Abukhalaf, J.E. Manno, B.R. Manno, D.D. Alford, M.E. McWilliams, F.E. Nixon, M.J. Fitzgerald, R.R. Reeves, M.J. Wood. Cannabinoids in humans. II. The influence of three methods of hydrolysis on the concentration of THC and two metabolites in urine. J. Anal. Toxicol. 1995, 19, 292.
133. W. Weinmann, S. Vogt, R. Goerke, C. Muller, A. Bromberger. Simultaneous determination of THC-COOH and THC-COOH-glucuronide in urine samples by LC/MS/MS. Forensic Sci. Int. 2000, 113, 381.
134. R. Yang, W. Xie. Determination of cannabinoids in biological samples using a new solid phase micro-extraction membrane and liquid chromatography-mass spectrometry. Forensic Sci. Int. 2006, 162, 135.
135. T.H. Marczylo, P.M. Lam, V. Nallendran, A.H. Taylor, J.C. Konje. A solid-phase method for the extraction and measurement of anandamide from multiple human biomatrices. Anal. Biochem. 2009, 384, 106.
136. A. Ozalp, B. Barroso. Simultaneous quantitative analysis of N-acylethanolamides in clinical samples. Anal. Biochem. 2009, 395, 68.
137. W.M. Bosker, M.A. Huestis. Oral fluid testing for drugs of abuse. Clin. Chem. 2009, 55, 1910.
138. G. Milman, D.M. Schwope, D.A. Gorelick, M.A. Huestis. Cannabinoids and metabolites in expectorated oral fluid following controlled smoked cannabis. Clin. Chim. Acta 2012, 413, 765.
139. H. Gjerde, A. Verstraete, Can the prevalence of high blood drug concentrations in a population be estimated by analysing oral fluid? A study of tetrahydrocannabinol and amphetamine. Forensic Sci. Int. 2010, 195, 153.
140. D. Lee, R. Vandrey, G. Milman, M. Bergamaschi, D.R. Mendu, J.A. Murray, A.J. Barnes, M.A. Huestis, Oral fluid/plasma cannabinoid ratios following controlled oral THC and smoked cannabis administration. Anal. Bioanal. Chem. 2013, 405, 7269.
141. K. Langel, C. Engblom, A. Pehrsson, T. Gunnar, K. Ariniemi, P. Lillsunde. Drug testing in oral fluid-evaluation of sample collection devices. J. Anal. Toxicol. 2008, 32, 393.
142. G. Milman, A.J. Barnes, D.M. Schwope, E.W. Schwilke, R.S. Goodwin, D.L. Kelly, D.A. Gorelick, M.A. Huestis. Cannabinoids and metabolites in expectorated oral fluid after 8 days of controlled around-the-clock oral THC administration. Anal. Bioanal. Chem. 2011, 401, 599.
143. M. Sergi, C. Montesano, S. Odoardi, L. Mainero Rocca, G. Fabrizi, D. Compagnone, R. Curini. 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 2013, 1301, 139.
144. D. Lee, G. Milman, D.M. Schwope, A.J. Barnes, D.A. Gorelick, M.A. Huestis. Cannabinoid stability in authentic oral fluid after controlled cannabis smoking. Clin. Chem. 2012, 58, 1101.
145. V. Cirimele, M. Villain, P. Mura, M. Bernard, P. Kintz. Oral fluid testing for cannabis: On-site OraLine IV s.a.t. device versus GC/MS. Forensic Sci. Int. 2006, 161, 180.
146. P.D. Lee, Y.J. Chang, K.L. Lin, Y.Z. Chang. Simultaneous determination of Delta9-tetrahydrocannabinol and 11-nor-9-carboxy-Delta9-tetrahydrocannabinol in oral fluid using isotope dilution liquid chromatography tandem mass spectrometry. Anal. Bioanal. Chem. 2012, 402, 851.
147. M. Laloup, M. Ramirez Fernandez Mdel, M. Wood, G. De Boeck, C. Henquet, V. Maes, N. Samyn. Quantitative analysis of delta9-tetrahydrocannabinol in preserved oral fluid by liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 2005, 1082, 15.
148. C. Tan, N. Gajovic-Eichelmann, W.F. Stocklein, R. Polzius, F.F. Bier. Direct detection of Delta9-tetrahydrocannabinol in saliva using a novel homogeneous competitive immunoassay with fluorescence quenching. Anal. Chim. Acta 2010, 658, 187.
149. A. Goodwin, C.E. Banks, R.G. Compton. Graphite micropowder modified with 4-Amino-2, 6-diphenylphenol supported on basal plane pyrolytic graphite electrodes: Micro sensing platforms for the indirect electrochemical detection of Δ9-Tetrahydrocannabinol in saliva. Electroanalysis 2006, 18, 1063.
150. H. Teixeira, P. Proenca, A. Castanheira, S. Santos, M. Lopez-Rivadulla, F. Corte-Real, E.P. Marques, D.N. Vieira. Cannabis and driving: The use of LC-MS to detect delta9-tetrahydrocannabinol (delta9-THC) in oral fluid samples. Forensic Sci. Int. 2004, 146, S61.
151. H. Teixeira, P. Proenca, A. Verstraete, F. Corte-Real, D.N. Vieira. Analysis of Delta9-tetrahydrocannabinol in oral fluid samples using solid-phase extraction and high-performance liquid chromatography-electrospray ionization mass spectrometry. Forensic Sci. Int. 2005, 150, 205.
152. G. Milman, A.J. Barnes, R.H. Lowe, M.A. Huestis. Simultaneous quantification of cannabinoids and metabolites in oral fluid by two-dimensional gas chromatography mass spectrometry. J. Chromatogr. A 2010, 1217, 1513.
153. J. Rohrich, S. Zorntlein, J. Becker, R. Urban. Detection of Delta9-tetrahydrocannabinol and amphetamine-type stimulants in oral fluid using the rapid stat point-of-collection drug-testing device. J. Anal. Toxicol. 2010, 34, 155.
154. N. Fucci, N. De Giovanni, M. Chiarotti. Simultaneous detection of some drugs of abuse in saliva samples by SPME technique. Forensic Sci. Int. 2003, 134, 40.
155. B.J. Hall, M. Satterfield-Doerr, A.R. Parikh, J.S. Brodbelt. Determination of cannabinoids in water and human saliva by solid-phase microextraction and quadrupole ion trap gas chromatography/mass spectrometry. Anal. Chem. 1998, 70, 1788.
156. A. Molnar, J. Lewis, P. Doble, G. Hansen, T. Prolov, S. Fu. A rapid and sensitive method for the identification of delta-9-tetrahydrocannabinol in oral fluid by liquid chromatography-tandem mass spectrometry. Forensic Sci. Int. 2012, 215, 92.
157. A.S. Goessaert, K. Pil, J. Veramme, A. Verstraete. Analytical evaluation of a rapid on-site oral fluid drug test. Anal. Bioanal. Chem. 2010, 396, 2461.
158. M. Concheiro, A. de Castro, O. Quintela, A. Cruz, M. Lopez-Rivadulla. Development and validation of a method for the quantitation of Delta9tetrahydrocannabinol in oral fluid by liquid chromatography electrospray-mass-spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2004, 810, 319.
159. D. Luo, F. Chen, K. Xiao, Y.Q. Feng. Rapid determination of Delta9-Tetrahydrocannabinol in saliva by polymer monolith microextraction combined with gas chromatography-mass spectrometry. Talanta 2009, 77, 1701.
160. S. Strano-Rossi, L. Anzillotti, E. Castrignano, M. Felli, G. Serpelloni, R. Mollica, M. Chiarotti. UHPLC-ESI-MS/MS method for direct analysis of drugs of abuse in oral fluid for DUID assessment. Anal. Bioanal. Chem. 2011, 401, 609.
161. K.A. Mortier, K.M. Clauwaert, W.E. Lambert, J.F. Van Bocxlaer, E.G. Van den Eeckhout, C.H. Van Peteghem, A.P. De Leenheer. Pitfalls associated with liquid chromatography/electrospray tandem mass spectrometry in quantitative bioanalysis of drugs of abuse in saliva. Rapid Commun. Mass Spectrom. 2001, 15, 1773.
162. C. Moore, C. Coulter, D. Uges, J. Tuyay, S. van der Linde, A. van Leeuwen, M. Garnier, J. Orbita, Jr. Cannabinoids in oral fluid following passive exposure to marijuana smoke. Forensic Sci. Int. 2011, 212, 227.
163. C. Coulter, M. Garnier, C. Moore. Analysis of tetrahydrocannabinol and its metabolite, 11-Nor-{Delta}9-Tetrahydrocannabinol-9-Carboxylic acid, in oral fluid using liquid chromatography with tandem mass spectrometry. J. Anal. Toxicol. 2012, 36, 413.
164. M. Sergi, E. Bafile, D. Compagnone, R. Curini, G. D'Ascenzo, F.S. Romolo. Multiclass analysis of illicit drugs in plasma and oral fluids by LC-MS/MS. Anal. Bioanal. Chem. 2009, 393, 709.
165. I. Matias, B. Gatta-Cherifi, A. Tabarin, S. Clark, T. Leste-Lasserre, G. Marsicano, P.V. Piazza, D. Cota. Endocannabinoids measurement in human saliva as potential biomarker of obesity. PLoS One 2012, 7, e42399.