Quantitative Determination of Cannabinoids in Cannabis and Cannabis Products Using Ultra-High-Performance Supercritical Fluid Chromatography and Diode Array/Mass Spectrometric Detection

Journal of Forensic Sciences

Volumn 62, Issue 3, 2017, Pages 602-611

  Wang, Mei ^a   Wang, Yan Hong ^a   Avula, Bharathi ^a   Radwan, Mohamed M ^a,b   Wanas, Amira S ^a,c   Mehmedic, Zlatko ^a   van Antwerp, John ^d   ElSohly, Mahmoud A ^a,e   Khan, Ikhlas A ^a,e,f  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b Alexandria University Faculty of Pharmacy   (Egypt)

^c Minia University   (Egypt)

^d WATERS CORPORATION   (United States)

^e UNIVERSITY OF MISSISSIPPI   (United States)

^f KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

cannabinoids; Cannabis sativa L.; chemometric analysis; forensic science; quantification and method validation; UHPSFC PDA MS

Indexed keywords

CANNABINOID; CANNABIS; PLANT EXTRACT;

CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; LEAST SQUARE ANALYSIS; LIMIT OF DETECTION; MASS SPECTROMETRY; PRINCIPAL COMPONENT ANALYSIS; SUPERCRITICAL FLUID CHROMATOGRAPHY;

CANNABINOIDS; CANNABIS; CHROMATOGRAPHY, SUPERCRITICAL FLUID; HUMANS; LEAST-SQUARES ANALYSIS; LIMIT OF DETECTION; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PLANT EXTRACTS; PRINCIPAL COMPONENT ANALYSIS;

EID: 85006741667     PISSN: 00221198     EISSN: 15564029     Source Type: Journal    
DOI: 10.1111/1556-4029.13341     Document Type: Article

References (49)

1. West ME, Homi J. Cannabis as a medicine. Br J Anaesth 1996;76(1):167.
2. Zuardi AW. History of cannabis as a medicine: a review. Rev Bras Psiquiatr 2006;28(2):153–7.
3. United Nations Office on Drug Crime (UNODC). Recommended method for the identification and analysis of cannabis and cannabis products. Vienna, Austria: UNODC, 2014;39–41.
4. Radwan MM, ElSohly MA, Slade D, Ahmed SA, Wilson L, El-Alfy AT, et al. Non-cannabinoid constituents from a high potency Cannabis sativa variety. Phytochemistry 2008;69(14):2627–33.
5. Radwan MM, Ross SA, Slade D, Ahmed SA, Zulfiqar F, ElSohly MA. Isolation and characterization of new cannabis constituents from a high potency variety. Planta Med 2008;74(3):267–72.
6. Radwan MM, ElSohly MA, Slade D, Ahmed SA, Khan IA, Ross SA. Biologically active cannabinoids from high-potency Cannabis sativa. J Nat Prod 2009;72(5):906–11.
7. Ahmed SA, Ross SA, Slade D, Radwan MM, Khan IA, ElSohly MA. Structure determination and absolute configuration of cannabichromanone derivatives from high potency Cannabis sativa. Tetrahedron Lett 2008;49(42):6050–3.
8. Ahmed SA, Ross SA, Slade D, Radwan MM, Zulfiqar F, Matsumoto RR, et al. Cannabinoid ester constituents from high-potency Cannabis sativa. J Nat Prod 2008;71(4):536–42.
9. Zulfiqar F, Ross SA, Slade D, Ahmed SA, Radwan MM, Ali Z, et al. Cannabisol, a novel Δ9-THC dimer possessing a unique methylene bridge, isolated from Cannabis sativa. Tetrahedron Lett 2012;53(28):3560–2.
10. Ibrahim AK, Radwan MM, Ahmed SA, Slade D, Ross SA, El Sohly MA, et al. Microbial metabolism of cannflavin A and B isolated from Cannabis sativa. Phytochemistry 2010;71(8–9):1014–9.
11. Radwan MM, ElSohly MA, El-Alfy AT, Ahmed SA, Slade D, Husni AS, et al. Isolation and pharmacological evaluation of minor cannabinoids from high-potency cannabis sativa. J Nat Prod 2015;78(6):1271–6.
12. Ahmed SA, Ross SA, Slade D, Radwan MM, Khan IA, ElSohly MA. Minor oxygenated cannabinoids from high potency Cannabis sativa L. Phytochemistry 2015;117:194–9.
13. ElSohly MA, Gul W, Salem M. Cannabinoids analysis: analytical methods for different biological specimens. Handb Anal Sep 2008;6(Forensic Science):203–41.
14. Pertwee RG, Thomas A, Stevenson LA, Ross RA, Varvel SA, Lichtman AH, et al. The psychoactive plant cannabinoid, Δ9-tetrahydrocannabinol, is antagonized by Δ8- and Δ9-tetrahydrocannabivarin in mice in vivo. Br J Pharmacol 2007;150(5):586–94.
15. ElSohly MA, Harland EC, Benigni DA, Waller CW. Cannabinoids in glaucoma. II: The effect of different cannabinoids on intraocular pressure of the rabbit. Curr Eye Res 1984;3(6):841–50.
16. Russo E. Cannabis for migraine treatment: the once and future prescription? An historical and scientific review. Pain 1998;76(1,2):3–8.
17. Baron EP. Comprehensive review of medicinal marijuana, cannabinoids, and therapeutic implications in medicine and headache: what a long strange trip it's been. Headache 2015;55(6):885–916.
18. Russo E, editor. Migraine. Philadelphia, PA: Haworth Press, 2002.
19. Volfe Z, Dvilansky A, Nathan I. Cannabinoids block release of serotonin from platelets induced by plasma from migraine patients. Int J Clin Pharmacol Res 1985;5(4):243–6.
20. Maurer M, Henn V, Dittrich A, Hofmann A. Delta-9-tetrahydrocannabinol shows antispastic and analgesic effects in a single case double-blind trial. Eur Arch Psychiatry Clin Neurosci 1990;240(1):1–4.
21. McLendon DM, Harris RT, Maule WF. Suppression of the cardiac conditioned response by Δ-9-tetrahydrocannabinol: a comparison with other drugs. Psychopharmacology 1976;50(2):159–63.
22. Mechoulam R, Parker LA, Gallily R. Cannabidiol: an overview of some pharmacological aspects. J Clin Pharmacol 2002;42(11 Suppl):11S–9S.
23. Schier A, Ribeiro N, Silva A, Hallak JEC, Crippa JAS, Nardi AE, et al. Cannabidiol, a Cannabis sativa constituent, as an anxiolytic drug. Rev Bras Psiquiatr 2012;34(Suppl 1):S104–10.
24. Porter BE, Jacobson C. Report of a parent survey of cannabidiol-enriched cannabis use in pediatric treatment-resistant epilepsy. Epilepsy Behav 2013;29(3):574–7.
25. Gambaro V, Dell'Acqua L, Fare F, Froldi R, Saligari E, Tassoni G. Determination of primary active constituents in cannabis preparations by high-resolution gas chromatography/flame ionization detection and high-performance liquid chromatography/UV detection. Anal Chim Acta 2002;468(2):245–54.
26. Caligiani A, Palla G, Bernardelli B. GC-MS analysis of hashish samples: a case of adulteration with colophony. J Forensic Sci 2006;51(5):1096–100.
27. Marsili R, Martello S, Felli M, Fiorina S, Chiarotti M. Hair testing for Δ9-THC-COOH by gas chromatography/tandem mass spectrometry in negative chemical ionization mode. Rapid Commun Mass Spectrom 2005;19(11):1566–8.
28. Huizer H. The use of gas chromatography for the detection and quantitation of abused drugs. In: Gough TA, editor. The analysis of drugs of abuse. New York, NY: John Wiley & Sons Ltd, 1991.
29. Omar J, Olivares M, Alzaga M, Etxebarria N. Optimisation and characterisation of marihuana extracts obtained by supercritical fluid extraction and focused ultrasound extraction and retention time locking GC-MS. J Sep Sci 2013;36(8):1397–404.
30. Fischedick JT, Hazekamp A, Erkelens T, Choi YH, Verpoorte R. Metabolic fingerprinting of Cannabis sativa L. cannabinoids and terpenoids for chemotaxonomic and drug standardization purposes. Phytochemistry 2010;71(17–8):2058–73.
31. Dussy FE, Hamberg C, Luginbuhl M, Schwerzmann T, Briellmann TA. Isolation of Δ9-THCA-A from hemp and analytical aspects concerning the determination of Δ9-THC in cannabis products. Forensic Sci Int 2005;149(1):3–10.
32. Groeger T, Schaeffer M, Puetz M, Ahrens B, Drew K, Eschner M, et al. Application of two-dimensional gas chromatography combined with pixel-based chemometric processing for the chemical profiling of illicit drug samples. J Chromatogr A 2008;1200(1):8–16.
33. Omar J, Olivares M, Amigo JM, Etxebarria N. Resolution of co-eluting compounds of Cannabis sativa in comprehensive two-dimensional gas chromatography/mass spectrometry detection with Multivariate Curve Resolution-Alternating Least Squares. Talanta 2014;121:273–80.
34. Hewavitharana AK, Golding G, Tempany G, King G, Holling N. Quantitative GC-MS analysis of D(9)-tetrahydrocannabinol in fiber hemp varieties. J Anal Toxicol 2005;29(4):258–61.
35. ElSohly MA, ElSohly HN, Jones AB, Dimson PA, Wells KE. Analysis of the major metabolite of Δ9-tetrahydrocannabinol in urine. II. A HPLC procedure. J Anal Toxicol 1983;7(6):262–4.
36. Grauwiler SB, Scholer A, Drewe J. 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 Anal Technol Biomed Life Sci 2007;850(1–2):515–22.
37. De Backer B, Debrus B, Lebrun P, Theunis L, Dubois N, Decock L, et al. Innovative development and validation of an HPLC/DAD method for the qualitative and quantitative determination of major cannabinoids in cannabis plant material. J Chromatogr B 2009;877(32):4115–24.
38. Aizpurua-Olaizola O, Omar J, Navarro P, Olivares M, Etxebarria N, Usobiaga A. Identification and quantification of cannabinoids in Cannabis sativa L. plants by high performance liquid chromatography-mass spectrometry. Anal Bioanal Chem 2014;406(29):7549–60.
39. Míguez-Framil M, Cocho JÁ, Tabernero MJ, Bermejo AM, Moreda-Piñeiro A, Bermejo-Barrera P. An improved method for the determination of ∆9-tetrahydrocannabinol, cannabinol and cannabidiol in hair by liquid chromatography–tandem mass spectrometry. Microchem J 2014;117:7–17.
40. Toyo'oka T, Kikura-Hanajiri R. A reliable method for the separation and detection of synthetic cannabinoids by supercritical fluid chromatography with mass spectrometry, and its application to plant products. Chem Pharm Bull 2015;63(10):762–9.
41. Backstrom B, Cole MD, Carrott MJ, Jones DC, Davidson G, Coleman K. A preliminary study of the analysis of cannabis by supercritical fluid chromatography with atmospheric pressure chemical ionization mass spectroscopic detection. Sci Justice 1997;37(2):91–7.
42. Later DW, Richter BE, Knowles DE, Andersen MR. Analysis of various classes of drugs by capillary supercritical fluid chromatography. J Chromatogr Sci 1986;24(6):249–53.
43. Breitenbach S, Rowe WF, McCord B, Lurie IS. Assessment of ultra high performance supercritical fluid chromatography as a separation technique for the analysis of seized drugs: applicability to synthetic cannabinoids. J Chromatogr A 2016;1440:201–11.
44. El-Alfy AT, Ivey K, Robinson K, Ahmed S, Radwan M, Slade D, et al. Antidepressant-like effect of Δ9-tetrahydrocannabinol and other cannabinoids isolated from Cannabis sativa L. Pharmacol Biochem Behav 2010;95(4):434–42.
45. Ahmed SA, Ross SA, Slade D, Radwan MM, Khan IA, ElSohly MA. Minor oxygenated cannabinoids from high potency Cannabis sativa L. Phytochemistry 2015;117:194–9.
46. Harmonization ICo. Validation of analytical procedures: text and methodology Q2 (R1). Geneva, Switzerland: ICH Harmonized Tripartite Guidelines, 2005.
47. Ambach L, Penitschka F, Broillet A, König S, Weinmann W, Bernhard W. Simultaneous quantification of delta-9-THC, THC-acid A, CBN and CBD in seized drugs using HPLC-DAD. Forensic Sci Int 2014;243:107–11.
48. Broseus J, Anglada F, Esseiva P. The differentiation of fibre- and drug type cannabis seedlings by gas chromatography/mass spectrometry and chemometric tools. Forensic Sci Int 2010;200(1–3):87–92.
49. Eriksson I, Johansson E, Kettaneh-Wold N, Wold S. Multi- and megavariate data analysis. Principles and applications [book review]. J Chemom 2002;16(5):261–2.