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DOI: 10.1055/s-0043-119361
Evaluation of Cannabinoid and Terpenoid Content: Cannabis Flower Compared to Supercritical CO2 Concentrate
Publication History
received 26 April 2017
revised 17 August 2017
accepted 01 September 2017
Publication Date:
19 September 2017 (online)
Abstract
A recent cannabis use survey revealed that 60% of cannabis users rely on smelling the flower to select their cannabis. Olfactory indicators in plants include volatile compounds, principally represented by the terpenoid fraction. Currently, medicinal- and adult-use cannabis is marketed in the United States with relatively little differentiation between products other than by a common name, association with a species type, and Δ-9 tetrahydrocannabinol/cannabidiol potency. Because of this practice, how terpenoid compositions may change during an extraction process is widely overlooked. Here we report on a comparative study of terpenoid and cannabinoid potencies of flower and supercritical fluid CO2 (SC-CO2) extract from six cannabis chemovars grown in Washington State. To enable this comparison, we employed a validated high-performance liquid chromatography/diode array detector methodology for quantification of seven cannabinoids and developed an internal gas chromatography-mass spectrometry method for quantification of 42 terpenes. The relative potencies of terpenoids and cannabinoids in flower versus concentrate were significantly different. Cannabinoid potency increased by factors of 3.2 for Δ-9 tetrahydrocannabinol and 4.0 for cannabidiol in concentrates compared to flower. Monoterpenes were lost in the extraction process; a ketone increased by 2.2; an ether by 2.7; monoterpene alcohols by 5.3, 7 and 9.4; and sesquiterpenes by 5.1, 4.2, 7.7, and 8.9. Our results demonstrate that the product of SC-CO2 extraction may have a significantly different chemotypic fingerprint from that of cannabis flower. These results highlight the need for more complete characterization of cannabis and associated products, beyond cannabinoid content, in order to further understand health-related consequences of inhaling or ingesting concentrated forms.
Supporting Information
- Supporting Information
Additional data on the method are provided as Supporting Information.
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References
- 1 Sexton M, Cuttler C, Finnell JS, Mischley LK. A cross-sectional survey of medical cannabis users: patterns of use and perceived efficacy. Cannabis Cannabinoid Res 2016; 1: 131-138
- 2 Vandrey R, Raber JC, Raber ME, Douglass B, Miller C, Bonn-Miller MO. Cannabinoid dose and label accuracy in edible medical cannabis products. JAMA 2015; 313: 2491-2493
- 3 Chan GCK, Hall W, Freeman TP, Ferris J, Kelly AB, Winstock A. User characteristics and effect profile of Butane Hash Oil: an extremely high-potency cannabis concentrate. Drug Alcohol Depend 2017; 178: 32-38
- 4 Medical user of marijuana, Chapter XIII of the Public Health Law, Section 3369-1, Part 1004. 2014
- 5 Canada H. Supreme Court of Canada decision R v. Smith. Marijuana for medical purposes regulations. 2015
- 6 Raber JC, Elzinga S, Kaplan C. Understanding dabs: contamination concerns of cannabis concentrates and cannabinoid transfer during the act of dabbing. J Toxicol Sci 2015; 40: 797-803
- 7 Pierre JM, Gandal M, Son M. Cannabis-induced psychosis associated with high potency “wax dabs”. Schizophr Res 2016; 172: 211-212
- 8 Perrotin-Brunela H, Cabeza Perez P, van Roosmalenb MJE, van Spronsena J, Geert-Jan W, Peters CJ. Solubility of delta 9-tetrahydrocannabinol in supercritical carbon dioxide: experiments and modeling. J Supercrit Fluids 2010; 52: 6-10
- 9 Aladić K, Jarni K, Barbirc T, Vidović S, Vladić J, Bilic M, Jokić S. Supercritical CO2 extraction of hemp (Cannabis sativa L.) seed oil. Ind Crops Prod 2015; 76: 472-478
- 10 Diaz-Reinoso B, Moure A, Dominguez H, Parajo JC. Supercritical CO2 extraction and purification of compounds with antioxidant activity. J Agric Food Chem 2006; 54: 2441-2469
- 11 Grotenhermen F, Muller-Vahl K. The therapeutic potential of cannabis and cannabinoids. Dtsch Arztebl Int 2012; 109: 495-501
- 12 Rothschild M, Wangberg S. Cannabis sativa: volatile compounds from pollen and entire male and female plants of two variants, Northern Lights and Hawaiian Indica. Bot J Linn Soc 2005; 147: 387-397
- 13 Ross SA, Elsohly MA. The volatile oil composition of fresh and air-dried buds of Cannabis sativa . J Nat Prod 1996; 59: 49-51
- 14 McPartland JM, Russo E. Cannabis and cannabis extracts: greater than the sum of their parts. J Cannabis Ther 2001; 3: 103-132
- 15 Maffei ME, Gertsch J, Appendino G. Plant volatiles: production, function and pharmacology. Nat Prod Rep 2011; 28: 1359-1380
- 16 Nerio LS, Olivero-Verbel J, Stashenko E. Repellent activity of essential oils: a review. Bioresour Technol 2010; 101: 372-378
- 17 Ormeno E, Fernandez C. Effect of soil nutrient on production and diversity of volatile terpenoids from plants. Curr Bioact Compd 2012; 8: 71-79
- 18 Loreto F, Barta C, Brilli F, Nogues I. On the induction of volatile organic compound emissions by plants as consequence of wounding or fluctuations of light and temperature. Plant Cell Environ 2006; 29: 1820-1828
- 19 Turner CE, Elsohly MA, Boeren EG. Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod 1980; 43: 169-234
- 20 Nigam MC, Handa IC, Nigam L. Essential oils and their constituents: XXIX. The essential oil of marijuana. Composition of genuine Indian Cannabis sativa . Can J Chem 1965; 43: 3372-3376
- 21 Hendriks H, Malingre TM, Batterman S, Bos R. Mono-terpene and sesqui-terpene hydrocarbons of the essential oil of Cannabis sativa . Phytochemistry 1975; 14: 814-815
- 22 Hillig KW, Mahlberg PG. A chemotaxonomic analysis of cannabinoid variation in cannabis (Cannabaceae). Am J Bot 2004; 91: 966-975
- 23 Rather MA, Dar BA, Sofi SN, Hassan T, Ali N, Lone AH, Shawl AS, Shah WA, Qurishi MA, Prakas P. Headspace solid phase microextraction (HS SPME) gas chromatography mass spectrometric analysis of the volatile constituents of Cannabis sativa L. from Kashmir. J Pharm Res 2011; 4: 2651-2653
- 24 Giese MW, Lewis MA, Giese L, Smith KM. Development and validation of a reliable and robust method for the analysis of cannabinoids and terpenes in cannabis. J AOAC Int 2015; 98: 1503-1522
- 25 Piomelli D, Russo EB. The Cannabis sativa versus Cannabis indica debate: an Interview with Ethan Russo, MD. Cannabis Cannabinoid Res 2016; 1: 44-46
- 26 Hazekamp A, Fischedick JT. Cannabis – from cultivar to chemovar. Drug Test Anal 2012; 4: 660-667
- 27 Bombastus PTA. Septem Defensiones – Complete Edition. Amazon Digital Services LLC: e-artnow; 2015
- 28 Romano LL, Hazekamp A. Cannabis oil: chemical evaluation of an upcoming cannabis-based medicine. Cannabinoids 2013; 1: 1-11
- 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: 1397-1404
- 30 Lee DC, Crosier BS, Borodovsky JT, Sargent JD, Budney AJ. Online survey characterizing vaporizer use among cannabis users. Drug Alcohol Depend 2016; 159: 227-233
- 31 Pacifico DM, Francesca M, Micheler M, Carboni A, Ranalli P, Mandolino G. Genetics and marker-assisted selection of the chemotype in Cannabis sativa L. Mol Breed 2006; 17: 257-268
- 32 Anikeev VI. Thermal transformations of some monoterpene compounds in supercritical lower alcohols. Flavour Fragr J 2010; 25: 443-455
- 33 Marchini M, Charvoz C, Dujourdy L, Baldovini N, Filippi JJ. Multidimensional analysis of cannabis volatile constituents: identification of 5, 5-dimethyl-1-vinylbicyclo[2.1.1]hexane as a volatile marker of hashish, the resin of Cannabis sativa L. J Chromatogr A 2014; 1370: 200-215
- 34 Yates AA, Erdman Jr. JW, Shao A, Dolan LC, Griffiths JC. Bioactive nutrients – time for tolerable upper intake levels to address safety. Regul Toxicol Pharmacol 2017; 84: 94-101
- 35 Smart R, Caulkins JP, Kilmer B, Davenport S, Midgette G. Variation in cannabis potency and prices in a newly-legal market: evidence from 30 million cannabis sales in Washington State. Addiction 27.05.2017; DOI: 10.1111/add.13886. [Epub ahead of print]
- 36 Russo EB. Current therapeutic cannabis controversies and clinical trial design issues. Front Pharmacol 2016; 7: 309
- 37 Stone D. Cannabis, pesticides and conflicting laws: the dilemma for legalized States and implications for public health. Regul Toxicol Pharmacol 2014; 69: 284-288
- 38 Loflin M, Earleywine M. A new method of cannabis ingestion: the dangers of dabs?. Addict Behav 2014; 39: 1430-1433
- 39 Budney AJ, Sargent JD, Lee DC. Vaping cannabis (marijuana): parallel concerns to e-cigs?. Addiction 2015; 110: 1699-1704
- 40 Ehrlich T. OʼNeill. Identifying health and safety concerns in a growing field; a needs assessment of employers and employees in Washington State Cannabis Grow Operations. Seattle: University of Washington; 2017
- 41 Citti C, Braghiroli D, Vandelli MA, Cannazza G. Pharmaceutical and biomedical analysis of cannabinoids: a critical review. J Pharm Biomed Anal 2017; DOI: 10.1016/j.jpba.2017.06.003.
- 42 Russo E. Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. Br J Pharmacol 2011; 163: 1344-1364
- 43 Schmidt L, Goen T. R-Limonene metabolism in humans and metabolite kinetics after oral administration. Arch Toxicol 2017; 91: 1175-1185
- 44 Schmidt L, Goen T. Human metabolism of α-pinene and metabolite kinetics after oral administration. Arch Toxicol 2017; 91: 677-687
- 45 De Backer B, Debrus B, Lebrun P, Theunis L, Dubois N, Decock L, Verstraete A, Hubert P, Charlier C. 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: 4115-4124