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A Quantitative 1H NMR Method for Screening Cannabinoids in CBD Oils

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toxics Article A Quantitative 1H NMR Method for Screening Cannabinoids in CBD Oils Ines Barthlott, Andreas Scharinger, Patricia Golombek, Thomas Kuballa and Dirk W. Lachenmeier * Chemisches und Veterinäruntersuchungsamt (CVUA) Karlsruhe, Weißenburger Straße 3, 76187 Karlsruhe, Germany; [email protected] (I.B.); [email protected] (A.S.); [email protected] (P.G.); [email protected] (T.K.) * Correspondence: [email protected]; Tel.: +49-721-926-5434 Abstract: Toxicologically relevant levels of the psychoactive D9-tetrahydocannabinol (D9-THC) as well as high levels of non-psychoactive cannabinoids potentially occur in CBD (cannabidiol) oils. For consumer protection in the fast-growing CBD oil market, facile and rapid quantitative methods to determine the cannabinoid content are crucial. However, the current standard method, i.e., liquid chromatography combined with tandem mass spectrometry (HPLC-MS/MS), requires a time- consuming multistep sample preparation. In this study, a quantitative nuclear magnetic resonance spectroscopy (qNMR) method for screening cannabinoids in CBD oils was developed. Contrary to the HPLC-MS/MS method, this qNMR features a simple sample preparation, i.e., only diluting the CBD oil in deuterochloroform. Pulse length-based concentration determination (PULCON) enables a direct quantification using an external standard. The signal intensities of the cannabinoids were enhanced during the NMR spectra acquisition by means of multiple suppression of the triglycerides which are a major component of the CBD oil matrix. The validation confirmed linearity for CBD, 9 8 Citation: Barthlott, I.; Scharinger, A.; cannabinol (CBN), D -THC and D -THC in hemp seed oil with sufficient recoveries and precision for Golombek, P.; Kuballa, T.; screening. Comparing the qNMR results to HPLC-MS/MS data for 46 commercial CBD oils verified Lachenmeier, D.W. A Quantitative the qNMR accuracy for D9-THC and CBD, but with higher limits of detection. The developed qNMR 1H NMR Method for Screening method paves the way for increasing the sample throughput as a complementary screening before Cannabinoids in CBD Oils. Toxics HPLC-MS/MS. 2021, 9, 136. https://doi.org/ 10.3390/toxics9060136 Keywords: cannabidiol (CBD); D9-tetrahydrocannabinol (D9-THC); cannabinol (CBN); D8-tetrahy- drocannabinol (D8-THC); cannabinoids; CBD oil; nuclear magnetic resonance spectroscopy (NMR); Academic Editors: Jana Pulkrabova PULCON methodology; 1H NMR; qNMR and Aristeidis Tsagkaris Received: 14 May 2021 Accepted: 5 June 2021 Published: 10 June 2021 1. Introduction In recent years, hemp products have experienced a strong increase in popularity. Publisher’s Note: MDPI stays neutral Besides hemp-based foods (e.g., hemp seed oil, hemp flour), consumer products containing with regard to jurisdictional claims in cannabidiol (CBD) and in particular “CBD oils” are currently high in demand [1] and published maps and institutional affil- the market for CBD-containing dietary supplements continues to grow [2]. The term iations. “CBD oil” originates from the non-psychoactive cannabidiol (CBD) which naturally occurs in the hemp plant. CBD is researched for a variety of pharmacological effects and is approved as medicinal product for treatment of certain epileptic conditions [3]. CBD is also marketed using unauthorized health or disease-related claims [1,2]. Despite the lack Copyright: © 2021 by the authors. of clinical evidence, CBD is advertised as a natural remedy for treating anxiety, depression, Licensee MDPI, Basel, Switzerland. pain, inflammatory and sleep disorders, and even cancer [2,4]. CBD oils are formulated This article is an open access article as mixtures of an edible oil with extracts of the leaves and flowers of the hemp plant distributed under the terms and Cannabis sativa L. Commercially available CBD oils usually declare a CBD content between conditions of the Creative Commons 5 and 20 wt.-% [4]. Oils with CBD content at this level can only be achieved by adding Attribution (CC BY) license (https:// a concentrated hemp extract to an edible oil, e.g., hemp seed oil or olive oil [4]. As the creativecommons.org/licenses/by/ extraction process for manufacturing so-called full spectrum hemp extracts is not CBD- 4.0/). Toxics 2021, 9, 136. https://doi.org/10.3390/toxics9060136 https://www.mdpi.com/journal/toxics Toxics 2021, 9, x 2 of 20 Toxics 2021, 9, 136 2 of 20 traction process for manufacturing so-called full spectrum hemp extracts is not CBD-se- selectivelective [4,5], [4,5], CBD oils oils contain contain a a wide wide spectrum spectrum of of cannabinoids cannabinoids naturally naturally occurring occurring in in the thehemp hemp plant. plant. TheThe substance substance class class of cannabinoids of cannabinoid referss refers to terpeno-phenolic to terpeno-phenolic C21 and C2221 compoundsand C22 com- thatpounds are exclusively that are exclusively found in found the hemp in the plant. hemp They plant. are They predominantly are predominantly formed formed in the in glandularthe glandular hairs ofhairs the femaleof the female hemp plant hemp [6 plan,7]. Thet [6,7]. occurrence The occurrence of a carboxyl of a carboxyl group allows group a furtherallows divisiona further into division two subclasses: into two cannabinoidsubclasses: cannabinoid acids featuring acids a carboxyl featuring group a carboxyl (e.g., D9group-tetrahydocannabinolic (e.g., ∆9-tetrahydocannabinolic acid (THCA) andacid cannabidiolic(THCA) and cannabidiolic acid (CBDA)) acid and the(CBDA)) neutral and cannabinoids.the neutral cannabinoids. More than 120 More different than cannabinoids 120 different andcannabinoids their carboxylic and their acid carboxylic analogs and acid conversionanalogs and products conversion are described products in are the described literature in [8 the]. The literature individual [8]. The cannabinoids individual differ canna- onlybinoids slightly differ in theironly structures.slightly in Thetheir modifications structures. The are modifications mainly limited are to mainly changes limited of the to 9 allylicchanges C5 side of the chain allylic (e.g., CD5 side-tetrahydrocannabivarin chain (e.g., ∆9-tetrahydrocannabivarin (THCV), in Figure (THCV),1), the substitution in Figure 1), ofthe a carboxylic substitution acid of or a hydroxylcarboxylic group, acid or or hydrox an additionalyl group, cyclization or an additional [9]. cyclization [9]. (a) (b) (c) (d) (e) (f) FigureFigure 1. 1.Chemical Chemical structures structures of of the the main main cannabinoids cannabinoids studied studied inin thisthis workwork including the applied applied numbering numbering system. system. (a) 9 9 (a)R R = =H: H: cannabidiol cannabidiol (CBD), (CBD), R = RCOOH: = COOH: cannabidiolic cannabidiolic acid (CBDA); acid (CBDA); (b) R = ( bH:) R∆ =-tetrahydrocannabinol H: D9-tetrahydrocannabinol (∆ -THC), (D R9 -THC),= COOH: 9 8 8 9 R =∆ COOH-tetrahydrocannabinolic: D9-tetrahydrocannabinolic acid A (THCA); acid ( Ac) (THCA);∆ -tetrahydrocannabinol (c) D8-tetrahydrocannabinol (∆ -THC); (d) cannabinol (D8-THC); ((CBN);d) cannabinol (e) ∆ -tetrahydro- (CBN); cannabivarin (THCV); (f) cannabigerol (CBG). (e) D9-tetrahydrocannabivarin (THCV); (f) cannabigerol (CBG). InIn the the hemp hemp plant, plant, CBD CBD andand D∆9-THC-THC are are the the most most abundant abundant cannabinoids cannabinoids beside beside can- cannabigerolnabigerol (CBG) (CBG) and and cannabinol cannabinol (CBN), (CBN), see see Figure Figure 1.1 While. While CBD CBD and and CBG CBG are are not not psy- psychoactive,choactive, ∆D9-THC9-THC induces induces intense intense states ofof intoxicationintoxication [ 8[8].]. Consequently, Consequently, the theD9 -THC∆9-THC contentcontent in in CBD CBD oil oil must must be be kept kept low low even even at at high high CBD CBD concentrations concentrations for for consumer consumer safety. safety. SinceSince the the hemp hemp extraction extraction is notis not typically typically cannabinoid-selective, cannabinoid-selective, the the naturally naturally occurring occurring contentcontent is is the the major major factor factor for forD9 ∆-THC9-THC contents. contents. InIn the the European European Union Union (EU), (EU), fiber fiber hemp hemp with with low lowD9 -THC∆9-THC content content (characterized (characterized by by ratioratio of of (THC (THC + CBN)/CBD+ CBN)/CBD < < 1) 1) is is used used for for the the production production of of hemp hemp extracts extracts [4 ][4] as as opposed opposed toto drug drug hemp hemp (ratio (ratio of of (THC(THC + CBN)/CBD CBN)/CBD > 1) > 1)[1,8,10]. [1,8,10 However,]. However, Lachenmeier Lachenmeier et al. et (2020) al. (2020)recently recently showed showed that some that someCBD products CBD products sold in sold Germany, in Germany, including including CBD oils, CBD exceeded oils, exceededthe acute the reference acute reference dose (ARfD) dose (ARfD)of 1 µg THC/ of 1 µkgg THC/kg body weight body established weight established by the European by the EuropeanFood Safety Food Authority Safety Authority (EFSA) (EFSA)[11]. Consequently, [11]. Consequently, these products these products were wereclassified classified in part inas part being as beingnot safe not for safe human for human consumption consumption [12]. Up [12 to]. 30 Up mg to ∆ 309-THC/daily mg D9-THC/daily dose was dose deter- was determined in the products [12]. As CBD oils may contain very high amounts of non- psychoactive cannabinoids and of the psychotropic cannabinoid D9-THC at toxicologically Toxics 2021, 9, 136 3 of 20 relevant
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  • Table of Natural Cannabinoids

    Table of Natural Cannabinoids

    Table of Natural Cannabinoids Scientific research continues to develop and further identify individual cannabinoids in cannabis strains and how they affect symptoms of illnesses suffered by patients. The table below identifies the chemical properties of the natural cannabinoids found in the average strains of cannabis. Levels of each of these chemicals will vary with varietal strain, growing method, and plant age. Individual cannabinoids can be enhanced or eliminated depending on need. Cannabigerol- type (CBG) Cannabigerol Cannabigerol Cannabigerovarin (E)-CBG-C monomethyl (E)-CBGV-C 5 Cannabinerolic 3 ether acid A (E)-CBGM-C 5 (Z)-CBGA-C A A 5 Cannabigerolic Cannabigerolic Cannabigerovarinic acid acid A acid A A (E)-CBGA-C5 A monomethyl (E)-CBGVA-C3 A ether (E)-CBGAM- C5 A Cannabichrom ene-type (CBC) (±)- (±)- Cannabichromen (±)- Cannabivarichromene, (±)- e Cannabichrome (±)- Cannabichrome CBC-C5 nic acid A Cannabichromevarin varinic CBCA-C5 A CBCV-C3 acid A CBCVA-C3 A Cannabidiol- type (CBD) 1 | Page (−)-Cannabidiol Cannabidiol Cannabidiol-C4 (−)- Cannabidiorc CBD-C5 momomethyl CBD-C4 Cannabidivarin ol ether CBDV-C3 CBD-C1 CBDM-C5 Cannabidiolic Cannabidivarini acid c acid CBDA-C5 CBDVA-C3 Cannabinodiol- type (CBND) Cannabinodiol Cannabinodivar CBND-C5 in CBND-C3 Tetrahydrocan nabinol-type (THC) 9 9 9 Δ - Δ - Δ - Δ9- Tetrahydrocanna Tetrahydrocan Tetrahydrocannabivarin 9 Tetrahydrocan binol nabinol-C4 Δ -THCV-C3 9 9 nabiorcol Δ -THC-C5 Δ -THC-C4 9 Δ -THCO-C1 9 9 Δ -Tetrahydro- Δ9-Tetrahydro- Δ -Tetrahydro- Δ9-Tetrahydro- cannabinolic