Electrochemical Oxidation of Δ-Tetrahydrocannabinol: A Simple Strategy for Marijuana Detection

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2020 Apr 25

PMID 32330051

Citations 2

Authors

Evan R Darzi

Neil K Garg

Affiliations

Soon will be listed here.

Abstract

Recently, it has been estimated that nearly 200 million people use marijuana with growing usage being attributed to the legalization and decriminalization of the drug around the world. A concerning implication of increased marijuana use is the alarming number of individuals who report driving under the influence of the drug, which has prompted the development of detection technologies. An electrochemical-based detection technology, akin to how the alcohol breathalyzer functions, would provide an attractive solution to this growing societal problem. The first step toward this goal is to develop a reaction that converts Δ-tetrahydrocannabinol (Δ-THC), the primary psychoactive substance in marijuana, to a derivative with diagnostic spectroscopic changes. We report the development of a mild electrochemical method for the oxidation of Δ-THC to its corresponding -quinone isomer. The photophysical and electrochemical properties of the resultant quinone show a dramatic shift in comparison to Δ-THC. This simple protocol provides the foundation for the development of an electrochemical-based marijuana breathalyzer.

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References

Hartman R, Huestis M . Cannabis effects on driving skills. Clin Chem. 2012; 59(3):478-92. PMC: 3836260. DOI: 10.1373/clinchem.2012.194381. View

Hanus L, Meyer S, Munoz E, Taglialatela-Scafati O, Appendino G . Phytocannabinoids: a unified critical inventory. Nat Prod Rep. 2016; 33(12):1357-1392. DOI: 10.1039/c6np00074f. View

Manolis A, McBurney L, Bobbie B . The detection of delta 9-tetrahydrocannabinol in the breath of human subjects. Clin Biochem. 1983; 16(4):229-33. DOI: 10.1016/s0009-9120(83)90070-x. View

Lenne M, Dietze P, Triggs T, Walmsley S, Murphy B, Redman J . The effects of cannabis and alcohol on simulated arterial driving: Influences of driving experience and task demand. Accid Anal Prev. 2010; 42(3):859-66. DOI: 10.1016/j.aap.2009.04.021. View

Hwang S, Franconi N, Rothfuss M, Bocan K, Bian L, White D . Tetrahydrocannabinol Detection Using Semiconductor-Enriched Single-Walled Carbon Nanotube Chemiresistors. ACS Sens. 2019; 4(8):2084-2093. DOI: 10.1021/acssensors.9b00762. View

Wanklyn C, Burton D, Enston E, Bartlett C, Taylor S, Raniczkowska A . Disposable screen printed sensor for the electrochemical detection of delta-9-tetrahydrocannabinol in undiluted saliva. Chem Cent J. 2016; 10:1. PMC: 4722664. DOI: 10.1186/s13065-016-0148-1. View

Karkas M . Electrochemical strategies for C-H functionalization and C-N bond formation. Chem Soc Rev. 2018; 47(15):5786-5865. DOI: 10.1039/c7cs00619e. View

Costanzo M, Boock J, Kemperman R, Wei M, Beekman C, Yost R . Portable FAIMS: Applications and Future Perspectives. Int J Mass Spectrom. 2018; 422:188-196. PMC: 5765550. DOI: 10.1016/j.ijms.2016.12.007. View

Ashton C . Adverse effects of cannabis and cannabinoids. Br J Anaesth. 2000; 83(4):637-49. DOI: 10.1093/bja/83.4.637. View

10.

Lai H, Corbin I, Almirall J . Headspace sampling and detection of cocaine, MDMA, and marijuana via volatile markers in the presence of potential interferences by solid phase microextraction-ion mobility spectrometry (SPME-IMS). Anal Bioanal Chem. 2008; 392(1-2):105-13. DOI: 10.1007/s00216-008-2229-z. View

11.

Dronova M, Smolianitski E, Lev O . Electrooxidation of New Synthetic Cannabinoids: Voltammetric Determination of Drugs in Seized Street Samples and Artificial Saliva. Anal Chem. 2016; 88(8):4487-94. DOI: 10.1021/acs.analchem.6b00368. View

12.

Nissim R, Compton R . Absorptive stripping voltammetry for cannabis detection. Chem Cent J. 2015; 9:41. PMC: 4493815. DOI: 10.1186/s13065-015-0117-0. View

13.

Himes S, Scheidweiler K, Beck O, Gorelick D, Desrosiers N, Huestis M . Cannabinoids in exhaled breath following controlled administration of smoked cannabis. Clin Chem. 2013; 59(12):1780-9. PMC: 4537523. DOI: 10.1373/clinchem.2013.207407. View

14.

Lynch K, Luo Y, Hooshfar S, Yun C . Correlation of Breath and Blood Δ-Tetrahydrocannabinol Concentrations and Release Kinetics Following Controlled Administration of Smoked Cannabis. Clin Chem. 2019; 65(9):1171-1179. DOI: 10.1373/clinchem.2019.304501. View

15.

Kingston C, Palkowitz M, Takahira Y, Vantourout J, Peters B, Kawamata Y . A Survival Guide for the "Electro-curious". Acc Chem Res. 2019; 53(1):72-83. PMC: 6996934. DOI: 10.1021/acs.accounts.9b00539. View

16.

Yan M, Kawamata Y, Baran P . Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance. Chem Rev. 2017; 117(21):13230-13319. PMC: 5786875. DOI: 10.1021/acs.chemrev.7b00397. View

17.

Hartman R, Brown T, Milavetz G, Spurgin A, Pierce R, Gorelick D . Cannabis effects on driving lateral control with and without alcohol. Drug Alcohol Depend. 2015; 154:25-37. PMC: 4536116. DOI: 10.1016/j.drugalcdep.2015.06.015. View

18.

Morales P, Vara D, Gomez-Canas M, Zuniga M, Olea-Azar C, Goya P . Synthetic cannabinoid quinones: preparation, in vitro antiproliferative effects and in vivo prostate antitumor activity. Eur J Med Chem. 2013; 70:111-9. DOI: 10.1016/j.ejmech.2013.09.043. View

19.

Mechoulam R, GAONI Y . Hashish--13. On the nature of the Beam test. Tetrahedron. 1968; 24(16):5615-24. DOI: 10.1016/0040-4020(68)88159-1. View

20.

Kogan N, Rabinowitz R, Levi P, Gibson D, Sandor P, Schlesinger M . Synthesis and antitumor activity of quinonoid derivatives of cannabinoids. J Med Chem. 2004; 47(15):3800-6. DOI: 10.1021/jm040042o. View