Disposable 3D Printed Electrode for the Electrochemical Detection of Delta-9-Tetrahydrocannabinol in Aqueous Solution and 11-Nor-9-Carboxy-Tetrahydrocannabinol in Saliva

Authors

  • Érica N. Oiye Henbak, Rua Chafic Maluf, 160, São Paulo, SP, Brazil / Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes, 3900, Ribeirão Preto, SP, Brazil
  • Maria Fernanda M. Ribeiro Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes, 3900, Ribeirão Preto, SP, Brazil
  • Bruno Ferreira Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes, 3900, Ribeirão Preto, SP, Brazil
  • Rodrigo C. B. Botelho Henbak, Rua Chafic Maluf, 160, São Paulo, SP, Brazil
  • Marcelo Firmino De Oliveira Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes, 3900, Ribeirão Preto, SP, Brazil

DOI:

https://doi.org/10.17063/bjfs9(4)y2020521-533

Keywords:

Forensic electroanalysis, Delta-9-tetrahydrocannabinol, Saliva, Voltammetry, 3D-printed electrode

Abstract

Currently, marijuana or cannabis is the most consumed drug worldwide, and is also the one with the highest number of seizures, with 354 tons seized in Brazil in 2017. The increase in its consumption has been called attention, not only by the authorities, due to accidents caused when driving under the influence of the drug, but also by companies that carry out toxicological analyzes on their employees. For this, rapid tests, such as colorimetric tests, are generally used to analyze the urine of users. The need for agile and proper identification of drugs of abuse has encouraged the scientific community to improve and to develop new methodologies. Electrochemical methods appear as a cheap, portable and easy to use alternative. The use of biodegradable materials for the development of disposable electrodes has become paramount today. The use of 3D printers emerges as an alternative for the manufacture of these electrodes and the use of saliva instead of urine, has also been a priority because it is a less invasive sample and difficult to adulterate. In this work, a three dimensional device was created in an innovative way containing the three electrodes, working, counter and reference, in conductive material. The device was then used to detect the active principle present in cannabis, delta-9-tetrahydrocannabinol, in aqueous solution, and its metabolite, 11-nor-9-carboxy-THC, in samples of real saliva, both through cyclic voltammetry. The positive results show that the proposed device can be used, as well as those already found on the market, for the identification of drug use and in the forensic field.

References

Bonini SA, Premoli M, Tambaro S, Kumar A, Maccarinelli G, Memo M, Mastinu A. Cannabis sativa: a comprehensive ethnopharmacological review of a medicinal plant with a long history. J Ethnopharmacol. 2018;227:300-315. https://doi.org/10.1016/j.jep.2018.09.004

United Nations Office on Drugs and Crime. World Drug Report 2019. Retrieved from https://wdr.unodc.org/wdr2019/.

Piluzza G, Delogu G, Cabras A, Marceddu A, Billitta S. Differentiation between fiber and drug types of hemp (Cannabis sativa L.) from a collection of wild and domesticated accessions. Genet Resour Crop Ev. 2013;60:2331-2342. https://doi.org/10.1007/s10722-013-0001-5

Kuddus M, Ginawi IAM, Al-Hazimi A. Cannabis sativa: an ancient wild edible plant of India. Emir J Food Agr. 2013;25(10):736-745. https://doi.org/10.9755/ejfa.v25i10.16400

D’Souza DC, Radhakrishnan R, Sherif M, Cortes-Briones J, Cahill J, Gupta S, Skosnik PD, Ranganathan M. Cannabinoids and psychosis. Curr Pharm Design. 2016;22:6380-6391. https://doi.org/10.2174/1381612822666160826105628

Fernández-Artamendi S, Fernández-Hermida JR, Secades-Villa R, Garcia-Portilla P. Cannabis and mental health. Actas Esp Psiquiatri. 2011;39(3):180-90.

United Nations Office on Drugs and Crime (UNODC). World Drug Report 2017. Retrieve from https://wdr.unodc.org/wdr2019/.

Polícia Federal. Estatística de Drogas Apreendidas. Retrieved from http://www.pf.gov.br/imprensa/estatistica/drogas/.

Lee D, Huestis MA. Current knowledge on cannabinoids in oral fluid. Drug Test Anal. 2014;6(0):88-111. https://doi.org/10.1002/dta.1514

Wille SMR, Ramírez-Fernandez MM, Samyn N, Boeck GD. Conventional and alternative matrices for driving under the influence of cannabis: recent progress and remaining challenges. Bioanalysis. 2010;2(4):791-806. https://doi.org/10.4155/bio.10.29

Huestis MA. Human cannabinoid pharmacokinetics. Chem Biodivers. 2007;4(8):1770-1804. https://doi.org/10.1002/cbdv.200790152

De Giovanni N, Fucci N. The state of the art on the use of oral fluid as alternative specimen in forensic toxicology. Curr Pharm Anal. 2008;4:258-273. https://doi.org/10.2174/157341208786306180

Bosker WM, Huestis MA. Oral fluid testing for drugs of abuse. Clin Chem. 2009;55(11):1910-1931. https://doi.org/10.1373/clinchem.2008.108670

Biermann T, Schwarze B, Zedler B, Betz P. On-site testing of illicit drugs: the use of th drug-testing device ‘‘Toxiquick®’’. Forensic Sci Int. 2004;143:21-25. https://doi.org/10.1016/j.forsciint.2004.01.013

Bondallaz P, Favrat B, Chtioui H, Fornari E, Maeder P, Giroud C. Cannabis and its effects on driving skills. Forensic Sci Int. 2016;268:92-102. https://doi.org/10.1016/j.forsciint.2016.09.007

Barthwell AG, Allgaier J, Egli K. Definitive urine drug testing in office-based opioid treatment: a literature review. Crit Rev Toxicol. 2018;48(10):815-838. https://doi.org/10.1080/10408444.2018.1553935

Allen KR. Screening for drugs of abuse: which matrix, oral fluid or urine?. Ann Clin Bioche. 2011;48:531-541. https://doi.org/10.1258/acb.2011.011116

Campos DR, Yonamine M, Moreau RLM. Marijuana as Doping in Sports. Sports Med. 2003;33(6):395-399. https://doi.org/10.2165/00007256-200333060-00001

Moore C, Crouch D. Oral fluid for the detection of drugs of abuse using immunoassay and LC–MS/MS. Bioanalysis. 2013;5(12):1555-1569. https://doi.org/10.4155/bio.13.115

Nie Z, Nijhuis CA, Gong J, Chen X, Kumachev A, Martinez AW, Narovlyansky M, Whitesides GM. Electrochemical sensing in paper-based microfluidic devices†. Lab Chip. 2010;10(4):477-483. https://doi.org/10.1039/B917150A

Wang Y, Xu H, Zhang J, Li G. Electrochemical sensors for clinic analysis. Sensors. 2008;8:2043-2081. https://doi.org/10.3390/s8042043

Crespi F. In vivo voltammetry and concomitant electrophysiology at a single micro-biosensor to analyse ischaemia, depression and drug dependence. J Neurosci Meth. 2002;119:173-184. https://doi.org/10.1016/S0165-0270(02)00176-0

Pavlova V, Mirceski V, Komorsky-Lovric S, Petrovska-Jovanovic S, Mitrevski B. Studying electrode mechanism and analytical determination of cocaine and its metabolites at the mercury electrode using square-wave voltammetry. Anal Chim Acta. 2004;512:49-56. https://doi.org/10.1016/j.aca.2004.02.035

Komorsky-Lovric S, Gagic S, Penovski R. Voltammetric determination of benzoylecgonine. Anal Chim Acta. 1999;389:219-223. https://doi.org/10.1016/S0003-2670(99)00091-4

Chen N, Trowbridge CG, Justice JB Jr. Voltammetric studies on mechanisms of dopamine efflux in the presence of substrates and cocaine from cells expressing human norepinephrine transporter. J. Neurochem. 1998;71(2):653-665. https://doi.org/10.1046/j.1471-4159.1998.71020653.x

Novak I, Mlakar M, Komorsky-Lovric S. Voltammetry of immobilized particles of cannabinoids. Electroanal. 2013;25(12):2631-2636. https://doi.org/10.1002/elan.201300410

Balbino MA, Menezes MMT, Eleotério IC, Saczk AA, Okumura LL, Tristão HM, Oliveira MF. Voltammetric determination of Δ9-THC in glassy carbon electrode: An important contribution to forensic electroanalysis. Forensic Sci Int. 2012;221:29-32. https://doi.org/10.1016/j.forsciint.2012.03.020

Balbino MA, Oliveira LS, Eleotério IC, Oiye EN, Ribeiro MFM, McCord BR, Ipolito AJ, Oliveira MF. The application of voltammetric analysis of Δ9-THC for the reduction of false positive results in the analysis of suspected marijuana plant matter. J Forensic Sci. 2016;61(4):1067-1073. https://doi.org/10.1111/1556-4029.13059

Balbino MA, Oiye EN, Ribeiro MFM, Junior JWC, Eleotério IC, Ipolito AJ, Oliveira MF. Use of screen-printed electrodes for quantification of cocaine and Δ9-THC: adaptions to portable systems for forensic purposes. J Solid State Electr. 2016;20:2435-2443. https://doi.org/10.1007/s10008-016-3145-3

Balbino MA, Eleotério IC, Oliveira LS, Menezes MMT, Andrade JF, Ipolito AJ, Oliveira MF. Comparative study between two different conventional working electrodes for detection of Δ9-Tetrahydrocannabinol using square-wave voltammetry: a new sensitive method for forensic analysis. J Brazil Chem Soc. 2014;25(3):589-596. https://doi.org/10.5935/0103-5053.20140040

Goodwin A, Banks CE, Compton RG. Graphite micropowder modified with 4-amino-2,6-diphenylphenol supported on basal plane Pprolytic graphite electrodes: micro sensing platforms for the indirect electrochemical detection of Δ9-Tetrahydrocannabinol in saliva. Electroanal. 2006;18(11):1063-1067. https://doi.org/10.1002/elan.200603518

Nissim R, Compton RG. Absorptive stripping voltammetry for cannabis detection. Chem Cent J. 2015;9:41. https://doi.org/10.1186/s13065-015-0117-0

Wanklyn C, Burton D, Enston E, Bartlett CA, Taylor S, Raniczkowska A, Black M, Murphy L. Disposable screen printed sensor for the electrochemical detection of delta‑9‑tetrahydrocannabinol in undiluted saliva. Chem Cent J. 2016;10:1-11. https://doi.org/10.1186/s13065-016-0148-1

Stephens B, Azimi P, El Orch Z, Ramos T. Ultrafine particle emissions from desktop 3D printers. Atmos Environ. 2013;79:334-339. https://doi.org/10.1186/s13065-016-0148-1

Palenzuela CLM, Novotný F, Krupička P, Sofer Z, Pumeraa M. 3D-Printed graphene/polylactic acid electrodes promise high sensitivity in electroanalysis. Anal Chem. 2018;90:5753-5757. https://doi.org/10.1021/acs.analchem.8b00083

Júnior PCG, Santos VB, Lopes AS, Souza JPI, Pina JRS, Junior GCAC, Marinho PSB. Determination of theobromine and caffeine in fermented and unfermented Amazonian cocoa (Theobroma cacao L.) beans using square wave voltammetry after chromatographic separation. Food Control. 2020;108:106887. https://doi.org/10.1016/j.foodcont.2019.106887

Katseli V, Economou A, Kokkinos C. A novel all-3D-printed cell-on-a-chip device as a useful electroanalytical tool: Application to the simultaneous voltammetric determination of caffeine and paracetamol. Talanta. 2020;208:120388. https://doi.org/10.1016/j.talanta.2019.120388

Oliveira MF, Balbino MA, “Método de análise química, direta qualitativa e quantativa de Δ9 tetraidrocanabinol”, Bazilian Patent PI 1104489-6, filed September 23, 2011, issued August 13, 2013.

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Published

2020-09-28

How to Cite

N. Oiye, Érica, M. Ribeiro, M. F., Ferreira, B., C. B. Botelho, R., & Marcelo Firmino De Oliveira. (2020). Disposable 3D Printed Electrode for the Electrochemical Detection of Delta-9-Tetrahydrocannabinol in Aqueous Solution and 11-Nor-9-Carboxy-Tetrahydrocannabinol in Saliva. Brazilian Journal of Forensic Sciences, Medical Law and Bioethics, 9(4), 521–533. https://doi.org/10.17063/bjfs9(4)y2020521-533

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Comunicação Breve