Metabolic profile of 4F-MDMB-BICA in human urine
- Authors: Kataev S.S.1, Dvorskaya O.N.2, Gofenberg M.A.3,4, Pospelova A.A.1, Tumilovich E.Y.5,6
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Affiliations:
- Hygienic and Epidemiological Center in Perm Region
- South Ural State Medical University
- Regional Narcological Hospital
- Sverdlovsk Regional Clinical Psychiatric Hospital
- Perm State Pharmaceutical Academy
- Parma Clinical LLC
- Issue: Vol 27, No 2 (2024)
- Pages: 22-34
- Section: Pharmaceutical chemistry
- URL: https://journals.eco-vector.com/1560-9596/article/view/627112
- DOI: https://doi.org/10.29296/25877313-2024-02-03
- ID: 627112
Cite item
Abstract
The purpose of the study is to study the metabolic profile of the cannabimimetic 4F-MDMB-BICA in the urine of consumers and to identify markers of 4F-MDMB-BICA use using gas chromatography with a mass spectrometric detector (GC-MS) and liquid chromatography with tandem mass spectrometry (LC-MS/ MS) in the urine of consumers of psychoactive substances, for chemical-toxicological and forensic chemical analysis.
Material and methods. The study of urine samples of 4F-MDMB-BICA cannabimimetic users using enzymatic hydrolysis in combination with solid-phase extraction and gas chromatography with mass spectrometric detection showed that the 4F-MDMB-BICA marker and, in some cases, its nor-metabolite are detected in the urine of consumers. The 4F-MDMB-BICA nor-metabolite is a common biotransformation product for the cannabimimetics 4F-MDMB-BICA and 5F-MDMB-PICA, resulting from the hydrolysis of the ester bond and N-dealkylation of the heterocyclic core.
Results. 35 compounds were identified by liquid chromatography with tandem mass spectrometry, including the original parent 4F-MDMB-BICA, 31 metabolites of biotransformation phases I and II, and 3 metabolite artifacts; it was found that the latter are the product of intramolecular cyclization of 4F-MDMB-BICA metabolites. 16 previously undescribed compounds, including 15 metabolites and one artifact were identified. The putative structures, mass spectra and some characteristics of the identified compounds are given, including retention time, MRM transitions, and relative peak area of the substance.
Conclusion. From the presented data, it can be seen that the main pathways of 4F-MDMB-BICA metabolism in the human body are hydrolysis of the ester group, hydroxylation of alkyl radicals and the heterocyclic core, oxidative defluorination, and N-dealkylation. The hydrolysis products of the ester bond and hydroxyl derivatives are subsequently conjugated with glucuronic acid.
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About the authors
S. S. Kataev
Hygienic and Epidemiological Center in Perm Region
Author for correspondence.
Email: forenschemist@narod.ru
ORCID iD: 0000-0001-6742-2054
Ph.D. (Chem.), Expert Chemist
Russian Federation, PermO. N. Dvorskaya
South Ural State Medical University
Email: dvoksnik@gmail.com
ORCID iD: 0000-0003-4774-8887
Dr.Sc. (Pharm.), Associate Professor, Head of Department of Pharmacy and Chemistry, Dean of the Faculty of Pharmacy
Russian Federation, ChelyabinskM. A. Gofenberg
Regional Narcological Hospital; Sverdlovsk Regional Clinical Psychiatric Hospital
Email: Hoffenberg@yandex.ru
ORCID iD: 0000-0003-2877-1301
Chemical-Toxicological Laboratory, Pharmacist-Analyst, Chemical-Toxicological Laboratory
Russian Federation, Ekaterinburg; EkaterinburgA. A. Pospelova
Hygienic and Epidemiological Center in Perm Region
Email: kuznecovaperm@yandex.ru
Ph.D. (Chem.), Expert Chemist
Russian Federation, PermE. Yu. Tumilovich
Perm State Pharmaceutical Academy; Parma Clinical LLC
Email: e.tumilovich@gmail.com
Ph.D. (Pharm.), Associate Professor, Department of Toxicological Chemistry, Senior Analytical Chemist
Russian Federation, Perm; PermReferences
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