nbsprotВестник войск РХБ защитыJournal of NBC Protection Corps2587-57283034-279127 Научный центр10.35825/2587-5728-2022-6-4-320-341eukkmsnbsprot-33Research ArticleПРОБЛЕМЫ СОБЛЮДЕНИЯ КОНВЕНЦИЙ ПО ЗАПРЕЩЕНИЮ ХИМИЧЕСКОГО И БИОЛОГИЧЕСКОГО ОРУЖИЯISSUES OF COMPLIANCE WITH CHEMICAL AND BIOLOGICAL WEAPONS CONVENTIONSСовременные психоактивные вещества и их обнаружение в биомедицинских пробахModern Psychoactive Substances and Their Detection in Biomedical SamplesГригорьевА. М.GrigoryevA. M.

Григорьев Андрей Михайлович. Старший научный сотрудник. Доктор химических наук.

111004, г. Москва, Проезд Энтузиастов, д. 19

Andrej Mihajlovich Grigoryev. Research associate. Grand PhD in Chemistry.

Entuziastov passage, 19, Moscow 111024

 

27nc_1@mil.ruФатеенковВ. Н.FateenkovV. N.

Фатеенков Дмитрий Николаевич. Начальник отдела. Кандидат военных наук, доцент, профессор АВН.

111004, г. Москва, Проезд Энтузиастов, д. 19

Dmitry Nikolaevich Fateenkov. Head of Department. PhD in Military Sciences, Associate Professor, Professor at the AMS.

Entuziastov passage, 19, Moscow 111024

27nc_1@mil.ruФедеральное государственное бюджетное учреждение «27 Научный центр» Министерства обороны Российской ФедерацииРоссияFederal State Budgetary Establishment «27 Scientific Centre» of the Ministry of Defence of the Russian FederationRussian Federation20221605202364320341Copyright © Григорьев А.М., Фатеенков В.Н., 20232023Григорьев А.М., Фатеенков В.Н.Grigoryev A.M., Fateenkov V.N.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.nbsprot.ru/jour/article/view/33

Научные и технологические достижения середины и конца ХХ в. привели к созданию большого количества новых психоактивных веществ (НПВ), разнообразных по составу и спектру действия. Первичными этапами борьбы с распространением НПВ являются информированность об их характеристиках, а также возможность обнаружения как самих веществ, так и биомаркеров их употребления (метаболитов) в биологических объектах человека. Цель работы – обзор психоактивных соединений и способов их обнаружения, выполняемых с диагностическими целями. В работе представлены краткие характеристики наиболее распространенных НПВ, а также особенности их метаболизма в организме человека. Показано, что анализ биопроб, отбираемых у предполагаемых потребителей наркотиков, сложен ввиду малого содержания аналитов, влияния матрицы, метаболизма и образования разнообразных артефактов. Общая схема скрининга биообъектов предполагает наличие двух стадий – предварительного экспресс-анализа, выполняемого с помощью иммунохимических тест-систем, и подтверждающего анализа, выполняемого методами газовой и жидкостной хроматомасс-спектрометрии. В статье рассмотрены возможности и ограничения целевого и нецелевого скрининга. Предметом специального рассмотрения стали проблемы применения хроматомасс-спектрометрических методов анализа НПВ в российских условиях – вопросы доступа к стандартным веществам, поисковым библиотекам и т.д. В работе также представлены краткие характеристики отдельных семейств НПВ – стимуляторов, синтетических каннабиноидов, синтетических опиоидов и галлюциногенов. Кроме того, в статье показано, что в ряде иностранных армий, в частности, в вооруженных силах Украины (ВСУ), наркотики и психостимуляторы используются для создания «бесстрашных солдат». Так, в пробах с объектов, доставленных с позиций ВСУ для анализа, были обнаружены метадон, амфетамин и другие психоактивные вещества, а также психотомиметик – структурное и фармакологическое подобие запрещенного BZ.

Scientific and technological advancement of the mid- and late twentieth century led to the creation of a large number of new psychoactive substances (NPS), diverse in composition and spectrum of action. The primary stages of fight the spread of NPS are awareness of their characteristics, as well as the possibility of detecting both the substances themselves and biomarkers of their use (metabolites) in human biological objects. The purpose of the work is to review psychoactive compounds and methods of their detection performed for diagnostic purposes. The paper presents brief characteristics of the most common NPS, as well as features of their metabolism in the human. It is shown that the analysis of biological specimens collected from susceptive drug users is difficult due to the low content of analytes, the matrix influences, metabolism and the formation of various artifacts. The general scheme of screening of biological objects assumes the presence of two stages – a preliminary express analysis performed using immunochemical test systems, and a confirmatory analysis performed by gas and liquid chromatography-mass spectrometry. The article discusses the possibilities and limitations of targeted and non-targeted screening. The subject of special consideration was the problems of using chromatography-mass spectrometry methods of NPS analysis in Russian – issues of accessibility of standard substances, search libraries, etc. The article also presents brief characteristics of individual families of NPS, such as stimulants, synthetic cannabinoids, synthetic opioids and hallucinogens. In addition, the article shows that in a number of foreign armies, in particular, in the Armed forces of Ukraine (AFU), drugs and psychostimulants are used to create «fearless soldiers». Thus, methadone, amphetamine and other psychoactive substances, as well as a psychotomimetic – a structural and pharmacological similarity of the prohibited BZ – were found in objects delivered from the positions of the AFU for analysis.

амфетаминбиообъектыгазовая хроматомасс-спектрометриягаллюциногеныжидкостная хроматомасс-спектрометрияиммунохимический анализметаболизмметадоннаркотические средствапсихоактивные веществаРоссиясинтетические каннабиноидысинтетические опиоидыскринингстимуляторыУкраинаэкспресс-анализBZamphetaminebiological objectgas chromatography-mass spectrometryhallucinogenliquid chromatography-mass spectrometryimmunochemical assaymetabolismmethadonenarcotic drugspsychoactive substancesRussiasynthetic cannabinoidssynthetic opioidsscreeningstimulatorsUkraineexpress analysisBZФедеральное государственное бюджетное учреждение «27 Научный центр» Министерства обороны Российской ФедерацииFederal State Budgetary Establishment «27 Scientific Centre» of the Ministry of Defence of the Russian Federation.ReferencesСимонов Е.А., Найденова Л.Ф., Ворнаков С.А. Наркотические средства и психотропные вещества, контролируемые на территории Российской Федерации. М.: «InterLab», 2003. 413 с.Simonov E.A., Naydenova L.F., Vornakov S.A. Narcotic drugs and psychotropic substances controlled on the territory of the Russian Federation. Moscow: «InterLab», 2003. 413 р. (in Russian).Еремин С.К., Изотов Б.Н., Веселовская Н.В. Анализ наркотических средств. М.: «Мысль», 1993. 272 с.Eremin S.K., Izotov B.N., Veselovskaya N.V. Analysis of drugs. Moscow: «Mysl», 1993. 272 p. (in Russian).Граник В.Г. Метаболизм экзогенных соединений. М.: «Вузовская книга», 2015. 526 с.Granik V.G. Metabolism of exogenous compounds. Moscow: «Vuzovskaya Kniga», 2015. 526 p. (in Russian).Smith D., van de Waterbeemd H., Walker D.K. Pharmacokinetics and metabolism in drug design. Weinheim: Wiley-VCH Verlag GmbH, 2001. 141 p.Smith D., van de Waterbeemd H., Walker D.K. Pharmacokinetics and metabolism in drug design. Weinheim: Wiley-VCH Verlag GmbH, 2001. 141 p.Григорьев А.М., Крупина Н.А., Никитин Е.В. и др. Исследование метаболизма нового синтетического каннабиноида MMB-022 в моделях in vivo и in vitro методом жидкостной хроматомасс-спектрометрии // Масс-спектрометрия. 2020. Т. 17. № 3. С. 151– 161. https://doi.org/10.25703/MS.2020.17.33Grigoryev A.M., Krupina N.A., Nikitin E.V. et al. Study of the metabolism of the new synthetic cannabinoid MMB-022 in in vivo and in vitro models by liquid chromatography-mass spectrometry // Mass Spectrometry. 2020. V. 17. № 3. P. 151–161. (in Russian). https://doi.org/10.25703/MS.2020.17.33Teske J., Weller J.P., Fieguth A. et al. Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in human serum by liquid chromatography– tandem mass spectrometry // J. Chromatogr. B. 2010. V. 878. P. 2959–2663.Teske J., Weller J.P., Fieguth A. et al. Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in human serum by liquid chromatography– tandem mass spectrometry // J. Chromatogr. B. 2010. V. 878. P. 2959–2663.Grigoryev A., Savchuk S., Melnik A. et al. Chromatography–mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures // J. Chromatogr. B. 2011. V. 879. P. 1126.Grigoryev A., Savchuk S., Melnik A. et al. Chromatography–mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures // J. Chromatogr. B. 2011. V. 879. P. 1126.Brenneisen R., Meyer P., Chtioui H. et al. Plasma and urine profiles of Δ9-tetrahydrocannabinol and its metabolites 11-hydroxy-Δ9-tetrahydrocannabinol and 11-nor-9-carboxy-Δ9-tetrahydrocannabinol after cannabis smoking by male volunteers to estimate recent consumption by athletes // Anal. Bioanal. Chem. 2010. V. 396. P. 2493–2502.Brenneisen R., Meyer P., Chtioui H. et al. Plasma and urine profiles of Δ9-tetrahydrocannabinol and its metabolites 11-hydroxy-Δ9-tetrahydrocannabinol and 11-nor-9-carboxy-Δ9-tetrahydrocannabinol after cannabis smoking by male volunteers to estimate recent consumption by athletes // Anal. Bioanal. Chem. 2010. V. 396. P. 2493–2502.Grigoryev A., Kavanagh P., Labutin A. et al. Tentative identification of the metabolites of (1‐(cyclohexylmethyl)‐1H‐indol‐3‐yl)‐(2,2,3,3‐ tetramethylcyclopropyl)methanone, and the product of its thermal degradation, by in vitro and in vivo methods // Drug Test Anal. 2019. V. 11. № 9. P. 1387–1402. https://doi.org/10.1002/dta.2668Grigoryev A., Kavanagh P., Labutin A. et al. Tentative identification of the metabolites of (1‐(cyclohexylmethyl)‐1H‐indol‐3‐yl)‐(2,2,3,3‐ tetramethylcyclopropyl)methanone, and the product of its thermal degradation, by in vitro and in vivo methods // Drug Test Anal. 2019. V. 11. № 9. P. 1387–1402. https://doi.org/10.1002/dta.2668Темердашев А.З., Григорьев А.М., Рыбальченко И.В. Наркотические средства природного происхождения и методы их определения // Ж. аналит. химии. 2016. Т. 71. № 1. С. 3–22. https://doi.org/10.7868/S004445021601014XTemerdashev A.Z., Grigoryev A.M., Rybalchenko I.V. Narcotic drugs of natural origin and methods for their determination // J. Anal. Chem. 2016. V. 71. № 1. P. 3–22. (in Russian). https://doi.org/10.7868/S004445021601014XТемердашев А.З., Григорьев А.М., Рыбальченко. И.В. Эволюция новых наркотических средств и методы их определения // Ж. аналит. химии. 2014. Т. 69. № 9. С. 1–28. https://doi.org/10.7868/S0044450214090114Temerdashev A.Z., Grigoryev A.M., Rybalchenko I.V. The evolution of new drugs and methods for their determination // J. Anal. Chem. 2014. V. 69. № 9. P. 1–28. (in Russian). https://doi.org/10.7868/S0044450214090114Flanagan R.J., Cuypers E., Maurer H.H., Whelpton R. Fundamentals of analytical toxicology. New York: John Wiley & Sons, Ltd, 2020. 599 p.Flanagan R.J., Cuypers E., Maurer H.H., Whelpton R. Fundamentals of analytical toxicology. New York: John Wiley & Sons, Ltd, 2020. 599 p.Григорьев А.М., Реброва С.Г., Крупина Н.А. Скрининговые процедуры при анализе объектов биологического происхождения методом жидкостной хроматографии/масс-спектрометрии: возможные затруднения // Наркология. 2016. № 10. С. 88–100.Grigoryev A.M., Rebrova S.G., Krupina N.A. Screening procedures in the analysis of objects of biological origin by liquid chromatography/mass spectrometry: possible difficulties // Narcology. 2016. № 10. P. 88–100. (in Russian).Hutter M., Kneisel S., Auwärter V., Neukamm M.A. Determination of 22 synthetic cannabinoids in human hair by liquid chromatographytandem mass spectrometry // J. Chromatogr. B. 2012. V. 903. P. 95–101. https://doi.org/10.1016/j.jchromb.2012.07.002Hutter M., Kneisel S., Auwärter V., Neukamm M.A. Determination of 22 synthetic cannabinoids in human hair by liquid chromatographytandem mass spectrometry // J. Chromatogr. B. 2012. V. 903. P. 95–101. https://doi.org/10.1016/j.jchromb.2012.07.002Maurer H.H. Multi-analyte procedures for screening for and quantification of drugs in blood, plasma, or serum by liquid chromatography-single stage or tandem mass spectrometry (LC-MS or LC-MS/MS) relevant to clinical and forensic toxicology // Clin. Biochem. 2005. V. 38. № 4. P. 310–318. https://doi.org/10.1016/j.clinbiochem.2005.01.014Maurer H.H. Multi-analyte procedures for screening for and quantification of drugs in blood, plasma, or serum by liquid chromatography-single stage or tandem mass spectrometry (LC-MS or LC-MS/MS) relevant to clinical and forensic toxicology // Clin. Biochem. 2005. V. 38. № 4. P. 310–318. https://doi.org/10.1016/j.clinbiochem.2005.01.014Kempf J., Traber J., Auwärter V., Huppertz L.M. ‘Psychotropics caught in a trap’ – adopting a screening approach to specific needs // Forensic Sci. Int. 2014. V. 243. P. 84–89. https://doi.org/10.1016/j.forsciint.2014.04.035Kempf J., Traber J., Auwärter V., Huppertz L.M. ‘Psychotropics caught in a trap’ – adopting a screening approach to specific needs // Forensic Sci. Int. 2014. V. 243. P. 84–89. https://doi.org/10.1016/j.forsciint.2014.04.035Wissenbach D.K., Meyer M.R., Remane D. et al. Drugs of abuse screening in urine as part of a metabolite-based LC-MSn screening concept // Anal. Bioanal. Chem. 2011. V. 40. № 10. P. 3481–3489. https://doi.org/10.1007/s00216-011-5032-1Wissenbach D.K., Meyer M.R., Remane D. et al. Drugs of abuse screening in urine as part of a metabolite-based LC-MSn screening concept // Anal. Bioanal. Chem. 2011. V. 40. № 10. P. 3481–3489. https://doi.org/10.1007/s00216-011-5032-1Broecker S., Herre S., Pragst F. General unknown screening in hair by liquid chromatographyhybrid quadrupole time-of-flight mass spectrometry (LC-QTOF-MS) // Forensic Sci. Int. 2012. V. 218. № 1-3. P. 68–81. https://doi.org/10.1016/j.forsciint.2011.10.004Broecker S., Herre S., Pragst F. General unknown screening in hair by liquid chromatographyhybrid quadrupole time-of-flight mass spectrometry (LC-QTOF-MS) // Forensic Sci. Int. 2012. V. 218. № 1-3. P. 68–81. https://doi.org/10.1016/j.forsciint.2011.10.004Li Z., Huang X., Wang X., Ren J., Xu B., Wang Y., Zou X., Wang L. Establishment and application of a screening method for 354 organic toxicants in blood and urine with high-performance liquid chromatographyhigh resolution orbitrap mass spectrometry // Anal. Bioanal. Chem. 2022. In press.Li Z., Huang X., Wang X., Ren J., Xu B., Wang Y., Zou X., Wang L. Establishment and application of a screening method for 354 organic toxicants in blood and urine with high-performance liquid chromatographyhigh resolution orbitrap mass spectrometry // Anal. Bioanal. Chem. 2022. In press.Recommended operating procedures for analysis in the verification of chemical disarmament / Ed. Vannien P. Helsinki: University of Helsinki, 2017. 809 p. http://www.helsinki.fi/veri-fin/bluebookRecommended operating procedures for analysis in the verification of chemical disarmament / Ed. Vannien P. Helsinki: University of Helsinki, 2017. 809 p. http://www.helsinki.fi/veri-fin/bluebookBadoud F., Grata E., Perrenoud L., Avois L. et al. Fast analysis of doping agents in urine by ultrahigh-pressure liquid chromatography–quadrupole time-of-flight mass spectrometry I. Screening analysis // J. Chromatogr. A. 2009. V. 1216. № 20. P. 4423–4433. https://doi.org/10.1016/j.chroma.2009.03.033Badoud F., Grata E., Perrenoud L., Avois L. et al. Fast analysis of doping agents in urine by ultrahigh-pressure liquid chromatography–quadrupole time-of-flight mass spectrometry I. Screening analysis // J. Chromatogr. A. 2009. V. 1216. № 20. P. 4423–4433. https://doi.org/10.1016/j.chroma.2009.03.033Maurer H.H. Systematic toxicological analysis of drugs and their metabolites by gas chromatographymass spectrometry // J. Chromatogr. B. 1992. V. 580. № 1-2. P. 3–41. https://doi.org/10.1016/0378-4347(92)80526-vMaurer H.H. Systematic toxicological analysis of drugs and their metabolites by gas chromatographymass spectrometry // J. Chromatogr. B. 1992. V. 580. № 1-2. P. 3–41. https://doi.org/10.1016/0378-4347(92)80526-vMaurer H.H. Systematic toxicological analysis procedures for acidic drugs and/or metabolites relevant to clinical and forensic toxicology and/or doping control // J. Chromatogr. B. 1999. V. 733. № 1-2. P. 3 –25. https://doi.org/10.1016/s0378-4347(99)00266-2Maurer H.H. Systematic toxicological analysis procedures for acidic drugs and/or metabolites relevant to clinical and forensic toxicology and/or doping control // J. Chromatogr. B. 1999. V. 733. № 1-2. P. 3 –25. https://doi.org/10.1016/s0378-4347(99)00266-2Grigoryev A., Kavanagh P., Dowling G., Rodin I. Tentative identification of etazene (etodesnitazene) metabolites in rat serum and urine by gas chromatography-mass spectrometry and accurate mass liquid chromatography-mass spectrometry // J. Anal. Toxicol. 2022. bkac001. https://doi.org/10.1093/jat/bkac001Grigoryev A., Kavanagh P., Dowling G., Rodin I. Tentative identification of etazene (etodesnitazene) metabolites in rat serum and urine by gas chromatography-mass spectrometry and accurate mass liquid chromatography-mass spectrometry // J. Anal. Toxicol. 2022. bkac001. https://doi.org/10.1093/jat/bkac001Papaseit E., Moltó J., Muga R. et al. Clinical pharmacology of the synthetic cathinone mephedrone // Curr. Top. Behav. Neurosci. 2017. V. 32. P. 313–332. https://doi.org/10.1007/7854_2016_61Papaseit E., Moltó J., Muga R. et al. Clinical pharmacology of the synthetic cathinone mephedrone // Curr. Top. Behav. Neurosci. 2017. V. 32. P. 313–332. https://doi.org/10.1007/7854_2016_61Заикина О.Л., Шилов В.В., Лодягин А.Н. и др. Установление структур свободных и глюкуронидированных метаболитов α-пирролидиновалерофенона в моче человека методом жидкостной хроматомасс-спектрометрии при измерении точных масс // Ж. аналит. химии. 2019. Т. 74. № 5. С. 381–396. https://doi.org/10.1134/S0044450219020130Zaikina O.L., Shilov V.V., Lodyagin A.N. et al. Establishment of the structures of free and glucuronidated metabolites of α-pyrrolidinovalerophenone in human urine by liquid chromatography-mass spectrometry when measuring accurate masses // J. Anal. Chem. 2019. V. 74. № 5. P. 381–396. https://doi.org/10.1134/S0044450219020130de la Torre R., Farré M., Roset P.N. et al. Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition // Ther. Drug Monit. 2004. V. 26. № 2. P. 137–144. (in Russian). https://doi.org/10.1097/00007691-200404000-00009de la Torre R., Farré M., Roset P.N. et al. Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition // Ther. Drug Monit. 2004. V. 26. № 2. P. 137–144. (in Russian). https://doi.org/10.1097/00007691-200404000-00009Olesti E., Farré M., Papaseit E. et al. Pharmacokinetics of mephedrone and its metabolites in human by LC-MS/MS // AAPS J. 2017. V. 19. № 6. P. 1766–1778. https://doi.org/10.1208/s12248-017-0132-2Olesti E., Farré M., Papaseit E. et al. Pharmacokinetics of mephedrone and its metabolites in human by LC-MS/MS // AAPS J. 2017. V. 19. № 6. P. 1766–1778. https://doi.org/10.1208/s12248-017-0132-2Kavanagh P., Gofenberg M., Shevyrin V. et al. Tentative identification of the phase I and II metabolites of two synthetic cathinones, MDPHP and α-PBP, in human urine // Drug Test. Anal. 2020. V. 12. № 10. P. 1442–1451. https://doi.org/10.1002/dta.2891Kavanagh P., Gofenberg M., Shevyrin V. et al. Tentative identification of the phase I and II metabolites of two synthetic cathinones, MDPHP and α-PBP, in human urine // Drug Test. Anal. 2020. V. 12. № 10. P. 1442–1451. https://doi.org/10.1002/dta.2891Никитин Е.В., Григорьев А.М., Грибкова С.Е. и др. Хроматомасс-спектрометрические характеристики новых дизайнерских катинонов, а также их метаболитов, полученных с помощью in vivo и in vitro методов // Масс-спектрометрия. 2020. Т. 17. № 2. С. 112–121. https://doi.org/10.25703/MS.2020.17.24Nikitin E.V., Grigoryev A.M., Gribkova S.E. et al. Chromatography-mass spectrometric characteristics of new designer cathinones, as well as their metabolites obtained using in vivo and in vitro methods // Mass spectrometry. 2020. V. 17. № 2. P. 112–121. (in Russian). https://doi.org/10.25703/MS.2020.17.24The cannabinoid receptors / Ed. Reggio P.H. New York: Humana Press, 2009. 396 p.The cannabinoid receptors / Ed. Reggio P.H. New York: Humana Press, 2009. 396 p.Makriyannis A., Deng H. Cannabimimetic Indole Derivatives. US Patent No. 208/0090871, 2008. 33. Гончаров Е.В., Кондрасенко А.А., Петерсон И.В. и др. Идентификация и аналитические профили синтетического каннабиноида 3,3-диметил2-(2-(1-(4-фторбензил)-1H-индол-3-ил)ацетамидо) бутанамида (ADB-FUBIATA, FUB-ACADB) // Бутлеровские сообщения. 2021. Т. 68. № 10. С. 133–140. https://doi.org/10.37952/ROI-jbc-01/21-68-10-133Makriyannis A., Deng H. Cannabimimetic Indole Derivatives. US Patent No. 208/0090871, 2008. 33. Гончаров Е.В., Кондрасенко А.А., Петерсон И.В. и др. Идентификация и аналитические профили синтетического каннабиноида 3,3-диметил2-(2-(1-(4-фторбензил)-1H-индол-3-ил)ацетамидо) бутанамида (ADB-FUBIATA, FUB-ACADB) // Бутлеровские сообщения. 2021. Т. 68. № 10. С. 133–140. https://doi.org/10.37952/ROI-jbc-01/21-68-10-133Goncharov E.V., Kondrasenko A.A., Peterson I.V. et al. Identification and analytical profiles of the synthetic cannabinoid 3,3-dimethyl-2-(2-(1-(4-fluorobenzyl)-1Hindol-3-yl)acetamido)butanamide (ADB-FUBIATA, FUB-ACADB) // Butlerov Readings. 2021. V. 68. № 10. P. 133–140. (in Russian). https://doi.org/10.37952/ROIjbc-01/21-68-10-133Goncharov E.V., Kondrasenko A.A., Peterson I.V. et al. Identification and analytical profiles of the synthetic cannabinoid 3,3-dimethyl-2-(2-(1-(4-fluorobenzyl)-1Hindol-3-yl)acetamido)butanamide (ADB-FUBIATA, FUB-ACADB) // Butlerov Readings. 2021. V. 68. № 10. P. 133–140. (in Russian). https://doi.org/10.37952/ROIjbc-01/21-68-10-133Liu C.-M., Hua Z.-D., Jia W., Li T. Identification of AD-18, 5F-MDA-19, and pentyl MDA-19 in seized materials after the class-wide ban of synthetic cannabinoids in China // Drug Test. Anal. 2022. V. 14. № 2. P. 307–316. https://doi.org/10.1002/dta.3185Liu C.-M., Hua Z.-D., Jia W., Li T. Identification of AD-18, 5F-MDA-19, and pentyl MDA-19 in seized materials after the class-wide ban of synthetic cannabinoids in China // Drug Test. Anal. 2022. V. 14. № 2. P. 307–316. https://doi.org/10.1002/dta.3185Kavanagh P., Pechnikov A., Nikolaev I. et al. Detection of ADB-BUTINACA metabolites in human urine, blood, kidney and liver // J. Anal. Toxicol. 2022. V. 46. № 6. P. 641–650. https://doi.org/10.1093/jat/bkab088Kavanagh P., Pechnikov A., Nikolaev I. et al. Detection of ADB-BUTINACA metabolites in human urine, blood, kidney and liver // J. Anal. Toxicol. 2022. V. 46. № 6. P. 641–650. https://doi.org/10.1093/jat/bkab088Meyer M.R., Maurer H.H. Absorption, distribution, metabolism and excretion pharmacogenomics of drugs of abuse // Pharmacogenomics. 2011. V. 12. № 2. P. 215–233. https://doi.org/10.2217/pgs.10.171Meyer M.R., Maurer H.H. Absorption, distribution, metabolism and excretion pharmacogenomics of drugs of abuse // Pharmacogenomics. 2011. V. 12. № 2. P. 215–233. https://doi.org/10.2217/pgs.10.171Higashikawa Y., Suzuki S. Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and its related compounds. VI. Structure– analgesic activity relationship for fentanyl, methylsubstituted fentanyls and other analogues // Forensic. Toxicol. 2008. V. 26. № 1. P. 1–5. https://doi.org/10.1007/s11419-007-0039-1Higashikawa Y., Suzuki S. Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and its related compounds. VI. Structure– analgesic activity relationship for fentanyl, methylsubstituted fentanyls and other analogues // Forensic. Toxicol. 2008. V. 26. № 1. P. 1–5. https://doi.org/10.1007/s11419-007-0039-1Заикина О.Л., Шилов В.В., Лодягин А.Н., Григорьев А.М. Особенности обнаружения производных фентанила в моче методами газовой и жидкостной хроматомасс-спектрометрии // Токсикологический вестник. 2016. № 3. С. 41–46. https://doi.org/10.36946/0869-7922-2016-3-41-46Zaikina O.L., Shilov V.V., Lodyagin A.N. et al. Features of the detection of fentanyl derivatives in urine by gas and liquid chromatography-mass spectrometry // Toxicological Bulletin. 2016. № 3. P. 41-46. (in Russian). https://doi.org/10.36946/0869-7922-2016-3-41-46Родин И.А., Грибкова С.Е., Григорьев А.М. и др. Обнаружение метаболитов нового психоактивного вещества фуранилфентанила в моче и сыворотке крови лабораторных крыс методом жидкостной хроматомасс-спектрометрии // Масс-спектрометрия. 2017. Т. 14. № 4. С. 242–251.Rodin I.A., Gribkova S.E., Grigoryev A.M. et al. Detection of metabolites of the new psychoactive substance furanylfentanyl in the urine and blood serum of laboratory rats by liquid chromatography-mass spectrometry // Mass spectrometry. 2017. V. 14. № 4. P. 242–251. (in Russian).Krotulski A.J., Papsun D.M., Kacinko S.L., Logan B.K. Isotonitazene quantitation and metabolite discovery in authentic forensic casework // J. Anal. Toxicol. 2020. V. 44. № 6. P. 521–530. https://doi.org/10.1093/jat/bkaa016Krotulski A.J., Papsun D.M., Kacinko S.L., Logan B.K. Isotonitazene quantitation and metabolite discovery in authentic forensic casework // J. Anal. Toxicol. 2020. V. 44. № 6. P. 521–530. https://doi.org/10.1093/jat/bkaa016Braden M.R., Parrish J.C., Naylor J.C., Nichols D.E. Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists // Mol. Pharmacol. 2006. V. 70. № 6. P. 1956–1964. https://doi.org/10.1124/mol.106.028720Braden M.R., Parrish J.C., Naylor J.C., Nichols D.E. Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists // Mol. Pharmacol. 2006. V. 70. № 6. P. 1956–1964. https://doi.org/10.1124/mol.106.028720Hansen M., Phonekeo K., Paine J.S. et al. Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists // ACS Chem. Neurosci. 2014. V. 5. № 3. P. 243–249. https://doi.org/10.1021/cn400216uHansen M., Phonekeo K., Paine J.S. et al. Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists // ACS Chem. Neurosci. 2014. V. 5. № 3. P. 243–249. https://doi.org/10.1021/cn400216uЗаикина О.Л., Шилов В.В., Лодягин А.Н. и др. Практические аспекты диагностики приема соединений группы NBOMe. Краткий обзор фармакологии, токсических свойств и психоактивных эффектов // Наркология. 2018. № 9. С. 78–89. https://doi.org/10.25557/1682-8313.2018.09.78-89Zaikina O.L., Shilov V.V., Lodyagin A.N. et al. Practical aspects of diagnosing the intake of compounds of the NBOMe group. Brief review of pharmacology, toxic properties and psychoactive effects // Narcology. 2018. № 9, P. 78–89. (in Russian). https://doi.org/10.25557/1682-8313.2018.09.78-89Заикина О.Л., Шилов В.В., Лодягин А.Н. и др. Практические аспекты диагностики приема соединений группы NBOMe. Обнаружение NBOMe и их метаболитов методами газовой и жидкостной хромато-масс-спектрометрии в биологических объектах // Наркология. 2018. № 10. С. 86–96. https://doi.org/10.25557/1682-8313.2018.10.85-96Zaikina O.L., Shilov V.V., Lodyagin A.N. et al. Practical aspects of diagnosing the intake of compounds of the NBOMe group. Detection of NBOMe and their metabolites by gas and liquid chromato-mass spectrometry in biological objects // Narcology. 2018. № 10. P. 86–96. (in Russian). https://doi.org/10.25557/1682-8313.2018.10.85-96Ellison D.H. Handbook of chemical and biological warfare agents. Second ed. Roca Raton, London: CRC Press, 2008.Ellison D.H. Handbook of chemical and biological warfare agents. Second ed. Roca Raton, London: CRC Press, 2008.

The authors declare that there are no conflicts of interest present.