Synthetic cannabinoid 3-benzyl-5-[1-(2-pyrrolidin-1-ylethyl)-1H-indol-3-yl]-1,2,4-oxadiazole. The first detection in illicit market of new psychoactive substances

Forensic Science International

Volumn 259, Issue , 2016, Pages 95-100

  Shevyrin, Vadim ^a   Melkozerov, Vladimir ^b   Eltsov, Oleg ^a   Shafran, Yuri ^a   Morzherin, Yuri ^a  

^a URAL FEDERAL UNIVERSITY   (Russian Federation)

^b Sverdlovsk Region Branch   (Russian Federation)

Author keywords

Analogues of 3 carbonylindoles; Designer drugs; Identification; Synthetic cannabinoids

Indexed keywords

3 BENZYL 5 [1 [2 PYRROLIDIN 1 YLETHYL] 1H INDOL 3 YL] 1,2,4 OXADIAZOLE; CANNABINOID; ILLICIT DRUG; PSYCHOTROPIC AGENT; UNCLASSIFIED DRUG; DESIGNER DRUG; OXADIAZOLE DERIVATIVE; STREET DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; DRUG TRAFFIC; INFRARED SPECTROSCOPY; MASS FRAGMENTOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SEIZURE; TANDEM MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

CANNABINOIDS; DESIGNER DRUGS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; OXADIAZOLES; PSYCHOTROPIC DRUGS; STREET DRUGS;

EID: 84952931259     PISSN: 03790738     EISSN: 18726283     Source Type: Journal    
DOI: 10.1016/j.forsciint.2015.12.019     Document Type: Article

References (27)

1. United Nation Office on Drugs and Crime (UNODC), World Drug Report 2013. http://www.unodc.org/unodc/secured/wdr/wdr2013/World_Drug_Report_2013.pdf.
2. United Nation Office on Drugs and Crime (UNODC), The challenge of new psychoactive substances. A Report from the Global SMART Programme March 2013. http://www.unodc.org/documents/scientific/NPS_2013_SMART.pdf.
3. European Monitoring Centre for Drugs and Drug Addiction, EMCDDA Europol 2014 Annual Report on the implementation of Council Decision 2005/387/JHA, Implementation Reports 2015, Publications Office of the European Union, Luxembourg, http://www.emcdda.europa.eu/attachements.cfm/att_240380_EN_TDAN15001ENN.pdf.
4. European Monitoring Centre for Drugs and Drug Addiction New Psychoactive Substances in Europe. An Update from the EU Early Warning System 2015, March, Publications Office of the European Union, Luxembourg, http://www.emcdda.europa.eu/attachements.cfm/att_235958_EN_TD0415135ENN.pdf.
5. United Nation Office on Drugs and Crime (UNODC), World Drug Report 2014. http://www.unodc.org/documents/data-and-analysis/WDR2014/World_Drug_Report_2014_web.pdf.
6. Castaneto M.S., Gorelick D.A., Desrosiers N.A., Hartman R.L., Pirard S., Huestis M.A. Synthetic cannabinoids: epidemiology, pharmacodynamics, and clinical implications. Drug Alcohol Depend. 2014, 144:12-41.
7. Presley B.C., Jansen-Varnum S.A., Logan B.K. Analysis of synthetic cannabinoids in botanical material: a review of analytical methods and findings. Forensic Sci. Rev. 2013, 25:27-46.
8. Shevyrin V., Morzherin Yu. Structure, activity and classification of cannabinoids. Bull. Russ. Acad. Sci. Chem. 2015, 6:1249-1266. (in Russian).
9. Uchiyama N., Kikura-Hanajiri R., Ogata J., Goda Y. Chemical analysis of synthetic cannabinoids as designer drugs in herbal products. Forensic Sci. Int. 2010, 198:31-38.
10. Uchiyama N., Kawamura M., Kikura-Hanajiri R., Goda Y. Identification and quantitation of two cannabimimetic phenylacetylindoles JWH-251 and JWH-250, and four cannabimimetic naphthoylindoles JWH-081, JWH-015, JWH-200, and JWH-073 as designer drugs in illegal products. Forensic Toxicol. 2011, 29:25-37.
11. Shanks K.G., Dahn T., Behonick G., Terrell A. Analysis of first and second generation legal highs for synthetic cannabinoids and synthetic stimulants by ultra-performance liquid chromatography and time of flight mass spectrometry. J. Anal. Toxicol. 2012, 36:360-371.
12. Banister S.D., Stuart J., Conroy T., Longworth M., Manohar M., Beinat C., Wilkinson S.M., Kevin R.C., Hibbs D.E., Glass M., Connor M., McGregor I.S., Kassiou M. Structure-activity relationships of synthetic cannabinoid designer drug RCS-4 and its regioisomers and C4 homologues. Forensic Toxicol. 2015, 33:355-366.
13. Banister S.D., Wilkinson S.M., Longworth M., Stuart J., Apetz N., English K., Brooker L., Goebel C., Hibbs D.E., Glass M., Connor M., McGregor I.S., Kassiou M. The Synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse. ACS Chem. Neurosci. 2013, 4:1081-1092.
14. Shevyrin V., Melkozerov V., Nevero A., Eltsov O., Morzherin Yu., Shafran Yu. Identification and analytical properties of new synthetic cannabimimetics bearing 2,2,3,3-tetramethylcyclopropanecarbonyl moiety. Forensic Sci. Int. 2013, 226:62-73.
15. Uchiyama N., Kawamura M., Kikura-Hanajiri R., Goda Y. Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products. Forensic Toxicol. 2012, 30:114-125.
16. Shevyrin V., Melkozerov V., Nevero A., Eltsov O., Shafran Yu. Analytical characterization of some synthetic cannabinoids, derivatives of indole-3-carboxylic acid. Forensic Sci. Int. 2013, 232:1-10.
17. Uchiyama N., Matsuda S., Kawamura M., Kikura-Hanajiri R., Goda Y. Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products. Forensic Toxicol. 2013, 31:223-240.
18. Shevyrin V., Melkozerov V., Nevero A., Eltsov O., Baranovsky A., Shafran Yu. Synthetic cannabinoids as designer drugs: new representatives of indol-3-carboxylates series and indazole-3-carboxylates as novel group of cannabinoids. Identification and analytical data. Forensic Sci. Int. 2014, 244:263-275.
19. Shevyrin V., Melkozerov V., Nevero A., Eltsov O., Morzherin Yu., Shafran Yu. 3-Naphthoylindazoles and 2-naphthoylbenzoimidazoles as novel chemical groups of synthetic cannabinoids: chemical structure elucidation, analytical characteristics and identification of the first representatives in smoke mixtures. Forensic Sci. Int. 2014, 242:72-80.
20. Uchiyama N., Shimokawa Y., Kawamura M., Kikura-Hanajiri R., Hakamatsuka T. Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products. Forensic Toxicol. 2014, 32:266-281.
21. Uchiyama N., Matsuda S., Wakana D., Kikura-Hanajiri R., Goda Y. New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA), identified as designer drugs. Forensic Toxicol. 2013, 31:93-100.
22. Shevyrin V., Melkozerov V., Nevero A., Eltsov O., Shafran Yu., Morzherin Yu., Lebedev A. Synthetic cannabinoids of indazole-3-carboxamide group bearing N-1-methoxycarbonylalkyl moiety as designer drugs. Anal. Bioanal. Chem. 2015, 407:6301-6315.
23. Uchiyama N., Asakawa K., Kikura-Hanajiri R., Tsutsumi T., Hakamatsuka T. A new pyrazole-carboxamide type synthetic cannabinoid AB-CHFUPYCA [N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxamide] identified in illegal products. Forensic Toxicol. 2015, 33:367-373.
24. Westphal F., Sönnichsen F.D., Knecht S., Auwärter V., Huppertz L. Two thiazolylindoles and a benzimidazole: novel compounds on the designer drug market with potential cannabinoid receptor activity. Forensic Sci. Int. 2015, 249:133-147.
25. Moloney G.P., Angus J.A., Robertson A.D., Stoermer M.J., Robinson M., Wright C.E., McRae K., Christopoulos A. Synthesis and cannabinoid activity of 1-substituted-indole-3-oxadiazole derivatives: novel agonists for the CB1 receptor. Eur. J. Med. Chem. 2008, 43:513-539.
26. G.P. Moloney, A.D. Robertson, 3-Oxadiazol-5-yl-1-aminoalkyl-1H-indole derivatives, Patent US0034073 (2004).
27. Stoliarov B.V., Savinov I.M., Vitenberg A.G., Kartsova L.A., Zenkevich I.G., Kalmanovsky V.I., Kalambet Y.A. Practical Gas and Liquid Chromatography 2002, 249-252. St. Petersburg University, St. Petersburg, (in Russian).