Identification of a new synthetic cannabinoid in a herbal mixture: 1-butyl-3-(2-methoxybenzoyl)indole

Forensic Toxicology

Volumn 31, Issue 2, 2013, Pages 187-196

  Park, Yujin ^a   Lee, Chul ^b   Lee, Heesang ^a   Pyo, Jaesung ^a   Jo, Jiyeong ^a   Lee, Jaesin ^a   Choi, Hyeyoung ^a   Kim, Suncheun ^a   Hong, Ran Seon ^b   Park, Yonghoon ^c   Hwang, Bang Yeon ^b   Choe, Sanggil ^a   Jung, Jee H ^c  

^a National Forensic Service   (South Korea)

^b Chungbuk National University   (South Korea)

^c Pusan National University   (South Korea)

Author keywords

1 Butyl 3 (2 methoxybenzoyl)indole; 1 Pentyl 3 (2 methoxybenzoyl)indole; NMR; RCS 4 isomer; Synthetic cannabinoids; TOF MS

Indexed keywords

1 BUTYL 3 (2 METHOXYBENZOYL)INDOLE; 1 BUTYLINDOLE DERIVATIVE; 2 METHOXYBENZOYL DERIVATIVE; 5 METHOXY N,N DIALLYLTRYPTAMINE; CANNABINOID DERIVATIVE; CARBON; DICHLOROMETHANE; HERBACEOUS AGENT; METHANOL; PHENAZEPAM; PROTON; TRYPTAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CORRELATION SPECTROSCOPY; ELECTROSPRAY MASS SPECTROMETRY; HETERONUCLEAR MULTIPLE BOND CORRELATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; MOLECULAR WEIGHT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SIGNAL TRANSDUCTION; SPECTROSCOPY; TIME OF FLIGHT MASS SPECTROMETRY;

EID: 84879800033     PISSN: 18608965     EISSN: 18608973     Source Type: Journal    
DOI: 10.1007/s11419-012-0173-2     Document Type: Article

References (29)

1. Dresen S, Ferreirós N, Pütz M, Westphal F, Zimmermann R, Auwärter V (2010) Monitoring of herbal mixtures potentially containing synthetic cannabinoids as psychoactive compounds. J Mass Spectrom 45:1186-1194
2. Kikura-Hanajiri R, Uchiyama N, Goda Y (2011) Survey of current trends in the abuse of psychotropic substances and plants in Japan. Legal Med 13:109-115
3. EMCDDA (2009) Action on new drugs briefing paper: understanding the 'Spice' phenomenon (a report from an EMCDDA expert meeting, 6 March 2009, Lisbon). Updated version, 13 Aug 2009
4. Auwärter V, Dresen S, Weinmann W, Müller M, Pütz M, Ferreirós N (2009) Spice and other herbal blends: harmless incense or cannabinoid designer drugs? J Mass Spectrom 44:832-837
5. Uchiyama N, Kikura-Hanajiri R, Kawahara N, Haishima Y, Goda Y (2009) Identification of a cannabinoid analog as a new type of designer drug in a herbal product. Chem Pharm Bull 57:439-441
6. Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y (2009) Identification of a cannabimimetic indole as a designer drug in a herbal product. Forensic Toxicol 27:61-66
7. Uchiyama N, Kikura-Hanajiri R, Ogata J, Goda Y (2010) Chemical analysis of synthetic cannabinoids as designer drugs in herbal products. Forensic Sci Int 198:31-38
8. Nycz JE, Malecki G, Zawiazalec M, Pazdziorek T, Skop P (2010) 1-Pentyl-3-(4-methoxy-1-naphthoyl)indol and 2-(2-methoxy-phenyl)-1-(1-pentyl-1H- indol-3-yl)-ethanone: X-ray structures and computational studies. Mol Struct 984:125-130
9. Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2011) 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 29:25-37
10. Nakajima J, Takahashi M, Seto T, Suzuki J (2011) Identification and quantitation of cannabimimetic compound JWH-250 as an adulterant in products obtained via the Internet. Forensic Toxicol 29:51-55
11. Nakajima J, Takahashi M, Seto T, Kanai C, Suzuki J, Yoshida M, Hamano T (2011) Identification and quantitation of two benzoylindoles AM-694 and (4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone, and three cannabimimetic naphthoylindoles JWH-210, JWH-122, and JWH-019 as adulterants in illegal products obtained via the Internet. Forensic Toxicol 29:95-110
12. 35S]GTPγS binding assays. Forensic Toxicol 29:132-141
13. Nakajima J, Takahashi M, Seto T, Yoshida M, Kanai C, Suzuki J, Hamano T (2012) Identification and quantitation of two new naphthoylindole drugs-of-Abuse, (1-(5-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone (AM-2202) and (1-(4-pentenyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone, with other synthetic cannabinoids in unregulated "herbal" products circulated in the Tokyo area. Forensic Toxicol 30:33-44
14. Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2012) 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 30:114-125
15. Kneisel S, Bisel P, Brecht V, Broecker S, Müller M, Auwärter V (2012) Identification of the cannabimimetic AM-1220 and its azepane isomer (N-methylazepan-3-yl)-3-(1-naphthoyl)indole in a research chemical and several herbal mixtures. Forensic Toxicol 30:126-134
16. 1 cannabinoid receptor. Bioorg Med Chem 11:539-549
17. 2 receptor agonists. Bioorg Med Chem 13:89-112
18. Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR (2005) 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg Med Chem Lett 15:4110-4113
19. Huffman JW, Lu J, Dai D, Kitaygorodskiy A, Wiley JL, Martin BR (2000) Synthesis and pharmacology of a hybrid cannabinoid. Bioorg Med Chem 8:439-447
20. 2 receptor. Bioorg Med Chem 14:2386-2397
21. 2 receptors. Bioorg Med Chem Lett 16:5432-5435
22. 8-tetrahydrocannabinols: new selective ligands for the CB receptor. Bioorg Med Chem 14:247-262
23. 2 receptor. Bioorg Med Chem Lett 15:3758-3762
24. Lindigkeit R, Boehme A, Eiserloh I, Luebbecke M, Wiggermann M, Ernst L, Beuerle T (2009) Spice: a never ending story? Forensic Sci Int 191:58-63
25. Vardakou I, Pistos C, Spiliopoulou Ch (2010) Spice drugs as a new trend: mode of action, identification and legislation. Toxicol Lett 197:157-162
26. Every-Palmer S (2011) Synthetic cannabinoid JWH-018 and psychosis: an explorative study. Drug Alcohol Depend 117:152-157
27. Corkery JM, Schifano F, Ghodse AH (2012) Phenazepam abuse in the UK: an emerging problem causing serious adverse health problems, including death. Hum Psychopharmacol 27:254-261
28. Maskell PD, Paoli GD, Seetohul LN, Pounder DJ (2012) Phenazepam: the drug that came in from the cold. J Forensic Legal Med 19:122-125
29. Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, Showalter VM, Abood ME, Martin BR (2000) Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding. Drug Alcohol Depend 60:133-140