Identification and quantitation of a benzoylindole (2-methoxyphenyl)(1- pentyl-1H-indol-3-yl)methanone and a naphthoylindole 1-(5-fluoropentyl-1H-indol- 3-yl)-(naphthalene-1-yl)methanone (AM-2201) found in illegal products obtained via the Internet and their cannabimimetic effects evaluated by in vitro [ 35S]GTPγS binding assays

Forensic Toxicology

Volumn 29, Issue 2, 2011, Pages 132-141

  Nakajima, Jun'Ichi ^a   Takahashi, Misako ^a   Nonaka, Ryouichi ^a   Seto, Takako ^a   Suzuki, Jin ^a   Yoshida, Masao ^a   Kanai, Chieko ^a   Hamano, Tomoko ^a  

^a TOKYO METROPOLITAN INSTITUTE OF PUBLIC HEALTH   (Japan)

Author keywords

(2 Methoxyphenyl)(1 pentyl 1H indol 3 yl)methanone; (4 Methoxyphenyl)(1 pentyl 1H indol 3 yl)methanone; 35S GTP S binding assay; AM 2201; Cannabimimetic indole; Designer drug

Indexed keywords

(2 METHOXYPHENYL)(1 PENTYL 1H INDOL 3 YL)METHANONE; (4 METHOXYPHENYL)(1 PENTYL 1H INDOL 3 YL)METHANONE; 1 (5 FLUOROPENTYL 1H INDOL 3 YL)(NAPTHTHALENE 1 YL)METHANONE; 3 (1 NAPHTHOYL) 1 PENTYLINDOLE; CANNABINOID RECEPTOR AGONIST; GUANINE NUCLEOTIDE BINDING PROTEIN; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); ILLICIT DRUG; INDOLE DERIVATIVE; JWH 019; JWH 122; JWH 210; SULFUR 35; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING ASSAY; BIOLOGICAL ACTIVITY; CANNABIS ADDICTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG DETERMINATION; IN VITRO STUDY; INTERNET; LIQUID CHROMATOGRAPHY; MALE; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN BINDING; RAT; ULTRAVIOLET SPECTROSCOPY;

EID: 79960613145     PISSN: 18608965     EISSN: 18608973     Source Type: Journal    
DOI: 10.1007/s11419-011-0114-5     Document Type: Article

References (23)

1. N Uchiyama R Kikura-Hanajiri N Kawahara Y Haishima Y Goda 2009 Identification of a cannabinoid analog as a new type of designer drug in a herbal product Chem Pharm Bull 57 439 441 19336947 10.1248/cpb.57.439 1:CAS:528:DC%2BD1MXmtl2qu74%3D
2. N Uchiyama R Kikura-Hanajiri N Kawahara Y Goda 2009 Identification of a cannabimimetic indole as a designer drug in a herbal product Forensic Toxicol 27 61 66 10.1007/s11419-009-0069-y 1:CAS:528:DC%2BD1MXos1Cgsrs%3D
3. R Kikura-Hanajiri M Kawamura T Maruyama M Kitajima M Takayama Y Goda 2009 Simultaneous analysis of mitragynine, 7-hydroxymitragynine, and other alkaloids in the psychotropic plant "kratom"(Mitragyna speciosa) by LC-ESI-MS Forensic Toxicol 27 67 74 10.1007/s11419-009-0070-5 1:CAS:528: DC%2BD1MXos1Cgsrk%3D
4. H Kikuchi N Uchiyama J Ogata R Kikura-Hanajiri Y Goda 2010 Chemical constituents and DNA sequence analysis of a psychotropic herbal product Forensic Toxicol 28 77 83 10.1007/s11419-010-0091-0 1:CAS:528:DC%2BC3cXpt1Oitb8%3D
5. N Uchiyama M Kawamura R Kikura-Hanajiri Y Goda 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 10.1007/s11419-010-0100-3 1:CAS:528:DC%2BC3MXhtVartr4%3D
6. J Nakajima M Takahashi T Seto J Suzuki 2011 Identification and quantitation of cannabimimetic compound JWH-250 as an adulterant in products obtained via the Internet Forensic Toxicol 29 51 55 10.1007/s11419-010-0101-2 1:CAS:528:DC%2BC3MXhtVarsbY%3D
7. 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. doi: 10.1007/s11419-011- 0108-3
8. Ministry of Health, Labour and Welfare of Japan (2011) http://search.e-gov.go.jp/servlet/Public?CLASSNAME=PCMMSTDETAIL&id= 495100324&Mode=0. Accessed 3 May 2011
9. Reggio PH (2009) The cannabinoid receptors. Humana Press, New York
10. 1 receptor activity in rat brain cryosections by functional autoradiography J Neurochem 101 972 981 17254014 10.1111/j.1471-4159.2006.04403.x (Pubitemid 46683863)
11. JC Martel AM Ormière N Leduc MB Assié D Cussac A Newman-Tancredi 2007 Native rat hippocampal 5-HT1A receptors show constitutive activity Mol Pharmacol 71 638 643 17167032 10.1124/mol.106.029769 1:CAS:528:DC%2BD2sXis1aqtL0%3D (Pubitemid 46294075)
12. MM Bradford 1976 A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal Biochem 72 248 254 942051 10.1016/0003-2697(76)90527-3 1:CAS:528: DyaE28XksVehtrY%3D
13. S Mato R Vidal E Castro A Diaz A Pazos EM Valdizán 2010 Long-term fluoxetine treatment modulates cannabinoid type 1 receptor-mediated inhibition of adenylyl cyclase in the rat prefrontal cortex through 5-hydroxytryptamine 1A receptor-dependent mechanisms Mol Pharmacol 77 424 434 19995940 10.1124/mol.109.060079 1:CAS:528:DC%2BC3cXjt1entL4%3D
14. 35S]GTPγS binding in rat brain membranes Biol Pharm Bull 30 2328 2333 18057721 10.1248/bpb.30.2328 1:CAS:528:DC%2BD1cXht1ymtb0%3D (Pubitemid 350223736)
15. Makriyannis A, Deng H (2005) Cannabimimetic indole derivatives. United States Patent, US 7,241,799 B2
16. 1 cannabinoid receptor ligand J Label Compd Radiopharm 46 799 804 10.1002/jlcr.720 1:CAS:528:DC%2BD3sXntFeisLk%3D (Pubitemid 37047668)
17. 2 receptor agonists Bioorg Med Chem 13 89 112 15582455 10.1016/j.bmc.2004.09.050 1:CAS:528:DC%2BD2cXhtVCgsbrL (Pubitemid 39575695)
18. 2 receptor binding Drug Alcohol Depend 60 133 140 10940540 10.1016/S0376-8716(99)00152-0 1:CAS:528:DC%2BD3cXlsFCis7o%3D (Pubitemid 30625016)
19. 1 cannabinoid receptor Bioorg Med Chem 11 539 549 12538019 10.1016/S0968-0896(02)00451-0 1:CAS:528:DC%2BD3sXlt1Oksg%3D%3D (Pubitemid 36132231)
20. JL Wiley DR Compton D Dai JA Lainton M Phillips JW Huffman BR Martin 1998 Structure-activity relationships of indole and pyrrole-derived cannabinoids J Pharmacol Exp Ther 285 995 1004 9618400 1:CAS:528:DyaK1cXjvFClt7g%3D (Pubitemid 28277896)
21. JW Huffman 1999 Cannabimimetic indoles, pyrroles and indenes Curr Med Chem 6 705 720 10469887 1:CAS:528:DyaK1MXltlKkurc%3D (Pubitemid 29399500)
22. EMCDDA (2009) Thematic papers: understanding the "Spice" phenomenon. http://www.emcdda.europa.eu/attachements.cfm/att-80086-EN- Spice%20Thematic%20paper%20%E2%80%94%20final%20version.pdf. Accessed 20 Jan 2011
23. ACMD (2009) Consideration of the major cannabinoid agonists. http://www.homeoffice.gov.uk/publications/drugs/acmd1/acmd-report-agonists?view= Binary. Accessed January 2011