Simultaneous determination of five naphthoylindole-based synthetic cannabinoids and metabolites and their deposition in human and rat hair

Journal of Pharmaceutical and Biomedical Analysis

Volumn 102, Issue , 2015, Pages 162-175

  Kim, Jihyun ^a,c   Park, Yuran ^a   Park, Meejung ^a   Kim, Eunmi ^a   Yang, Wonkyung ^a   Baeck, Seungkyung ^a   Lee, Sooyeun ^b   Han, Sangbeom ^c  

^a National Forensic Service   (South Korea)

^b Keimyung University   (South Korea)

^c Chung Ang University   (South Korea)

Author keywords

AM 2201; Drug abuse; Hair analysis; JWH 122; MAM 2201

Indexed keywords

1 BUTYL 3 (1 NAPHTHOYL)INDOLE; 3 (1 NAPHTHOYL) 1 PENTYLINDOLE; AM 2201; CANNABINOID; CANNABINOID DERIVATIVE; DRONABINOL; DRUG METABOLITE; INDOLE DERIVATIVE; JWH 122; MAM 2201; UNCLASSIFIED DRUG; (4-METHYL-1-NAPHTHYL)-(1-PENTYLINDOL-3-YL)METHANONE; 1-((5-FLUOROPENTYL)-1H-INDOL-3-YL)-(NAPHTHALEN-1-YL)METHANONE; 1-(5-FLUOROPENTYL)-3-(4-METHYL-1-NAPHTHOYL)INDOLE; 1-PENTYL-3-(1-NAPHTHOYL)INDOLE; JWH-073; NAPHTHALENE DERIVATIVE; STREET DRUG;

ANALYTIC METHOD; ANIMAL EXPERIMENT; ARTICLE; CANNABIS ADDICTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG ABUSE; FORENSIC TOXICOLOGY; HAIR ANALYSIS; HUMAN; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; METABOLITE; NONHUMAN; QUANTITATIVE ANALYSIS; RAT; VALIDATION STUDY; ANIMAL; CHEMISTRY; HAIR; LIMIT OF DETECTION; PROCEDURES; SUBSTANCE ABUSE; TANDEM MASS SPECTROMETRY;

ANIMALS; CANNABINOIDS; CHROMATOGRAPHY, LIQUID; HAIR; HUMANS; INDOLES; LIMIT OF DETECTION; NAPHTHALENES; RATS; STREET DRUGS; SUBSTANCE ABUSE DETECTION; TANDEM MASS SPECTROMETRY;

EID: 84907758775     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2014.09.013     Document Type: Article

References (27)

1. Seely K.A., Lapoint J., Moran J.H., Fattore L. Spice drugs are more than harmless herbal blends: a review of the pharmacology and toxicology of synthetic cannabinoids. Prog. Neuropsychopharmacol. Biol. Psychiatry 2012, 39:234-243.
2. Vardakou I., Pistos C., Spiliopoulou Ch. Spice drugs as a new trend: mode of action, identification and legislation. Toxicol. Lett. 2010, 197:157-162.
3. Schaefer N., Peters B., Bregel D., Kneisel S., Auwärter V., Schmidt P.H., Ewald A.H. A fatal case involving several synthetic cannabinoids. Toxichem Krimtech. 2013, 80:248.
4. Patton A.L., Chimalakonda K.C., Moran C.L., McCain K.R., Radominska-Pandya A., James L.P., Kokes C., Moran J.H. K2 toxicity: fatal case of psychiatric complications following AM2201 exposure. J. Forensic Sci. 2013, 58:1676-1680.
5. McQuade D., Hudson S., Dargan P.I., Wood D.M. First European case of convulsions related to analytically confirmed use of the synthetic cannabinoid receptor agonist AM-2201. Eur. J. Clin. Pharmacol. 2012, 69:373-376.
6. Saito T., Namera A., Miura N., Ohta S., Miyazaki S., Osawa M., Inokuchi S. A fatal case of MAM-2201 poisoning. Forensic Toxicol. 2013, 31:333-337.
7. 13 2013.
8. Lin C.Y., Wheelock A.M., Morin D., Baldwin R.M., Lee M.G., Taff A., Plopper C., Buckpitt A., Rohde A. Toxicity and metabolism of methylnaphthalenes: comparison with naphthalene and 1-nitronaphthalene. Toxicology 2009, 260:16-27.
9. Brents L.K., Gallus-Zawada A., Radominska-Pandya A., Vasiljevik T., Prisinzano T.E., Fantegrossi W.E., Moran J.H.J.H., Prather P.L. Monohydroxylated metabolites of the K2 synthetic cannabinoid JWH-073 retain intermediate to high cannabinoid 1 receptor (CB1R) affinity and exhibit neutral antagonist to partial agonist activity. Biochem. Pharmacol. 2012, 83:952-961.
10. United Nations Office on Drugs and Crime Recommended methods for the identification and analysis of synthetic cannabinoid receptor agonists in seized materials 2013.
11. Nakajima J., Takahashi M., Nonaka R., Seto T., Suzuki J., Yoshida M., Kanai C., Hamano T. 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]GTP(S binding assays. Forensic Toxicol. 2011, 29:132-141.
12. Huffman J.W., Zengin G., Wu M.J., Lu J., Hynd G., Bushell K., Thompson A.L., Bushell S., Tartal C., Hurst D.P., Reggio P.H., Selley D.E., Cassidy M.P., Wiley J.L., Martin B.R. Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists. Bioorg. Med. Chem. 2005, 13:89-112.
13. Hutter M., Broecker S., Kneisel S., Auwärter V. Identification of the major urinary metabolites in man of seven synthetic cannabinoids of the aminoalkylindole type present as adulterants in 'herbal mixtures' using LC-MS/MS techniques. J. Mass Spectrom. 2012, 47:54-65.
14. Chimalakonda K.C., Seely K.A., Bratton S.M., Brents L.K., Moran C.L., Endres G.W., James L.P., Hollenberg P.F., Prather P.L., Radominska-Pandya A., Moran J.H. Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands. Drug Metab. Dispos. 2012, 40:2174-2184.
15. Hutter M., Moosmann B., Kneisel S., Auwärter V. Characteristics of the designer drug and synthetic cannabinoid receptor agonist AM-2201 regarding its chemistry and metabolism. J. Mass Spectrom. 2013, 48:885-894.
16. Kim J., In S., Park Y., Park M., Kim E., Lee S. Deposition of JWH-018, JWH-073 and their metabolites in hair and effect of hair pigmentation. Anal. Bioanal. Chem. 2013, 405:9769-9778.
17. Pragst F., Balikova M.A. State of the art in hair analysis for detection of drug and alcohol abuse. Clin. Chim. Acta 2006, 370:17-49.
18. Peters F.T., Drummer O.H.O.H., Musshoff F. Validation of new methods. Forensic Sci. Int. 2007, 165:216-224.
19. Matuszewski B.K., Constanzer M.L., Chavez-Eng C.M. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Anal. Chem. 2003, 75:3019-3030.
20. Hutter M., Kneisel S., Auwärter V., Neukamm M.A. Determination of 22 synthetic cannabinoids in human hair by liquid chromatography-tandem mass spectrometry. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 2012, 903:95-101.
21. Salomone A., Gerace E., D'Urso F., Di Corcia D., Vincenti M. Simultaneous analysis of several synthetic cannabinoids, THC, CBD and CBN, in hair by ultra-high performance liquid chromatography tandem mass spectrometry. Method validation and application to real samples. J. Mass Spectrom. 2012, 47:604-610.
22. Hubbard D.L., Wilkins D.G., Rollins D.E. The incorporation of cocaine and metabolites into hair: effects of dose and hair pigmentation. Drug Metab. Dispos. 2000, 28:1464-1469.
23. Nakahara Y., Takahashi K., Kikura R. Hair analysis for drugs of abuse. X. Effect of physicochemical properties of drugs on the incorporation rates into hair. Biol. Pharm. Bull. 1995, 18:1223-1227.
24. Stout P.R., Ruth J.A. Deposition of [3H]cocaine, [3H]nicotine, and [3H]flunitrazepam in mouse hair melanosomes after systemic administration. Drug Metab. Dispos. 1999, 27:731-735.
25. Han E., Park Y., Kim E., In S., Yang W., Lee S., Choi H., Lee S., Chung H., Song J.M. Simultaneous analysis of (9)-tetrahydrocannabinol and 11-nor-9-carboxy-tetrahydrocannabinol in hair without different sample preparation and derivatization by gas chromatography-tandem mass spectrometry. J. Pharm. Biomed. Anal. 2011, 55:1096-1103.
26. Salomone A., Luciano C., Di Corcia D., Gerace E., Vincenti M. Hair analysis as a tool to evaluate the prevalence of synthetic cannabinoids in different populations of drug consumers. Drug Test. Anal. 2014, 6:126-134.
27. Salomone A., Gerace E., Luciano C., Di Corcia D., Vincenti M. O22. Quantification of 22 synthetic cannabinoids and 10 metabolites in human hair. Toxicologie Analytique et Clinique 2014, 26:S14.