Tentative identification of phase I metabolites of HU-210, a classical synthetic cannabinoid, by LC-MS/MS

Journal of Pharmaceutical and Biomedical Analysis

Volumn 64-65, Issue , 2012, Pages 26-34

  Kim, Unyong ^a,b   Jin, Ming Ji ^c   Lee, Jaeick ^a   Han, Sang Beom ^b   In, Moon Kyo ^d   Yoo, Hye Hyun ^c  

^a Korea Institute of Science and Technology   (South Korea)

^b Chung Ang University   (South Korea)

^c Hanyang University   (South Korea)

^d Supreme Prosecutors' Office   (South Korea)

Author keywords

HU 210; LC MS MS; Metabolism; Synthetic cannabinoid

Indexed keywords

DEXANABINOL; DRUG METABOLITE;

ACCURACY; ARTICLE; CHEMICAL STRUCTURE; DRUG METABOLISM; HUMAN; HYDROXYLATION; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; OXYGENATION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

BIOTRANSFORMATION; CANNABINOIDS; CHROMATOGRAPHY, LIQUID; HUMANS; MASS SPECTROMETRY; METABOLIC DETOXICATION, PHASE I; MICROSOMES, LIVER; MOLECULAR STRUCTURE; TETRAHYDROCANNABINOL;

EID: 84862784914     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.02.007     Document Type: Article

References (21)

1. Mechoulam R., Lander N., Breuer A., Zahalka J. Synthesis of the individual, pharmacologically distinct, enantiomers of a tetrahydrocannabinol derivative. Tetrahedron: Asymmetry 1990, 1:315-318.
2. 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.
3. Auwärter V., Dresen S., Weinmann W., Müller M., Pütz M., Ferreirós N. 'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs?. J. Mass. Spectrom. 2009, 44:832-837.
4. HU-210 [(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c] chromen-1-ol] [Purported Ingredient of " Spice" ], U.S. Department of Justice Drug Enforcement Administration Office of Diversion Control, 2009.
5. Lambert D.M., Fowler C.J. The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications. J. Med. Chem. 2005, 48:5059-5087.
6. Ovadia H., Wohlman A., Mechoulam R., Weidenfeld J. Characterization of the hypothermic effect of the synthetic cannabinoid HU-210 in the rat. Relation to the adrenergic system and endogenous pyrogens. Neuropharmacology 1995, 34:175-180.
7. Little P.J., Compton D.R., Mechoulam R., Martin B.R. Stereochemical effects of 11-OH-[Delta]8-THC-dimethylheptyl in mice and dogs. Pharmacol. Biochem. Behav. 1989, 32:661-666.
8. Giuliani D., Ferrari F., Ottani A. The cannabinoid agonist HU 210 modifies rat behavioural responses to novelty and stress. Pharmacol. Res. 2000, 41:45-51.
9. Ottani A., Giuliani D. HU 210: a potent tool for investigations of the cannabinoid system. CNS Drug Rev. 2001, 7:131-145.
10. Zhang Q., Ma P., Cole R.B., Wang G. Identification of in vitro metabolites of JWH-015, an aminoalkylindole agonist for the peripheral cannabinoid receptor (CB2) by HPLC-MS/MS. Anal. Bioanal. Chem. 2006, 386:1345-1355.
11. Sobolevsky T., Prasolov I., Rodchenkov G. Detection of JWH-018 metabolites in smoking mixture post-administration urine. Forensic Sci. Int. 2010, 200:141-147.
12. Möller I., Wintermeyer A., Bender K., Jübner M., Thomas A., Krug O., Schänzer W., Thevis M. Screening for the synthetic cannabinoid JWH-018 and its major metabolites in human doping controls. Drug Test. Anal. 2011, 3:609-620.
13. Leighty E.G. Metabolism and distribution of cannabinoids in rats after different methods of administration. Biochem. Pharmacol. 1973, 22:1613-1621.
14. Harvey D.J., Brown N.K. Comparative in vitro metabolism of the cannabinoids. Pharmacol. Biochem. Behav. 1991, 40:533-540.
15. Maralikova B., Weinmann W. Simultaneous determination of Δ9-tetrahydrocannabinol, 11-hydroxy-Δ9-tetrahydrocannabinol and 11-nor-9-carboxy-Δ9-tetrahydrocannabinol in human plasma by high-performance liquid chromatography/tandem mass spectrometry. J. Mass Spectrom. 2004, 39:526-531.
16. Jung J., Meyer M.R., Maurer H.H., Neusüß C., Weinmann W., Auwärter V. Studies on the metabolism of the Δ9-tetrahydrocannabinol precursor Δ9-tetrahydrocannabinolic acid A (Δ9-THCA-A) in rat using LC-MS/MS, LC-QTOF MS and GC-MS techniques. J. Mass Spectrom. 2009, 44:1423-1433.
17. Maralikova B., Weinmann W. Simultaneous determination of Delta9-tetrahydrocannabinol, 11-hydroxy-Delta9-tetrahydrocannabinol and 11-nor-9-carboxy-Delta9-tetrahydrocannabinol in human plasma by high-performance liquid chromatography/tandem mass spectrometry. J. Mass Spectrom. 2004, 39:526-531.
18. Bijlsma L., Sancho J.V., Hernández F., Niessen W.M. Fragmentation pathways of drugs of abuse and their metabolites based on QTOF MS/MS and MS(E) accurate-mass spectra. J. Mass Spectrom. 2011, 46:865-875.
19. Wintermeyer A., Möller I., Thevis M., Jübner M., Beike J., Rothschild M.A., Bender K. In vitro phase I metabolism of the synthetic cannabimimetic JWH-018. Anal. Bioanal. Chem. 2010, 398:2141-2153.
20. Moran C.L., Le V.H., Chimalakonda K.C., Smedley A.L., Lackey F.D., Owen S.N., Kennedy P.D., Endres G.W., Ciske F.L., Kramer J.B., Kornilov A.M., Bratton L.D., Dobrowolski P.J., Wessinger W.D., Fantegrossi W.E., Prather P.L., James L.P., Radominska-Pandya A., Moran J.H. Quantitative measurement of JWH-018 and JWH-073 metabolites excreted in human urine. Anal. Chem. 2011, 83:4228-4236.
21. Grigoryev A., Savchuk S., Melnik A., Moskaleva N., Dzhurko J., Ershov M., Nosyrev A., Vedenin A., Izotov B., Zabirova I., Rozhanets V. Chromatography-mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 2011, 879:1126-1136.