Chromatography-mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences

Volumn 879, Issue 15-16, 2011, Pages 1126-1136

  Grigoryev, Andrej ^a   Savchuk, Sergey ^b   Melnik, Aleksandra ^a   Moskaleva, Natal'ja ^c   Dzhurko, Jurij ^d   Ershov, Mihail ^d   Nosyrev, Aleksandr ^b   Vedenin, Aleksandr ^c   Izotov, Boris ^b   Zabirova, Irina ^e   Rozhanets, Vladimir ^e  

^a Bureau of Forensic Medical Expertise   (Russian Federation)

^b I M SECHENOV FIRST MOSCOW STATE MEDICAL UNIVERSITY   (Russian Federation)

^c Interlab Inc   (Russian Federation)

^d Clinical Narcological Hospital   (Russian Federation)

^e Nacional Research Center on Addictions   (Russian Federation)

Author keywords

GC MS; Herbal mixture; JWH 018; JWH 073; LC MS; Metabolites

Indexed keywords

GC-MS; HERBAL MIXTURES; JWH-018; JWH-073; LC-MS;

BIOMOLECULES; BODY FLUIDS; CARBOXYLATION; GAS CHROMATOGRAPHY; HYDROXYLATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; MIXTURES; ORGANIC POLYMERS; RATS;

METABOLISM;

3 (1 NAPHTHOYL) 1 PENTYLINDOLE; CANNABINOID; JWH 073; UNCLASSIFIED DRUG;

ARTICLE; CARBOXYLATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DEALKYLATION; DIHYDROXYLATION; GAS CHROMATOGRAPHY; HERBAL MEDICINE; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; METABOLITE; NONHUMAN; PRIORITY JOURNAL; RUSSIAN FEDERATION; SMOKING; URINALYSIS;

ALKYLATION; ANIMALS; CHROMATOGRAPHY, LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; HYDROXYLATION; INDOLES; MARIJUANA SMOKING; NAPHTHALENES; RATS; RATS, WISTAR; RECEPTOR, CANNABINOID, CB1; STREET DRUGS;

RATTUS;

EID: 79955031826     PISSN: 15700232     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jchromb.2011.03.034     Document Type: Article

References (18)

1. Consideration of the major cannabinoid agonists. Advisory Council on the Misuse of Drugs (ACMD), London. Website: , 2009 (accessed 10.07.10). http://www.homeoffice.gov.uk/publications/drugs/acmd1/acmd-report-agonists%3Fview=Binary.
2. Wiley W.L., Compton D.R., Dai D., et al. Structure-activity relationships of indole- and pyrrole-derived cannabinoids. J. Pharmacol. Exp. Ther. 1998, 285:995.
3. Huffman J.W. Cannabimimetic indoles, pyrroles, and indenes: structure-activity relationships and receptor interactions. The Cannabinoid Receptors 2009, 49. Humana Press, NJ. P.H. Reggio (Ed.).
4. Mustata C., Torrens M., Pardo R., Perez C. The Psychonaut web mapping group, M. Farre, spice drugs: cannabinoids as a new designer drugs. Adicciones 2009, 21:181.
5. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA), Thematic paper-Understanding the 'Spice' phenomenon, Luxembourg, 2009, pp. 37.
6. 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.
7. Lindigkeit R., Boehme A., Eiserloh I., Lubbecke M., Wiggermann M., Ernst L., Beuerle T. Spice: a never ending story?. Forensic Sci. Int. 2009, 191:58.
8. Uchiyama N., Kikura-Hanajiri R., Kawahara N., Goda Y. Identification of a cannabimimetic indole as a designer drug in a herbal product. Forensic Toxicol. 2009, 27:61.
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.
10. Atwood B.K., Huffman J.W., Straiker A., Mackie K. JWH018, a common constituent of 'Spice' herbal blends, is a potent and efficacious cannabinoid CB1 receptor agonist. Br. J. Pharmacol. 2010, 1.
11. Teske J., Weller J.P., Fieguth A., Rothämel T., Schulz Y., Tröger H.D. Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in human serum by liquid chromatography-tandem mass spectrometry. J Chromatogr. B 2010, 878. 2959-2663.
12. Kraemer T., Meyer M., Wissenbach D., Rust K., Bregel D., Hopf M., Maurer H., Wilske J. Distinctive features and symptoms of deficiency of drivers with blood samples positive for JWH-018, the pharmacologically active ingredient of different misused incenses (" spice" ), in suspected DUID cases. ABSTRACTS-VORTRÄGE HAUPTSYMPOSIUM 2008, 91.
13. Neukamm M.A., Mürdter T.E., Wehner H.-D., Wehner F., Renger M., Ratge D., Sachs H., Knabbe C. Quantitative determination of the active 'spice' ingredient JWH-018 in blood and hair by liquid chromatography-tandem mass spectrometry. Ann. Toxicol Anal. 2009, 21(S1):21.
14. 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.
15. Kraemer T., Rust K.Y., Meyer M., Wissenbach D., Bregel D., Hopf M., Maurer H., Wilske J. Studies on the metabolism of JWH-018 and of a homologue of CP 47,497, pharmacologically active ingredients of different misused incense (" spice" ) using GC-MS and LCMSn techniques. Ann. Toxicol. Anal. 2009, 21(S1):21.
16. Sobolevsky T., Prasolov I., Rodchenkov G. Detection of JWH-018 metabolites in smoking mixture post-administration urine. Forensic Sci. Int. 2010, 200:141.
17. Pertwee R.G. Cannabinoid pharmacology: the first 66 years. Br. J. Pharmacol. 2006, 147(S1):163.
18. Martin B.R., Jefferson R., Winckler R., Wiley J.L., Huffman J.W., Crocker P.J., Saha B., Razdan R.K. Manipulation of the tetrahydrocannabinol side chain delineastes agonists, partial agonists, and antagonists. J. Pharmacol. Exp. Ther. 1999, 290:1065.