Detection of synthetic cannabimimetics JWH-018 and JWH-073 by gas chromatography-mass spectrometry of metabolites dezalkilirovannyh
Keywords:
synthetic cannabimimetics JWH-018, JWH-073, metabolites, GC-MS, LC-MS/MS.
Abstract
The analysis of urine for the presence of metabolites cannabimimetics JWH-018 and JWH-073
by gas chromatography-mass spectrometry with acid deconjugation of metabolites and derivatization
methylation considered. Given gas chromatography-mass spectrometric characteristics defined
metabolites.
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References
1. Synthetic cannabinoids in herbal products. United Nations Office on Drugs and Crime
(UNODC). Available at:
http://www.unodc.org/documents/scientific/Synthetic_Cannabinoids.pdf (проверено
07.07.2013).
2. Lindigkeit R., Boehme A., Eiserloh I., Lubbecke M., Wiggermann M., Ernst L.,
Beuerle T. Spice: A never ending story? //Forensic Sci. Int. 2009, V. 191, р. 58-63.
3. Uchiyama N., Kikura-Hanajiri R., Ogata J., Goda Y.. Chemical analysis of synthetic
cannabinoids as designer drugs in herbal products //Forensic Sci. Int. 2010, V. 198, р. 31-38.
4. Uchiyama N., Kawamura M., Kikura-Hanajiri R., Goda Y. 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. 2011, V.29, р. 25-37.
5. Hudson S., Ramsey J. The emergence and analysis of synthetic cannabinoids //Drug
Testing Anal. 2011, V.3, p. 466-478.
6. Dresen S., Ferreirós N., Pütz M., Westphal F., Zimmermann R., Auwärter V.
Monitoring of herbal mixtures potentially containing synthetic cannabinoids as
psychoactive compounds. J. Mass Spectrom. 2010, V.45, р. 1186-1194.
7. Aung M.M., Griffin G., Huffman J.W,. Wu M.-J, Keel C., Yang B., Showalter V.M.,
Abood M. E., Martin B.R.. Influence of the N-1 alkyl chain length of cannabimimetic
indoles upon CB1 and CB2 receptor binding//Drug Alcohol Depend. 2000, V. 60, p. 133-
140.
8. Wiley J.L., Compton D.R., Dai D., Lainton J.A.H., Phillips M., Huffman J.W., Martin
B.R. Structure-Activity Relationships of Indole- and Pyrrole-Derived Cannabinoids//J.
Pharmacol. Exp. Ther. 1998, V. 285, p. 995-1004.
9. Brents L.K., Gallus-Zawada A., Radominska-Pandya A., Vasiljevik T., Prisinzano
T.E., Fantegrossi W.E., Moran 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, V.83, p. 952-961.
10. Schneir A.B., Cullen J., Ly B.T.. “Spice” Girls: Synthetic Cannabinoid
Intoxication//J. Emerg. Med. 2011, V.40, p. 296-299.
11. Simmons J.R., Cookman L., Kang C., Skinner C.. Three cases of “spice”
exposure//Clin. Toxicol. 2011, V. 49, p. 431-433.
12. Zimmermann U.S., Winkelmann P.R., Pilhatsch M., Nees J.A., Spanagel R., Schulz
K. Withdrawal phenomena and dependence syndrome after the consumption of ‘Spice
Gold’//Dtsch Arztebl Int. 2009, V.106, p. 464-467.
13. Kraemer T., Rust K.Y., Meyer M.R., Wissenbach D.K., Bregel D., Hopf M., Maurer
H.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, V.21(S1), p. O43-45.
14. Sobolevsky T., Prasolov I., Rodchenkov G. Detection of JWH-018 metabolites in
smokingmixture post-administration urine//Forensic Sci. Int. 2010, V. 200, p.141-147.
15. 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 Testing Anal. 2011, V.3, p. 609-620.
16. 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. 2011. V.879, p. 1126-
1136.
17. Григорьев А.М., Савчук С.А., Мельник А.А., Ершов М.Б., Джурко Ю.А.,
Веденин А.Н., Носырев А.Е., Изотов Б.Н., Рожанец В.В. Установление факта приема
синтетического каннабиноида JWH-018 хромато-масс-спектрометрическими
методами//Журн. аналит. химии. 2012. Т.67, c. 995-1004.
18. Grigoryev A., Melnik A., Savchuk S., Simonov A., Rozhanets V. Gas and liquid
chromatography–mass spectrometry studies on the metabolism of synthetic
phenylacetylindole cannabimimetic JWH-250, psychoactive components of smoking
mixtures, J. Chromatogr. B. 2011, V. 879, p. 2519-2526.
19. Grigoryev A., Kavanagh P., Melnik A. The detection of the urinary metabolites of 3-
[(adamantan-1-yl)carbonyl]-1-pentylindole (AB-001), a novel cannabimimetic, by gas
chromatography/mass spectrometry//Drug Test. Anal. 2012, V.4. p.519-524.
20. Kavanagh P., Grigoryev A., Melnik A., Simonov A. The identification of the urinary
metabolites of 3-(4-methoxybenzoyl)-1-pentylindole (RCS-4), a novel cannabimimetic, by
gas chromatography/mass spectrometry//J. Anal. Toxicol. 2012, V.36. p. 303-311.
21. Grigoryev A., Kavanagh P., Melnik A. The detection of the urinary metabolites of 1-
[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone (AM-694), a high affinity
cannabimimetic, by gas chromatography – mass spectrometry//Drug Test. Anal. 2013, V.5.
p. 110-115.
22. 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, V.398, p. 2141-2153.
23. Beuck S., Möller I., Thomas A., Klose A., Schlörer N., Schänzer W., Thevis M.
Structure characterisation of urinary metabolites of the cannabimimetic JWH-018 using
chemically synthesised reference material for the support of LC-MS/MS-based drug
testing//Anal. Bioanal. Chem. 2011, V.401, p. 493-505.
24. Chimalakonda K.C., Bratton S.M., Vi-Huyen Le, Kan Hui Yiew, Dineva A., Moran
C.L., James L.P., Moran J.H., Radominska-Pandya A. Conjugation of Synthetic
Cannabinoids JWH-018 and JWH-073, Metabolites by Human UDPGlucuronosyltransferases//
Drug. Metab. Dispos. 2011, V.39, p. 1967-1976.
25. Dresen S., Kneisel S., Weinmann W., Zimmermann R., Auwärter V. Development
and validation of a liquid chromatography–tandem mass spectrometry method for the
quantitation of synthetic cannabinoids of the aminoalkylindole type and methanandamide
in serum and its application to forensic samples//J. Mass. Spectrom. 2011, V.46, p. 163-
171.
26. J. Teske, J.P. Weller, A. Fieguth, T. Rothämel, Y. Schulz, H.D. Tröger, 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, V.878, p. 2959-2963.
27. 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, V.83, p. 4228-4236.
28. Chimalakonda K.C., Moran C.L., Kennedy P.D., Endres G.W., Uzieblo A.,
Dobrowolski P.J., Fifer E.K., Lapoint J., Nelson L.S., Hoffman R.S., James L.P.,
Radominska-Pandya A., Moran J.H. Solid-Phase Extraction and Quantitative Measurement
of Omega and Omega-1 Metabolites of JWH-018 and JWH-073 in Human Urine//Anal.
Chem. 2011, V.83, p. 6381-6388.
29. 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,
V.47, p.54-65.
30. Wissenbach D.K., Meyer M.R., Remane D., Philipp A.A., Weber A.A., Maurer H.H.
Drugs of abuse screening in urine as part of a metabolite-based LC-MSn screening
concept//Anal. Bioanal. Chem. 2011, V.400, p. 79-88.
31. 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 HPLCMS/
MS//Anal. Bioanal. Chem. 2006. V.386. p. 1345-134-55.
(UNODC). Available at:
http://www.unodc.org/documents/scientific/Synthetic_Cannabinoids.pdf (проверено
07.07.2013).
2. Lindigkeit R., Boehme A., Eiserloh I., Lubbecke M., Wiggermann M., Ernst L.,
Beuerle T. Spice: A never ending story? //Forensic Sci. Int. 2009, V. 191, р. 58-63.
3. Uchiyama N., Kikura-Hanajiri R., Ogata J., Goda Y.. Chemical analysis of synthetic
cannabinoids as designer drugs in herbal products //Forensic Sci. Int. 2010, V. 198, р. 31-38.
4. Uchiyama N., Kawamura M., Kikura-Hanajiri R., Goda Y. 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. 2011, V.29, р. 25-37.
5. Hudson S., Ramsey J. The emergence and analysis of synthetic cannabinoids //Drug
Testing Anal. 2011, V.3, p. 466-478.
6. Dresen S., Ferreirós N., Pütz M., Westphal F., Zimmermann R., Auwärter V.
Monitoring of herbal mixtures potentially containing synthetic cannabinoids as
psychoactive compounds. J. Mass Spectrom. 2010, V.45, р. 1186-1194.
7. Aung M.M., Griffin G., Huffman J.W,. Wu M.-J, Keel C., Yang B., Showalter V.M.,
Abood M. E., Martin B.R.. Influence of the N-1 alkyl chain length of cannabimimetic
indoles upon CB1 and CB2 receptor binding//Drug Alcohol Depend. 2000, V. 60, p. 133-
140.
8. Wiley J.L., Compton D.R., Dai D., Lainton J.A.H., Phillips M., Huffman J.W., Martin
B.R. Structure-Activity Relationships of Indole- and Pyrrole-Derived Cannabinoids//J.
Pharmacol. Exp. Ther. 1998, V. 285, p. 995-1004.
9. Brents L.K., Gallus-Zawada A., Radominska-Pandya A., Vasiljevik T., Prisinzano
T.E., Fantegrossi W.E., Moran 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, V.83, p. 952-961.
10. Schneir A.B., Cullen J., Ly B.T.. “Spice” Girls: Synthetic Cannabinoid
Intoxication//J. Emerg. Med. 2011, V.40, p. 296-299.
11. Simmons J.R., Cookman L., Kang C., Skinner C.. Three cases of “spice”
exposure//Clin. Toxicol. 2011, V. 49, p. 431-433.
12. Zimmermann U.S., Winkelmann P.R., Pilhatsch M., Nees J.A., Spanagel R., Schulz
K. Withdrawal phenomena and dependence syndrome after the consumption of ‘Spice
Gold’//Dtsch Arztebl Int. 2009, V.106, p. 464-467.
13. Kraemer T., Rust K.Y., Meyer M.R., Wissenbach D.K., Bregel D., Hopf M., Maurer
H.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, V.21(S1), p. O43-45.
14. Sobolevsky T., Prasolov I., Rodchenkov G. Detection of JWH-018 metabolites in
smokingmixture post-administration urine//Forensic Sci. Int. 2010, V. 200, p.141-147.
15. 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 Testing Anal. 2011, V.3, p. 609-620.
16. 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. 2011. V.879, p. 1126-
1136.
17. Григорьев А.М., Савчук С.А., Мельник А.А., Ершов М.Б., Джурко Ю.А.,
Веденин А.Н., Носырев А.Е., Изотов Б.Н., Рожанец В.В. Установление факта приема
синтетического каннабиноида JWH-018 хромато-масс-спектрометрическими
методами//Журн. аналит. химии. 2012. Т.67, c. 995-1004.
18. Grigoryev A., Melnik A., Savchuk S., Simonov A., Rozhanets V. Gas and liquid
chromatography–mass spectrometry studies on the metabolism of synthetic
phenylacetylindole cannabimimetic JWH-250, psychoactive components of smoking
mixtures, J. Chromatogr. B. 2011, V. 879, p. 2519-2526.
19. Grigoryev A., Kavanagh P., Melnik A. The detection of the urinary metabolites of 3-
[(adamantan-1-yl)carbonyl]-1-pentylindole (AB-001), a novel cannabimimetic, by gas
chromatography/mass spectrometry//Drug Test. Anal. 2012, V.4. p.519-524.
20. Kavanagh P., Grigoryev A., Melnik A., Simonov A. The identification of the urinary
metabolites of 3-(4-methoxybenzoyl)-1-pentylindole (RCS-4), a novel cannabimimetic, by
gas chromatography/mass spectrometry//J. Anal. Toxicol. 2012, V.36. p. 303-311.
21. Grigoryev A., Kavanagh P., Melnik A. The detection of the urinary metabolites of 1-
[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone (AM-694), a high affinity
cannabimimetic, by gas chromatography – mass spectrometry//Drug Test. Anal. 2013, V.5.
p. 110-115.
22. 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, V.398, p. 2141-2153.
23. Beuck S., Möller I., Thomas A., Klose A., Schlörer N., Schänzer W., Thevis M.
Structure characterisation of urinary metabolites of the cannabimimetic JWH-018 using
chemically synthesised reference material for the support of LC-MS/MS-based drug
testing//Anal. Bioanal. Chem. 2011, V.401, p. 493-505.
24. Chimalakonda K.C., Bratton S.M., Vi-Huyen Le, Kan Hui Yiew, Dineva A., Moran
C.L., James L.P., Moran J.H., Radominska-Pandya A. Conjugation of Synthetic
Cannabinoids JWH-018 and JWH-073, Metabolites by Human UDPGlucuronosyltransferases//
Drug. Metab. Dispos. 2011, V.39, p. 1967-1976.
25. Dresen S., Kneisel S., Weinmann W., Zimmermann R., Auwärter V. Development
and validation of a liquid chromatography–tandem mass spectrometry method for the
quantitation of synthetic cannabinoids of the aminoalkylindole type and methanandamide
in serum and its application to forensic samples//J. Mass. Spectrom. 2011, V.46, p. 163-
171.
26. J. Teske, J.P. Weller, A. Fieguth, T. Rothämel, Y. Schulz, H.D. Tröger, 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, V.878, p. 2959-2963.
27. 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, V.83, p. 4228-4236.
28. Chimalakonda K.C., Moran C.L., Kennedy P.D., Endres G.W., Uzieblo A.,
Dobrowolski P.J., Fifer E.K., Lapoint J., Nelson L.S., Hoffman R.S., James L.P.,
Radominska-Pandya A., Moran J.H. Solid-Phase Extraction and Quantitative Measurement
of Omega and Omega-1 Metabolites of JWH-018 and JWH-073 in Human Urine//Anal.
Chem. 2011, V.83, p. 6381-6388.
29. 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,
V.47, p.54-65.
30. Wissenbach D.K., Meyer M.R., Remane D., Philipp A.A., Weber A.A., Maurer H.H.
Drugs of abuse screening in urine as part of a metabolite-based LC-MSn screening
concept//Anal. Bioanal. Chem. 2011, V.400, p. 79-88.
31. 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 HPLCMS/
MS//Anal. Bioanal. Chem. 2006. V.386. p. 1345-134-55.
Published
2019-11-22
How to Cite
Grigoriev, A. M., Daniluyk, A. A., Savchuk, S. A., & Rudakov, O. B. (2019). Detection of synthetic cannabimimetics JWH-018 and JWH-073 by gas chromatography-mass spectrometry of metabolites dezalkilirovannyh. Sorbtsionnye I Khromatograficheskie Protsessy, 13(6). Retrieved from https://journals.vsu.ru/sorpchrom/article/view/1707
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