Determination of major metabolites of MAM-2201 and JWH-122 in in vitro and in vivo studies to distinguish their intake

Forensic Science International

Volumn 244, Issue , 2014, Pages 85-91

  Jang, Moonhee ^a   Shin, Ilchung ^a   Yang, Wonkyung ^a   Chang, Hyejin ^a   Yoo, Hye Hyun ^b   Lee, Jaesin ^a   Kim, Eunmi ^a  

^a National Forensic Service   (South Korea)

^b Hanyang University   (South Korea)

Author keywords

In vitro metabolism; JWH 122; MAM 2201; Synthetic cannabinoid; Urine

Indexed keywords

CANNABINOID DERIVATIVE; CARBOXYLATED JWH 122 METABOLITE; DRUG METABOLITE; JWH 122; MAM 2201; N 4 HYDROXYLATED JWH 122 METABOLITE; N 4 HYDROXYLATED MAM 2201 METABOLITE; N 5 HYDROXYLATED JWH 122 METABOLITE; N CARBOXYLATED MAM 2201 METABOLITE; UNCLASSIFIED DRUG; (4-METHYL-1-NAPHTHYL)-(1-PENTYLINDOL-3-YL)METHANONE; 1-(5-FLUOROPENTYL)-3-(4-METHYL-1-NAPHTHOYL)INDOLE; INDOLE DERIVATIVE; NAPHTHALENE DERIVATIVE; STREET DRUG;

ARTICLE; CARBOXYLATION; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG ABUSE; DRUG DETERMINATION; DRUG METABOLISM; DRUG STRUCTURE; HUMAN; HUMAN CELL; HYDROXYLATION; IN VITRO STUDY; IN VIVO STUDY; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; TANDEM MASS SPECTROMETRY; URINALYSIS; VALIDATION STUDY; CHEMICAL STRUCTURE; CHEMISTRY;

HUMANS; HYDROXYLATION; IN VITRO TECHNIQUES; INDOLES; MICROSOMES, LIVER; MOLECULAR STRUCTURE; NAPHTHALENES; STREET DRUGS;

EID: 84907735372     PISSN: 03790738     EISSN: 18726283     Source Type: Journal    
DOI: 10.1016/j.forsciint.2014.08.008     Document Type: Article

References (23)

1. Gurney S.M.R., Scott K.S., Kacinko S.L., Presley B.C., Logan B.K. Pharmacology, toxicology, and adverse effects of synthetic cannabinoid drugs. Forensic Sci. Rev. 2014, 26:53-78.
2. Camp N.E. Synthetic cannabinoids. J. Emerg. Nurs. 2011, 37:292-293.
3. Wells D.L., Ott C.A. The new marijuana. Ann. Pharmacother. 2011, 45:414-417.
4. Lewin A.H., Seltzman H.H., Carroll F.I., Mascarella S.W., Reddy P.A. Emergence and properties of spice and bath salts: a medicinal chemistry perspective. Life Sci. 2013, 97:9-19.
5. 35S]GTP(S binding assays. Forensic Toxicol. 2011, 29:132-141.
6. Dziadosz M., Klintschar M., Teske J. Mixed consumption of cannabis and spice. Forensic Sci. Int. 2014, 235:e1-e2.
7. Simolka K., Lindigkeit R., Schiebel H.M., Papke U., Ernst L., Beuerle T. Analysis of synthetic cannabinoids in "spicelike" herbal highs: snapshot of the German market in summer 2011. Anal. Bioanal. Chem. 2012, 404:157-171.
8. Moosmann B., Kneisel S., Girreser U., Brecht V., Westphal F., Auwärter V. Separation and structural characterization of the synthetic cannabinoids JWH-412 and 1-[(5-fluoropentyl)-1H-indol-3yl]-(4-methylnaphthalen-1-yl)methanone using GC-MS, NMR analysis and a flash chromatography system. Forensic Sci. Int. 2012, 220:e17-e22.
9. Chung H., Choi H., Heo S., Kim E., Lee J. Synthetic cannabinoids abused in South Korea: drug identifications by the National Forensic Service from 2009 to June 2013. Forensic Toxicol. 2013, 32:82-88.
10. Derungs A., Schwaninger A.E., Mansella G., Bingisser R., Kraemer T., Liechti M.E. Symptoms, toxicities, and analytical results for a patient after smoking herbs containing the novel synthetic cannabinoid MAM-2201. Forensic Toxicol. 2013, 31:164-171.
11. 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.
12. 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.
13. Sobolevsky T., Prasolov I., Rodchenkov G. Detection of urinary metabolites of AM-2201 and UR-144, two novel synthetic cannabinoids. Drug Test. Anal. 2012, 4:745-753.
14. Jang M., Yang W., Shin I., Choi H., Chang H., Kim E. Determination of AM-2201 metabolites in urine and comparison with JWH-018 abuse. Int. J. Legal Med. 2014, 128:285-294.
15. Jang M., Yang W., Choi H., Chang H., Lee S., Kim E., Chung H. Monitoring of urinary metabolites of JWH-018 and JWH-073 in legal cases. Forensic Sci. Int. 2013, 231:13-19.
16. Food and Drug Administration Guidance for industry, bioanalytical method validation 2001, FDA, U.S. Department of Health and Human Services, Available from: http://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/ucm070107.pdf Accessed 30.04.14.
17. Chimalakonda K.C., Moran C.L., Kennedy P.D., Endres G.W., Uzieblo A., Doborowolski 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, 83:6381-6388.
18. Chimalakonda K.C., Bratton S.M., Le V.H., Yiew K.H., 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 UDP-glucuronosyltransferases. Drug Metab. Dispos. 2011, 39:1967-1976.
19. 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.
20. De Brabanter N., Esposito S., Geldof L., Lootens L., Meuleman P., Leroux-Roels G., Deventer K., Van Eenoo P. In vitro and in vivo metabolisms of 1-pentyl-3-(4-methyl-1-naphthoyl) indole (JWH-122). Forensic Toxicol. 2013, 31:212-222.
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, 5:110-115.
22. Patton A.L., Seely K.A., Chimalakonda K.C., Tran J.P., Trass M., Miranda A., Fantegrossi W.E., Kennedy P.D., Dobrowolski P., Radominska-Pandya A., McCain K.R., James L.P., Endres G.W., Moran J.H. Targeted metabolomic approach for assessing human synthetic cannabinoid exposure and pharmacology. Anal. Chem. 2013, 85:9390-9399.
23. Scheidweiler K.B., Huestis M.A. Simultaneous quantification of 20 synthetic cannabinoids and 21 metabolites, and semi-quantification of 12 alkyl hydroxy metabolites in human urine by liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 2014, 1327:105-117.