메뉴 건너뛰기




Volumn 17, Issue 3, 2015, Pages 660-677

Pentylindole/Pentylindazole Synthetic Cannabinoids and Their 5-Fluoro Analogs Produce Different Primary Metabolites: Metabolite Profiling for AB-PINACA and 5F-AB-PINACA

Author keywords

5 fluoro AB PINACA; AB PINACA; in silico prediction; metabolism; synthetic cannabinoids

Indexed keywords

INDAZOLE DERIVATIVE; N-(1-AMINO-3-METHYL-1-OXOBUTAN-2-YL)-1-(5-FLUOROPENTYL)-1H-INDAZOLE-3-CARBOXAMIDE; N-(1-AMINO-3-METHYL-1-OXOBUTAN-2-YL)-1-PENTYL-1H-INDAZOLE-3-CARBOXAMIDE; VALINE;

EID: 84939934149     PISSN: None     EISSN: 15507416     Source Type: Journal    
DOI: 10.1208/s12248-015-9721-0     Document Type: Article
Times cited : (100)

References (36)
  • 1
    • 84939957904 scopus 로고    scopus 로고
    • European Monitoring Centre for Drugs and Drug Addiction. Perspectives on drugs: synthetic cannabinoids in Europe. 2014
    • European Monitoring Centre for Drugs and Drug Addiction. Perspectives on drugs: synthetic cannabinoids in Europe. 2014.
  • 2
    • 84962628550 scopus 로고    scopus 로고
    • Synthetic marijuana data
    • American Association of Poison Control Centers. Synthetic marijuana data, updated January 31, 2015. https://aapcc.s3.amazonaws.com/files/library/Syn_Marijuana_Web_Data_through_1.2015.pdf
    • (2015) updated January 31
  • 4
    • 84894061625 scopus 로고    scopus 로고
    • Synthetic cannabinoids: analysis and metabolites
    • COI: 1:CAS:528:DC%2BC2cXhvFGgtbs%3D, PID: 24412391
    • ElSohly MA, Gul W, Wanas AS, Radwan MM. Synthetic cannabinoids: analysis and metabolites. Life Sci. 2014;97(1):78–90.
    • (2014) Life Sci , vol.97 , Issue.1 , pp. 78-90
    • ElSohly, M.A.1    Gul, W.2    Wanas, A.S.3    Radwan, M.M.4
  • 5
    • 84867684839 scopus 로고    scopus 로고
    • Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands
    • COI: 1:CAS:528:DC%2BC38XhsFKkt7rJ, PID: 22904561
    • Chimalakonda KC, Seely KA, Bratton SM, Brents LK, Moran CL, Endres GW, et al. Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands. Drug Metab Dispos. 2012;40(11):2174–84.
    • (2012) Drug Metab Dispos , vol.40 , Issue.11 , pp. 2174-2184
    • Chimalakonda, K.C.1    Seely, K.A.2    Bratton, S.M.3    Brents, L.K.4    Moran, C.L.5    Endres, G.W.6
  • 8
    • 84888014152 scopus 로고    scopus 로고
    • First characterization of AKB-48 metabolism, a novel synthetic cannabinoid, using human hepatocytes and high-resolution mass spectrometry
    • COI: 1:CAS:528:DC%2BC3sXhsFOgsr7M, PID: 23913126
    • Gandhi A, Zhu M, Pang S, Wohlfarth A, Scheidweiler K, Liu H-f, et al. First characterization of AKB-48 metabolism, a novel synthetic cannabinoid, using human hepatocytes and high-resolution mass spectrometry. AAPS J. 2013;15(4):1091–9.
    • (2013) AAPS J , vol.15 , Issue.4 , pp. 1091-1099
    • Gandhi, A.1    Zhu, M.2    Pang, S.3    Wohlfarth, A.4    Scheidweiler, K.5    Liu, H.-F.6
  • 9
    • 84924726627 scopus 로고    scopus 로고
    • High-resolution mass spectrometric metabolite profiling of a novel synthetic designer drug, N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide (STS-135), using cryopreserved human hepatocytes and assessment of metabolic stability with human liver microsomes
    • Gandhi AS, Wohlfarth A, Zhu M, Pang S, Castaneto M, Scheidweiler KB, et al. High-resolution mass spectrometric metabolite profiling of a novel synthetic designer drug, N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide (STS-135), using cryopreserved human hepatocytes and assessment of metabolic stability with human liver microsomes. Drug Test Anal. 2014. doi:10.1002/dta.1662.
    • (2014) Drug Test Anal
    • Gandhi, A.S.1    Wohlfarth, A.2    Zhu, M.3    Pang, S.4    Castaneto, M.5    Scheidweiler, K.B.6
  • 10
    • 84904624043 scopus 로고    scopus 로고
    • Metabolite profiling of RCS-4, a novel synthetic cannabinoid designer drug, using human hepatocyte metabolism and time of flight mass spectrometry
    • COI: 1:CAS:528:DC%2BC2cXhtFyntrfE, PID: 25046048
    • Gandhi AS, Zhu M, Pang S, Wohlfarth A, Scheidweiler KB, Huestis MA. Metabolite profiling of RCS-4, a novel synthetic cannabinoid designer drug, using human hepatocyte metabolism and time of flight mass spectrometry. Bioanalysis. 2014;6(11):1471–85.
    • (2014) Bioanalysis , vol.6 , Issue.11 , pp. 1471-1485
    • Gandhi, A.S.1    Zhu, M.2    Pang, S.3    Wohlfarth, A.4    Scheidweiler, K.B.5    Huestis, M.A.6
  • 11
    • 84873746662 scopus 로고    scopus 로고
    • 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
    • COI: 1:CAS:528:DC%2BC38XlvVKltr4%3D, PID: 22522907
    • 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(2):110–5.
    • (2013) Drug Test Anal , vol.5 , Issue.2 , pp. 110-115
    • Grigoryev, A.1    Kavanagh, P.2    Melnik, A.3
  • 12
    • 84863104962 scopus 로고    scopus 로고
    • The detection of the urinary metabolites of 3-[(adamantan-1-yl)carbonyl]-1-pentylindole (AB-001), a novel cannabimimetic, by gas chromatography-mass spectrometry
    • COI: 1:CAS:528:DC%2BC3MXhsVOqsr7E, PID: 22102533
    • 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;4(6):519–24.
    • (2012) Drug Test Anal , vol.4 , Issue.6 , pp. 519-524
    • Grigoryev, A.1    Kavanagh, P.2    Melnik, A.3
  • 13
    • 84860422185 scopus 로고    scopus 로고
    • Gas and liquid chromatography-mass spectrometry studies on the metabolism of the synthetic phenylacetylindole cannabimimetic JWH-250, the psychoactive component of smoking mixtures
    • COI: 1:CAS:528:DC%2BC3MXhtVKlsLnO, PID: 21803006
    • Grigoryev A, Melnik A, Savchuk S, Simonov A, Rozhanets V. Gas and liquid chromatography-mass spectrometry studies on the metabolism of the synthetic phenylacetylindole cannabimimetic JWH-250, the psychoactive component of smoking mixtures. J Chromatogr B Analyt Technol Biomed Life Sci. 2011;879(25):2519–26.
    • (2011) J Chromatogr B Analyt Technol Biomed Life Sci , vol.879 , Issue.25 , pp. 2519-2526
    • Grigoryev, A.1    Melnik, A.2    Savchuk, S.3    Simonov, A.4    Rozhanets, V.5
  • 14
    • 79955031826 scopus 로고    scopus 로고
    • Chromatography-mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures
    • COI: 1:CAS:528:DC%2BC3MXltFyisL0%3D, PID: 21481654
    • Grigoryev A, Savchuk S, Melnik A, Moskaleva N, Dzhurko J, Ershov M, et al. 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(15–16):1126–36.
    • (2011) J Chromatogr B Analyt Technol Biomed Life Sci , vol.879 , Issue.15-16 , pp. 1126-1136
    • Grigoryev, A.1    Savchuk, S.2    Melnik, A.3    Moskaleva, N.4    Dzhurko, J.5    Ershov, M.6
  • 15
    • 84856349177 scopus 로고    scopus 로고
    • 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
    • COI: 1:CAS:528:DC%2BC38Xht1ymsbY%3D, PID: 22282090
    • 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(1):54–65.
    • (2012) J Mass Spectrom , vol.47 , Issue.1 , pp. 54-65
    • Hutter, M.1    Broecker, S.2    Kneisel, S.3    Auwärter, V.4
  • 16
    • 84879902232 scopus 로고    scopus 로고
    • Characteristics of the designer drug and synthetic cannabinoid receptor agonist AM-2201 regarding its chemistry and metabolism
    • COI: 1:CAS:528:DC%2BC3sXhtVOjsb3F, PID: 23832945
    • 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(7):885–94.
    • (2013) J Mass Spectrom , vol.48 , Issue.7 , pp. 885-894
    • Hutter, M.1    Moosmann, B.2    Kneisel, S.3    Auwärter, V.4
  • 17
    • 84865846893 scopus 로고    scopus 로고
    • The identification of the urinary metabolites of 3-(4-methoxybenzoyl)-1-pentylindole (RCS-4), a novel cannabimimetic, by gas chromatography-mass spectrometry
    • COI: 1:CAS:528:DC%2BC38XntVSntL8%3D, PID: 22582265
    • 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;36(5):303–11.
    • (2012) J Anal Toxicol , vol.36 , Issue.5 , pp. 303-311
    • Kavanagh, P.1    Grigoryev, A.2    Melnik, A.3    Simonov, A.4
  • 18
    • 84868194464 scopus 로고    scopus 로고
    • Detection of urinary metabolites of AM-2201 and UR-144, two novel synthetic cannabinoids
    • COI: 1:CAS:528:DC%2BC38XhsVKgsrfP, PID: 23042760
    • 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(10):745–53.
    • (2012) Drug Test Anal , vol.4 , Issue.10 , pp. 745-753
    • Sobolevsky, T.1    Prasolov, I.2    Rodchenkov, G.3
  • 19
    • 84898045894 scopus 로고    scopus 로고
    • Metabolism of synthetic cannabinoids PB-22 and its 5-fluoro analog, 5F-PB-22, by human hepatocyte incubation and high-resolution mass spectrometry
    • COI: 1:CAS:528:DC%2BC2cXitF2jurc%3D, PID: 24518903
    • Wohlfarth A, Gandhi A, Pang S, Zhu M, Scheidweiler K, Huestis M. Metabolism of synthetic cannabinoids PB-22 and its 5-fluoro analog, 5F-PB-22, by human hepatocyte incubation and high-resolution mass spectrometry. Anal Bioanal Chem. 2014;406(6):1763–80.
    • (2014) Anal Bioanal Chem , vol.406 , Issue.6 , pp. 1763-1780
    • Wohlfarth, A.1    Gandhi, A.2    Pang, S.3    Zhu, M.4    Scheidweiler, K.5    Huestis, M.6
  • 20
    • 84903195324 scopus 로고    scopus 로고
    • Metabolism of RCS-8, a synthetic cannabinoid with cyclohexyl structure, in human hepatocytes by high-resolution MS
    • COI: 1:CAS:528:DC%2BC2cXhtVWms7jL, PID: 24946920
    • Wohlfarth A, Pang S, Zhu M, Gandhi AS, Scheidweiler KB, Huestis MA. Metabolism of RCS-8, a synthetic cannabinoid with cyclohexyl structure, in human hepatocytes by high-resolution MS. Bioanalysis. 2014;6(9):1187–200.
    • (2014) Bioanalysis , vol.6 , Issue.9 , pp. 1187-1200
    • Wohlfarth, A.1    Pang, S.2    Zhu, M.3    Gandhi, A.S.4    Scheidweiler, K.B.5    Huestis, M.A.6
  • 21
    • 84887082348 scopus 로고    scopus 로고
    • First metabolic profile of XLR-11, a novel synthetic cannabinoid, obtained by using human hepatocytes and high-resolution mass spectrometry
    • COI: 1:CAS:528:DC%2BC3sXhslGht7vE, PID: 24014837
    • Wohlfarth A, Pang S, Zhu M, Gandhi AS, Scheidweiler KB, Liu H-F, et al. First metabolic profile of XLR-11, a novel synthetic cannabinoid, obtained by using human hepatocytes and high-resolution mass spectrometry. Clin Chem. 2013;59(11):1638–48.
    • (2013) Clin Chem , vol.59 , Issue.11 , pp. 1638-1648
    • Wohlfarth, A.1    Pang, S.2    Zhu, M.3    Gandhi, A.S.4    Scheidweiler, K.B.5    Liu, H.-F.6
  • 22
    • 33750458384 scopus 로고    scopus 로고
    • Identification of in vitro metabolites of JWH-015, an aminoalkylindole agonist for the peripheral cannabinoid receptor (CB2) by HPLC-MS/MS
    • COI: 1:CAS:528:DC%2BD28XhtFegtLvJ, PID: 16955257
    • Zhang Q, Ma P, Cole R, 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(5):1345–55.
    • (2006) Anal Bioanal Chem , vol.386 , Issue.5 , pp. 1345-1355
    • Zhang, Q.1    Ma, P.2    Cole, R.3    Wang, G.4
  • 24
    • 84872685862 scopus 로고    scopus 로고
    • New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA) identified as designer drugs in illegal products
    • COI: 1:CAS:528:DC%2BC3sXhsVCnsL0%3D
    • Uchiyama N, Matsuda S, Wakana D, Kikura-Hanajiri R, Goda Y. New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA) identified as designer drugs in illegal products. Forensic Toxicol. 2013;31(1):93–100.
    • (2013) Forensic Toxicol , vol.31 , Issue.1 , pp. 93-100
    • Uchiyama, N.1    Matsuda, S.2    Wakana, D.3    Kikura-Hanajiri, R.4    Goda, Y.5
  • 25
    • 84939965549 scopus 로고    scopus 로고
    • European Monitoring Centre for Drugs and Drug Addiction. EMCDDA—Europol 2013 annual report on the implementation of Council Decision 2005/387/JHA2014
    • European Monitoring Centre for Drugs and Drug Addiction. EMCDDA—Europol 2013 annual report on the implementation of Council Decision 2005/387/JHA2014.
  • 26
    • 84962688004 scopus 로고    scopus 로고
    • Indazole derivatives
    • Pfizer Inc. Indazole derivatives, patent WO/2009/106982. 2009.
    • (2009) patent WO/2009/106982
  • 27
    • 84939986538 scopus 로고    scopus 로고
    • Schedules of controlled substances: temporary placement of three synthetic cannabinoids into schedule I (AB-CHMINACA, AB-PINACA, THJ-2201)
    • Drug Enforcement Administration. Schedules of controlled substances: temporary placement of three synthetic cannabinoids into schedule I (AB-CHMINACA, AB-PINACA, THJ-2201). Fed Register. 2014;79(244):75767–71.
    • (2014) Fed Register , vol.79 , Issue.244 , pp. 75767-75771
    • Drug Enforcement Administration1
  • 28
    • 84901441981 scopus 로고    scopus 로고
    • UPLC/ESI-MS/MS-based determination of metabolism of several new illicit drugs, ADB-FUBINACA, AB-FUBINACA, AB-PINACA, QUPIC, 5F-QUPIC and α-PVT, by human liver microsome
    • COI: 1:CAS:528:DC%2BC2cXosFaqsrs%3D, PID: 24861751
    • Takayama T, Suzuki M, Todoroki K, Inoue K, Min JZ, Kikura-Hanajiri R, et al. UPLC/ESI-MS/MS-based determination of metabolism of several new illicit drugs, ADB-FUBINACA, AB-FUBINACA, AB-PINACA, QUPIC, 5F-QUPIC and α-PVT, by human liver microsome. Biomed Chromatogr. 2014;28(6):831–8.
    • (2014) Biomed Chromatogr , vol.28 , Issue.6 , pp. 831-838
    • Takayama, T.1    Suzuki, M.2    Todoroki, K.3    Inoue, K.4    Min, J.Z.5    Kikura-Hanajiri, R.6
  • 30
    • 33748636018 scopus 로고    scopus 로고
    • Introduction to in vitro estimation of metabolic stability and drug interactions of new chemical entities in drug discovery and development
    • COI: 1:CAS:528:DC%2BD28XhtlarsbnM, PID: 16963792
    • Baranczewski P, Stanczak A, Sundberg K, Svensson R, Wallin A, Jansson J, et al. Introduction to in vitro estimation of metabolic stability and drug interactions of new chemical entities in drug discovery and development. Pharmacol Rep. 2006;58(4):453–72.
    • (2006) Pharmacol Rep , vol.58 , Issue.4 , pp. 453-472
    • Baranczewski, P.1    Stanczak, A.2    Sundberg, K.3    Svensson, R.4    Wallin, A.5    Jansson, J.6
  • 31
    • 40749151480 scopus 로고    scopus 로고
    • An automated liquid chromatography-mass spectrometry process to determine metabolic stability half-life and intrinsic clearance of drug candidates by substrate depletion
    • COI: 1:CAS:528:DC%2BD1cXjtFKqtbs%3D, PID: 18336089
    • McNaney CA, Drexler DM, Hnatyshyn SY, Zvyaga TA, Knipe JO, Belcastro JV, et al. An automated liquid chromatography-mass spectrometry process to determine metabolic stability half-life and intrinsic clearance of drug candidates by substrate depletion. Assay Drug Dev Technol. 2008;6(1):121–9.
    • (2008) Assay Drug Dev Technol , vol.6 , Issue.1 , pp. 121-129
    • McNaney, C.A.1    Drexler, D.M.2    Hnatyshyn, S.Y.3    Zvyaga, T.A.4    Knipe, J.O.5    Belcastro, J.V.6
  • 32
    • 0030911863 scopus 로고    scopus 로고
    • The use of human hepatocytes to select compounds based on their expected hepatic extraction ratios in humans
    • PID: 9090701
    • Lavé T, Dupin S, Schmitt C, Valles B, Ubeaud G, Chou RC, et al. The use of human hepatocytes to select compounds based on their expected hepatic extraction ratios in humans. Pharm Res. 1997;14(2):152–5.
    • (1997) Pharm Res , vol.14 , Issue.2 , pp. 152-155
    • Lavé, T.1    Dupin, S.2    Schmitt, C.3    Valles, B.4    Ubeaud, G.5    Chou, R.C.6
  • 33
    • 7744224004 scopus 로고    scopus 로고
    • Standardization of a LC/MS/MS method for the determination of acyl glucuronides and their isomers
    • COI: 1:CAS:528:DC%2BD38XovF2ku74%3D
    • Bolze S, Lacombe O, Durand G, Chaimbault P, Massiere F, Gay-Feutry C, et al. Standardization of a LC/MS/MS method for the determination of acyl glucuronides and their isomers. Curr Sep. 2002;20(2):55–9.
    • (2002) Curr Sep , vol.20 , Issue.2 , pp. 55-59
    • Bolze, S.1    Lacombe, O.2    Durand, G.3    Chaimbault, P.4    Massiere, F.5    Gay-Feutry, C.6
  • 34
    • 0037306174 scopus 로고    scopus 로고
    • Acyl glucuronide drug metabolites: toxicological and analytical implications
    • COI: 1:CAS:528:DC%2BD3sXmtVWgsA%3D%3D, PID: 12548138
    • Shipkova M, Armstrong VW, Oellerich M, Wieland E. Acyl glucuronide drug metabolites: toxicological and analytical implications. Ther Drug Monit. 2003;25(1):1–16.
    • (2003) Ther Drug Monit , vol.25 , Issue.1 , pp. 1-16
    • Shipkova, M.1    Armstrong, V.W.2    Oellerich, M.3    Wieland, E.4
  • 35
    • 84886540118 scopus 로고    scopus 로고
    • The nonenzymatic reactivity of the acyl-linked metabolites of Mefenamic acid toward amino and thiol functional group bionucleophiles
    • COI: 1:CAS:528:DC%2BC3sXhslSqsLvF, PID: 23975029
    • Horng H, Benet LZ. The nonenzymatic reactivity of the acyl-linked metabolites of Mefenamic acid toward amino and thiol functional group bionucleophiles. Drug Metab Dispos. 2013;41(11):1923–33.
    • (2013) Drug Metab Dispos , vol.41 , Issue.11 , pp. 1923-1933
    • Horng, H.1    Benet, L.Z.2
  • 36
    • 0028074997 scopus 로고
    • Effects of fluorine substitution on drug metabolism: pharmacological and toxicological implications
    • COI: 1:CAS:528:DyaK2cXmslSqtbc%3D, PID: 7924905
    • Park BK, Kitteringham NR. Effects of fluorine substitution on drug metabolism: pharmacological and toxicological implications. Drug Metab Rev. 1994;26(3):605–43.
    • (1994) Drug Metab Rev , vol.26 , Issue.3 , pp. 605-643
    • Park, B.K.1    Kitteringham, N.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.