LC/QQQ Screening for ~ 300 Designer Drugs and Metabolites
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1 LC/QQQ Screening for ~ 300 Designer Drugs and Metabolites Anthony P. DeCaprio, Ph.D. Associate Professor Ana-Michelle Broomes M.S.F.S. Student Dept. of Chemistry & Biochemistry International Forensic Research Institute Florida International University Miami, FL
2 Acknowledgements Madeleine Swortwood, Josh Seither (FIU Ph.D. students). Ana-Michelle Broomes (FIU MSFS student). Dr. Luis Arroyo (Manager, IFRI Forensic & Analytical Toxicology Facility). Dr. Lee Hearn, Mr. George Hime, and Dr. Diane Boland (MDME Toxicology Department). Agilent Technologies, Inc. Cayman Chemical. Ralph Hindle; Vogon Laboratory Services. National Institute of Justice grant 2011-DN-BX-K559.
3 Designer Drugs Drugs that are created (or marketed, if they had already existed) so as to avoid the provisions of existing drug laws, usually by preparing analogs or derivatives of existing drugs by modifying their chemical structure to varying degrees, or less commonly by finding drugs with entirely different chemical structures that produce similar subjective effects to illegal recreational drugs. ( See and PiHKAL ( Phenethylamines I Have Known and Loved ) and TiHKAL ( Tryptamines I Have Known and Loved ) books by Dr. Alexander Shulgin.
4 Wohlfarth and Weinmann, 2010.
5 Designer Drug Forensic Toxicology Issues Lack of objective information on pharmacological and clinical action, toxicokinetics, lethal levels. Possible high potency. Variable legal status. Unknown or new entities. Street drugs are often misrepresented. Cross-reactivity (or lack of) in immunoassays.
6 Cross-Reactivity of Commercial Immunoassays (±)-Amphetamine Immunalysis Neogen Randox Orasure Drug Amp Meth Amp (±)-Methamphetamine 2C-E (±)-DOET (±)-DOM (±)-TMA (±)-MDA (±)-MDEA (±)-MDMA (±)-Ethylamphetamine (±)-MDPV (±)-Mephedrone (±)-Cathinone (±)-Methcathinone (±)-Methylone (±)-4-MEC (±)-Flephedrone (±)-Butylone mcpp (±)-Methedrone 5-MeO-DiPT (±)-DOB 2C-B DMT BZP AMT 2C-I 2C-T-7 TFMPP 2C-T-4 AMP Specific Amp Ultra BZP Ketamine MPD Meth/ MDMA MPT MDPV Meph/ Mcath PCP Cotinine Amp Specific Meth Target analyte Cross-reactive at concentrations <650 ng/ml Swortwood, Amp - amphetamine; M.J., Hearn, BZP - benzylpiperazine; W.L., and DeCaprio, Meph - A.P. mephedrone; (2013). Meth Cross-reactivity - methamphetamine; of cathinone Mcath - methcathinone; derivatives and MPD other - methylphenidate; designer drugs MPT in - commercial mephentermine enzyme-linked immunosorbent assays. American Academy of Forensic Sciences 65th Annual Meeting, Washington, DC; February 22.
7 Designer Drug Forensic Toxicology Issues Lack of objective information on pharmacological and clinical action, toxicokinetics, lethal levels. Possible high potency. Variable legal status. Unknown or new entities. Street drugs often misrepresented. Cross-reactivity (or lack of) in immunoassays. No comprehensive analytical methods available.
8 MS-Based Screening of Designer Drugs: Previous Work Peters, F.T., et al. (2003). J.Mass Spectrom. 38, (18 amphetamines and piperazines) Kölliker, S., and Oehme, M. (2004). Anal.Bioanal.Chem. 378, (55 phenethylamines) Takahashi, M., et al. (2009). Talanta 77, (104 analytes) Wohlfarth, A., et al. (2010). Anal.Bioanal.Chem. 396, (35 analytes) Shanks, K.G., et al. (2012). J.Anal.Toxicol. 36, (33 cannabinoids; 26 cathinones/phenethylamines) Ammann, J., et al. (2012). J.Anal.Toxicol. 36, (23 cannabinoids) Ammann, D., et al. (2012). J.Anal.Toxicol. 36, (25 cathinones and phenethylamines) Guale, F., et al. (2013). J.Anal.Toxicol. 37, (32 cannabinoids/cathinones)
9 Evolution of Method Development Develop designer drug screening/confirmation methods that are comprehensive, sensitive, and rapid. 1. LC-QQQ-MS/MS screening method for 32 designer drugs. 2. Designer drug Master List. 3. LC-QTOF-MS based database and analytical method (~300 drugs). 4. GC-MS and GC-QQQ-MS database and analytical methods (~300 drugs). 5. LC-QQQ Enhanced Dynamic MRM database and analytical method for selected groups of designer drugs ( DEA and Japan lists; expansion to ~300 drugs). 6. LC-QQQ Triggered MRM database and analytical method for ~300 drugs.
10 QQQ-MS MRM Modes Standard MRM: Typically 2 to 4 transitions are selected for confirmation and quantitative analysis. Requires the use of time segmentation, where the method is divided into a series of time segments. Dynamic MRM: Ion transitions and a retention time window for each analyte are part of the analytical method. Constant sampling time across peak, individual MRM dwell time is adjusted accordingly, fewer concurrent ion transitions, individual cycle times are reduced. Triggered MRM: Both primary and secondary transitions are defined for each target analyte in the method. When the signal of one of the primary transitions exceeds a threshold level, the secondary transitions are triggered and acquired in a specified number of scans. Comparison to tmrm spectral library (with match score ) allows identification of unknowns; selectivity approaches that of high mass accuracy instruments.
11 Triggered MRM Library Spectra
12 LC-QQQ-MS/MS Based Designer Drug Screening SPE from serum or whole blood. Agilent 1290 Infinity Binary Pump UHPLC. Agilent 6460 QQQ-MS. Electrospray Ionization (ESI) with Jet Streaming technology. Data acquired in Dynamic MRM mode with positive ESI.
13 Chromatographic Separation Eluent A: 2 mm ammonium formate with 0.1% formic acid. Eluent B: 0.1% formic acid in MeCN:H 2 O (90:10). Six-minute gradient. Agilent Zorbax Rapid Resolution HD Eclipse Plus C 18 column (50 x 2.1 mm, 1.8 μm particle size)
14 Results Selective for targeted analytes. Interfering peaks from matrix were negligible; no co-elutions. LODs in the range of pg/ml. LOQs in the range of 1-10 ng/ml. Linear between LOQ and 250 ng/ml. Analytes stable for the length of the batch run. Method was fully evaluated for the analysis of 32 designer drug analytes in serum.
15 Designer Drug Master List Master List of current or potential designer drugs/metabolites, identified from: Published literature. Government documentation. Commercial standard supplier listings. PiHKAL and TiHKAL by Alexander & Ann Shulgin. Online drug forums: Currently at 769 unique entries.
16 Designer Drug Master List Information collected: Structure. Molecular formula. Accurate mass. IUPAC name. Common name or abbreviation. CAS and Chemspider number (if available). Literature citations. Unique ID assigned and data compiled into a Personal Compound Database Library (PCDL; Agilent Technologies). Standards available for 275 compounds (target 300).
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20 Designer Drug Spectral Databases: Current Status Collection of LC-QTOF MS/MS data and construction of PCDL completed. Spectra from 258 designer drug standards added to the PCDL. 17 designer drug standards did not produce a 1000-count base peak. Collection of LC-QQQ MS/MS data by Dynamic MRM completed for DEA and Japan lists. Collection of LC-QQQ MS/MS data by Triggered MRM underway for all compounds. SPE and chromatography (RT) studies underway for all compounds.
21 Questions?
22 Development of a Comprehensive LC-QQQ-MS/MS Designer Drug Spectral Database and Screening/Confirmatory Method
23 Designer Drug LC-QQQ-MS Method Development Work Flow FIA Confirmation of the precursor ion using flow injection analysis in MS2 full scan mode for all standards. Optimizer/ MRM Optimization of fragmentor voltages and collision energies using Mass Hunter MS Optimizer software. Acquisition of precursor-to-product ion transitions (4-10 for each drug) in dynamic and/or triggered MRM mode. Chromatography On-column separation of designer drug mixes to obtain retention times (Zorbax Eclipse Plus C 18 column, 2.1 x 100 mm, 1.8 mm). Designer Drug Library Compilation of fragmentation data and retention times to generate MRM database. Validation against QTOF database.
24 DEA Mix 4-Methylmethcathinone (4-MMC) 2C-H 2C-D 2C-E 2C-C 2C-P 2C-N 2C-T-2 2C-T-4 MDPV 2C-I (±)-CP-47,497 RCS-4 JWH-073 (±)-CP-47,497-C8-homolog JWH-250 JWH-203 JWH-018 JWH-122 JWH-019 AM2201 JWH-081 JWH-398 RCS-8 JWH-200 AM694 Japan Mix 4-Methylmethcathinone (4-MMC) 3,4-Dimethylmethcathinone (3,4-DMMC) Methoxetamine MDPV (±)-CP-47,497-C8-homolog JWH-022 (AM2201 N-(4-pentenyl) analog) JWH-018 JWH-018 adamantyl carboxamide (2NE1) AKB48 CB-13 Cannabipiperidiethanone AM1220 AM2233 Supermix Evolving mix that contains as many designer drugs and metabolites as possible (currently at 275 analytes). Divided into 25 individual calibration mixes for validation purposes ( ng/ml).
25 Flow Injection Analysis Screening (DEA mix) Injection volume: Mobile phase A (20%): Mobile phase B (80%): LC Conditions (FIA) 1µl of 1ppm JWH-081 in MeOH solution 5mM Ammonium Formate, 0.1% Formic Acid, H 2 O 0.1% Formic acid, Methanol Fig. 1b: Mass Spectrum confirming molecular [M+H] + ion of JWH-081(C 25 H 25 NO 2 ) Flow: Stoptime: Fig. 1a: Full Scan TIC of JWH-081(4- methoxy- 1- naphthalenyl)(1- pentyl- 1H- indol- 3- yl)- methanone) 0.4ml/min 1minute
26 Flow Injection Analysis Screening (Japan Mix) Fig. 2a: Full Scan TIC of AM1220([1-[[(2R)-1- methyl-2-piperidyl]methyl]indol-3-yl]-(1-naphthyl) methanone) Fig. 2b: Mass Spectrum confirming molecular [M+H] + ion of AM1220(C 26 H 26 N 2 O) Injection volume: Mobile phase A (20%): Mobile phase B (80%): Flow: Stoptime: LC Conditions (FIA) 1µl of 1ppm JWH-081 in MeOH solution 5mM Ammonium Formate, 0.1% Formic Acid, H 2 O 0.1% Formic acid, Methanol 0.4ml/min 1minute
27 MRM Optimization/Confirmation Mass Hunter Optimizer Software: Optimizer Parameters Fragmentor Coarse Range V Collision Energy Range 0-60 V Cell Accelerator Voltage 7 Table 1. Excerpt from Summary Table of Optimization data for DEA list which shows 4 transitions for each compound, optimized fragmentor voltages and collision energies and the abundance of each product ion.
28 MRM Optimization/Confirmation (DEA Mix) Table. 2 Optimized transitions of JWH-081 Compound Name Formula Mass Precursor Product Frag CE Rel % JWH-081 C25H25NO JWH-081 C25H25NO JWH-081 C25H25NO JWH-081 C25H25NO Fig. 3 Shows the correlating product ion peaks produced following CID of [M+H] + ion during optimization
29 MRM Optimization/Confirmation (Japan Mix) Compound Name Formula Mass Precursor Product Frag CE Rel % AM-1220 C26H26N2O AM-1220 C26H26N2O AM-1220 C26H26N2O AM-1220 C26H26N2O Table. 3 Optimized transitions for AM-1220 Fig. 4 Shows the correlating product ion peaks produced following CID of [M+H] + ion during optimization
30 QTOF Confirmation Fig.5a MH Optimizer product ions of AM-1220 Fig. 5b QTOF fragmentation pattern at 40eV of AM-1220
31 Chromatographic Separation (DEA MIX B) DEA MIX B 2C-N JWH 019 2C-I AM2201 RCS-4 JWH 398 JWH 203 JWH 200 (±)-CP 47,497-C8-homolog (non-ionizable) Column: Injection volume: LC Conditions for Column Separation Zorbax Eclipse Plus C18 column, 2.1 x 100mm, 1.8 µm 20µl of 10ng/ml DEA MIX B solution in H 2 O Gradient: 1.0 min Mobile phase A (95%) Mobile phase B (5%) Flow: Stoptime: 9.5 min Mobile phase A (10%) Mobile phase B (90%) 0.4ml/min. 14 mins. Temperature: C Fig. 6 Chromatographic separation of DEA MIX B
32 Chromatographic Separation (Dynamic MRM Complete DEA MIX) LC Conditions for Column Separation Column: Injection volume: Gradient: 1.0 min Zorbax Eclipse Plus C18 column, 2.1 x 100mm, 1.8 µm 20µl of 100ng/ml DEA MIX B solution in H 2 O Mobile phase A (95%) Mobile phase B (5%) 9.5 min Mobile phase A (10%) Mobile phase B (90%) Flow: Stoptime: 0.4ml/min. 14 mins. Temperature: C Table 4. Summary Table of Optimization data for DEA list which shows 4 transitions for each compound, optimized fragmentor voltages and collision energies, relative abundances reported as percentages and retention times.
33 Chromatographic Separation (Dynamic MRM Complete DEA MIX) JWH-081 Fig. 7 shows the on-column separation of 23 of 26 compounds recently scheduled by the DEA NB of the 3 compounds missing: 2 are non-ionizable (CP family) and 1 shows inadequate chromatography
34 Chromatographic Separation (Dynamic MRM Complete DEA MIX) Compounds Ret. time [M+H] + Fig. 8 Enlarged view of co-eluting compounds in DEA mix 2C-N C-H MMC C-C MDPV C-T C-I
35 Chromatographic Separation (Dynamic MRM Complete DEA MIX) JWH-081 Fig. 7 shows the on-column separation of 23 of 26 compounds recently scheduled by the DEA NB of the 3 compounds missing: 2 are non-ionizable (CP family) and 1 shows inadequate chromatography
36 Chromatographic Separation (Dynamic MRM Complete DEA MIX) Figs. 9a and 9b - Enlarged view of co-eluting compounds in DEA mix Fig. Fig. 9b 9a Compounds Ret. time [M+H] + Compounds JWH-122 Ret time [M+H] RCS-4 JWH JWH JWH JWH-019 JWH Is there cross-talk?
37 Is there Crosstalk between JWH-122 and JWH-019? Common precursor with no response for unique products = NO CROSSTALK
38 Unique Products for Common Precursor Because the main 2 transitions for each of JWH-019 and JWH-022 are unique, the correct identities can be determined even though they co-elute
39 Chromatographic Separation (Dynamic MRM Complete Japan MIX) Fig. 10 shows the on-column separation of12 of 13 compounds recently scheduled in Japan NB the missing compound (1) is non-ionizable (CP family)
40 Chromatographic Separation (Dynamic MRM Complete Japan MIX) Fig Enlarged view of co-eluting compounds in JAPAN mix Compounds Ret. time [M+H] + MDPV ,4-DMMC CANNABIPIPERIDIETHANONE AM
41 Quantitation Results Table 5 shows the respective line equations, R 2 values, and limit of quantitation ranges for each designer drug. DEA and Japan Mixes Compound name Equation of the line R 2 value LOQ (ng/ml) DEA JWH C-P C-T C-E C-I C-T C-D MDPV C-C MMC C-H C-N JAPAN 4-MMC MXE ,4-DMMC MDPV
42 Quantitation DEA Mix Fig. 12 Calibration curve of 2C-D showing acceptable linearity of over a concentration range of ng/ml
43 Quantitation Results DEA and Japan Mixes Compound name Equation of the line R 2 value LOQ (ng/ml) DEA JWH C-P C-T C-E C-I C-T C-D MDPV C-C MMC C-H C-N JAPAN 4-MMC MXE ,4-DMMC MDPV Table 5 shows the respective line equations, R 2 values, and limit of quantitation ranges for each designer drug.
44 Quantitation Japan Mix Fig. 13 Calibration curve of MDPV showing acceptable linearity of over the concentration range of ng/ml
45 Conclusions LC-QQQ-MS is effective in producing characteristic MS/MS spectra and chromatography specific to designer drugs. The LC-QQQ analytical method is able to effectively screen and confirm 24 designer drugs recently scheduled by the DEA and 12 designer drugs scheduled in Japan. Quantification data for the majority of the designer drugs studied showed concentrations in the parts per billion range with adequate linearity. This comprehensive analytical method is applicable for use in Forensic Toxicology.
46 Ongoing Research Development of a comprehensive analytical method for approximately 300 designer drugs using the new Agilent software platform (REVB.06.00) to collect up to 10 transitions per drug. Creation of a spectral database which can positively identify unknown designer drug entities via score match.
47 Questions?
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