Institute of Toxicology Clinical Toxicology and Pharmacology Berliner Betrieb für Zentrale Gesundheitliche Aufgaben, Berlin
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1 LOGO Institute of Toxicology Clinical Toxicology and Pharmacology Berliner Betrieb für Zentrale Gesundheitliche Aufgaben, Berlin Rapid Quantification of Tilidine, Nortilidine and Bisnortilidine in Urine by automated online-spe-lc-ms/ms Christoph Köhler Thomas Grobosch Torsten Binscheck 48th Annual Meeting of the International Association of Forensic Toxicologists Conference in Bonn August 29 - September 2, 2010
2 Tilidine introduction Synthetic opioid analgesic Strong analgesic effect of its main metabolite nortilidine [2]. Hepatically N-demethylation of tilidine to nortilidine and bisnortilidine (CYP3A4, CYP2C19, CYP2D6) [1] In commercially available preparations tilidine is combined with the µ-opioid-receptor antagonist naloxone preventing opioid abuse [2]. HO (+)-tilidine O CH 3 O CH 3 N CH 3 O CH 3 O NH CH 3 (+)-nortilidine O CH 3 O O N OH naloxone (1S,5R,13R,17S) CH 2 O NH 2 (+)-bisnortilidine Source: [1] Clin. Chem. 24/2, (1978) [2] Fachinfo Valorone N, Fa. Pfizer;
3 Aims introduction Sensitive quantification of tilidine and its metabolites in urine samples No immunoassay for the detection of tilidine abuse is available! Offline-LLE LC QTrap Increasing number of samples (max. 100 samples/d!) consumed much time and human resources for the LLE (max. 180 min/d!). Online-SPE LC QTrap 3
4 Online-SPE-LC introduction Highly automated sample preparation Automatization: 1. IS-mixing procedure 2. Complete SPE procedure Chromatography Analytical column: Luna phenyl-hexyl 50x2 mm 5 µm Mobile phase: 0.2% FA + MeOH (gradient elution) Total run time: 3.5 min Symbiosis Pico Spark Holland Online-SPE LC 4
5 SPE Optimization SPE method development Mix setup: SPE sorbent: 100 µl Aqueous analyte solution of tilidine, nortilidine and naloxone (c = 50 µg/l) + 100µL 100 mm NH 4 Ac-solution (ph 6); IS PCP-D 5 (c=100 ng/ml) OASIS WCX 10x1mm Generic SPE procedure: SPE step solvent volume (µl) flow rate (ml/min) Conditioning MeOH Equilibration Loading 10 mm NH 4 Ac-solution ph Clean up Elution Mobile phase
6 SPE Optimization SPE method development Mix setup: SPE sorbent: 100 µl Aqueous analyte solution of tilidine, nortilidine and naloxone (c = 50 µg/l) + 100µL 100 mm NH 4 Ac-solution (ph 6); IS PCP-D 5 (c=100 ng/ml) OASIS WCX 10x1mm Generic SPE procedure: SPE step solvent volume (µl) flow rate (ml/min) Conditioning MeOH Equilibration mm NH 4 Ac-solution ph 6 Loading Clean up?? 1.0 Elution Mobile phase? 0.3 6
7 Results (wash solution) SPE method development Wash solution: 10 mm NH 4 Ac-solution ph 6 + 0/10/15/20/40% MeOH 100 recovery (%) tilidine nortilidine naloxone IS MeOH in wash solution (%) Conclusion: 10% MeOH 7
8 Results (wash volume) SPE method development Wash solution: 10 mm NH 4 Ac-solution ph % MeOH Wash volume: 500/1000/1500 µl 100 %) recovery ( tilidine nortilidine naloxone IS wash volume (µl) Conclusion: 500 µl 60 bed volumes 8
9 Results (elution volume) SPE method development Wash solution: 10 mm NH 4 Ac-solution ph % MeOH Elution volume: 150/300/600/900/1200 µl 100 recovery (% %) tilidine nortilidine naloxone IS elution volume (µl) Conclusion: 600 µl 2 min elution time 9
10 Final SPE method SPE method development Mix setup: SPE sorbent: 100 µl sample (urine) + 100µL 100 mm NH 4 Ac-solution (ph 6); c(pcp-d 5 )=100 ng/ml OASIS WCX 10x1mm Generic SPE procedure: SPE step solvent volume (µl) flow rate (ml/min) Conditioning MeOH Equilibration mm NH4 Ac-solution ph 6 Loading Clean up 10 mm NH 4 Ac-solution ph % MeOH 500 (1000) 1.0 Elution Mobile phase 600 (1050)
11 Untitled 18 (Nortilidin 1): "Linear Through Zero" Regression ("No" weighting): y = x (r = ) Validation data of the new method Validation and routine work Selectivity: no interference by matrix peaks Ionsuppression: < 10% for all analytes Recovery: > 80% for all analytes and IS Intra-assay precision (n=6 per conc.): coefficient of variation: 6% Inter-assay precision (n=6 per conc.): coefficient of variation: 7% LLOQ: 1.0 µg/l for all analytes Linearity: µg/l Analyte Area / IS Area Analyte Area / IS Area Analyte Area / IS Area Untitled 18 (Tilidin 1): "Linear Through Zero" Regression ("No" weighting): y = x (r = ) Calibration curves of the analytes tilidine R = Analyte Conc. / IS Conc nortilidine R = Analyte Conc. / IS Conc. Untitled 18 (Bisnortilidin 1): "Linear Through Zero" Regression ("No" weighting): y = x (r = ) bisnortilidine R = Analyte Conc. / IS Conc. Society of Toxicological and Forensic Chemistry (GTFCH) Guidance in forensic quality terms Toxichem Krimtech 2009; 76 (3):
12 Implementation in routine Reduction of the manual preparation time by the factor 10 Positive result: c (tilidine) and c (nortilidine) > 1.0 µg/l (cutoff) c (nortilidine) and c (bisnortilidine) > 1.0 µg/l (cutoff) or Analysis of 3665 samples from correctional facilities: - 55 positive results (1.5 %) - positive samples: c (bisnortilidine) > c (nortilidine) could the detection of bisnortilidine increase the drug detection window? 12
13 Urinary Excretion of Tilidine Tilidine A single oral dose of Valoron N solution (50 mg T-HCl and 4 mg NX-HCl) was administered to a male volunteer (age: 28 years; body height: 175 cm; body weight: 72 kg) g Analyte Drug detection window (d) - ß-glucuronidase + ß-glucuronidase Tilidine Nortilidine Bisnortilidine positive result
14 Chromatograms 1.81 L Intensity, cps 2.0e4 1.5e4 1.0e4 Tilidine (c=7.63 µg/l) m/z L Intensity, cps 1.00e5 8.00e4 6.00e4 4.00e4 Bisnortilidine (c=96.5 µg/l) m/z e Time, min Time, min L Intensity, cps Tilidine m/z L Intensity, cps 6.0e4 5.0e4 4.0e4 3.0e4 2.0e4 1.0e4 Bisnortilidine m/z Time, min Time, min Concentration: N/A Calculated Conc: 5.44 ng/ml Proc. Algorithm: Analyst Classic Intensity, cps 6.0e4 5.0e4 4.0e4 3.0e4 2.0e4 Nortilidine (c=36.9 µg/l) m/z e Time, min Concentration: N/A Calculated Conc: 5.17 ng/ml Proc. Algorithm: Analyst Classic Intensity, cps Nortilidine m/z Concentration: 1.00 ng/ml Calculated Conc: N/A Proc. Algorithm: Analyst Classic Intensity, cps 7.0e5 6.0e5 5.0e5 4.0e5 3.0e5 2.0e IS Phencyclidine-D 5 (c=33.33 µg/l) m/z e Time, min Time, min
15 Conclusion An highly sensitive method for the determination of tilidine, nortilidine and bisnortilidine in urine was developed and validated on an online- SPE-LC-QTrap Due to the automatization of the online-spe the manual preparation time of the new method is 20 min/100 samples authentic samples were analyzed resulting in 55 positive results. The LLOQ of 1 µg/l allowed detecting a single oral dose of a tilidine preparation up to 5 days after administration. 15
16 Aknowledgements Martin Sibum(Spark Holland) for technical support Dr. Goebel (Medizinisches Labor Bremen) for delivering Bisnortilidine Thank you for your attention 16
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