Simultaneous Quantitation of 43 Drugs in Human Urine with a Dilute-and-Shoot LC-MS/MS Method

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1 Simultaneous Quantitation of 4 Drugs in Human Urine with a Dilute-and-Shoot LC-MS/MS Method Xiang He and Marta Kozak, Thermo Fisher Scientific, San Jose, CA Application Note 76 Key Words TSQ Quantum Access MAX, forensic toxicology, drugs of abuse, pain management drugs, urine, quantitation Goal The goal of this work was to develop a simple dilute-and-shoot liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the simultaneous quantitation of 4 drugs of abuse, including pain management drugs, in human urine for forensic toxicology purposes. The drugs to be analyzed included opioids, amphetamines, benzodiazepines, cocaine, buprenorphine, methadone, and some of their metabolites. An additional objective was to use ultra-high-pressure liquid chromatography (UHPLC) to improve throughput and sensitivity of the method. Introduction LC-MS/MS has become more accepted as the tool for quantitative analysis of drugs in forensic toxicology laboratories. This technique enables simultaneous detection of multiple analytes of interests and is compatible with a simple dilute-and-shoot sample preparation method for urine samples. Methods Sample Preparation Nine individual human urine and pure water samples were spiked with and of the 4 drugs of abuse, pain management drugs, and with internal standards (IS). The samples were then mixed with β-glucuronidase and incubated at 6 C for hydrolysis. Methanol was added to the mixture and the supernatant was diluted with water. The final dilution factor was. The mixture was centrifuged at 17, g for minutes. Fifty microliter injections of the supernatant were analyzed by LC-MS/MS. LC-MS/MS Conditions LC-MS/MS analysis was performed on a Thermo Scientific Accela 12 pump and Accela Open autosampler coupled to a Thermo Scientific TSQ Quantum Access MAX triple stage quadrupole mass spectrometer. The analytical column was a Thermo Scientific Accucore PFP column ( 2.1 mm, 2.6 µm particle size) maintained at room temperature. Details of the LC gradient and mobile phases (MP) are as follows: Time Flow rate Gradient MPA MPB MPC (min) (ml/min) (%) (%) (%)..7 Step 9..7 Ramp Ramp Step Step Step 9 MPA: 1 mm NH 4 Ac and.1% formic acid in water MPB: 1 mm NH 4 Ac and.1% formic acid in methanol MPC: acetonitrile/isopropanol/acetone 9:9:2 (v/v/v) The mass spectrometer was operated with a heated electrospray ionization (HESI-II) source in positive ionization mode. The MS conditions were as follows: Spray voltage (V) 4 Vaporizer temperature ( C) Sheath gas pressure (arbitrary units) Auxiliary gas pressure (arbitrary units) 1 Capillary temperature ( C) Blank human urine was used as the matrix for calibration samples. The concentrations of the calibrators were 1, 2,, 1,,, 1,,, and 1. Concentration of the internal standards in all samples was 2.

2 2 Data were acquired in selected-reaction monitoring (SRM) mode. SRM transitions for the 4 drugs and their internal standards are shown in Table 1. For each analyte and internal standard, two SRM transitions were monitored. One of transition was used as the quantifier and the other as the qualifier. The signal ratio between the qualifier and the quantifier was used to evaluate the validity of the results. Validation The validation procedure included tests for the following: 1) matrix effects; 2) lower limit of quantitation (LLOQ), linear range, accuracy, and precision; and ) carryover. Table 1. Drug analytes, their corresponding internal standards, and the SRM transitions for both analytes and internal standards Analyte Precursor Quantifier Qualifier Ratio (%) Corresponding Internal Standard Precursor Quantifier Qualifier 6-MAM MAM-d Amino-clonazepam Amino-clonazepam-d Amino-flunitrazepam Amino-flunitrazepam-d Aminonitrazepam Amino-clonazepam-d a-hydroxy-alprazolam α-hydroxy-alprazolam-d Alprazolam Temazepam-d Amphetamine Amphetamine-d Benzoylecgonine Benzoylecgonine-d Benzylpiperazine Benzylpiperazine-d Buprenorphine Diazepam-d Carisprodol α-hydroxy-alprazolam-d Clonazepam Temazepam-d Cocaine Amphetamine-d Codeine Codeine-d Diazepam Diazepam-d EDDP Temazepam-d Fentanyl Temazepam-d Flunitrazepam Temazepam-d Flurazepam Temazepam-d Hydrocodone MDA-d Hydromorphone Benzylpiperazine-d Lorazepam α-hydroxy-alprazolam-d MDA MDA-d MDEA Nordiazepam-d MDMA MDMA-d Meperidine Diazepam-d Methadone Diazepam-d Methamphetamine Methamphetamine-d Midazolam Diazepam-d Morphine Morphine-d Naloxone Amino-clonazepam-d Naltrexone MDA-d Norbuprenorphine Temazepam-d Nordiazepam Nordiazepam-d Norfentanyl MDMA-d Normeperidine Temazepam-d Oxazepam Oxazepam-d Oxycodone Benzoylecgonine-d Oxymorphone Amino-clonazepam-d PCP Diazepam-d Propoxyphene Diazepam-d Temazepam Temazepam-d Tramadol Temazepam-d

3 Results and Discussion Matrix Effects Matrix effects were assessed with the nine individual human urine samples. Absolute recovery was determined by comparing the signals of unlabeled drugs in urine and water samples. Relative recovery was determined by comparing the analyte/is ratio in urine and water samples. The recovery/matrix effects results are summarized in Table 2. Summary of matrix effects Drug Average Absolute Recovery (%, n=9) Table 2. All 4 drugs had almost full absolute recovery (between 8% and 1%), except morphine for which the matrix effect was compensated by the use of its internal standard, morphine-d. The observed precision from the nine individual human urine samples was below 1% for most of the 4 drugs. CV (%, n=9) Average Relative Recovery (%, n=9) CV (%, n=9) 6-MAM Amino-clonazepam Amino-flunitrazepam Aminonitrazepam a-hydroxy-alprazolam Alprazolam Amphetamine Benzoylecgonine Benzylpiperazine Buprenorphine Carisprodol Clonazepam Cocaine Codeine Diazepam EDDP Fentanyl Flunitrazepam Flurazepam Hydrocodone Hydromorphone Lorazepam MDA MDEA MDMA Meperidine Methadone Methamphetamine Midazolam Morphine Naloxone Naltrexone Norbuprenorphine Nordiazepam Norfentanyl Normeperidine Oxazepam Oxycodone Oxymorphone PCP Propoxyphene Temazepam Tramadol

4 4 Lower Limit of Quantitation, Linear Range, Accuracy, and Precision The LLOQ of these 4 drugs and other aspects of analytical performances of this method are summarized in Table. Linear fit with 1/X weighting was used for calibration curves of all the 4 drugs. The LLOQ for these 4 drugs was determined to be between 2 and except for tramadol, which was. At the LLOQ, the accuracy ranged between 89.9% and 118.4%, and precision ranged between.6% and 19.%. The method was linear to 1 for all the drugs. Figure 1 shows the calibration curves of six typical pain management drugs in human urine. Table. Lower limit of quantitation, linear range, accuracy, and precision Drug Retention Time (min) LLOQ () Accuracy at LLOQ (%, n=4) CV at LLOQ (%, n=4) Linear Range () R 2 Precision (%, n=6) Precision (%, n=6) 6-MAM Amino-clonazepam Amino-flunitrazepam Aminonitrazepam a-hydroxy-alprazolam Alprazolam Amphetamine Benzoylecgonine Benzylpiperazine Buprenorphine Carisprodol Clonazepam Cocaine Codeine Diazepam EDDP Fentanyl Flunitrazepam Flurazepam Hydrocodone Hydromorphone Lorazepam MDA MDEA MDMA Meperidine Methadone Methamphetamine Midazolam Morphine Naloxone Naltrexone Norbuprenorphine Nordiazepam Norfentanyl Normeperidine Oxazepam Oxycodone Oxymorphone PCP Propoxyphene Temazepam Tramadol NA 2.

5 Aminoclonazepam Benzoylecogonine 16 Fentanyl Concentration () Concentration () Concentration () 14 Hydrocodone Midazolam. Morphine Concentration () Concentration (). Concentration () Figure 1. Calibration curves of six selected drugs in spiked human urine Method precision was also assessed with spiked human urine samples at low and high quality control (QC) concentrations of and, respectively (Table 2). Precision values at low ( ) and high ( ) quality control concentrations ranged between 1.1% and 1.9% (Table 2). Figure 2 shows both the quantifier and qualifier SRM chromatograms of selected pain management drugs spiked at in human urine. 1 Methadone 8 EDDP Relative Abundance (%) 6 4 Codeine 6-MAM Benzoylecgonine Oxycodone Hydrocodone MDA PCP Fentanyl Cocaine Meperidine MDEA Carisprodol 7-Aminonitrazepam Hydromorphone Oxymorphone Methamphetamine MDMA Morphine Time (min) Figure 2. SRM chromatograms of selected drugs at in spiked human urine

6 Carryover The lowest calibrator was analyzed after the highest calibrator. No carryover causing elevated measurements of the drugs in the lowest calibrator was observed. Conclusion The developed method provides a simple, fast, and sensitive way for forensic toxicology labs to simultaneously quantify 4 drugs of abuse, including pain management drugs, in human urine by LC-MS/MS. The method provided LLOQ values of 2 for 42 of the 4 drugs, and was linear to 1. Minimal ion suppression and no carryover were observed in matrix samples. At the LLOQ, the accuracy ranged between 89.9% and 118.4%. Method precision ranged between 1.1% and 1.9% at low and high QC samples. Application Note 76 For forensic toxicology use only Thermo Fisher Scientific Inc. All rights reserved. ISO is a trademark of the International Standards Organization. All other trademarks are the property of Thermo Fisher Scientific Inc. and its subsidiaries. This information is presented as an example of the capabilities of Thermo Fisher Scientific Inc. products. It is not intended to encourage use of these products in any manners that might infringe the intellectual property rights of others. Specifications, terms and pricing are subject to change. Not all products are available in all countries. Please consult your local sales representative for details. Thermo Fisher Scientific, San Jose, CA USA is ISO Certified. Africa-Other Australia Austria Belgium Canada China Denmark Europe-Other Finland/Norway/Sweden France Germany India Italy Japan Latin America Middle East Netherlands New Zealand Russia/CIS South Africa Spain Switzerland UK USA AN6686_E 11/12S

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