Comparison of the Stability of Stock Solutions of Drugs of Abuse and Other Drugs Stored in a Freezer, Refrigerator, and at Ambient Temperature

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1 Comparison of the Stability of Stock Solutions of Drugs of Abuse and Other Drugs Stored in a Freezer,, and at for Up to One Year Technical Note Ritva Karinen 1, *, Elisabeth Leere Øiestad 1, Wenche Andresen 1, Anne Smith-Kielland 2, and Asbjørg Christophersen 1 1 Division of Forensic Toxicology and Drug Abuse, Norwegian Institute of Public Health, P.O. Box 4404, Nydalen, 0403 Oslo, Norway and 2 The Department for Quality, Norwegian Institute of Public Health, P.O. Box 4404, Nydalen, 0403 Oslo, Norway Abstract The aim of this study was to evaluate the stability of stock solutions of a variety of illegal and medicinal drugs, important in forensic analysis, when stored refrigerated or at ambient temperature compared to solutions stored in a freezer. Stock solutions in methanol, acetonitrile, or a mixture of acetonitrile/methanol were transferred to autosampler vials and analyzed after storage for one month, three months, six months, and one year at ambient temperature, in a refrigerator, and in a freezer. Some of the compounds investigated, such as morphine and amitriptyline, showed to be stable for at least one year when stored at ambient temperature, but others, such as prometazine and olanzapine, nearly vanished when stored at ambient temperature for one month. Introduction Stock solutions made in organic solvents are, as a rule, stored in a freezer ( 20 C) (1). To make working solutions, it is necessary to bring the stock solutions to room temperature before taking out an aliquot. An even greater disadvantage, from our experience, is that some compounds, such as tadalafil and lamotrigine, for example, have a tendency to precipitate when stored in the freezer at 20 C or even in a refrigerator at 4 6 C. Before use, these solutions have to be placed in an ultrasonic bath for an extended period to dissolve again. Therefore, the question is if it is necessary to store stock solutions in the freezer. * Author to whom correspondence should be addressed. rika@fhi.no. Short- or long-term stability studies, especially of injection solutions of medicinal drugs, have been published for many compounds (2 5). Stability of stock solutions in itself, working solutions, sample extracts, analyte stability in authentic/fortified biological matrix (e.g., blood, urine, etc.), and in sampling assay might be included in papers describing analytical methods or as independent studies (1,6 10). However, to the best of our knowledge, no previous comprehensive studies on the influence of storage methods on the stability of drug concentrations in stock solutions have been published. We therefore designed a study with the aim to evaluate alternative storage conditions, that is, in a refrigerator or at ambient temperature compared to in a freezer, for a selection of stock solutions of different drugs. The selected compounds included benzodiazepines, opiates and opioids, psychostimulants, antidepressants, antipsychotics, and some miscellaneous drugs. In this study, we did not evaluate the stability of stock solutions in themselves by comparing frozen with freshly made solutions. Methods and Reagents Methanol (HPLC grade) and acetonitrile (for UV HPLC) were purchased from LAB-SCAN (Dublin, Ireland). Crimp Top Tapered autosampler vials [06-CTV(A)] and caps (8-AC6) were supplied from CHROMACOL (Welwyn Garden City, U.K.). Reference substances were delivered from commercial suppliers: 7-aminoclonazepam, 7-aminoflunitrazepam, 7-aminonitrazepam, bromazepam, lorazepam, nordiazepam, temazepam, zopiclone, 6-MAM, codeine, pethidine, tramadol, amphetamine, benzoylecgonine, MDA, MDMA, methamphetamine, olanzapine, and LSD from Cerilliant (Round Rock, TX); alprazolam, Reproduction (photocopying) of editorial content of this journal is prohibited without publisher s permission. 583

2 clonazepam, diazepam, flunitrazepam, nitrazepam, oxazepam, zolpidem, dextropropoxyfene, methadone, morphine, amisulpride, chlorprotixene, clozapine, haloperidol, levomepromazine, risperidone, amitriptyline, citalopram, clomipramine, doxepin, fluoxetine, fluvoxamine, mianserin, mirtazapine, nortriptylene, reboxetin, trimipramine, cocaine, carbamazepine, carisoprodol, chlorpromazine, ketamine, meprobamate, orphenadrine, phenobarbital, prometazine, and salicylic acid from Sigma-Aldrich Norway AS (Oslo, Norway); flupentixol, moclobemide, sertraline, and venlafaxine from Promochem (Borås, Sweden); fenazepam from Chiron (Trondheim, Norway); dixyrazine and ketobemidone from NMD (Oslo, Norway); MDEA from Alltech (Deerfield, IL); zuclopenthixol from Lundbeck (Copenhagen, Denmark); alimemazine from Rhone-Poulenc Rorer (Collegeville, PA); paroxetine from Chemos (Regenstauf, Germany); and nefazodone from Bristol- Myers Squibb (New Brunswick, NJ). The internal standards morphine-d 3, amphetamine-d 11, metamphetamine-d 11, benzoylecgonine-d 8, MDMA-d 5, 7-aminoflunitrazepam-d 7, nordiazepam-d 5, methadone-d 9, and imipramine-d 3 were purchased from Cerilliant. Stock solutions for a selection of drugs of abuse and other psychoactive or medicinal drugs commonly found in forensic cases in Norway (Table I) were prepared in methanol, except for Table I. List of the Compounds Studied with their Stock Solution Concentration and Therapeutic Range Stock Solution Therapeutic Concentration* Stock Solution Therapeutic Concentration* Compound (mg/l) (mg/l) Compound (mg/l) (mg/l) Benzodiazepines and related compounds Antidepressants 7-Aminoclonazepam 0.7 Amitriptyline serum 7-Aminoflunitrazepam 0.5 Citalopram plasma 7-Aminonitrazepam 0.6 Clomipramine serum Alprazolam serum Doxepin plasma Bromazepam serum Fluoxetine serum Clonazepam plasma Fluvoxamine serum Diazepam plasma Mianserin serum Fenazepam 0.9 Mirtazapine serum Flunitrazepam serum Moclobemide serum Lorazepam serum Nortriptyline serum Nitrazepam serum Paroxetine serum Nordiazepam serum Reboxetin 0.9 Oxazepam serum Sertraline serum Temazepam serum Trimipramine serum Zolpidem serum Venlafaxine serum Zopiclone serum Opiates and opioids Psychostimulants 6-MAM 0.6 Amphetamine serum Codeine serum Benzoylecgonine 0.4 Dextropropoxyphene plasma Cocaine serum Ketobemidone plasma MDA 0.2 Methadone serum MDEA 0.2 Morphine serum MDMA 0.2 Pethidine serum Metamphetamine serum Tramadol blood Antipsychotic agents Miscellaneous drugs Amisulpride plasma Alimemazine serum Chlorprotixene serum Carbamazepine serum Clozapine serum Carisoprodol serum Flupentixol serum Dixyrazine 1.1 approx. 0.3 blood Haloperidol serum Ketamine serum Levomepromazine serum LSD 0.03 Olanzapine serum Meprobamate serum Risperidone serum Nefazodone 1.5 approx plasma Zuclopenthixol plasma Orphenadrine plasma Phenobarbital serum Prometazine serum Salicylic acid serum * Therapeutic concentrations compiled from TIAFT Therapeutic and Toxic Drug Concentrations ( accessed August 2010). 584

3 the solutions for zopiclone and zolpidem, which were prepared in acetonitrile and acetonitrile/methanol (50:50), respectively. Four aliquots of each stock solution were transferred into amber autosampler vials and capped. One set of vials was stored in a freezer ( 20 C) for one, three, and six months and one year. Equivalent sets of vials were stored in a refrigerator (4 6 C) and in the dark at ambient temperature for the same time periods. The samples were analyzed after dilution with water or water/acetonitrile mixture to a working concentration and internal standards were added. The techniques used were highperformance liquid chromatography mass spectrometry (HPLC MS) [antidepressants, dextropropoxyphene, ketobemidone, pethidine, tramadol, antipsychotic agents, and miscellaneous drugs (except carisoprodol, meprobamate and LSD); internal standard used was imipramin-d 3 ] (11), or tandem MS (benzodiazepines and related compounds, psychostimulants, 6- MAM, codeine, methadone, morphine, meprobamate, and carisoprodol; internal standard used was a mixture of morphine-d 3, amphetamine-d 11, metamphetamine-d 11, benzoylecgonine-d 8, MDMA-d 5, 7-aminoflunitrazepam-d 7, nordiazepamd 5, and methadone-d 9 ) (12). The samples stored at ambient temperature, in the refrigerator and freezer were analysed within the same series and with 10 injections from each sample. A two-tailed, paired Student s T-test was performed to check Table II. Benzodiazepines and Related Drugs: Deviation (%) from Target Value Sorted in Groups of ±10%, ±20%, and Above ±20% After One Year and Six, Three, or One Month of Storage at and in 7-Aminoclonazepam Aminoflunitrazepam Aminonitrazepam Alprazolam 27.3* 4.9 Bromazepam Clonazepam Diazepam 17.8* 8.8 Fenazepam Flunitrazepam 29.0* 2.7 Lorazepam 95.4* 22.4* Nitrazepam 35.5* 22.4 Nordiazepam Oxazepam 84.5* 20.0* Temazepam Zolpidem Zopiclone Alprazolam 28.4* Diazepam 7.8 Flunitrazepam 32.5* Lorazepam 87.9* 27.6* Nitrazepam 27.1* 18.3 Oxazepam 66.0* 18.5* Temazepam 16.5 Three months Alprazolam 10.4 Flunitrazepam +7.6 Lorazepam 60.7* 10.8 Nitrazepam Oxazepam 42.6* +0.9 Temazepam 17.1 One month Lorazepam 24.8* Oxazepam 12.3 Temazepam

4 Table III. Antidepressants: Deviation (%) from Target Value Sorted in Groups of ±10%, ±20%, and Above ±20% After One Year and Six, Three, or One Month of Storage at and in Amitriptyline * Citalopram 14.5* 12.9* Clomipramine +2.0* +3.7* Doxepin +5.3* +4.1* Fluoxetine 43.1* 45.3* Fluvoxamine +3.3* +18.6* Mianserin +7.4* +5.6* Mirtazapine +6.5* +3.5* Moclobemide 6.1* 1.7 Nortriptyline +11.5* +19.8* Paroxetine +12.4* +9.4* Reboxetin 7.0* +2.7* Sertraline +3.6* +24.8* Trimipramine * Venlafaxine +7.3* +7.0* Amitriptyline +8.5* Citalopram 10.8* 3.9* Fluoxetine Fluvoxamine 0.6 Nortriptyline +9.4* +7.3* Paroxetine 2.0 Sertraline +10.3* Trimipramine 0.1 Three months Citalopram +4.1 Sertraline +5.9* Table IV. Opiates and Opioids: Deviation (%) from Target Value Sorted in Groups of ±10%, ±20%, and Above ±20% After One Year and Six, Three, or One Month of Storage at and in 6-MAM Codeine Dextropropoxyphene Ketobemidone +17.0* 1.6 Methadone +9.8* 0.8 Morphine Pethidine +2.8* +4.4* Tramadol +64.2* +35.3* Ketobemidone +1.7* Tramadol 4.3*

5 if the observed differences in the results were due to storage conditions or just simply due to random effects. A value of p < 0.05 was considered statistically significant. Results and Discussion The results for the various drugs are presented in Tables II VII. The tables have been divided into three columns, where the columns represent a mean deviation from the target value (the samples stored in the freezer) after storage either at ambient temperature or in the refrigerator within ±10%, ±20%, and above ±20%, respectively. Statistically significant differences (p < 0.05) are marked with an asterisk in Tables II VII. They are based on the average of 10 replicates. Internal standard was used to correct possible inaccuracy in sample injections. For stability testing of the stock solution in itself, it is recommended that the acceptable difference between the fresh and aged solutions lies between 5 and 7% (13). On the other hand, a difference between ±20% has been acknowledged (14), and we have set our acceptance criteria for stability in our study at ±20%. Table V. Psychostimulants: Deviation (%) from Target Value Sorted in Groups of ±10%, ±20%, and Above ±20% After One Year and Six, Three, or One Month of Storage at and in Amphetamine Benzoylecgonine 8.1* 4.5 Cocaine MDA MDEA 11.4* 2.5 MDMA 7.6* 0.3 Metamphetamine MDEA 6.1* Table VI. Antipsychotic Agents: Deviation (%) from Target Value Sorted in Groups of ±10%, ±20%, and Above ±20% After One Year and Six, Three, or One Month of Storage at and in Amisulpride 6.5* 2.6 Chlorprotixene * Clozapine Flupentixol 5.0* 6.3* Haloperidol Levomepromazine Olanzapine Risperidone Zuclopenthixol Olanzapine 99.8* 76.2* Three months Olanzapine 67.5* 21.3* One month Olanzapine 23.4*

6 It is important to take into consideration the purpose of analysis for which the stock solutions are used. A higher degree of accuracy might be necessary in cases such as therapy control, clinical applications, or forensic toxicological analysis of blood and urine from the drivers suspected of driving under the influence of drugs (duid) than in forensic autopsy samples for toxicological analysis, where for instance, postmortem changes can take place. Benzodiazepines and related compounds The results are shown in Table II. The most affected compounds in this group are lorazepam and oxazepam, where concentrations had decreased dramatically already after three months of storage at ambient temperature, and nearly disappeared after one year of storage. Lorazepam showed a significant concentration loss ( 25%) already after one month of storage at ambient temperature. For both compounds a statistically significant decrease in concentration of approximately 20% was seen after more than three months of storage in the refrigerator. Alprazolam, flunitrazepam, and nitrazepam concentrations were not stable for more than three months when stored at ambient temperature. When stored in the refrigerator they seemed to be stable for at least one year. Nitrazepam had a decrease of around 20% after six months, but the difference is not statistically significant. The rest of the compounds in this group seemed to tolerate storage at ambient temperature for up to one year. Antidepressants The results for this group are shown in Table III. Fluoxetine showed to be stable only up to six months when stored at ambient temperature or in the refrigerator. Subsequently, the concentration decreased more than 40%. For most of the compounds, the T-test showed a statistically significant alteration in concentration, but the results are within our criteria of deviations ±20%, and we conclude that the rest of the substances tolerated storage for a period of one year at ambient temperature. Opiates and opioids These results are shown in Table IV. All the compounds in this group proved to tolerate storage at ambient temperature for at least one year, except tramadol. For tramadol, the results increased approximately 65% and 35% after storage for one year at ambient temperature and in the refrigerator, respectively, compared to the stock solution in the freezer, whereas the results after six months of storage were satisfactory. One possible explanation can be that tramadol precipitates more ex- Table VII. Miscellaneous Drugs: Deviation (%) from Target Value Sorted in Groups of ±10%, ±20%, and Above ±20% After One Year and Six, Three, or One Month of Storage at and in Alimemazine Carbamazepine +75.5* +26.8* Carisoprodol Dixyrazine Ketamine LSD Meprobamate Nefazodone 37.1* 26.1* Orphenadrine Phenobarbital Prometazine 99.1* 65.5* Salicylic acid Alimemazine 1.0 Carbamazepine 9.8* 7.5* LSD Nefazodone 8.4* 7.7* Orfenadrine 7.5* Prometazine 96.5* 40.1* Salicylic acid +2.6* 2.4* Three months Prometazine 97.1* 26.8* One month Prometazine 80.4* 15.5* 588

7 tensively in stock solution stored in a freezer for one year compared with six months and is more difficult to re-dissolve, thus leading to erroneous large positive deviations for the solutions stored at ambient temperature and in the refrigerator. Psychostimulants The results are shown in Table V. The results were very stable with deviations between ±10% for all the compounds studied, except MDEA. MDEA showed a small, but statistically significant, tendency to decrease during one year s storage at ambient temperature. Antipsychotic agents The results are shown in Table VI. Olanzapine proved to be unstable already after one month of storage at ambient temperature, after three months in the refrigerator, and had disappeared completely during one year of storage. The rest of the compounds studied were stable for up to one year at both storage conditions. Miscellaneous drugs The results are shown in Table VII. Two compounds, promethazine and nefazodone, did not give acceptable results. Promethazine started to decompose already after one month of storage both at ambient temperature and in the refrigerator. Nefazodone was stable for up to six months at both storage conditions. Carbamazepine concentration increased significantly (25 80%) when stored in the refrigerator or at ambient temperature for one year. This could most likely have the same explanation as we proposed for tramadol with extensive precipitation in the stock solution stored in the freezer, and consequently problems with dissolution. The rest of the compounds in this group proved to be stable. Storage vessels For tramadol and carbamazepine, with large increases in measured concentrations, an explanation for the positive deviation could be that the vials stored in the freezer for one year were not shaken well enough before taking out an aliquot to make working solutions. In order to avoid multiple reopenings of the solutions during the study the stock solutions were stored in small aliquots. We chose tapered form and amber-colored vials for this experiment, which unfortunately made it difficult to notice possible precipitation of drugs or separated phases in the vials. We usually store stock solutions in glass bottles/tubes with volumes of 10 ml or more, in which it is easier to discover problems with precipitation. Conclusions The compounds which showed a significant concentration loss (> 20%) during storage for one year at ambient temperature were alprazolam, flunitrazepam, lorazepam, nitrazepam, oxazepam, fluoxetine, olanzapine, nefazodone, and prometazine. In addition, some of these compounds decreased to a variable extent in the refrigerator. For tramadol and carbamazepine, we are unable to come to a conclusion with regards to the stability after six months, probably due to problems with solubility. We have set our stability acceptance criteria to ±20% to be certain not to infer inherent instability from analytical inaccuracy. For many compounds differences below ±20% were, however, significant by the T-test, and smaller variation criteria can be applied for applications where necessary. Altogether, we included 67 compounds important in forensic science in our study. Of these, 46 (69%) showed to have remarkably stable results, with deviation of ±10% or less, after one year of storage at ambient temperature. This shows that many stock solutions of illegal and medicinal drugs can be safely stored in a refrigerator, if not at ambient temperature, instead of storage in a freezer. Acknowledgments We want to thank Inger Hasvold, Gerd-Wenche Brochman, Ada Rognerud, and Ida Nord for technical assistance and Ilah Le Nygaard and Jørg Mørland for valuable comments and for critical reading of the manuscript. References 1. S. Croubels, S. De Baere, and P. De Backer, Practical approach for the stability testing of veterinary drugs in solutions and in biological matrices during storage. Anal. Chim. Acta 483: (2003). 2. M. Vehabovic, S. Hadzovic, F. Stambolic, A. Hadzic, E. Vranjes, and E. Haracic. Stability of ranitidine in injectable solutions. Int. J. Pharm. 256: (2003). 3. A. Vermeire and J.P. Remon. The solubility of morphine and the stability of concentrated morphine solutions in glass, polypropylene syringes and PVC containers. Int. J. Pharm. 146: (1997). 4. A. Vermeire and J.P. Remon. Stability and compatibility of morphine. Int. J. Pharm. 187: (1999). 5. K.M. Wilson, J.J. Schneider, and P.J. Ravenscroft. Stability of midazolam and fentanyl in infusion solutions. J. Pain Symptom. Manage. 16: (1998). 6. E.J. Avramides. Long-term stability of pure standards and stock standard solutions for the determination of pesticide residues using gas chromatography. J. Chromatogr. A 1080: (2005). 7. R. Karinen, J.M. Andersen, A. Ripel, I. Hasvold, A.B. Hopen, J. Mørland, and A.S. Christophersen. Determination of heroin and its main metabolites in small sample volumes of whole blood and brain tissue by reversed-phase liquid chromatography tandem mass spectrometry. J. Anal. Toxicol. 33: (2009). 8. R. Karinen, E.L. Øiestad, W. Andresen, G. Wethe, A. Smith-Kielland, and A. Christophersen. Comparison of ethanol and other drugs of abuse concentrations in whole blood stored in venoject glass and plastic and venosafe plastic evacuated tubes. J. Anal. Toxicol. 34: (2010). 9. J. Martens-Lobenhoffer. Stability of thiopental and pentobarbital in human plasma determined with a new easy and specific gas chromatography mass spectrometry assay. Pharmazie 54: (1999). 589

8 10. E.L. Øiestad, U. Johansen, O.M. Stokke, S. Bergan, and A.S. Christophersen. Determination of digoxin and digitoxin in whole blood. J. Anal. Toxicol. 33: (2009). 11. M. Krogh, P.V. Syversen, I. Hasvol, M. Gulliksen, L.J.U. Johansen, L.H. Olsen, Å. Ripel, and A.S. Christophersen. LC MS analyses for screening, conformation and quantification of about 60 drugs in whole blood from autopsy cases. Abstracts from TIAFT XIV, Volume 3, 2002, p E.L. Øiestad, U. Johansen, and A.S. Christophersen. Drug screening of preserved oral fluid by liquid chromatography tandem mass spectrometry. Clin. Chem. 53: (2007). 13. W. Nowatzke and E. Woolf. Best practices during bioanalytical method validation for the characterization of assay reagents and the evaluation of analyte stability in assay standards, quality controls, and study samples. AAPS J. 9: E117 E122 (2007). 14. T. Gunnar, S. Mykkänen, K. Ariniemi, and P. Lillsunde. Validated semiquantitative/quantitative screening of 51 drugs in whole blood as silylated derivatives by gas chromatography selected ion monitoring mass spectrometry and gas chromatography electron capture detection. J. Chromatogr. B 806: (2004). Manuscript received March 21, 2011; revision received May 10,

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