T2007 Seattle, Washington

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1 T2007 Seattle, Washington Stable Isotopes (δ 13 C): A Proposed Means of Identifying the Source of Gamma- Hydroxybutyric Acid (GHB) Bill Guthery *1, David E.G. Shuker 2, Colin T. Pillinger 1, Mabs A. Gilmour 1, Silvia Valussi 3, John Wicks 4, Lolita Tsanaclis 4 and Geraint H. Morgan 1 1 Planetary and Space Sciences Research Institute, The pen University, Milton Keynes, UK, 2 Department of Chemistry, The pen University, Milton Keynes, UK, 3 Forensic Science Service Ltd., R & D Physical Sciences, 109 Lambeth Road, London SE1 7LP, UK, 4 TrichoTech Ltd., No. 1 Pentwyn Business Centre, Cardiff CF23 7HB, UK Abstract Stable isotope measurements have the potential to differentiate endogenous from exogenous gamma-hydroxybutyric acid (GHB) in biological matrices. We propose a clean-up method from urine using solid phase extraction (SPE) and analysis using gas chromatographycombustion-isotope ratio mass spectrometry (GC-C-IRMS). We have determined δ 13 C ( ) values for three different reference standards of GHB (10 μg/ml sodium salt) derivatised with N,-bis(trimethylsilyl)trifluoroacetamide (BSTFA) (#1 mean ; σ n ; n=3: #2 mean ; σ n ; n=3: #3 mean ; σ n ; n=3). Urine samples (<1.62 μg/ml endogenous GHB) were spiked with 10 μg/ml of GHB standard, extracted from the matrix using SPE and derivatised with BSTFA, and the δ 13 C ( ) values (#1 mean ; σ n ; n=3: #2 mean ; σ n ; n=3: #3 mean ; σ n ; n=3) compared with the standard preparation. Gamma-hydroxyvalerate (GHV) was used as an internal standard for quantitation purposes and as a control for isotopic measurements. GHB standards were also derivatised with N-methyl-N-(t-butyldimethylsilyl) trifluoroacetamide (MTBSTFA). The same batches of the derivatisation agents were used throughout the study. Introduction GHB is produced naturally in the human body and is also a Class C controlled substance in the UK under the Misuse of Drugs Act It is notorious because of its association with drug facilitated sexual assaults (DFSA). Studies have indicated that large variations in urinary and blood concentrations of endogenous GHB occur across population groups 1, 2. At present the recognised cut off values of 10 μg/ml in urine and 5 μg/ml in blood may only provide reliable evidence if the sample was taken <12 hours after ingestion because GHB is rapidly metabolised and excreted from the body 3. A recent study, using GC-C-IRMS, found a significant difference (>13.5 ) in the values of δ 13 C found in endogenous GHB in five post-mortem blood samples (range: μg/ml) compared to synthetically produced GHB with the implication that stable isotope measurements could significantly increase time frames of detection in reported DFSA 4. The concentration of GHB in these samples was much higher than the recognised cut-off values. GHB has been found to be elevated in post-mortem biological fluids due to the putrefaction process 5.

2 The aim of this study was to determine the δ 13 C values of GHB in human urine at the 10 μg/ml cut-off level. If sufficient precision and sensitivity could be achieved, the next stage would be to extract and analyse GHB in urine below the recognised cut-off values to identify if it is from a natural or a synthetic source. The symbol δ is a standard notation and refers to the carbon isotope ratio measured against a known reference standard (Equation 1). δ 13 C( ) = ( C/ C) - ( C/ C) sample ( C/ C) standard standard x 1000 Equation 1 Method Summary Standard Preparation (GC-C-IRMS) 10 μl GHB (1 mg/ml methanolic) and 10 μl GHV (1 mg/ml methanolic) were added to 1 ml deionised water and evaporated to dryness. The dried residues were derivatised with BSTFA: TMCS (99:1) or MTBSTFA. The excess solvent was removed and reconstituted in 200 μl hexane. 1 μl aliquot was injected into the GC. Sample preparation (GC-C-IRMS) 0 or 10 μl GHB (1 mg/ml methanolic) and 10 μl GHV (1 mg/ml methanolic) were added to 1 ml urine (collected on the day of analysis). GHB was extracted using CLEAN SCREEN SPE cartridges. The extracts were evaporated and derivatised with BSTFA: TMCS (99:1). The rest of the procedure was as previously described. Standard Preparation (GC-MS) Standard solutions of GHB (50, 25, 10, 5, 2, 1, 0.5, 0.1 μg) and GHV (10 μg) were prepared in 1 ml de-ionised water. The standard solutions were evaporated and derivatised with BSTFA: TMCS (99:1). The rest of the procedure was as previously described. Analysis GC-C-IRMS The instrument used was a Thermo Finnigan MAT 253 IR-MS with Trace Ultra GC and Combustion III Interface. The separation was performed with a J&W DB-5 (30m x 0.25mm x 0.25 μm). GC-MS The instrument used was a Thermo Focus/Polaris Q (Ion Trap) with AS3000 Autosampler. The separation was performed with a Restek Rtx-5MS (15m x 0.25mm x 0.25 μm).

3 Results and Discussion Three separate urine samples, taken on different days from the same volunteer, were found to contain 1.62, 1.50 and 1.31 μg/ml, quantitated against a 7-point calibration curve (0.1 to 50 μg/ml; R 2 =0.997) with GHV (10 μg/ml) used as an internal standard. The quantitation ions used were GHB di-tms (m/z 233), GHV di-tms (m/z 247). The urine samples were spiked with 10 μg/ml of the three synthetic standards, respectively, and the δ 13 C ( ) values obtained were compared against values obtained for the synthetic standards prepared from water with no clean-up (Tables 1 to 4). The endogenous concentration was not expected to significantly alter the δ 13 C ( ) values. The chromatograms obtained from the GC-C-IRMS have shown that GHB and GHV derivatives can be separated sufficiently from the matrix interferences (Figure 1 and 2). The method was not sensitive enough to obtain δ 13 C ( ) values for endogenous GHB. Table 1. δ13c ( ) values of GHB di-tms (10 μg/ml standard preparation) Run Standard #1 Standard #2 Standard # Mean σ n Table 2. δ13c ( ) values of GHV di-tms controls (10 μg/ml ) Run #1 #2 # Mean σ n Table 3. δ13c ( ) values of GHB di-tms (10 μg/ml spikes in urine) Run Standard #1 Standard #2 Standard # Mean σ n

4 Table 4. δ13c ( ) values of GHV di-tms controls (10 μg/ml spikes in urine) Run #1 #2 # Mean σ n GHB derivatised with N-methyl-N-(t-butyldimethylsilyl)trifluoroacetamide (MTBSTFA) was also evaluated as an alternative to BSTFA. GHB di-tbdms δ 13 C values were found to be more reproducible (Table 5) compared with GHB di-tms. This is almost certainly due to isotopic fractionation during the silylation reaction or in the injector port which is not as prevalent with the TBDMS derivatives which form more stable compounds with much higher boiling points. However, the addition of carbon atoms to the analyte has the effect of diluting the δ 13 C values. Silylated GHB is the carbon-weighted average of the isotope values of GHB and TMS (or TBDMS) (Equation 2 and 3). Table 5. δ13c ( ) values of GHB di-tbdms (10 μg/ml standard preparation) Run Standard #1 Standard #2 Standard #3 GHV di-tbdms Mean σ n

5 CH H 3 3 C Si H 3 C CH 3 Si CH 3 H 3 C GHB di-tms δ C GH B di-tms = 4 δ C GHB + 6 δ C Equation 2 di-tms CH H 3 3 C CH 3 Si H 3 C H 3 C CH 3 CH Si 3 H 3 C CH H 3 C 3 GHB di-tbdms δ C GHB di-tbdms = 4 δ C GHB + 12 δ C Equation 3 di-tbdms GHB di-tms GHV di-tms Figure 1 GHB standard 10 μg/ml P 4 tri-tms GHV di-tms GHB di-tms Figure 2 GHB 10 μg/ml spike in urine

6 Conclusion The work so far has demonstrated that GHB, derivatised with BSTFA and MTBSTFA, can be effectively analysed by GC-C-IRMS. δ 13 C ( ) values were successfully obtained for 10 μg/ml spikes in urine. However, it has been reported that only ~1% of administered GHB is excreted unchanged in urine 3. Further work will be required to determine if δ 13 C ( ) values of synthetic GHB are altered during this process. The issue of sensitivity also requires further investigation. It has not been possible, thus far, to obtain δ 13 C ( ) values for endogenous GHB in urine. This could possibly be achieved by using a larger sample volume but this will also have the effect of adding more matrix interferences to the sample which could overload the SPE cartridge or the GC column. Also because all of the organic compounds are converted to carbon dioxide prior to analysis these matrix interferences may affect the isotopic values. We have overcome this problem by using a slow oven ramp rate (5 C/min) to obtain the best separation but this does not guarantee that the target analyte will always be clearly visible in the chromatogram. Compounds found in urine will be different across the population range. This problem may be overcome by creating an antibody specific to the GHB to selectively remove GHB from the matrix using immunoaffinity column chromatography. This would have the advantage of selectively removing GHB from the matrix and therefore would allow more sample to be used. This could greatly increase the sensitivity of the method. To our knowledge immunoassays are not available for GHB and so this would involve the synthesis of an immunising antigen. GHB is a small molecule so it may not be possible to obtain specific binding sites for GHB on an antibody. KEY WRDS: GHB, Isotopes, Endogenous w.guthery@open.ac.uk References (1) Elian, A. A. Forensic Science International 2002, 128, (2) LeBeau, M. A.; Montgomery, M. A.; Morris-Kukowski, C.; Schaff, J. E.; Deakin, A. Journal of Analytical Toxicology 2006, 30, (3) Kavanagh, P. V.; Kenny, P.; Feely, J. Journal of Pharmacy and Pharmacology 2001, 53, (4) Saudan, C.; Augsburger, M.; Kintz, P.; Saugy, M.; Mangin, P. Journal of Analytical Toxicology 2005, 29, (5) Elliot, S.; Lowe, P.; Symonds, A. Forensic Science International 2004, 139,

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