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Rapid Screening for and Simultaneous Semiquantitative Analysis of Thirty Abused Drugs in Human Urine Samples Using Gas Chromatography-Mass Spectrometry Journal of Analytical Toxicology, Vol. 30, September 2006 Rapid Screeningfor and SimultaneousSemiquantitative Analysisof Thirty Abused Drugs in Human Urine Samples Using Gas Chromatography- Mass Spectrometry Downloaded from https://academic.oup.com/jat/article/30/7/468/711520 by guest on 01 October 2021 Tomomi Ishida 1, Keiko Kudo 1, Hiromasa Inoue 1, Akiko Tsuji1, Takashi Kojima 2, and Noriaki Ikeda 1,* 1Department of Forensic Pathology and Sciences, Graduate School of Medical Sciences, Kyushu University, Fukuoka 812-8582, Japan and 2Kanagawa Prefectural Institute of Public Health, Kanagawa 253-0087, Japan Abstract[ signer drugs, piperazine, tryptamine, and phenethylamine derivatives, are being widely abused among juveniles (1). Also, illicit use of opiates and the anesthetic drug ketamine (KET), In Japan, a wide variety of designer drugs became popular among which is known as or "Special is spreading (2,3). These juveniles because of their availability via the Internet and mobile "K" K', phones. Hence, it is necessary to develop simple and rapid designer drugs are sold as tablets or powder and are easily screening method for these drugs. We devised a rapid screening purchased via the Internet and mobile phones. method for and simultaneous semiquantitative analysis of 30 It is said that the classical stimulants, amphetamine (AP) abused drugs, including amphetamines, amphetamine-, and MA, mainly enhance dopamine-mediated neurotransmis- piperazine-, tryptamine-, and pbenethylamine-derived designer sion, leading to potent stimulant effects (4,5), whereas newer drugs and opiates in human urine. The urine sample was digested designer drugs such as amphetamine, piperazine, tryptamine, with urease, and the drugs were analyzed by gas chromatography- and phenethylamine derivatives mainly enhance serotonin- mass spectrometry in the scan mode after solid-phase extraction mediated neurotransmission, leading to psychedelic experi- with a FocusTM column and acetylation. The retention time ence and "feeling euphoria" (6-9). In recent years, a number of obtained with the use of a retention time locking technique and severe and even fatal intoxications attributable to these de- three qualifier ions were used to obtain positive results. As the signer drugs have been reported (10-18). Focus column requires only simple extraction steps and can retain various drugs of a wide range of polarity, screening of 30 abused Numerous methods for the determination of AP, MA, and drugs was feasible within 3 h. The calibration curves were linear amphetamine-derivatives using gas chromatography (GC), in the concentration range of 100-5000 ng/mL in most drugs with GC-mass spectrometry (MS), liquid chromatography (LC), correlation coefficients exceeding 0.99. The absolute recoveries and LC-MS have been reported and described in review articles for all drugs in urine samples were 6.9-125.4% at the (19,20). Several analytical methods for newer designer drugs concentration 1000 ng/mL. This method will be most useful such as piperazine (21-25), tryptamine (26,27), and phenethy- to confirm the presence of many abused drugs in urine in lamine (28,29) derivatives have been reported. However, no clinical and forensic cases. screening procedure for all drugs described is reported. De- signer drugs are often sold as a mixture of several drugs (2), and there are cases where results of immunoassay screening Introduction were negative but intoxication of these drugs is strongly sus- pected. In such cases, the analysis for a respective class of In Japan, methamphetamine (MA) has been the most ex- drugs is not easy. Therefore, it is necessary to develop a second tensively used illicit drug. In the latter half of the 1990s, the screening method that can detect a wide ranging class of drugs abuse of other drugs such as 3,4-methylenedioxymetham- simultaneously. Furthermore, it is more convenient if the phetamine (MDMA) and p-methoxyamphetamine (PMA) has method can roughly estimate the concentration of drugs at the also been on the rise. These drugs are generally called "club same time. drugs" or "designer drugs". More recently, varieties of de- We developed a rapid screening and semiquantitative method for 30 abused drugs (shown in Table I) in human * Author to whom correspondence should be addressed. urine using solid-phase extraction (SPE) with a Focus column E-maih [email protected],ac,jp. followed by acetylation and GC-MS analysis. 468 Reproduction (photocopying)of editorialcontent of this journal is prohibitedwithout publisher'spermission. Journal of Analytical Toxicology, Vol. 30, September 2006 Experimental hydrochloride was purchased from Sankyo Co. (Tokyo,Japan). Codeine (COD) phosphate and dihydrocodeine (DCO) phos- Chemicals and reagents phate were purchased from Takeda Pharmaceutica] Co. (Osaka, MA hydrochloride was purchased from Dainippon Pharma- Japan). 1-(3-Trifluoromethyphenyl)piperazine (TFMPP) hy- ceutical Co. (Osaka, Japan). Phenylpropanolamine (PPA) hy- drochloride was purchased from Avocado Research Chemicals drochloride, 4-bromo-2,5-dimethoxy-[3-phenetylamine(2C-B) (Lancashire, U.K.). AP sulfate was a generous gift from De- hydrochloride, mescaline hydrochloride, and 5-methoxy-N,N- partment of Forensic Medicine, Fukuoka University School of dimethyltryptamine (5MeO-DMT) were purchased from Medicine. N-Methyl-l-(3,4-methylenedioxyphenyl)-2-bu- Sigma-Aldrich Co. (St. Louis, MO). Methylephedrine (ME), or tanamine (MBDB) was purchased from Cerilliant (Austin, TX). methyltryptamine (AMT), N-benzylpiperazine (BZP), and 1- Medazepam hydrochloride was provided by Shionogi & Co. (4-methoxyphenyl)piperazine (4MPP) were purchased from (Osaka, Japan). 1-(3-Chlorophenyl)piperazine (3CPP) hy- Aldrich Chemical Co. (Milwaukee,WI). 2,5-Dimethoxy-4-iodo- drochloride and KET hydrochloride were purchased from ~-phenethylamine hydrochloride (2C-I), 2,5-dimethoxy-4- Wako Pure Chemical Industries (Osaka, Japan). ethylthio-[3-phenethylamine (2C-T-2) hydrochloride, Trifluoroacetic acid (TFA), urease from Jack Bean (activity, Downloaded from https://academic.oup.com/jat/article/30/7/468/711520 by guest on 01 October 2021 2,5-dimethoxy-4-(n)-propylthio-~-phenethylamine (2C-T-7) 133 units/mg), and ethylacetate were purchased from Wako hydrochloride, 5-methoxy-cz-methyltryptamine (5MeO-AMT) Pure Chemical Industries (Osaka, Japan). Urease (200 rag) hydrochloride, and 5-methoxy-N,N-diisopropyltryptamine was dissolved in 10 mL of distilled water. Acetic anhydride (5MeO-DIPT) hydrochloride were synthesized by Chemical was purchased from Sigma-Aldrich Co. Pyridine (silylation Soft R&D (Kyoto, Japan). 3,4-Methylenedioxyamphetamine grade) was purchased from Pierce (Milwaukee,WI). Focus was (MDA) hydrochloride, MDMA hydrochloride, dimethylam- purchased from Varian (Lake Forest, CA). The other chemicals phetamine (DMA) hydrochloride, PMA hydrochloride, p- were of analytical reagent grade. methoxymethamphetamine (PMMA) hydrochloride, 4MTA hydrochloride, and psilocin were synthesized in our laboratory Standard solutions using previouslypublished methods (29-31). Morphine (MOR) Most drugs (5 mg as free base) were dissolved in methanol, and the volume was adjusted to 5 mL to obtain a concentration of 1000 ng/tJL. This solution was further diluted in methanol Table I. Thirty Abused Drugs and Their Abbreviations to 100, 10, and 1 ng/IJL. PPA, EP, MOR, COD, and DCO were dissolved in 0.01M hydrochloric acid. ME was dissolved in Compound Abbreviation 0.01M hydrochloric acid containing 0.05% methanol. Amphetamine AP Biological samples Methamphetamine MA Dimethylamphetamine DMA Urine samples were obtained from healthy Japanese volun- Phenylpropanolamine PPA teers and stored at -20~ until analysis. Ephedrine EP Methylephedrine ME Extraction and derivatization procedure 3,4-Methylenedioxyamphetamine MDA One milliliter of urine sample was mixed with 1 lJL IS solu- 3,4-Methylenedioxymethamphetamine MDMA tion (1 lJg medazepam) in a centrifuge tube (10 mE) and di- N-Methyl-l-(3,4-methylenedioxyphenyl)-2-butanamine MBDB gested with 200 units of urease at 37~ for 10 rain. One N-Benzylpiperazine BZP milliliter of 0.05M sodium borate/0.1M potassium dihydrogen 1-(3-Trifluoromethylphenyl)piperazine TFMPP phosphate buffer (pH 9.0) was added, and the mixture was 1-(3-Chlorophenyl)piperazine 3CPP vortex mixed for 10 s and centrifuged at 850 xg for 5 min. The 1-(4-Methoxyphenyl)piperazine 4MPP supernatant was applied to Focus column conditioned se- 0~-Methyltryptamine AMT 5-Methoxy-~-methyltryptamine 5MeO-AMT quentially with 1 mL of methanol and I mL of distilled water. 5-Methoxy-N,N-dimethyltryptamine 5MeO-DMT The column was rinsed sequentially with 1 mL of distilled 5-Methoxy-N,N-diisopropyltryptamine 5MeO-DIPT water and 1 mL of 30% acetonitrile (ACN). The analytes were Psilocin eluted with 1 mL of ACN/distilled water/TFA (90:10:0.1, v/v). 4-Bromo-2,5-dimethoxy-~-phenethylamine 2C- Then the eluate was evaporated to dryness under a stream of 2,5-Dimethoxy-4-iodo-~-phenethylamine 2C-I nitrogen. The residue was dissolved in 50 l~L of pyridine, and 2,5-Dimethoxy-4-ethylthio-~-phenethylamine 2C-T-2 50 lJL of acetic anhydride was added to the solution for acety- 2,5-Dimethoxy-4-(n)-propylthio-ig-phenethylamine 2C-T-7 lation. The mixture was kept at 60~ for 30 min, and then the p-Methoxyamphetamine PMA solvent was evaporated to dryness. The residue was dissolved in p-Methoxymetamphetamine PMMA 100 lJL of ethyl acetate, and a 2-1JL aliquot of the solution was 4-Methylthioamphetamine 4MTA injected into the GC-MS apparatus. Mescaline Morphine MOR Codeine COD GC-MS condition Dihydrocodeine DCO The apparatus used was an Agilent 6980 GC combined with Ketamine KET an Agilent 5973 MS. An HP-lms fused-silica capillary column (30 m x 0.25-mm i.d., 0.25-1Jm film thickness) coated with 469 Journal of Analytical Toxicology, Vol. 30, September 2006 1 ] 100 .s Z .~s DMA EP-2AC ~ "o~s < 91 15 148 , ,IL L .... ~....... ) ..... 9 i ..... I00 200 3O0 4OO I00 200 300 4OO m/z m/z 8 ~ 118 AP-AC 8 ] ,,.C,s s Ioo ~o ~ c~ o Downloaded from https://academic.oup.com/jat/article/30/7/468/711520 by guest on 01 October 2021 < < 121 9 . .', ....... , 9 I00 200 3O0 40o .,[.,.,[ .I.
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