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Analysis of Benzylpiperazine-Like Compounds Hiroyuki Inoue 1

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Analysis of Benzylpiperazine-Like Compounds Hiroyuki Inoue 1 鑑識科学，9(2)，165―184(2004) 165 ―Technical Note― Analysis of Benzylpiperazine-like Compounds Hiroyuki Inoue1,YukoT.Iwata1, Tatsuyuki Kanamori1, Hajime Miyaguchi1, Kenji Tsujikawa1, Kenji Kuwayama1, Hiroe Tsutsumi2, Munehiro Katagi2, Hitoshi Tsuchihashi2 and Tohru Kishi1 National Research Institute of Police Science 631, Kashiwanoha, Kashiwa, Chiba 2770882, Japan1 Forensic Science Laboratory, Osaka Prefectural Police H. Q. 1318, Hommachi, Chuo-ku, Osaka, Osaka 5410053, Japan2 (Received 6 January 2004; accepted 6 March 2004) 1-Benzylpiperazine (BZP) and 1-(3-tri‰uoromethylphenyl)piperazine, newly controlled as narcotics in Japan on 2003, and their analogues were analyzed. The analytical data with color test, thin layer chromatography (TLC), infrared spectroscopy (IR), gas chromatography/mass spectrometry (GC/MS) and liquid chromatography/mass spectrometry (LC/MS) are presented. The BZP-like compounds were less sensitive to Simon's reagent than amphetamine type stimulants on spot plates. Using on-site screening kit based on Simon's test (X-Checker), BZP indicated almost the same result as methamphetamine. For TLC, the solvent system, methanol －25 aqueous ammonia (100 : 1.5), was the best among the systems examined. Iodoplatinate reagent was the most sensitive one to detect BZP. The IR spectra showed su‹cient diŠerences to make identiˆcation. Trimethylsilylation was the most appropriate choice for the GC/MS analysis of BZP-like compounds in terms of the peak shapes, separation and stability (using a J&W DB-5MS column). In LC/MS analysis, the gradient elution (10 mM formic acid and acetonitrile) using a Waters Symmetry Shield C18 column achieved discrimination of isomers except for 1-(2-‰uorophenyl) piperazine and 1-(4-‰uorophenyl)piperazine. The cone voltage of 30 V was recommended for the LC/MS screening. The information would be useful for identiˆcation of piperazines in conˆscated powders, liquids or tablets. Key words: piperazine, TLC, IR, GC/MS, LC/MS Introduction (2C-B), 4-methylthioamphetamine (4-MTA), 4- Recent information technology makes hydroxybutylic acid (GHB) and magic dramatic progress in popularization of the mushrooms (fungi containing psilocybin and/or Internet. Although the Internet is undoubtedly psilocin), and in recent years, these are our valuable source of knowledge, it also controlled under Narcotic and Psychotropic facilitates widespread of various kinds of drugs Drug Control Law in Japan. of abuse even in the young people. These drugs More recently, piperazine derivatives, 1- include 4-bromo-2,5-dimethoxyphenethylamine benzylpiperazine (BZP) and 1-(3-tri‰uoromethy- 166166 Hiroyuki Inoue et al lphenyl)piperazine (mTFMPP) (Fig. 1), have mTFMPP is a 5HT-releasing agent and binds to been found on the illicit market as a new group 5HT receptors in the brain10,11).Afatalcase of designer drugs14). They are often sold as associated with BZP and MDMA had been ``BZP'', ``A2'', ``legal E'' or ``legal X''. BZP reported in 200112). There are no recognized and mTFMPP, with their easy availability and therapeutic uses of these substances in Japan and their so-called legal status, are becoming drugs the United States. Four kinds of psychoactive of abuse worldwide. Both of piperazine piperazines, BZP, mTFMPP, 1-(4-methoxy- derivatives had been placed temporarily into phenyl)piperazine (pMeOPP), 1-(3-chloro- Schedule I of the Controlled Substances Act in phenyl)piperazine (mCPP), have been found in the United State on September 2002, in order to Japan and they are also sold as a mixed form avoid an imminent hazard to the public safety5). with BZP in some cases. The scheduling is still valid at the present A few study on identiˆcation of piperazines moment. BZP and mTFMPP are controlled in in tablets and powders as well as biological Japan after October 2003. matrices are reported1,1316),however,itshould BZP was ˆrst synthesized in 1944 as a be noted that there are several isomers in the potential anthelmintic agent. BZP also shows a piperazine derivatives which would have quite central serotoninomimetic action that involves 5- similar chromatographic and mass spectrometric HT uptake-inhibition and 5-HT1 receptor properties to each other. In the present study, agonistic eŠects6).BZPactsasastimulant analytical data of BZP-like compounds similar to 3,4-methylenedioxymethamphetamine appeared on the illicit market and available (MDMA) or amphetamine, producing euphoria isomers in Japan using color tests, thin layer and inducing cardiovascular eŠects in humans, chromatography (TLC), infrared spectroscopy including increased heart rate and systolic blood (IR), gas chromatography/mass spectrometry pressure7,8). mTFMPP shows hallucinogenic (GC/MS) and liquid chromatography/mass eŠects similar to those produced by MDMA9). spectrometry (LC/MS) are presented. Fig. 1 Chemical structures of benzylpiperazine-like compounds used in this study. Analysis of Benzylpiperazine-like Compounds 167 Materials and Methods Pyridine (anhydrous) was obtained from Aldrich 1Chemicals Co. (Milwaukee, WI). HPLC-grade acetonitrile (1) BZP-like compounds was obtained from Wako Pure Chemical BZP and 1-(3-tri‰uoromethylphenyl) Industries. X-Checker(on-site screening kit for piperazine monohydrochloride (mTFMPP･HCl) MA, based on Simon's test) was obtained from were obtained from Lancaster Synthesis Taisho Rika (Saitama, Japan). Glass plates (20 (Lancashire, UK). BZP dihydrochloride was cm×20 cm) precoated to a depth of 0.25 mm prepared from BZP. mTFMPP, 1-(2-methoxy- with silica gel 60F254 was obtained from Merck phenyl)piperazine (oMeOPP), 1-(4-methoxy- (Darmstadt, Germany). A Milli-Q Simpli Lab- phenyl)piperazine dihydrochloride (pMeOPP･ UV system (Millipore, Billerica, MA) was used 2HCl), 1-(3-chlorophenyl)piperazine monohy- to prepare pure water throughout the study. All drochloride (mCPP･HCl), 1-(4-chlorophenyl) other chemicals used were analytical reagent piperazine monohydrochloride (pCPP･HCl), grade. 1-(2-‰uorophenyl)piperazine monohydrochlo- 2 Methods ride (oFPP･HCl) and 1-(4-‰uorophenyl) (1) Color tests piperazine dihydrochloride (pFPP･2HCl) were The samples (3 or 10 mg) were tested by obtained from Tokyo Kasei Kogyo (Tokyo, following reagents20).Blanktests(reagentsonly) Japan). 1-(2-Tri‰uoromethylphenyl)piperazine were also carried out. (oTFMPP) and 1-(4-tri‰uoromethylphenyl) (1)-1 Simon's reagent piperazine (pTFMPP) were from Fluorochem Solution A. 20 aqueous sodium (Derbyshire, UK). carbonate solution (2) Reference compounds Solution B. 50 ethanolic acetaldehyde d-Methamphetamine hydrochloride (MA･ solution HCl) was obtained from Dainippon Solution C. 1 aqueous sodium Pharmaceutical (Osaka, Japan). dl-MDMA nitroprusside solution hydrochloride (MDMA･HCl) was synthesized as a. Spots test previously reported17). 4-Bromo-2,5-dimethoxy- A sample was placed in a depression of spot phenethylamine hydrochloride (2C-B･HCl) was plates and mixed with 1 drop (20 mLapprox.)of synthesized as previously reported18). d- solutionA.OnedropofsolutionBandthatof Dimethylamphetamine hydrochloride (DMA･ solution C were added subsequently. HCl) was synthesized from l-norephedrine b. X-Checker hydrochloride (Wako Pure Chemical Industries, The kit is a capped plastic tube which Osaka, Japan) as previously reported19).Stock contains 2 sealed capillaries (enclosed Solution B solutions were prepared at concentrations of 1 andC)andasmallpieceofˆlterpapersoaked mg/mL in methanol. with Solution A. (3) Reagents Test was carried out according to an Sodium nitroprusside and hydrogen instruction manual attached to the kit21) (Fig. 2): hexachloroplatinate hexahydrate were obtained (1) 10 mg of sample is put into the plastic tube. from Kanto Chemical (Tokyo, Japan). p- (2) Bend the plastic tube to crack the sealed Dimethylaminobenzaldehyde (p-DMAB) was capillaries and the sample will be mixed with obtained from Kokusan Chemical (Tokyo, Solution B and C. The mixed solution will be Japan). Ferric chloride was obtained from soaked to the ˆlter paper. (3) If MA presents, the Nacalai Tesque (Kyoto, Japan). N,O- contents of the tube will turn blue in a few Bis(trimethylsilyl)tri‰uoroacetamide (BSTFA) seconds. was obtained from GL Sciences (Tokyo, Japan). (1)-2 Marquis reagent Trimethylchlorosilane (TMCS) was obtained The reagent was prepared by adding 1 drop from Pierce Chemical Co. (Rockford, IL). of formaldehyde to 1 mL of concentrated 168168 Hiroyuki Inoue et al reagents. b. DragendorŠ reagent Preparation of the reagent is as described in the section ``13 DragendorŠ reagent''. c. Simon's reagent The reagent was prepared by mixing equal volumes of the Solution A and the Solution C described in the section ``11 Simon's reagent''. The plates were exposed to acetaldehyde gas Fig. 2 Schematics of how to use X-Checker. after spraying the reagent. d. Iodoplatinate reagent Solution A: aqueous 10 hydrogen sulfuric acid. A sample was placed in a hexachloroplatinate hexahydrate solution depression of a spot plate, and 3 drops of the Solution B: aqueous 4 potassium iodide reagent were added. solution. (1)-3 DragendorŠ reagent The Solution A, B and water were mixed in One gram of bismuth subnitrate was the ratio of 1 : 25 : 24 by volume. dissolved in a small amount of concentrated e. 1 Iodine-methanol solution hydrochloric acid; 25 aqueous ammonia was f. p-DMAB solution added until the precipitation (Bi(OH)3 )ˆnished; 0.125 g of p-DMAB was dissolved in 100 the supernatant was removed and the residue mL of 65 sulfuric acid and 0.1 mL of 5 waswashedwithwater;theresiduewasdissolved ferric chloride
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