Abstract
PurposePhenethylamines constitute the majority of drug-related arrests in Japan. Recently, the smuggling of tert-butoxycarbonyl (t-Boc)-protected phenethylamines has become of increasing concern, because of the difficult identification of these masked substances.MethodsIn this study, a rapid and accurate method for the detection of t-Boc-methamphetamine (t-Boc-MP) by direct analysis in real time–time-of-flight-mass spectrometry (DART–TOF-MS) was developed. The efficiency of the method was evaluated by comparison with conventional gas chromatography–MS (GC–MS) and liquid chromatography–TOF-MS (LC–TOF-MS) techniques.ResultsDuring GC–MS analysis of t-Boc-MP, MP was generated in the injection port, which can lead to an analytical error. In the LC–TOF-MS spectrum, fragment ions were detected, which were generated by McLafferty rearrangement in the ion source. On the other hand, in the DART–TOF-MS analysis of t-Boc-MP, pyrolysis could be suppressed by using a micro-syringe injection method, and the fragment ions generated by McLafferty rearrangement were still observed. Moreover, protonated t-Boc-MP could be detected.ConclusionsHence, DART–TOF-MS provides a rapid and accurate method for the detection of t-Boc-MP, allowing suppression of the pyrolysis reaction and identification of both fragment ions and protonated t-Boc-MP. To our knowledge, this is the first report for detecting t-Boc-MP by MS techniques.
Highlights
In Japan, methamphetamine (MP), amphetamine, and their salts are strictly regulated by the Stimulants Control Law, and represent the majority of drug-related arrests
The synthesized t-Boc-MP was analyzed by gas chromatography–MS (GC–MS), and the obtained mass spectrum was compared to that of t-BocMP reported by Collins et al [4]
MP was detected in the total ion current chromatogram (TICC) by GC–MS for the synthesized t-Boc-MP, and was presumably generated by pyrolysis of t-Boc-MP in the injection port of the instrument
Summary
In Japan, methamphetamine (MP), amphetamine, and their salts are strictly regulated by the Stimulants Control Law, and represent the majority of drug-related arrests. MP is Narcotics Control Department, Kanto-Shin’etsu Regional Bureau of Health and Welfare Ministry of Health, Labour and Welfare, 1‐2‐1 Kudan‐Minami, Chiyoda‐ku, Tokyo 102‐8309, Japan. Narcotics Control Department, Tohoku Regional Bureau of Health and Welfare Ministry of Health, Labour and Welfare, 3‐2‐23 Honchou, Aoba, Sendai 980‐0014, Japan. The t-Boc group is one of the most commonly used amino-protecting groups in organic synthesis, such as peptide synthesis, because of the simple protection-deprotection procedures [7]. Seizures of t-Boc-protected MDMA and MP, phenethylamines containing secondary amino groups, have been reported. In view of the simple protection-deprotection procedures, a variety of phenethylamine drugs could be masked by t-Boc protection of the amino group. No analytical data for t-Boc-protected phenethylamines is available to date, making drug detection difficult and inaccurate. In order to prevent their distribution worldwide, a rapid and accurate analytical method for the detection of t-Boc-masked drugs is needed to quickly provide the administrative authorities with the drug data
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