Purpose Various phenylethylamines have been detected lately in dietary or sports supplements. N-Methyl-2-phenylpropan-1-amine (phenpromethamine) and 2-phenylpropan-1-amine (β-methylphenylethylamine, BMPEA) are known to produce mass spectra almost identical to those produced by methamphetamine (MA) and amphetamine (AP), respectively, when analyzed by liquid chromatography/mass spectrometry (LC/MS). They may interfere with the analysis of MA and AP. The aims of the present study were to determine whether some substances other than phenpromethamine and BMPEA give mass spectra similar to those given by MA or AP and to develop an analytical method of distinguishing phenpromethamine from MA and BMPEA from AP by derivatization. Methods Twenty isomers of MA or AP were selected to be analyzed using LC/MS. Six reagents were examined for derivatization of MA, AP, phenpromethamine, and BMPEA. Three mass spectrometers from two manufacturers were evaluated for their ability to reproduce the data. Results All isomers except phenpromethamine and BMPEA were shown to be distinguishable from MA and AP by their mass spectra. For the discrimination of isomeric pairs, derivatization using N-succinimidyl-4-nitrophenylacetate was found to be the best for tandem mass spectrometry and that using 4-nitrobenzoyl chloride was the best for in-source collision-induced dissociation. One or more ions from each pair of isomers gave adequate difference in their relative intensities according to the World Anti-Doping Agency criteria. Conclusions The newly developed method was proved to be usable for discriminating among those phenylethylamines.

Illegal distribution of cannabis products, such as cannabis-infused foods and eliquids, are increasing in Japan. The main component of cannabis is tetrahydrocannabinol (THC). THC extracted from cannabis is regulated by the Cannabis Control Act, and chemically synthesized THC is regulated by the Narcotics and Psychotropics Control Act; therefore, it is important to identify the source of THC for judicial appraisal. Recently, the crime of cultivating cannabis has occurred frequently in Japan. Illegal cultivation is diŠicult to discover because there are cases in which cannabis is cultivated secretly in a room in apartments, etc. Cannabis is a plant that emits unique odors. Detection of the odor constituents can provide a breakthrough for the criminal investigation of cannabis cultivation. The purpose of this study was to identify cannabis products and utilize them for the criminal investigation of cannabis cultivation. Cannabis plants were cultivated from seeds and analyzed using both solid-phase microextraction (SPME) and solvent extraction. Fifty kinds of volatile components were detected by SPME and 21 kinds of refractory components were detected by solvent extraction in fresh cannabis plants. We found that terpenes were detected more strongly in cannabis buds than in cannabis leaves. Furthermore, sesquiterpenes were strongly detected from cannabis leaves and monoterpenes were strongly detected from cannabis buds. The most abundant components were b myrcene, cis b ocimene, terpinolene, b caryophyllene, trans a bergamotene, humu-