Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012

Kikura‐Hanajiri, Ruri; Uchiyama, Nahoko; Kawamura, Maiko; Goda, Yukihiro

doi:10.1007/s11419-012-0165-2

Cited by 87 publications

(49 citation statements)

References 25 publications

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“…In recent years, synthetic cannabinoids [1][2][3][4][5] and cathinones [6][7][8][9] have become widely distributed, and are now causing social problems throughout many parts of the world. Although the traditional marijuana and hashish containing D 9 -tetrahydrocannabinol as the psychoactive compound have been associated with almost no fatalities thus far, two reports have described fatalities caused by the synthetic cannabinoids MAM-2201 [10] and NNEI [11].…”

Section: Introductionmentioning

confidence: 99%

Identification and quantitation of 5-fluoro-ADB, one of the most dangerous synthetic cannabinoids, in the stomach contents and solid tissues of a human cadaver and in some herbal products

et al. 2014

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Since late September 2014, there have been approximately 10 cases in Japan where people have died from inhaling smoke from herbal blends containing a newly emerged synthetic cannabinoid. Although the drug was tentatively identified by some drug-monitoring institutions as 5-fluoro-ADB, to our knowledge, its data have not been published in any scientific context. We recently encountered an autopsy case in which 5-fluoro-ADB was involved. The deceased was a 34-year-old man who was found dead in his room. The postmortem interval was estimated at 35-40 h. The direct cause of the death was asphyxia due to aspiration of stomach contents into the trachea, which likely took place during vomiting under low-consciousness conditions provoked by inhalation of the 5-fluoro-ADB smoke. The cadaver was subjected to autopsy at our department. Femoral vein blood, right heart blood, left heart blood, urine, stomach contents, and nine solid tissues including the adipose tissue were collected and frozen until analysis. The extraction of 5-fluoro-ADB and internal standard 5-fluoro-AMB was performed using a modified QuEChERS method plus filtration through Captiva ND Lipids cartridges, followed by liquid chromatography-tandem mass spectrometry (LC-MS-MS) analysis. Because this study dealt with various kinds of human matrices, we used the standard addition method for quantitation to overcome the matrix effects. The levels of 5-fluoro-ADB in the cadaver specimens were generally low; it could not be detected from blood or urine specimens. The levels of 5-fluoro-ADB in solid tissues were 1.17-7.95 ng/g. Because the highest levels were found for the adipose tissue and heart muscle, the final extracts of the adipose tissue and/or heart muscle were concentrated 10-and 200-fold to obtain product ion mass spectra of 5-fluoro-ADB using LC-MS-MS and its mass spectrum by gas chromatography-mass spectrometry, respectively. Both spectra completely coincided with those obtained from the reference standard 5-fluoro-ADB, confirming that the target compound was 5-fluoro-ADB. The quantitative results obtained by selected reaction monitoring of LC-MS-MS showed the highest level, at 7.95 ng/g, in the adipose tissue, followed by stomach contents, brain, heart muscle, pancreas, and spleen. For the lung, liver, kidney, and skeletal muscle, levels were below the quantitation limit (about 0.5 ng/g), although very small peaks above the detection limit (about 0.1 ng/g) could be observed for all of the above solid tissues. The low levels of 5-fluoro-ADB in the solid tissues were likely as a result of only a small amount of 5-fluoro-ADB incorporated into the body via the lungs due to the short period from the beginning of smoking the herb to the fatal asphyxia resulting from aspiration of a massive amount of stomach contents into the trachea under low-consciousness conditions. In addition, we measured the content of 5-fluoro-ADB in three packages, all of which were opened, that were found under a pillow near the deceased; their levels of 5-fluoro-ADB were 49.2 mg/g, ...

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Section: Introductionmentioning

confidence: 99%

Identification and quantitation of 5-fluoro-ADB, one of the most dangerous synthetic cannabinoids, in the stomach contents and solid tissues of a human cadaver and in some herbal products

et al. 2014

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“…However, herbal mixtures called ''Spice'' containing synthetic cannabinoids as synthetic additives have gained popularity globally since 2008 [1][2][3][4]. These mixtures are sold at head shops and gas stations and can be accessed via the Internet and even vending machines as incenses or air fresheners.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry

et al. 2015

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Despite efforts by legal authorities to control the abuse of synthetic cannabinoids, new derivatives have continually emerged on the market to circumvent regulations, and its abuse has become a threat to public health. Thus, development of analytical methods for confirming drug intake in biological fluids is essential to ensure effective drug control and to address further drug intoxication cases. Herein, a sensitive and reliable liquid chromatography-tandem mass spectrometry method was established and validated for the simultaneous determination of 37 synthetic cannabinoid metabolites, such as N-hydroxypentyl and carboxy metabolites, using 100 ll of urine. Urine specimens were treated by enzymatic hydrolysis and solid-phase extraction. Limits of detection for the evaluated drugs ranged from 0.1 to 1 ng/ml, and the linear range spanned from 0.25 or 1 to 100 ng/ml. Precision and accuracy bias were 1.4-12.1 % and -7.2-7.2 %, respectively. Matrix effects biases were in the range of 0.4 to 10.1 %, and extraction recoveries were 65-99 %. In addition, all analytes were stable under storage conditions of 4°C and -20°C for 14 days, and after three freeze-thaw cycles. The developed method was successfully applied to actual urine specimens obtained from synthetic cannabinoid users. The present method enabled simultaneous quantification of 37 synthetic cannabinoid metabolites, including their regioisomers, in urine in the field of clinical and forensic toxicology.

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“…In recent years, several new psychoactive substances (NPS) have been found and identified in illicit drug products [1][2][3][4][5][6][7]. Among the NPS, synthetic cannabinoids and synthetic cathinones are most frequently detected and have become serious social problems [1,7].…”

Section: Introductionmentioning

confidence: 99%

Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products

et al. 2015

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Recently, thienyl derivatives of cathinones have appeared on the market as new psychoactive substances (NPS). In this study, identification and characterization of 2-(pyrrolidin-1-yl)-1-(thiophen-2-yl)pentan-1-one (a-PVT), 2-(pyrrolidin-1-yl)-1-(thiophen-2-yl)butan-1-one (a-PBT), and their bromothienyl analogs disclosed in illicit products are described. In our analysis, some analogous compounds of a-PVT, which had a bromine substitution on the thiophene ring, were identified in the samples containing a-PVT; 1-(4-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one, 1-(5-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one, and 1-(4,5-dibromothiophen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one by comparing the analytical data with synthetic reference standards. We also observed 1-(4-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)butan-1-one and 1-(5-bromothiophen-2-yl)-2-(pyrrolidin-1-yl)butan-1-one from a powder product, in which a-PBT was detected. The brominated a-PVTs were also found when overbrominated 1-(thiophen-2-yl)pentan-1-one reacted with pyrrolidine, and they are suspected to be the by-products of a-PVT synthesis. In Japan, cathinone derivatives with a phenyl group as the aromatic ring have been widely controlled by generic scheduling. To escape from such a regulation, analogs with different aromatic groups such as a-PVT and a-PBT appeared on the illicit market of psychoactive compounds. To our knowledge, this is the first report describing identification of a-PBT, and bromothienyl analogs of both a-PVT and a-PBT in illicit drug products. The synthetic method and analytical data shown in this study will be useful for identification of the thienyl derivatives of cathinone analogs.

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Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012

Cited by 87 publications

References 25 publications

Identification and quantitation of 5-fluoro-ADB, one of the most dangerous synthetic cannabinoids, in the stomach contents and solid tissues of a human cadaver and in some herbal products

Identification and quantitation of 5-fluoro-ADB, one of the most dangerous synthetic cannabinoids, in the stomach contents and solid tissues of a human cadaver and in some herbal products

Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry

Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products

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