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Erschienen in: Forensic Toxicology 1/2015

01.01.2015 | Original Article

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

verfasst von: Koutaro Hasegawa, Amin Wurita, Kayoko Minakata, Kunio Gonmori, Itaru Yamagishi, Hideki Nozawa, Kanako Watanabe, Osamu Suzuki

Erschienen in: Forensic Toxicology | Ausgabe 1/2015

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Abstract

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, 12.2 μg/g, and 0.77 μg/g. To our knowledge, this is the first reported identification and quantitation of 5-fluoro-ADB in human specimens and herbal products.
Literatur
1.
Zurück zum Zitat Zuba D, Byrska B (2013) Analysis of the prevalence and coexistence of synthetic cannabinoids in “herbal high” products in Poland. Forensic Toxicol 31:21–30CrossRef Zuba D, Byrska B (2013) Analysis of the prevalence and coexistence of synthetic cannabinoids in “herbal high” products in Poland. Forensic Toxicol 31:21–30CrossRef
2.
Zurück zum Zitat Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2013) Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012. Forensic Toxicol 31:44–53CrossRef Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2013) Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012. Forensic Toxicol 31:44–53CrossRef
3.
Zurück zum Zitat Chung H, Choi H, Heo S, Kim E, Lee J (2014) Synthetic cannabinoids abused in South Korea: drug identification by the National Forensic Service from 2009 to June 2013. Forensic Toxicol 32:82–88CrossRef Chung H, Choi H, Heo S, Kim E, Lee J (2014) Synthetic cannabinoids abused in South Korea: drug identification by the National Forensic Service from 2009 to June 2013. Forensic Toxicol 32:82–88CrossRef
4.
Zurück zum Zitat Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products. Forensic Toxicol 32:105–115CrossRef Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products. Forensic Toxicol 32:105–115CrossRef
5.
Zurück zum Zitat Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T (2014) Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products. Forensic Toxicol 32:266–281CrossRef Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T (2014) Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products. Forensic Toxicol 32:266–281CrossRef
6.
Zurück zum Zitat Namera A, Urabe S, Saito T, Torikoshi-Hatano A, Shiraishi H, Arima Y, Nagao M (2013) A fatal case of 3,4-methylenedioxypyrovalerone poisoning: coexistence of α-pyrrolidinobutiophenone and α-pyrrolidinovalerophenone in blood and/or hair. Forensic Toxicol 31:338–343CrossRef Namera A, Urabe S, Saito T, Torikoshi-Hatano A, Shiraishi H, Arima Y, Nagao M (2013) A fatal case of 3,4-methylenedioxypyrovalerone poisoning: coexistence of α-pyrrolidinobutiophenone and α-pyrrolidinovalerophenone in blood and/or hair. Forensic Toxicol 31:338–343CrossRef
7.
Zurück zum Zitat Namera A, Konuma K, Kawamura M, Saito T, Nakamoto A, Yahata M, Ohta S, Miyazaki S, Shiraishi H, Nagao M (2014) Time-course profile of urinary excretion of intravenously administered α-pyrrolidinovalerophenone and α-pyrrolidinobutiophenone in a human. Forensic Toxicol 32:68–74CrossRef Namera A, Konuma K, Kawamura M, Saito T, Nakamoto A, Yahata M, Ohta S, Miyazaki S, Shiraishi H, Nagao M (2014) Time-course profile of urinary excretion of intravenously administered α-pyrrolidinovalerophenone and α-pyrrolidinobutiophenone in a human. Forensic Toxicol 32:68–74CrossRef
8.
Zurück zum Zitat Hasegawa K, Suzuki O, Wurita A, Minakata K, Yamagishi I, Nozawa H, Gonmori K, Watanabe K (2014) Postmortem distribution of α-pyrrolidinovalerophenone and its metabolite in body fluids and solid tissues in a fatal poisoning case measured by LC–MS–MS with the standard addition method. Forensic Toxicol 32:225–234CrossRef Hasegawa K, Suzuki O, Wurita A, Minakata K, Yamagishi I, Nozawa H, Gonmori K, Watanabe K (2014) Postmortem distribution of α-pyrrolidinovalerophenone and its metabolite in body fluids and solid tissues in a fatal poisoning case measured by LC–MS–MS with the standard addition method. Forensic Toxicol 32:225–234CrossRef
9.
Zurück zum Zitat Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Suzuki O, Watanabe K (2014) Identification and quantitation of a new cathinone designer drug PV9 in an “aroma liquid” product, antemortem whole blood and urine specimens, and a postmortem whole blood specimen in its fatal poisoning case. Forensic Toxicol 32:243–250CrossRef Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Suzuki O, Watanabe K (2014) Identification and quantitation of a new cathinone designer drug PV9 in an “aroma liquid” product, antemortem whole blood and urine specimens, and a postmortem whole blood specimen in its fatal poisoning case. Forensic Toxicol 32:243–250CrossRef
10.
Zurück zum Zitat Saito T, Namera A, Miura N, Ohta S, Miyazaki S, Osawa M, Inokuchi S (2013) A fatal case of MAM-2201 poisoning. Forensic Toxicol 31:333–337CrossRef Saito T, Namera A, Miura N, Ohta S, Miyazaki S, Osawa M, Inokuchi S (2013) A fatal case of MAM-2201 poisoning. Forensic Toxicol 31:333–337CrossRef
11.
Zurück zum Zitat Sasaki C, Saito T, Shinozuka T, Irie W, Murakami C, Maeda K, Nakamaru N, Oishi M, Nakamura S, Kurihara K (2014) A case of death caused by abuse of a synthetic cannabinoid N-1-naphthalenyl-1-pentyl-1H-indole-3-carboxamide. Forensic Toxicol. doi:10.1007/s11419-014-0246-5 Sasaki C, Saito T, Shinozuka T, Irie W, Murakami C, Maeda K, Nakamaru N, Oishi M, Nakamura S, Kurihara K (2014) A case of death caused by abuse of a synthetic cannabinoid N-1-naphthalenyl-1-pentyl-1H-indole-3-carboxamide. Forensic Toxicol. doi:10.​1007/​s11419-014-0246-5
12.
Zurück zum Zitat Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O (2014) Postmortem distribution of AB-CHMINACA, 5-fluoro-AMB and diphenidine in body fluids and solid tissues in a fatal poisoning case: usefulness of the adipose tissue for detection of the drugs in unchanged forms. Forensic Toxicol. doi:10.1007/s11419-014-0245-6 Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O (2014) Postmortem distribution of AB-CHMINACA, 5-fluoro-AMB and diphenidine in body fluids and solid tissues in a fatal poisoning case: usefulness of the adipose tissue for detection of the drugs in unchanged forms. Forensic Toxicol. doi:10.​1007/​s11419-014-0245-6
13.
Zurück zum Zitat Kudo K, Ishida T, Hikiji W, Hayashida M, Uekusa K, Usumoto Y, Tsuji A, Ikeda N (2009) Construction of calibration-locking databases for rapid and reliable drug screening by gas chromatography-mass spectrometry. Forensic Toxicol 27:21–31CrossRef Kudo K, Ishida T, Hikiji W, Hayashida M, Uekusa K, Usumoto Y, Tsuji A, Ikeda N (2009) Construction of calibration-locking databases for rapid and reliable drug screening by gas chromatography-mass spectrometry. Forensic Toxicol 27:21–31CrossRef
14.
Zurück zum Zitat Wurita A, Hasegawa K, Minakata K, Watanabe K, Suzuki O (2014) A large amount of new designer drug diphenidine coexisting with a synthetic cannabinoid 5-fluoro-AB-PINACA found in a dubious herbal product. Forensic Toxicol 32:331–337CrossRef Wurita A, Hasegawa K, Minakata K, Watanabe K, Suzuki O (2014) A large amount of new designer drug diphenidine coexisting with a synthetic cannabinoid 5-fluoro-AB-PINACA found in a dubious herbal product. Forensic Toxicol 32:331–337CrossRef
15.
Zurück zum Zitat Bonilla E (1978) Flameless atomic absorption spectrophotometric determination of manganese in rat brain and other tissues. Clin Chem 24:471–474PubMed Bonilla E (1978) Flameless atomic absorption spectrophotometric determination of manganese in rat brain and other tissues. Clin Chem 24:471–474PubMed
16.
Zurück zum Zitat Wurita A, Suzuki O, Hasegawa K, Gonmori K, Minakata K, Yamagishi I, Nozawa H, Watanabe K (2013) Sensitive determination of ethylene glycol, propylene glycol and diethylene glycol in human whole blood by isotope dilution gas chromatography–mass spectrometry, and the presence of appreciable amounts of the glycols in blood of healthy subjects. Forensic Toxicol 31:272–280CrossRef Wurita A, Suzuki O, Hasegawa K, Gonmori K, Minakata K, Yamagishi I, Nozawa H, Watanabe K (2013) Sensitive determination of ethylene glycol, propylene glycol and diethylene glycol in human whole blood by isotope dilution gas chromatography–mass spectrometry, and the presence of appreciable amounts of the glycols in blood of healthy subjects. Forensic Toxicol 31:272–280CrossRef
17.
Zurück zum Zitat Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Suzuki O, Watanabe K (2014) Postmortem distribution of α-pyrrolidinobutiophenone in body fluids and solid tissues of a human cadaver. Legal Med 16:241–246PubMedCrossRef Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Suzuki O, Watanabe K (2014) Postmortem distribution of α-pyrrolidinobutiophenone in body fluids and solid tissues of a human cadaver. Legal Med 16:241–246PubMedCrossRef
Metadaten
Titel
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
verfasst von
Koutaro Hasegawa
Amin Wurita
Kayoko Minakata
Kunio Gonmori
Itaru Yamagishi
Hideki Nozawa
Kanako Watanabe
Osamu Suzuki
Publikationsdatum
01.01.2015
Verlag
Springer Japan
Erschienen in
Forensic Toxicology / Ausgabe 1/2015
Print ISSN: 1860-8965
Elektronische ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-014-0259-0

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