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A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N-OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products.

Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T - Forensic Toxicol (2015)

Bottom Line: Compound 6 is considered to be a by-product of the preparation of NNEI indazole analog from compound 5 and 1-pentyl-1H-indazole.A phenethylamine derivative, N-OH-EDMA [N-hydroxy-3,4-ethylenedioxy-N-methylamphetamine, 7], and a cathinone derivative, dimethoxy-α-PHP (dimethoxy-α-pyrrolidinohexanophenone, 8), were newly identified in illegal products.Among them, compounds 1 and 8 have been controlled as designated substances (Shitei-Yakubutsu) under the Pharmaceutical Affairs Law in Japan since August and November 2014, respectively.

View Article: PubMed Central - PubMed

Affiliation: Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo, 158-8501 Japan.

ABSTRACT

Six new psychoactive substances were identified together with two other substances (compounds 1-8) in illegal products by our ongoing survey in Japan between January and July 2014. A new synthetic cannabinoid, FDU-NNEI [1-(4-fluorobenzyl)-N-(naphthalen-1-yl)-1H-indole-3-carboxamide, 2], was detected with the newly distributed synthetic cannabinoid FDU-PB-22 (1). Two 2H-indazole isomers of synthetic cannabinoids, AB-CHMINACA 2H-indazole analog (3) and NNEI 2H-indazole analog (4), were newly identified with 1H-indazoles [AB-CHMINACA and NNEI indazole analog (MN-18)]. In addition, 2-methylpropyl N-(naphthalen-1-yl) carbamate (5) and isobutyl 1-pentyl-1H-indazole-3-carboxylate (6) were detected in illegal products. Compound 6 is considered to be a by-product of the preparation of NNEI indazole analog from compound 5 and 1-pentyl-1H-indazole. A phenethylamine derivative, N-OH-EDMA [N-hydroxy-3,4-ethylenedioxy-N-methylamphetamine, 7], and a cathinone derivative, dimethoxy-α-PHP (dimethoxy-α-pyrrolidinohexanophenone, 8), were newly identified in illegal products. Among them, compounds 1 and 8 have been controlled as designated substances (Shitei-Yakubutsu) under the Pharmaceutical Affairs Law in Japan since August and November 2014, respectively.

No MeSH data available.


LC-MS and GC–MS analyses of product B. LC–UV-PDA chromatogram (a), TIC (b), extracted-ion chromatograms at m/z 395 (c) and 397 (d), and ESI mass and UV spectra of peak 2 (e) are shown. TIC (f) and EI mass spectrum of peak 2 (g) obtained by GC–MS are also presented
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Fig3: LC-MS and GC–MS analyses of product B. LC–UV-PDA chromatogram (a), TIC (b), extracted-ion chromatograms at m/z 395 (c) and 397 (d), and ESI mass and UV spectra of peak 2 (e) are shown. TIC (f) and EI mass spectrum of peak 2 (g) obtained by GC–MS are also presented

Mentions: In the LC–MS and GC–MS analyses, an unknown peak 2 was detected with a synthetic cannabinoid (FUB-PB-22), its synthetic component 8-quinolinol, and a cathinone derivative (4-methylbuphedrone) in product B (Figs. 1b, 3a, b, d, f). By GC–MS analysis, peak 2 showed a molecular ion at m/z 394 (Fig. 3g). The major fragment ions of peak 2 (m/z 109 and 252) are the same as those of FDU-PB-22 (1) except for the molecular ion of compound 1 at m/z 395 (Fig. 2g). In the LC–MS analysis, peak 2 showed the protonated molecular ion at m/z 395 ([M + H]+) (Fig. 3c, e). However, the major fragment ion at m/z 252 of FDU-PB-22 (1) given by cleavage of an ester group (Fig. 2d) was not observed in the mass spectrum of peak 2 (Fig. 3e). The accurate mass spectrum obtained by LC–QTOF–MS gave an ion peak at m/z 395.1565, suggesting that the protonated molecular formula of compound 2 was C26H20N2OF (calcd. 395.1560).Fig. 3


A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N-OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products.

Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T - Forensic Toxicol (2015)

LC-MS and GC–MS analyses of product B. LC–UV-PDA chromatogram (a), TIC (b), extracted-ion chromatograms at m/z 395 (c) and 397 (d), and ESI mass and UV spectra of peak 2 (e) are shown. TIC (f) and EI mass spectrum of peak 2 (g) obtained by GC–MS are also presented
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Related In: Results  -  Collection

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Fig3: LC-MS and GC–MS analyses of product B. LC–UV-PDA chromatogram (a), TIC (b), extracted-ion chromatograms at m/z 395 (c) and 397 (d), and ESI mass and UV spectra of peak 2 (e) are shown. TIC (f) and EI mass spectrum of peak 2 (g) obtained by GC–MS are also presented
Mentions: In the LC–MS and GC–MS analyses, an unknown peak 2 was detected with a synthetic cannabinoid (FUB-PB-22), its synthetic component 8-quinolinol, and a cathinone derivative (4-methylbuphedrone) in product B (Figs. 1b, 3a, b, d, f). By GC–MS analysis, peak 2 showed a molecular ion at m/z 394 (Fig. 3g). The major fragment ions of peak 2 (m/z 109 and 252) are the same as those of FDU-PB-22 (1) except for the molecular ion of compound 1 at m/z 395 (Fig. 2g). In the LC–MS analysis, peak 2 showed the protonated molecular ion at m/z 395 ([M + H]+) (Fig. 3c, e). However, the major fragment ion at m/z 252 of FDU-PB-22 (1) given by cleavage of an ester group (Fig. 2d) was not observed in the mass spectrum of peak 2 (Fig. 3e). The accurate mass spectrum obtained by LC–QTOF–MS gave an ion peak at m/z 395.1565, suggesting that the protonated molecular formula of compound 2 was C26H20N2OF (calcd. 395.1560).Fig. 3

Bottom Line: Compound 6 is considered to be a by-product of the preparation of NNEI indazole analog from compound 5 and 1-pentyl-1H-indazole.A phenethylamine derivative, N-OH-EDMA [N-hydroxy-3,4-ethylenedioxy-N-methylamphetamine, 7], and a cathinone derivative, dimethoxy-α-PHP (dimethoxy-α-pyrrolidinohexanophenone, 8), were newly identified in illegal products.Among them, compounds 1 and 8 have been controlled as designated substances (Shitei-Yakubutsu) under the Pharmaceutical Affairs Law in Japan since August and November 2014, respectively.

View Article: PubMed Central - PubMed

Affiliation: Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo, 158-8501 Japan.

ABSTRACT

Six new psychoactive substances were identified together with two other substances (compounds 1-8) in illegal products by our ongoing survey in Japan between January and July 2014. A new synthetic cannabinoid, FDU-NNEI [1-(4-fluorobenzyl)-N-(naphthalen-1-yl)-1H-indole-3-carboxamide, 2], was detected with the newly distributed synthetic cannabinoid FDU-PB-22 (1). Two 2H-indazole isomers of synthetic cannabinoids, AB-CHMINACA 2H-indazole analog (3) and NNEI 2H-indazole analog (4), were newly identified with 1H-indazoles [AB-CHMINACA and NNEI indazole analog (MN-18)]. In addition, 2-methylpropyl N-(naphthalen-1-yl) carbamate (5) and isobutyl 1-pentyl-1H-indazole-3-carboxylate (6) were detected in illegal products. Compound 6 is considered to be a by-product of the preparation of NNEI indazole analog from compound 5 and 1-pentyl-1H-indazole. A phenethylamine derivative, N-OH-EDMA [N-hydroxy-3,4-ethylenedioxy-N-methylamphetamine, 7], and a cathinone derivative, dimethoxy-α-PHP (dimethoxy-α-pyrrolidinohexanophenone, 8), were newly identified in illegal products. Among them, compounds 1 and 8 have been controlled as designated substances (Shitei-Yakubutsu) under the Pharmaceutical Affairs Law in Japan since August and November 2014, respectively.

No MeSH data available.