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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 C. The LC–UV-PDA chromatogram (a), TIC (b), and ESI mass and UV spectra of peak 3 (c) and the authentic AB-CHMINACA (d) are shown. TIC (e), and EI mass spectra of peaks 3 (f) and the authentic AB-CHMINACA (g) obtained by the GC–MS analysis are also shown
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Fig5: LC–MS and GC–MS analyses of product C. The LC–UV-PDA chromatogram (a), TIC (b), and ESI mass and UV spectra of peak 3 (c) and the authentic AB-CHMINACA (d) are shown. TIC (e), and EI mass spectra of peaks 3 (f) and the authentic AB-CHMINACA (g) obtained by the GC–MS analysis are also shown

Mentions: We detected an unknown peak 3 together with seven peaks of five known synthetic cannabinoids (AB-CHMINACA, 5-fluoro-AMB, FUB-PB-22, AM-2201 indazole analog and NNEI indazole analog), a known cathinone derivative DL-4662, and 8-quinolinol in the LC–MS and GC–MS chromatograms for product C (Fig. 5a, b, e). In the LC–MS and GC–MS analysis, the unknown peak 3 showed a protonated molecular ion signal at m/z 357 [M + H+] (Fig. 5c) and a molecular ion signal at m/z 356 [M+] (Fig. 5f). The accurate mass spectrum obtained by LC–QTOF–MS gave an ion signal at m/z 357.2282, suggesting that the protonated molecular formula of compound 3 was C20H29N4O2 (calcd. 357.2291). The presumed molecular formula of compound 3 (C20H28N4O2: 356) was thus the same as that of AB-CHMINACA (Fig. 1b). However, the LC–MS and GC–MS spectra patterns, in addition to each retention time, were different (Fig. 5c, d, f, g).Fig. 5


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 C. The LC–UV-PDA chromatogram (a), TIC (b), and ESI mass and UV spectra of peak 3 (c) and the authentic AB-CHMINACA (d) are shown. TIC (e), and EI mass spectra of peaks 3 (f) and the authentic AB-CHMINACA (g) obtained by the GC–MS analysis are also shown
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Fig5: LC–MS and GC–MS analyses of product C. The LC–UV-PDA chromatogram (a), TIC (b), and ESI mass and UV spectra of peak 3 (c) and the authentic AB-CHMINACA (d) are shown. TIC (e), and EI mass spectra of peaks 3 (f) and the authentic AB-CHMINACA (g) obtained by the GC–MS analysis are also shown
Mentions: We detected an unknown peak 3 together with seven peaks of five known synthetic cannabinoids (AB-CHMINACA, 5-fluoro-AMB, FUB-PB-22, AM-2201 indazole analog and NNEI indazole analog), a known cathinone derivative DL-4662, and 8-quinolinol in the LC–MS and GC–MS chromatograms for product C (Fig. 5a, b, e). In the LC–MS and GC–MS analysis, the unknown peak 3 showed a protonated molecular ion signal at m/z 357 [M + H+] (Fig. 5c) and a molecular ion signal at m/z 356 [M+] (Fig. 5f). The accurate mass spectrum obtained by LC–QTOF–MS gave an ion signal at m/z 357.2282, suggesting that the protonated molecular formula of compound 3 was C20H29N4O2 (calcd. 357.2291). The presumed molecular formula of compound 3 (C20H28N4O2: 356) was thus the same as that of AB-CHMINACA (Fig. 1b). However, the LC–MS and GC–MS spectra patterns, in addition to each retention time, were different (Fig. 5c, d, f, g).Fig. 5

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.