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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 D. The LC–UV-PDA chromatogram (a), TIC (b) and an extracted-ion chromatogram at m/z 358 (c) are shown, along with the ESI mass and UV spectra of peaks 4 (d), 5 (f), 6 (h), the authentic NNEI indazole analog (e) and the authentic 2-methylpropyl N-(naphthalen-1-yl) carbamate (g). TIC (i) and EI mass spectra of peaks 4 (j), 5 (l), 6 (n), the authentic NNEI indazole analog (k) and the authentic 2-methylpropyl N-(naphthalen-1-yl) carbamate (m) obtained by the GC–MS analysis are also indicated
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Fig7: LC–MS and GC–MS analyses of product D. The LC–UV-PDA chromatogram (a), TIC (b) and an extracted-ion chromatogram at m/z 358 (c) are shown, along with the ESI mass and UV spectra of peaks 4 (d), 5 (f), 6 (h), the authentic NNEI indazole analog (e) and the authentic 2-methylpropyl N-(naphthalen-1-yl) carbamate (g). TIC (i) and EI mass spectra of peaks 4 (j), 5 (l), 6 (n), the authentic NNEI indazole analog (k) and the authentic 2-methylpropyl N-(naphthalen-1-yl) carbamate (m) obtained by the GC–MS analysis are also indicated

Mentions: Three unknown peaks 4, 5, and 6 were detected along with a synthetic cannabinoid NNEI indazole analog in the LC–MS and GC–MS chromatograms for product D (Figs. 7a, b, i, 1b). In the LC–MS and GC–MS analysis, the unknown peak 4 showed a protonated molecular ion signal at m/z 358 [M + H+] (Fig. 7c, d) and a molecular ion signal at m/z 357 [M+] (Fig. 7j). The accurate mass spectrum obtained by LC–QTOF–MS gave an ion signal at m/z 358.1916, suggesting that the protonated molecular formula of compound 4 was C23H24N3O (calcd. 358.1919). Hence, the presumed molecular formula of compound 4 (C23H23N3O: 357) was the same as that of NNEI indazole analog. However, the GC–MS and LC–MS spectra patterns and each retention time of both compounds were different (Fig. 7d, e, j, k).Fig. 7


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 D. The LC–UV-PDA chromatogram (a), TIC (b) and an extracted-ion chromatogram at m/z 358 (c) are shown, along with the ESI mass and UV spectra of peaks 4 (d), 5 (f), 6 (h), the authentic NNEI indazole analog (e) and the authentic 2-methylpropyl N-(naphthalen-1-yl) carbamate (g). TIC (i) and EI mass spectra of peaks 4 (j), 5 (l), 6 (n), the authentic NNEI indazole analog (k) and the authentic 2-methylpropyl N-(naphthalen-1-yl) carbamate (m) obtained by the GC–MS analysis are also indicated
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Related In: Results  -  Collection

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Fig7: LC–MS and GC–MS analyses of product D. The LC–UV-PDA chromatogram (a), TIC (b) and an extracted-ion chromatogram at m/z 358 (c) are shown, along with the ESI mass and UV spectra of peaks 4 (d), 5 (f), 6 (h), the authentic NNEI indazole analog (e) and the authentic 2-methylpropyl N-(naphthalen-1-yl) carbamate (g). TIC (i) and EI mass spectra of peaks 4 (j), 5 (l), 6 (n), the authentic NNEI indazole analog (k) and the authentic 2-methylpropyl N-(naphthalen-1-yl) carbamate (m) obtained by the GC–MS analysis are also indicated
Mentions: Three unknown peaks 4, 5, and 6 were detected along with a synthetic cannabinoid NNEI indazole analog in the LC–MS and GC–MS chromatograms for product D (Figs. 7a, b, i, 1b). In the LC–MS and GC–MS analysis, the unknown peak 4 showed a protonated molecular ion signal at m/z 358 [M + H+] (Fig. 7c, d) and a molecular ion signal at m/z 357 [M+] (Fig. 7j). The accurate mass spectrum obtained by LC–QTOF–MS gave an ion signal at m/z 358.1916, suggesting that the protonated molecular formula of compound 4 was C23H24N3O (calcd. 358.1919). Hence, the presumed molecular formula of compound 4 (C23H23N3O: 357) was the same as that of NNEI indazole analog. However, the GC–MS and LC–MS spectra patterns and each retention time of both compounds were different (Fig. 7d, e, j, k).Fig. 7

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.