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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.


Results of HH COSY, HMBC, selected NOE correlations (a), 1H-15N HMBC correlations (b) and deuterium-induced isotope shift of NH protons for the 13C NMR signals of compound 4 (NNEI 2H-indazole analog) in CD3OD (c). HH COSY and HMBC correlations (d) and 1H-15N HMBC correlations (e) for compound 6 (isobutyl 1-pentyl-1H-indazole-3-carboxylate), are also shown
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Fig8: Results of HH COSY, HMBC, selected NOE correlations (a), 1H-15N HMBC correlations (b) and deuterium-induced isotope shift of NH protons for the 13C NMR signals of compound 4 (NNEI 2H-indazole analog) in CD3OD (c). HH COSY and HMBC correlations (d) and 1H-15N HMBC correlations (e) for compound 6 (isobutyl 1-pentyl-1H-indazole-3-carboxylate), are also shown

Mentions: The 1H and 13C NMR spectra (Table 4), HH COSY, HMQC, HMBC and 15N HMBC correlations of compound 4 suggested the presence of N-pentyl-indazole and N-(naphthalen-1-yl)carboxamide moieties (Fig. 8a, b). Therefore, the connectivity of the two moieties (positions 1 and 3′) was not observed. On the other hand, the 13C NMR chemical shifts of compound 4 at the C-3′ (δc 127.1), C-7′ (δc 119.0) and C-7′a (δc 147.3) positions were different from those of NNEI indazole analog [C-3′ (δc 137.3), C-7′ (δc 109.4), and C-7′a (δc 141.1)] (Table 4). Comparing the 15N NMR chemical shifts between the two compounds showed that the 15N chemical shifts at the N-1′ (δN −82.7) and N-2′ (δN −147.4) of the indazole moiety in compound 4 were different from those of the 1H-indazole moiety in NNEI indazole analog [N-1′ (δN −187.8) and N-2′ (δN −62.0)] (Table 3). However, their shifts of compound 4 were similar to those of 2-methyl-2H-indazole [N-1′ (δN −91.2) and N-2′ (δN −161.0)] (Table 3) [14]. Therefore, it was revealed that compound 4 has a 2-pentyl-2H-indazole moiety.Table 4


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)

Results of HH COSY, HMBC, selected NOE correlations (a), 1H-15N HMBC correlations (b) and deuterium-induced isotope shift of NH protons for the 13C NMR signals of compound 4 (NNEI 2H-indazole analog) in CD3OD (c). HH COSY and HMBC correlations (d) and 1H-15N HMBC correlations (e) for compound 6 (isobutyl 1-pentyl-1H-indazole-3-carboxylate), are also shown
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Related In: Results  -  Collection

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Fig8: Results of HH COSY, HMBC, selected NOE correlations (a), 1H-15N HMBC correlations (b) and deuterium-induced isotope shift of NH protons for the 13C NMR signals of compound 4 (NNEI 2H-indazole analog) in CD3OD (c). HH COSY and HMBC correlations (d) and 1H-15N HMBC correlations (e) for compound 6 (isobutyl 1-pentyl-1H-indazole-3-carboxylate), are also shown
Mentions: The 1H and 13C NMR spectra (Table 4), HH COSY, HMQC, HMBC and 15N HMBC correlations of compound 4 suggested the presence of N-pentyl-indazole and N-(naphthalen-1-yl)carboxamide moieties (Fig. 8a, b). Therefore, the connectivity of the two moieties (positions 1 and 3′) was not observed. On the other hand, the 13C NMR chemical shifts of compound 4 at the C-3′ (δc 127.1), C-7′ (δc 119.0) and C-7′a (δc 147.3) positions were different from those of NNEI indazole analog [C-3′ (δc 137.3), C-7′ (δc 109.4), and C-7′a (δc 141.1)] (Table 4). Comparing the 15N NMR chemical shifts between the two compounds showed that the 15N chemical shifts at the N-1′ (δN −82.7) and N-2′ (δN −147.4) of the indazole moiety in compound 4 were different from those of the 1H-indazole moiety in NNEI indazole analog [N-1′ (δN −187.8) and N-2′ (δN −62.0)] (Table 3). However, their shifts of compound 4 were similar to those of 2-methyl-2H-indazole [N-1′ (δN −91.2) and N-2′ (δN −161.0)] (Table 3) [14]. Therefore, it was revealed that compound 4 has a 2-pentyl-2H-indazole moiety.Table 4

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.