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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 incredible natural abundance double-quantum transfer experiment (INADEQUATE), HMBC, selected NOE correlations (a) and 1H-15N HMBC correlations (b) for compound 3 (AB-CHMINACA 2H-indazole analog)
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Fig6: Results of incredible natural abundance double-quantum transfer experiment (INADEQUATE), HMBC, selected NOE correlations (a) and 1H-15N HMBC correlations (b) for compound 3 (AB-CHMINACA 2H-indazole analog)

Mentions: The observed 1H and 13C NMR spectra (Table 2), HH COSY, HMQC, HMBC and 15N HMBC correlations for compound 3 indicated the presence of N-cyclohexylmethyl-indazole and N-(1-amino-3-methyl-1-oxobutan-2-yl)-carboxamide moieties (Fig. 6a, b). Additionally, 2D-INADEQUATE correlation revealed that the cyclohexylmethyl-indazole moiety is connected at the 3′-position of the indazole to the carboxamide (C-1″′). Nevertheless, the 13C NMR chemical shifts of compound 3 were significantly different at the C-3′ (δc 129.1), C-7′ (δc 117.4) and C-7′a (δc 146.4) positions from those of AB-CHMINACA [C-3′ (δc 136.4), C-7′ (δc 110.6) and C-7′a (δc 141.2) as shown in Table 2.Table 2


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 incredible natural abundance double-quantum transfer experiment (INADEQUATE), HMBC, selected NOE correlations (a) and 1H-15N HMBC correlations (b) for compound 3 (AB-CHMINACA 2H-indazole analog)
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4525202&req=5

Fig6: Results of incredible natural abundance double-quantum transfer experiment (INADEQUATE), HMBC, selected NOE correlations (a) and 1H-15N HMBC correlations (b) for compound 3 (AB-CHMINACA 2H-indazole analog)
Mentions: The observed 1H and 13C NMR spectra (Table 2), HH COSY, HMQC, HMBC and 15N HMBC correlations for compound 3 indicated the presence of N-cyclohexylmethyl-indazole and N-(1-amino-3-methyl-1-oxobutan-2-yl)-carboxamide moieties (Fig. 6a, b). Additionally, 2D-INADEQUATE correlation revealed that the cyclohexylmethyl-indazole moiety is connected at the 3′-position of the indazole to the carboxamide (C-1″′). Nevertheless, the 13C NMR chemical shifts of compound 3 were significantly different at the C-3′ (δc 129.1), C-7′ (δc 117.4) and C-7′a (δc 146.4) positions from those of AB-CHMINACA [C-3′ (δc 136.4), C-7′ (δc 110.6) and C-7′a (δc 141.2) as shown in Table 2.Table 2

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.