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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 correlation spectroscopy (HH COSY), heteronuclear multiple-bond correlation (HMBC), selected nuclear Overhauser effect (NOE) correlations (a), 1H-15N HMBC correlations (b) and deuterium-induced isotope shift of NH protons for the 13C nuclear magnetic resonance (NMR) signals of compound 2 (FDU-NNEI) in CD3OD (c)
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Fig4: Results of HH correlation spectroscopy (HH COSY), heteronuclear multiple-bond correlation (HMBC), selected nuclear Overhauser effect (NOE) correlations (a), 1H-15N HMBC correlations (b) and deuterium-induced isotope shift of NH protons for the 13C nuclear magnetic resonance (NMR) signals of compound 2 (FDU-NNEI) in CD3OD (c)

Mentions: The structure of compound 2 was elucidated by NMR analysis (Fig. 4; Table 1). The analyses by 1H and 13C NMR, HH COSY, HMQC, HMBC, 15N HMBC and 1D-NOE spectra of compound 2 revealed the presence of a 1-(4-fluorobenzyl)-1H-indole (positions 1′ to 7′a and positions 1″ to 7″) and a N-(naphthalen-1-yl)-carboxamide moieties (position 1 and positions 1″′ to 8″′a) as shown in Fig. 4a, b. However, no HBMC correlation between the two moieties was observed. We, therefore, measured the deuterium isotope effect on the NH amide proton on the 13C chemical shift to determine the connection between the two moieties.Fig. 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 correlation spectroscopy (HH COSY), heteronuclear multiple-bond correlation (HMBC), selected nuclear Overhauser effect (NOE) correlations (a), 1H-15N HMBC correlations (b) and deuterium-induced isotope shift of NH protons for the 13C nuclear magnetic resonance (NMR) signals of compound 2 (FDU-NNEI) in CD3OD (c)
© Copyright Policy
Related In: Results  -  Collection

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

Fig4: Results of HH correlation spectroscopy (HH COSY), heteronuclear multiple-bond correlation (HMBC), selected nuclear Overhauser effect (NOE) correlations (a), 1H-15N HMBC correlations (b) and deuterium-induced isotope shift of NH protons for the 13C nuclear magnetic resonance (NMR) signals of compound 2 (FDU-NNEI) in CD3OD (c)
Mentions: The structure of compound 2 was elucidated by NMR analysis (Fig. 4; Table 1). The analyses by 1H and 13C NMR, HH COSY, HMQC, HMBC, 15N HMBC and 1D-NOE spectra of compound 2 revealed the presence of a 1-(4-fluorobenzyl)-1H-indole (positions 1′ to 7′a and positions 1″ to 7″) and a N-(naphthalen-1-yl)-carboxamide moieties (position 1 and positions 1″′ to 8″′a) as shown in Fig. 4a, b. However, no HBMC correlation between the two moieties was observed. We, therefore, measured the deuterium isotope effect on the NH amide proton on the 13C chemical shift to determine the connection between the two moieties.Fig. 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.