Identification and quantitation of two benzoylindoles AM-694 and (4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone, and three cannabimimetic naphthoylindoles JWH-210, JWH-122, and JWH-019 as adulterants in illegal products obtained via the Internet

Abstract

During our careful surveillance of unregulated drugs, we found five new compounds used as adulterants in herbal and drug-like products obtained via the Internet. These compounds were identified by liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, accurate mass spectrometry, and nuclear magnetic resonance spectroscopy. The first compound identified was a benzoylindole AM-694, which is 1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone (1). The second compound was (4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone (2), which was also classified as a benzoylindole. The three other compounds were identified as naphthoylindoles JWH-210 (4-ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone; 3), JWH-122 (4-methylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone; 4), and JWH-019 (1-hexyl-3-(naphthalen-1-oyl)-indole; 5). All compounds except compound 2 had been reported to be cannabinoid receptor agonists. For quantitation of the five compounds and previously reported compounds, each product was extracted with methanol under ultrasonication to prepare a test solution for analysis by liquid chromatography with ultraviolet detection. Each compound detected in 43 commercial products showed large variation in content ranging from 4.0 to 359 mg per pack.

Analytical characterization of some synthetic cannabinoids, derivatives of indole-3-carboxylic acid

“…Beginning in October 2012, new type of synthetic cannabinoids, a structural modification of compounds from 3-naphthoylindole series [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] has begun to be seized by police regularly, on the territory of Russia and Belarus.…”

Identification and analytical properties of new synthetic cannabimimetics bearing 2,2,3,3-tetramethylcyclopropanecarbonyl moiety

“…The processes described earlier are accompanied by a McLafferty rearrangement of compounds 9-12, which leads to additional intense peak with m/z [MÀC 6 H 10 ] + (Fig. 6).…”

“…The (7) 118.00 (4) 118.74 (5) 122.56 (2) 122.95 (6) 139.30 (7') 221.66 (1a ) resolution was higher than 20,000, which enabled us to determine exact masses of ions formed from a molecule. Based on these data, the chemical formulas of unknown substances were ascertained by means of MassHunter Qualitative Analysis B.05.00 software.…”

“…Numerous occurrences of these 'designer drugs' were detected in many countries including Russia and Belarus. These compounds are basically indole derivatives such as 3-naphthoylindoles, 3-phenylacetylindoles, 3-benzoylindoles and 3-adamantoylindoles [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19].…”

“…We have identified that since the summer 2011 most popular compounds, from the class, were: 'TMCP-018' (2), parent 3-(2,2,3,3-tetramethylcyclopropanecarbonyl)indole (1) and the other derivatives thereof (3)(4)(5)(6)(7), as well as {N-[3-(2-methoxyethyl)-4,5-dimethylthiazol-2(3H)-ylidene]-2,2,3,3-tetramethylcyclopropanecarboxamide} (8) ('A-836,339'), a thiazolidene analog of the compounds under discussion (Fig. 1).…”