1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles

Identification of a Novel Cannabimimetic Phenylacetylindole, Cannabipiperidiethanone, as a Designer Drug in a Herbal Product and Its Affinity for Cannabinoid CB1 and CB2 Receptors

“…However, 1 has a mixed structure of known cannabimimetic compounds, JWH-250 and AM-2233 (a racemic compound), and both compounds have been reported to possess affinity to cannabinoid CB 1 and CB 2 receptors (JWH-250: K i ϭ11, 33 nM, respectively; AM-2233: K i ϭ2.8, 2.9 nM, respectively). 13,14) Therefore, we thought that 1 might have some cannabinoid receptor-binding activity. Subsequently, the binding affinity of 1 to cannabinoid CB 1 and CB 2 receptors was determined in competition with agonist [ Table 2.…”

“…The NMR spectra were obtained on ECA-600 spectrometers (JEOL). Assignments were made via 1 H-NMR, 13 C-NMR, heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), double quantum filtered correlation spectroscopy (DQF-COSY), one-dimensional total correlation spectroscopy (1D-TOCSY), and rotating frame nuclear Overhauser effect (ROE) spectra. For isolation of the compound, recycling preparative HPLC (Japan Analytical Industry, Tokyo, Japan) was used with a JAIGEL-GS310 column (500 mmϫ20 mm i.d.…”

Gas and liquid chromatography–mass spectrometry studies on the metabolism of the synthetic phenylacetylindole cannabimimetic JWH-250, the psychoactive component of smoking mixtures

“…JWH-250 (1-pentyl-3-(2-methoxyphenylacetyl)indole) was synthesised by Huffman et al [6] and first identified in May 2009 by the German Federal Criminal Police [2,7] as an ingredient of herbal smoking mixtures. This match was confirmed in a series of publications [8][9][10].…”

Determination of 22 synthetic cannabinoids in human hair by liquid chromatography–tandem mass spectrometry

“…This is because they have been adulterated with synthetic cannabinoid receptor agonists [1]. Most of the synthetic cannabinoids identified in herbal mixtures, for instance the aminoalkylindole JWH-018, feature high binding affinity to the cannabinoid receptor type 1 [2][3][4][5], thus inducing similar effects as 9 -tetrahydrocannabinol (THC).…”