Identification and quantitation of JWH-213, a cannabimimetic indole, as a designer drug in a herbal product

Abstract

In our survey of designer drugs in the Japanese market, a cannabimimetic indole was identified as a new active compound in a herbal product. The structure of this compound was elucidated by liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS), gas chromatography-mass spectrometry (GC-MS), high-resolution MS, and nuclear magnetic resonance (NMR) analyses. The compound was finally identified as (4-ethyl-1-naphthalenyl)(2-methyl-1-pentyl-1H-indol-3-yl)methanone (JWH-213), an indole-based cannabinoid receptor ligand. To our knowledge, this is the first finding of JWH-213 as a designer drug in a herbal product. The quantitative LC-PDA analysis showed that the JWH-213 content in the product was 252 mg/pack.Keywords (4-Ethyl-1-naphthalenyl)(2-methyl-1-pentyl-1H-indol-3-yl)methanone Á JWH-213 Á Designer drug Á Synthetic cannabinoid Á Drug of abuse

The Synthesis and Pharmacological Evaluation of Adamantane-Derived Indoles: Cannabimimetic Drugs of Abuse

“…Dozens of indole cannabinoids have been identified as components of Spice-like products from around the world, and in some cases the structures were previously unprecedented in the scientific literature. − In 2010, adamantan-1-yl(1-pentyl-1 H -indol-3-yl)methanone ( 5 , AB-001) was identified in products originating from Ireland, and subsequently reported to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) via the Early Warning System (EWS) . AB-001 was contemporaneously identified in bulk powders seized by the Hungary Customs and Finance Guard, and spectroscopic characterization and human metabolites were reported, although no synthetic details or pharmacological evaluation of this compound exist in the scientific literature. ,, In 2012, N -(adamtan-1-yl)-1-pentyl-1 H -indole-3-carboxamide ( 6 , SDB-001), was detected in products obtained by the National Institute of Health Sciences in Japan and, like AB-001, no synthetic preparation or pharmacological assessment of this compound has been published to date. , …”

Direct analysis in real time—Mass spectrometry (DART‐MS) in forensic and security applications

“…Areas of interest for the forensic drug applications of DART have included screening for THC (tetrahydrocannabinol) or its derivatives, synthetic cannabinoids, and cannabimimetics (Blackledge, ; Musah et al, ,; Takahashi et al, ; Duvivier et al, ; Jacobs & Steiner, ; Lesiak et al, ); detecting adulterations and contaminants in drugs (Fernández et al, ; Newton et al, ,; Nyadong et al, ; Chernetsova et al, ; Samms et al, ; Zhou et al, ; Vaclavik, Krynitsky, & Rader, ); determining the nature or amount of the active ingredient in various known drugs or unknown pharmaceutical samples (Cody, Laramee, & Durst, ; Ropero‐Miller et al, ; Howlett & Steiner, ; Likar et al, ; Lesiak et al, , ; Easter & Steiner, ; Musah et al, ; Kuki et al, ); identifying synthetic precursors to drugs of abuse (Steiner, ); and detecting drug residues on surfaces, in fingerprints, or in liquid matrices (Cody, Laramee, & Durst, ; Blackledge, ; Bennett & Steiner, ; Grange & Sovocool, ; Lim et al, ).…”