Identification and quantitation of two new naphthoylindole drugs-of-abuse, (1-(5-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone (AM-2202) and (1-(4-pentenyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone, with other synthetic cannabinoids in unregulated “herbal” products circulated in the Tokyo area

Nakajima, Jun; Takahashi, Misako; Seto, Takako; Yoshida, Masao; Kanai, Chieko; Suzuki, Jin; Hamano, Tomoko

doi:10.1007/s11419-011-0130-5

Cited by 53 publications

(30 citation statements)

References 13 publications

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“…This is a typical fragmentation observed for naphthoyl alkylindole cannabinoids. [17] Similar observations were made for ESI-MS/MS data (Figure 3 A2) comparing JWH-122 [12] and JWH-122-pentenyl (see fragment ions 141, 144, 169, 212 vs 214 amu). An ion containing the structural information of the whole N-alkyl-chain (298 amu) is common in JWH-122-pentenyl and [1-(4-pentenyl)-1H-indol-3-yl](naphthalen-1-yl) methanone.…”

Section: Jwh-122-pentenylsupporting

confidence: 74%

Identification and quantification of synthetic cannabinoids in ‘spice‐like’ herbal mixtures: A snapshot of the German situation in the autumn of 2012

Langer

Lindigkeit

Schiebel

et al. 2013

Drug Testing and Analysis

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Synthetic compounds mimicking cannabis-like effects are a recent trend. Currently, these so-called synthetic cannabinoids are the largest and fastest growing class of newly appearing designer drugs. Many national authorities are continuously adapting their regulations to keep pace with the permanently changing variety of compounds. We have analyzed eight herbal smoking blends containing synthetic cannabinoids. Altogether, nine compounds could be identified, namely AM-2201, AM-2201-pMe (MAM-2201), AM-1220, AM-1220-azepane, UR-144, XLR-11, JWH-122-pentenyl, AM-2232, and STS-135. Newly appearing compounds were isolated by column chromatography and their structures elucidated by 1D- and 2D-nuclear magnetic resonance (NMR) experiments. In addition, the compounds were investigated by electron ionization-mass spectrometry (EI-MS) and electrospray ionization-tandem mass spectrometry (ESI-MS/MS) to complete the physicochemical dataset. Based on the purified compounds a universal gas chromatography-mass spectrometry (GC-MS) method was developed for the identification and quantification of these compounds in commercial smoking blends. By applying this method, up to five different compounds could be found in such products showing total concentrations from 72 to 303 mg/g smoking blend while individual compounds ranged from 0.4 to 303 mg/g. (1)H NMR spectra of the chiral compounds AM-1220 and its azepane-isomer recorded in the presence of 1 equivalent of (R)-(+)-α-methoxy-α-trifluoromethylphenylacetic acid (MTPA, Mosher's acid) showed them to be racemic mixtures.

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Section: Jwh-122-pentenylsupporting

confidence: 74%

Identification and quantification of synthetic cannabinoids in ‘spice‐like’ herbal mixtures: A snapshot of the German situation in the autumn of 2012

Langer

Lindigkeit

Schiebel

et al. 2013

Drug Testing and Analysis

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“…As some cannabis users consume ‘herbal mixtures’ as a legal alternative to cannabis products in order to circumvent drug testing, there is an urgent need for comprehensive methods suitable for the analysis of synthetic cannabinoids in human specimens, particularly in the fields of clinical and forensic toxicology. However, considering the enormous diversity of synthetic cannabinoids which have already been identified in ‘Spice’ products, the timely development of such methods is challenging. The development of selective immunochemical‐based detection methods is difficult due to the considerable structural variety of this group of substances.…”

Section: Introductionmentioning

confidence: 99%

Analysis of 30 synthetic cannabinoids in serum by liquid chromatography‐electrospray ionization tandem mass spectrometry after liquid‐liquid extraction

2012

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The analysis of synthetic cannabinoids in human matrices is of particular importance in the fields of forensic and clinical toxicology since cannabis users partly shift to the consumption of 'herbal mixtures' as a legal alternative to cannabis products in order to circumvent drug testing. However, comprehensive methods covering the majority of synthetic cannabinoids already identified on the drug market are still lacking. In this article, we present a fully validated method for the analysis of 30 synthetic cannabinoids in human serum utilizing liquid-liquid extraction and liquid chromatography-electrospray ionization tandem mass spectrometry. The method proved to be suitable for the quantification of 27 substances. The limits of detection ranged from 0.01 to 2.0 ng/mL, whereas the lower limits of quantification were in the range from 0.1 to 2.0 ng/mL. The presented method was successfully applied to 833 authentic serum samples during routine analysis between August 2011 and January 2012. A total of 227 (27%) samples was tested positive for at least one of the following synthetic cannabinoids: JWH-018, JWH-019, JWH-073, JWH-081, JWH-122, JWH-200, JWH-203, JWH-210, JWH-307, AM-2201 and RCS-4. The most prevalent compounds in positive samples were JWH-210 (80%), JWH-122 (63%) as well as AM-2201 (29%). Median serum concentrations were all below 1.0 ng/mL. These findings demonstrate a significant shift of the market of synthetic cannabinoids towards substances featuring a higher CB(1) binding affinity and clearly emphasize that the analysis of synthetic cannabinoids in serum or blood samples requires highly sensitive analytical methods covering a wide spectrum of substances.

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“…For identification of novel cannabinoids from the naphthoylindole family, liquid chromatography-quadrupole-time-of-flight-mass spectrometry (LC-QTOF-MS) was proposed by Sekuła et al [9]; based on the mass spectra of 12 representatives, the authors proposed the fragmentation route and predicted the spectra of 35 other substances. A number of novel ingredients of herbal high products available on the Japanese market have been disclosed by combination techniques of time-of-flight (TOF)-MS and nuclear magnetic resonance (NMR) analyses [10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Analysis of the prevalence and coexistence of synthetic cannabinoids in “herbal high” products in Poland

Zuba

Byrska

2012

Forensic Toxicol

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Herbal highs'' are a group of products marketed in recent years as legal substitutes for marijuana. This article presents the results of examinations performed on samples seized in ''head shops'' and from individuals during a 3.5-year period, between mid-2008 and the end of 2011 in Poland. Of over 2000 samples delivered for analysis, 420 preparations were selected for this study. Gas chromatography-mass spectrometry and liquid chromatography-quadrupole-time-of-flight-mass spectrometry were used for identification of psychoactive components, and high-performance liquid chromatography was used for their quantitation. The most common ingredients of herbal highs were: JWH-081 (144 products), JWH-018 (103), RCS-4 (92), JWH-073 (89), JWH-250 (75), JWH-122 (69), cannabicyclohexanol (55), and JWH-210 (38). Over 50 % of the products contained two or more active ingredients; 136 products (32.4 %) contained two; 56 products (13.3 %) contained three; and 22 (5.2 %) contained more than three. Common combinations of ingredients were investigated by the graph method; substances coexisted mainly with those introduced into the drug market in a similar period of time. The most common dual combinations were JWH-081 ? RCS-4 (18 products), JWH-073 ? JWH-250 (16), and JWH-081 ? JWH-250 (12). JWH-081 was blended with almost all detected synthetic cannabinoids. The main risks of the use of these substances were due to ignorance of great variation in the content and composition of synthetic cannabinoids even if the products had identical labels. This inconsistency could cause serious health damage to users, while ignorance of the fact that more than one third of the products being sold at head shops contain illicit compound(s) could result in unexpected arrest.

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Cited by 53 publications

References 13 publications

Identification and quantification of synthetic cannabinoids in ‘spice‐like’ herbal mixtures: A snapshot of the German situation in the autumn of 2012

Identification and quantification of synthetic cannabinoids in ‘spice‐like’ herbal mixtures: A snapshot of the German situation in the autumn of 2012

Analysis of 30 synthetic cannabinoids in serum by liquid chromatography‐electrospray ionization tandem mass spectrometry after liquid‐liquid extraction

Analysis of the prevalence and coexistence of synthetic cannabinoids in “herbal high” products in Poland

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