Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group

@article{Shevyrin2015IdentificationAA,
  title={Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group},
  author={Vadim A. Shevyrin and Vladimir Melkozerov and Alexander Nevero and Oleg S. Eltsov and Yu. M. Shafran and Yuri Yu Morzherin and Albert T. Lebedev},
  journal={Analytical and Bioanalytical Chemistry},
  year={2015},
  volume={407},
  pages={6301-6315}
}
Illicit new psychoactive substances (NPS) are a serious threat to health throughout the world. Such NPS do not usually pass preliminary pharmacological trials. In 2014, we identified a series of five new synthetic cannabinoids with an indazole-3-carboxamide structure bearing an N-1-methoxycarbonylalkyl group. The compounds have very high cannabimimetic activity which has caused mass severe intoxication and deaths. The compounds were identified by means of gas chromatography–mass spectrometry… 
Identification of new synthetic cannabinoid analogue APINAC (adamantan-1-yl 1-pentyl-1H-indazole-3-carboxylate) with other synthetic cannabinoid MDMB(N)-Bz-F in illegal products
Two synthetic cannabinoid analogues were detected using high-performance liquid chromatography (HPLC)–diode array detector, and gas chromatography–time-of-flight-mass spectrometry during the
Identification of the Synthetic Cannabinoid 1-(4-cyanobutyl)-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide (CUMYL-4CN-BINACA) in Plant Material and Quantification in Post-Mortem Blood Samples.
  • Oya Yeter
  • Chemistry
    Journal of analytical toxicology
  • 2017
TLDR
An ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS-MS) method was developed to determine its presence in blood samples and has been validated in terms of linearity, selectivity, intra- and inter-assay accuracy and precision.
Identification of three cannabimimetic indazole and pyrazole derivatives, APINACA 2H-indazole analogue, AMPPPCA, and 5F-AMPPPCA.
TLDR
Analytical properties of three cannabimimetic indazole and pyrazole derivatives seized from a clandestine laboratory are reported, making this the first report on these compounds.
Elucidation of the Chemical Structure of a Gas Chromatographic Artifact of Synthetic Cannabinoid N-(1-Carbamoyl-2-Methylpropyl)-1-(Cyclohexylmethyl)-1H-Indazol-3Ccarboxamide by High-Resolution Mass Spectrometry
  • V. Shevyrin
  • Chemistry
    Journal of Analytical Chemistry
  • 2017
Synthetic cannabinoids are the most popular psychoactive compounds on the illegal market. In the gas chromatographic determination, some synthetic cannabinoids undergo chemical transformations
In vitro Phase I metabolism of indazole carboxamide synthetic cannabinoid MDMB-CHMINACA via human liver microsome incubation and high-resolution mass spectrometry.
TLDR
The authors propose that CHM-monohydroxylated metabolites specific to MDMB-CHMINACA are the most suitable candidates for implementation into bioanalytical assays to demonstrate consumption of this synthetic cannabinoid.
...
...

References

SHOWING 1-10 OF 27 REFERENCES
Identification of the cannabimimetic AM-1220 and its azepane isomer (N-methylazepan-3-yl)-3-(1-naphthoyl)indole in a research chemical and several herbal mixtures
Recently, a large number of synthetic cannabinoids have been identified in herbal mixtures. Moreover, an even higher number of cannabimimetic compounds are currently distributed as research chemicals
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
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
Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in
Two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA, 1) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA, 2), have been identified as designer
Qualitative analysis of seized synthetic cannabinoids and synthetic cathinones by gas chromatography triple quadrupole tandem mass spectrometry.
TLDR
In this study, the qualitative identification of 34 designer drugs were performed by gas chromatography-triple quadrupole-tandem mass spectrometry with two different ionization techniques only focusing on qualitative seized-drug analysis, not from the toxicological point of view.
Identification and quantitation of two cannabimimetic phenylacetylindoles JWH-251 and JWH-250, and four cannabimimetic naphthoylindoles JWH-081, JWH-015, JWH-200, and JWH-073 as designer drugs in illegal products
Six cannabimimetic indoles have been identified as adulterants in herbal or chemical products being sold illegally in Japan, with four of the compounds being new as adulterants to our knowledge. The
...
...