1 H-15 N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F-MDMB-P7AICA.

  title={1 H-15 N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F-MDMB-P7AICA.},
  author={Bruno A Martek and Mateja Mihela{\vc} and Martin Gazvoda and Miha Virant and Damijana Urankar and Marko Krivec and T Gostic and B. Němec and Bojana Ko{\vs}trun and Mojca Jane{\vz}i{\vc} and Sonja Klemenc and Janez Ko{\vs}mrlj},
  journal={Drug testing and analysis},
  volume={11 4},
The high frequency of the synthetic cannabinoid receptor agonists (SCRAs) emergence renders this group of new psychoactive compounds particularly demanding in terms of detection, identification, and responding. Without the available reference material, one of the specific problems is differentiation and structure elucidation of constitutional isomers. Herein, we report a simple and efficient flow chart diagram applicable for a rapid nuclear magnetic resonance (NMR) identification and… Expand
4 Citations
7-Azaindole-3-carboxylic acid and its Pt(II) and Pd(II) complexes: Crystal structure of the ligand, vibrational spectra, DFT calculations and in vitro antiproliferative activity
Abstract The crystal and molecular structure of 7-azaindole-3-carboxylic acid (7AI3CAH2) has been determined by a single-crystal X-ray diffraction analysis (space group Pca21, a = 14.247(3), b =Expand
Can A Recently Developed Pig Model Be Used for In Vivo Metabolism Studies of 7-Azaindole Derived Synthetic Cannabinoids? A Study Using 5F-MDMB-P7AICA.
The used pig model seems to be a suitable alternative for in vivo metabolism studies of 7-azaindole-derived SC, and the main metabolites recommended in previous studies as urinary targets were confirmed by using pig urine. Expand
Mass-Spectrometry-Based Identification of Synthetic Drug Isomers Using Infrared Ion Spectroscopy
It is demonstrated the ability of IRIS to distinguish closely related NPS using three isomers of fluoroamphetamine and two ring-isomers of both MDA and MDMA, and computationally predicted infrared spectra are shown to correspond with experimental spectra. Expand
Adding more "Spice" to the pot; a review of the chemistry and pharmacology of newly emerging heterocyclic synthetic cannabinoid receptor agonists.
This review highlights the importance of continued research in the field of SCRA chemistry and pharmacology, as recreational SCRA use remains a global public health issue and represents a serious control challenge for law enforcement agencies. Expand


Synthesis and pharmacology of new psychoactive substance 5F-CUMYL-P7AICA, a scaffold- hopping analog of synthetic cannabinoid receptor agonists 5F-CUMYL-PICA and 5F-CUMYL-PINACA.
Five scaffold-hopping SCRAs, including 5F-CUMYL-P7AICA, were synthesized and characterized and found to exert potent cannabimimetic effects in mice, inducing hypothermia through a CB1 -dependent mechanism. Expand
Identification and analytical characterization of six synthetic cannabinoids NNL-3, 5F-NPB-22-7N, 5F-AKB-48-7N, 5F-EDMB-PINACA, EMB-FUBINACA, and EG-018.
The analytical characterization of these six synthetic cannabinoids was described, so as to assist forensic laboratories in identifying these compounds or other substances with similar structure in their case work. Expand
Structural characterization of the new synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA.
Five new synthetic cannabinoids containing a cumyl moiety as a linked group were identified and the article contains all analytical data for a proper identification and differentiation of the five cumyl compounds. Expand
Metabolic fate of the new synthetic cannabinoid 7'N-5F-ADB in rat, human, and pooled human S9 studied by means of hyphenated high-resolution mass spectrometry.
7'N-5F-ABD was extensively metabolized in rat and human with minor species differences observed and a differentiation of both compounds was possible due to different retention times and fragmentation patterns. Expand
Identification and analytical characterization of four synthetic cannabinoids ADB-BICA, NNL-1, NNL-2, and PPA(N)-2201.
The analytical properties and structure elucidation of four cannabimimetic derivatives in seized material are reported on, making this the first report on these compounds. Expand
In vitro metabolism of the synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA.
Several constitutional isomers containing either an indazole or azaindole core structure were detected, which should be differentiated by retention time rather than by their mass spectra alone and should not be used as marker for the intake of a particular parent compound. Expand
Pharmacological evaluation of new constituents of “Spice”: synthetic cannabinoids based on indole, indazole, benzimidazole and carbazole scaffolds
All compounds showed high CB receptor selectivity, mostly interacting with both subtypes, CB1 and CB2, and will be useful to assess the compounds’ toxicological risks and to guide legislation. Expand
1H and 13C NMR studies of 7-azaindole and related compounds
The 1H and 13C chemical shifts, proton-proton coupling constants, and one-bond carbon-hydrogen coupling constants have been obtained for 7-azaindole, 1-methyl-7-azaindole, their corresponding methylExpand
The synthesis and characterization of the 'research chemical' N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxamide (3,5-AB-CHMFUPPYCA) and differentiation from its 5,3-regioisomer.
The pyrazole core indicates a bioisosteric replacement of an indazole ring that is frequently associated with synthetic cannabinoids of the PINACA, FUBINACA, and CHMINACA series and both isomers were synthesized using two specific routes which supported the correct identification of the 'research chemical' as 3,5-AB-CHMFUPPYCA. Expand
Metabolism and toxicological analysis of synthetic cannabinoids in biological fluids and tissues.
This comprehensive review describes the history of the appearance of the drugs in the United States, discusses the naming conventions emerging to designate new structures, and describes the most prominent new compounds linked to the adverse effects now associated with their use. Expand