A new pyrazole-carboxamide type synthetic cannabinoid AB-CHFUPYCA [N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxamide] identified in illegal products

@article{Uchiyama2015ANP,
  title={A new pyrazole-carboxamide type synthetic cannabinoid AB-CHFUPYCA [N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxamide] identified in illegal products},
  author={Nahoko Uchiyama and Kazuhiro Asakawa and Ruri Kikura-Hanajiri and Taizou Tsutsumi and Takashi Hakamatsuka},
  journal={Forensic Toxicology},
  year={2015},
  volume={33},
  pages={367-373}
}
A new pyrazole-carboxamide type synthetic cannabinoid, AB-CHFUPYCA (1), was detected in illegal herbal products by our ongoing survey in Japan. The structure of 1 was identified by gas chromatography–mass spectrometry (GC–MS), liquid chromatography–mass spectrometry (LC–MS), liquid chromatography–high-resolution-mass spectrometry (LC–HR-MS) and nuclear magnetic resonance (NMR) analyses. Compound 1 showed a molecular weight of 400, and accurate mass measurement using LC–HR-MS revealed its… 

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.

Comprehensive analytical characteristics of N-(adamantan-1-yl)-1- (cyclohexylmethyl)-1H-indazole-3-carboxamide (ACHMINACA)

Purpose The aim of this study was to clarify the most essential analytical features of N -(adamantan-1-yl)-1-(cyclohexylmethyl)-1 H -indazole-3-carboxamide (one of the newest cannabimimetics called

In vitro metabolism of the synthetic cannabinoid 3,5-AB-CHMFUPPYCA and its 5,3-regioisomer and investigation of their thermal stability.

TLDR
Biotransformation to monohydroxylated metabolites of high abundance confirmed that these species might serve as suitable targets for urine analysis and the stability of both isomers was assessed under smoking conditions.

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.

TLDR
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.

Analytical differentiation of quinolinyl- and isoquinolinyl-substituted 1-(5-fluoropentyl)-1H-indole-3-carboxylates: 5F-PB-22 and its ten isomers

TLDR
This is the first report on mass spectrometric differentiation of 5F-PB-22 and its ten isomers and the analytical properties of these molecules and methods of differentiation are reported.

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.

TLDR
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.

The 2-alkyl-2H-indazole regioisomers of synthetic cannabinoids AB-CHMINACA, AB-FUBINACA, AB-PINACA, and 5F-AB-PINACA are possible manufacturing impurities with cannabimimetic activities

Indazole-derived synthetic cannabinoids (SCs) featuring an alkyl substituent at the 1-position and l-valinamide at the 3-carboxamide position (e.g., AB-CHMINACA) have been identified by forensic

References

SHOWING 1-10 OF 26 REFERENCES

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

Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products

Two new types of synthetic cannabinoids, an AM-2201 benzimidazole analog (FUBIMINA, 1) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM, 2), and three newly emerged

Identification of a cannabimimetic indole as a designer drug in a herbal product

A cannabimimetic indole has been identified as a new adulterant in a herbal product being sold illegally in Japan for its expected narcotic effect. Liquid chromatography-mass spectrometry and gas

A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N–OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products

Six new psychoactive substances were identified together with two other substances (compounds 1–8) in illegal products by our ongoing survey in Japan between January and July 2014. A new synthetic

Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products

We identified two new-type cannabimimetic quinolinyl carboxylates, quinolin-8-yl 1-pentyl-(1H-indole)-3-carboxylate (QUPIC, 1) and quinolin-8-yl 1-(cyclohexylmethyl)-1H-indole-3-carboxylate (QUCHIC,

Identification of a cannabinoid analog as a new type of designer drug in a herbal product.

A new type of designer drug, a cannabinoid analog (1), was found in a herbal product distributed on the illegal drug market in Japan in expectation of its narcotic effect. The structure of 1 was

Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists.

TLDR
The iodinated nature of this compound offers additional utility as a gamma-enriching SPECT (single photon emission computed tomography) ligand that may be useful in characterizing brain CB1 receptor binding in vivo.