Identification of N,N-bis(1-pentylindol-3-yl-carboxy)naphthylamine (BiPICANA) found in an herbal blend product in the Tokyo metropolitan area and its cannabimimetic effects evaluated by in vitro [35S]GTPγS binding assays

@article{Nakajima2014IdentificationON,
  title={Identification of N,N-bis(1-pentylindol-3-yl-carboxy)naphthylamine (BiPICANA) found in an herbal blend product in the Tokyo metropolitan area and its cannabimimetic effects evaluated by in vitro [35S]GTP$\gamma$S binding assays},
  author={Jun’ichi Nakajima and Misako Takahashi and Nozomi Uemura and Takako Seto and Haruhiko Fukaya and Jin Suzuki and Masao Yoshida and Maiko Kusano and Hiroshi Nakayama and Kei Zaitsu and Akira Ishii and Takako Moriyasu and Dai Nakae},
  journal={Forensic Toxicology},
  year={2014},
  volume={33},
  pages={84-92}
}
During our careful survey of unregulated psychotropic drugs in June 2013 in the Tokyo metropolitan area, we found a new compound in a herbal product. It was identified as an analog of NNEI (MN-24) and differed in that its molecule possessed another N-pentyl indole-carbonyl group: N, N-bis(1-pentylindol-3-yl-carboxy)naphtylamine (BiPICANA, compound 2). Compound 2 was purified by silica and octadecyl group bonded type silica gel (C18, ODS) columns and confirmed by liquid chromatography–mass… 

Identification of (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (DP-UR-144) in a herbal drug product that was commercially available in the Tokyo metropolitan area

We encountered during our investigation a case of herbal drug products commercially available in the Tokyo metropolitan area in 2014, in which a small unknown peak was detected, along with the

Evaluation of carboxamide-type synthetic cannabinoids as CB1/CB2 receptor agonists: difference between the enantiomers

TLDR
This is the first report to show that the (R)-enantiomers of the carboxamide-type synthetic cannabinoids have the potency to activate CB1 and CB2 receptors.

Cannabimimetic activities of cumyl carboxamide-type synthetic cannabinoids

TLDR
This study synthesized seven cumyl carboxamide-type synthetic cannabinoids and evaluated their activities as CB1 and CB2 receptor agonists and showed the analytical characterization of these compounds using gas chromatography–electron ionization-mass spectrometry.

In vitro metabolism of synthetic cannabinoid AM1220 by human liver microsomes and Cunninghamella elegans using liquid chromatography coupled with high resolution mass spectrometry

TLDR
Three most abundant metabolites in both human liver microsomes and Cunninghamella elegans were desmethyl, dihydrodiol and hydroxy metabolites, despite different isomers of dihydroxy metabolites in each model, which can potentially be useful markers in urine testing for AM1220 intake.

Evaluation of carboxamide-type synthetic cannabinoids on the functional activities at cannabinoid receptors and biological effects via inhalation exposure test

TLDR
It was suggested that 5F-MDMB-PICA was the strongest CB1 and CB2 receptor agonist in comparison with synthetic cannabinoids evaluated in the past, considering their way of inhalation and thermal degradation.

The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonist New Psychoactive Substances: Evolution.

TLDR
This chapter will chart the evolution of recently identified SCRA NPS chemotypes, as well as their putative manufacturing by-products and thermolytic degradants, and describe structure-activity relationships within each class.

Metabolites of synthetic cannabinoids in hair—proof of consumption or false friends for interpretation?

AbstractThe detection of drug metabolites in hair is widely accepted as a proof for systemic uptake of the drug, unless the metabolites can be formed as artefacts. However, regarding synthetic

High-resolution mass spectrometric determination of the synthetic cannabinoids MAM-2201, AM-2201, AM-2232, and their metabolites in postmortem plasma and urine by LC/Q-TOFMS

TLDR
Quantitation results suggest that defluorination is a major metabolic pathway for MAM-2201, and N-dealkylation is a common but minor pathway for the naphthoylindole-type synthetic cannabinoids in human.

Chemoinformatic Consideration of Novel Psychoactive Substances: Compilation and Preliminary Analysis of a Categorised Dataset

TLDR
A dataset composed of 690 distinct acknowledged NPS, complete with defined chemical structures, has been constructed, and classification was performed in accordance with their key molecular structural features, subjective effect profiles and pharmacological mechanisms of action.

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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

During our continual surveillance of unregulated drugs in May–June 2011, we found two new compounds as adulterants in herbal products obtained at shops in the Tokyo area. These compounds were

Identification and quantitation of a benzoylindole (2-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone and a naphthoylindole 1-(5-fluoropentyl-1H-indol-3-yl)-(naphthalene-1-yl)methanone (AM-2201) found in illegal products obtained via the Internet and their cannabimimetic effects evaluated by in vitr

During our careful surveillance of unregulated drugs in January to February 2011, we found two new compounds used as adulterants in herbal products obtained via the Internet. These compounds were

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

Analysis of azepane isomers of AM-2233 and AM-1220, and detection of an inhibitor of fatty acid amide hydrolase [3′-(aminocarbonyl)(1,1′-biphenyl)-3-yl]-cyclohexylcarbamate (URB597) obtained as designer drugs in the Tokyo area

During our careful survey of unregulated drugs from November 2011 to January 2012 in the Tokyo area, we found two new compounds in commercial products. The first was identified as the benzoylindole

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 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

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

Identification of a synthetic cannabinoid A-836339 as a novel compound found in a product

As a part of the work conducted in our laboratory, we encountered a case in which new chemical compound was contained in a certain product. This compound was found to have a molecular weight of 310

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

Identification of two new-type designer drugs, piperazine derivative MT-45 (I-C6) and synthetic peptide Noopept (GVS-111), with synthetic cannabinoid A-834735, cathinone derivative 4-methoxy-α-PVP, and phenethylamine derivative 4-methylbuphedrine from illegal products

TLDR
Two new-type designer drugs, piperazine derivative MT-45 and synthetic peptide Noopept and synthetic cannabinoids A-834735 and QUPIC N-(5-fluoropentyl) analog (synonym: 5-fluoro-PB-22, 4), are identified in chemical and herbal products.