Forensic Toxicology

, Volume 35, Issue 1, pp 146–152 | Cite as

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

  • Yoko Ichikawa
  • Jun’ichi Nakajima
  • Misako Takahashi
  • Nozomi Uemura
  • Masao Yoshida
  • Atsuko Suzuki
  • Jin Suzuki
  • Dai Nakae
  • Takako Moriyasu
  • Mitsugu Hosaka
Short Communication
First Online:
Received:
Accepted:

Abstract

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 intense peak of FUB-144, by liquid chromatography–ultraviolet detection. The present study was conducted to identify and clarify the pharmacological characteristics of the compound present in this small peak. We isolated a compound using a silica gel column from the peak, which was then identified to have a molecular weight of 241 Da by liquid chromatography–mass spectrometry and gas chromatography–mass spectrometry. The accurate mass measurement suggested an elementary composition of C16H19NO. Using these mass data together with those obtained by the nuclear magnetic resonance analysis, the compound was finally identified as (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (despentyl-UR-144; DP-UR-144). In addition, this compound was revealed to have affinities for cannabinoid receptors CB1 and CB2 with EC50s of 2.36 × 10−6 and 2.79 × 10−8 M, respectively. To our knowledge, there is no information in the scientific literature on structural or pharmacological properties of this chemical. These results suggest that the components present in small amounts can contribute to the effects of a major component in their mother product, if they have sufficient pharmacological activities, and, therefore, even such small amounts of components should be precisely characterized and well evaluated to control illegal and potentially illegal drug products.

Keywords

(1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (DP-UR-144) FUB-144 Synthetic cannabinoid [35S]GTPγS binding assays Small amounts of drugs having psychotropic activities 
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Notes

Acknowledgments

The authors express their gratitude to Ms. Takako Seto and Ms. Tomoko Urade for their expert support in the instrumental analysis. This work was supported by the Pharmaceutical Affairs Section, the Tokyo Metropolitan Government, Tokyo, Japan.

Compliance with ethical standards

Conflict of interest

There are no financial or other relations that could lead to a conflict of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

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Copyright information

© Japanese Association of Forensic Toxicology and Springer Japan 2016

Authors and Affiliations

  • Yoko Ichikawa
    • 1
  • Jun’ichi Nakajima
    • 1
  • Misako Takahashi
    • 1
  • Nozomi Uemura
    • 1
  • Masao Yoshida
    • 1
  • Atsuko Suzuki
    • 1
  • Jin Suzuki
    • 1
  • Dai Nakae
    • 2
  • Takako Moriyasu
    • 1
  • Mitsugu Hosaka
    • 1
  1. 1.Department of Pharmaceutical and Environmental SciencesTokyo Metropolitan Institute of Public HealthTokyoJapan
  2. 2.Department of Nutritional Science and Food Safety, Faculty of Applied BiosciencesTokyo University of AgricultureTokyoJapan

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