Skip to main content
SpringerLink
Log in

Cannabimimetic activities of cumyl carboxamide-type synthetic cannabinoids

  • Short Communication
  • Published:
Forensic Toxicology Aims and scope Submit manuscript

A Correction to this article was published on 21 July 2020

This article has been updated

Abstract

1-Pentyl-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide (CUMYL-PINACA) is a carboxamide-type synthetic cannabinoid comprising a cumylamine moiety. Recently, the detection of CUMYL-PINACA and some analogs in illicit drug products has been reported by the European Monitoring Centre for Drugs and Drug Addiction. In this study, we synthesized seven cumyl carboxamide-type synthetic cannabinoids (CUMYL-PINACA, CUMYL-5F-PINACA, CUMYL-PICA, CUMYL-5F-PICA, CUMYL-THPINACA, CUMYL-BICA, and CUMYL-5F-P7AICA) and evaluated their activities as CB1 and CB2 receptor agonists. We also showed the analytical characterization of these compounds using gas chromatography–electron ionization-mass spectrometry. All of the evaluated compounds exhibited moderate to strong activities as agonists acting on both CB1 and CB2 receptors with EC50 values in the range of 8.1 × 10−10–7.8 × 10−7 mol/L for CB1 and from 2.5 × 10−10 to 9.1 × 10−6 mol/L for CB2. The EC50 data presented will be helpful to understand the effects of these compounds in the forensic cases. Furthermore, other new cumyl carboxamide-type synthetic cannabinoids, which will be potentially distributed in the future, will probably have the activities as agonists acting on both CB1 and CB2 receptors.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Change history

  • 21 July 2020

    There were some mistakes.

References

  1. United Nations Office on Drugs and Crime (UNODC) (2016) World Drug Report 2016. Vienna. www.unodc.org/doc/wdr2016/WORLD_DRUG_REPORT_2016_web.pdf. Accessed 6 April 2017

  2. Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2013) Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012. Forensic Toxicol 31:44–53

    Article  Google Scholar 

  3. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA)—Europol (2015) EMCDDA–Europol 2014 Annual Report on the implementation of Council Decision 2005/387/JHA. Lisbon. www.emcdda.europa.eu/system/files/publications/1018/TDAN15001ENN.pdf. Accessed 28 April 2017

  4. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) –Europol (2016) EMCDDA–Europol 2015 Annual Report on the implementation of Council Decision 2005/387/JHA. Lisbon. http://www.emcdda.europa.eu/system/files/publications/2880/TDAS16001ENN.pdf. Accessed 28 April 2017

  5. Dobaja M, Grenc D, Kozelj G, Brvar M (2017) Occupational transdermal poisoning with synthetic cannabinoid cumyl-PINACA. Clin Toxicol 55:193–195

    Article  CAS  Google Scholar 

  6. Sveriges Riksdag, Förordning (1999) om förbud mot vissa hälsofarliga varor. https://www.riksdagen.se/sv/dokument-lagar/dokument/svensk-forfattningssamling/forordning-199958-om-forbud-mot-vissa_sfs-1999-58. Accessed 28 April 2017

  7. Ministry of Justice (2017) Pharmaceutical Affairs Law. http://www.japaneselawtranslation.go.jp/law/detail/?id=2766&vm=&re=&new=1. Accessed 28 April 2017

  8. Bowden MJ, Williamson JPB (2014) Cannabinoid compounds. Patent WO 2014/167530 A1

  9. Buchler IP, Hayas MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, TenBrink RE, Wu KK (2009) Indazole derivatives. Patent WO 2009/106982

  10. Banister SD, Wilkinson SM, Longworth M, Stuart J, Apetz N, English K, Brooker L, Goebel C, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M (2013) The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse. ACS Chem Neurosci 4:1081–1092

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Asada A, Doi T, Tagami T, Takeda A, Sawabe Y (2017) Isomeric discrimination of synthetic cannabinoids by GC–EI–MS: 1-adamantyl and 2-adamantyl isomers of N-adamantyl carboxamides. Drug Test Anal 9:378–388

    Article  CAS  PubMed  Google Scholar 

  12. Nakajima J, Takahashi M, Uemura N, Sato T, Fukaya H, Suzuki J, Yoshida M, Kusano M, Nakayama H, Zaitsu K, Ishii A, Moriyasu T, Nakae D (2015) 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. Forensic Toxicol 33:84–92

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This study was partly supported by JSPS KAKENHI Grant number JP25860475 and JP15K08834.

Author information

Authors and Affiliations

  1. Osaka Institute of Public Health, 1-3-69 Nakamichi, Higashinari-ku, Osaka, 537-0025, Japan

    Akiko Asada, Takahiro Doi, Takaomi Tagami, Akihiro Takeda, Yuka Satsuki, Masami Kawaguchi, Akihiko Nakamura & Yoshiyuki Sawabe

Authors
  1. Akiko Asada
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Takahiro Doi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Takaomi Tagami
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Akihiro Takeda
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yuka Satsuki
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Masami Kawaguchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Akihiko Nakamura
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Yoshiyuki Sawabe
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Akiko Asada.

Ethics declarations

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.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Asada, A., Doi, T., Tagami, T. et al. Cannabimimetic activities of cumyl carboxamide-type synthetic cannabinoids. Forensic Toxicol 36, 170–177 (2018). https://doi.org/10.1007/s11419-017-0374-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11419-017-0374-9

Keywords

Search

Navigation