Skip to main content
SpringerLink
Log in

Identification of new synthetic cannabinoid analogue APINAC (adamantan-1-yl 1-pentyl-1H-indazole-3-carboxylate) with other synthetic cannabinoid MDMB(N)-Bz-F in illegal products

  • Original Article
  • Published:
Forensic Toxicology Aims and scope Submit manuscript

Abstract

Two synthetic cannabinoid analogues were detected using high-performance liquid chromatography (HPLC)–diode array detector, and gas chromatography–time-of-flight-mass spectrometry during the inspection of illegal products in an airmail package. The analogues were separated by semi-preparative HPLC, and their structures were determined by performing liquid chromatography–high-resolution-mass spectrometry, infrared analysis, and nuclear magnetic resonance spectroscopy. Compound 1 was MDMB(N)-Bz-F, which has been reported previously. Compound 2 was elucidated as adamantan-1-yl 1-pentyl-1H-indazole-3-carboxylate (APINAC), in which the amide group of APINACA was replaced with an ester group. Because there has been no chemical or pharmacological data about this compound until now, this is the first report of its detection in illegal products.

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
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Huffman JW (2009) Cannabimimetic indoles, pyrroles, and indenes: structure-activity relationships and receptor interactions. In: Reggio PH (ed) The cannabinoid receptors. Humana Press, New York, pp 49–94

  2. Benford DM, Caplan JP (2011) Psychiatric sequelae of spice, K2 and synthetic cannabinoid receptor agonists. Psychosomatics 52:295

    Article  PubMed  Google Scholar 

  3. Every-Palmer S (2010) Warning: legal synthetic cannabinoid-receptor agonists such as JWH-018 may precipitate psychosis in vulnerable individuals. Addiction 105:1859–1860

    Article  PubMed  Google Scholar 

  4. Gandhi AS, Zhu M, Pang S, Wohlfarth A, Scheidweiler KB, Liu HF, Huestis MA (2013) First characterization of AKB-48 metabolism, a novel synthetic cannabinoid, using human hepatocytes and high-resolution mass spectrometry. J AAPS 15:1091–1098

    Article  CAS  Google Scholar 

  5. Spaderna M, Addy PH, D’Souza DC (2013) Spicing things up: synthetic cannabinoids. Psychopharmacology 228:525–540

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products. Forensic Sci Int 227:21–32

    Article  CAS  PubMed  Google Scholar 

  7. Chung H, Choi H, Heo S, Kim E, Lee J (2014) Synthetic cannabinoids abused in South Korea: drug identifications by the 123 National Forensic Service from 2009 to June 2013. Forensic Toxicol 32:82–88

    Article  CAS  Google Scholar 

  8. Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2012) 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 illegal products. Forensic Toxicol 30:114–125

    Article  CAS  Google Scholar 

  9. Vikingsson S, Josefsson M, Gre´en H (2015) Identification of AKB-48 and 5F-AKB-48 metabolites in authentic human urine samples using human liver microsomes and time of flight mass spectrometry. J Anal Toxicol 39:426–435

    Article  CAS  PubMed  Google Scholar 

  10. Thornton SL, Wood C, Friesen MW, Gerona RR (2013) Synthetic cannabinoid use associated with acute kidney injury. Clin Toxicol 51:189–190

    Article  Google Scholar 

  11. Seely KA, Lapoint J, Moran JH, Fattore L (2012) Spice drugs are more than harmless herbal blends: a review of the pharmacology and toxicology of synthetic cannabinoids. Prog Neuropsychopharmacol Biol Psychiatry 29:234–243

    Article  Google Scholar 

  12. Ashton AC (1999) Adverse effects of cannabis and cannabinoids. Br J Anaesth 83:637–649

    Article  CAS  PubMed  Google Scholar 

  13. Kronstrand R, Roman M, Andersson M, Eklund A (2013) Toxicological findings of synthetic cannabinoids in recreational users. J Anal Toxicol 37:534–541

    Article  CAS  PubMed  Google Scholar 

  14. Vardakou I, Pistos C, Spiliopoulou C (2010) Spice drugs as a new trend: mode of action, identification and legislation. Toxicol Lett 197:157–162

    Article  CAS  PubMed  Google Scholar 

  15. UNODC (2012) World drug report 2012. United Nations Office on Drugs and Crime, Vienna

    Google Scholar 

  16. Choi JY, Hea S, Yoo GJ, Park SK, Yoon CY, Baek SY (2015) Development and validation of an LC-MS/MS method for the simultaneous analysis of 28 specific narcotic adulterants used in dietary supplements. Food Addit Contam A 32:1029–1039

    Article  CAS  Google Scholar 

  17. Penn HJ, Langman LJ, Unold D, Shields J, Nichols JH (2011) Detection of synthetic cannabinoids in herbal incense products. Clin Biochem 44:1163–1165

    Article  CAS  PubMed  Google Scholar 

  18. Harris CR, Brown A (2013) Synthetic cannabinoid intoxication: a case series and review. J Emerg Med 44:360–366

    Article  PubMed  Google Scholar 

  19. Grotenhermen F (2007) The toxicology of cannabis and cannabis prohibition. Chem Biodivers 4:1744–1769

    Article  CAS  PubMed  Google Scholar 

  20. Seely KA, Patton AL, Moran CL, Womack ML, Prather PL, Fantegrossi WE, Radominska-Pandya A, Endres GW, Channell KB, Smith NH, McCain KR, James LP, Moran JH (2013) Forensic investigation of K2, spice, and ‘‘bath salt’’ commercial preparations: a 3-year study of new designer drug products containing synthetic cannabinoid, stimulant, and hallucinogenic compounds. Forensic Sci Int 233:416–422

    Article  CAS  PubMed  Google Scholar 

  21. 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 

  22. Namera A, Kawamura M, Nakamoto A, Saito T, Nagao M (2013) Comprehensive review of the detection methods for synthetic cannabinoids and cathinones. Forensic Toxicol 33:175–194

    Article  Google Scholar 

  23. Uchiyama N, Kikura-Hanajiri R, Kawahara N, Haishima Y, Goda Y (2009) Identification of a cannabinoid analog as a new type of designer drug in a herbal product. Chem Pharm Bull 57:439–441

    Article  CAS  PubMed  Google Scholar 

  24. Amato J, Iaccarino N, Pagano B, Compagnone V, Di Rosa F, Peluso G, Novellino E, Randazzo A (2014) NMR assignment of N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide seized as herbal incense for the first time in Italy. J Forensic Sci Criminol 2(1):103. doi:10.15744/2348-9804.1.403

    Google Scholar 

  25. EMCDDA (2015) New psychoactive substances in Europe: an update from the EU early warning system. European Monitoring Centre for Drugs and Drug Addiction. http://www.emcdda.europa.eu/publications/2015/new-psychoactive-substances. Accessed 8 June 2016

  26. Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, Lebedv AT (2015) Identification and analytical characteristics of synthetic caanabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group. Anal Bioanal Chem 407:3601–3615

    Article  Google Scholar 

  27. Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) 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. Forensic Toxicol 31:223–240

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research was supported by Research Grants (15181MFDS521 and 15182MFDS523) from the Ministry of Food and Drug Safety (MFDS) in Korea. We thank the Central Laboratory of Kangwon National University for providing us with technical assistance on the spectroscopic experiments.

Author information

Author notes

    Authors and Affiliations

    1. Advanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Cheongju-si, Chungcheongbuk-do, 28159, Republic of Korea

      Ji Hyun Lee, Han Na Park, Sooyeul Cho & Sun Young Baek

    2. Laboratory and Scientific Service, Incheon Airport Customs, Korea Customs Service, Incheon, 22381, Republic of Korea

      Tan-Soon Leem & Joo-hyoung Jeon

    3. College of Pharmacy, Kangwon National University, 1 Kangwondaehak-gil Chuncheon, Gangwon-do, 24341, Republic of Korea

      Jongkook Lee

    Authors
    1. Ji Hyun Lee
      View author publications

      You can also search for this author in PubMed Google Scholar

    2. Han Na Park
      View author publications

      You can also search for this author in PubMed Google Scholar

    3. Tan-Soon Leem
      View author publications

      You can also search for this author in PubMed Google Scholar

    4. Joo-hyoung Jeon
      View author publications

      You can also search for this author in PubMed Google Scholar

    5. Sooyeul Cho
      View author publications

      You can also search for this author in PubMed Google Scholar

    6. Jongkook Lee
      View author publications

      You can also search for this author in PubMed Google Scholar

    7. Sun Young Baek
      View author publications

      You can also search for this author in PubMed Google Scholar

    Corresponding authors

    Correspondence to Jongkook Lee or Sun Young Baek.

    Ethics declarations

    Conflict of interest

    The authors declare that they have no conflict of interest.

    Ethical approval

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

    Additional information

    J. H. Lee and H. N. Park contributed equally.

    Electronic supplementary material

    Below is the link to the electronic supplementary material.

    Supplementary material 1 (DOCX 65828 kb)

    Rights and permissions

    Reprints and permissions

    About this article

    Check for updates. Verify currency and authenticity via CrossMark

    Cite this article

    Lee, J.H., Park, H.N., Leem, TS. et al. Identification of new synthetic cannabinoid analogue APINAC (adamantan-1-yl 1-pentyl-1H-indazole-3-carboxylate) with other synthetic cannabinoid MDMB(N)-Bz-F in illegal products. Forensic Toxicol 35, 45–55 (2017). https://doi.org/10.1007/s11419-016-0331-z

    Download citation

    • Received:

    • Accepted:

    • Published:

    • Issue Date:

    • DOI: https://doi.org/10.1007/s11419-016-0331-z

    Keywords

    Search

    Navigation