Skip to main content
Springer Nature Link
Log in

Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products

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

Abstract

From November 2013 to May 2014, 19 newly distributed designer drugs were identified in 104 products in our ongoing survey of illegal products in Japan. The identified compounds included 8 synthetic cannabinoids, FUB-PB-22 (1), 5-fluoro-NNEI indazole analog (5-fluoro-MN-18, 2), AM-2201 indazole analog (THJ-2201, 3), XLR-12 (4), 5-fluoro-AB-PINACA (5), 5-chloro-AB-PINACA (6), AB-CHMINACA (7), and 5-fluoro-AMB (8); 5 cathinone derivatives, DL-4662 (9), α-PHP (10), 4-methoxy-α-POP (11), 4-methoxy-α-PHPP (12), and 4-fluoro-α-PHPP (13); and 6 other substances, namely, the benzofuran derivative 2-(2-ethylaminopropyl)benzofuran (2-EAPB, 14), nitracaine (15), diclofensine (16), diphenidine (17), 1-benzylpiperidine (18), and acetylfentanyl (19). To our knowledge, this is the first report on the chemical properties of compounds 9–11 and 14. A total of 33 designer drugs, including compounds 1–19, were detected in the 104 illegal products, in 60 different combination patterns. The numbers of detected compounds per product ranged from 1 to 7. In addition, several products contained three different types of compounds, such as synthetic cannabinoids, cathinone derivatives, and phenethylamine derivatives per product. It is apparent that the types of compounds emerging as illegal products are becoming more diverse, as are their combinations.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
€34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Germany)

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
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y (2009) Identification of a cannabimimetic indole as a designer drug in a herbal product. Forensic Toxicol 27:61–66

    Article  CAS  Google Scholar 

  2. 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 

  3. 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 

  4. Uchiyama N, Matsuda S, Wakana D, Kikura-Hanajiri R, Goda Y (2013) New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA), identified as designer drugs. Forensic Toxicol 31:93–100

    Article  CAS  Google Scholar 

  5. Takahashi K, Uchiyama N, Fukiwake T, Hasegawa T, Saijou M, Motoki Y, Kikura-Hanajiri R, Goda Y (2013) Identification and quantitation of JWH-213, a cannabimimetic indole, as a designer drug in a herbal product. Forensic Toxicol 31:145–150

    Article  CAS  Google Scholar 

  6. 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 

  7. UNODC (2014) 2014 Global synthetic drugs assessment. Amphetamine-type stimulants and new psychoactive substances, May 2014. http://www.unodc.org/documents/scientific/2014_Global_Synthetic_Drugs_Assessment_web.pdf. Accessed May 2014

  8. EMCDDA (2014) European drug report 2014: trends and developments, May 2014. http://www.emcdda.europa.eu/attachements.cfm/att_228272_EN_TDAT14001ENN.pdf. Accessed May 2014

  9. Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) Identification of two new-type designer drugs, a piperazine derivative MT-45 (I-C6) and a synthetic peptide Noopept (GVS-111), with a synthetic cannabinoid A-834735, a cathinone derivative 4-methoxy-α-PVP and a phenethylamine derivative 4-methylbuphedrine from illegal products. Forensic Toxicol 32:9–18

    Article  CAS  Google Scholar 

  10. Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) 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. Forensic Toxicol 32:105–117

    Article  CAS  Google Scholar 

  11. Uchiyama N, Matsuda S, Kawamura M, Shimokawa Y, Kikura-Hanajiri R, Aritake K, Urade Y, Goda Y (2014) Characterization of four new designer drugs, 5-chloro-NNEI, NNEI indazole analog, α-PHPP and α-POP, with 11 newly distributed designer drugs in illegal products. Forensic Sci Int 243:1–13

    Article  CAS  Google Scholar 

  12. 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 

  13. Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, El-Kouhen OF, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD (2010) Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB2 cannabinoid receptor activity. J Med Chem 53:295–315

  14. Buchler IP, Hayes MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RE, Wu KK (2009) Indazole derivatives as CB1 receptor modulators and their preparation and use in treatment of diseases. Patent: WO/2009/106980 September, 2009

  15. Iversen L, Gibbons S, Treble R, Sedtola V, Huang X-P, Rolth BL (2013) Neurochemical profiles of some novel psychoactive substances. Eur J Pharmacol 700:147–151

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  16. Advisory Council on the Misuse of Drugs (ACMD) (2013) Benzofurans: a review of the evidence of use and harm. ACMD, London. https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/261783/Benzofuran_compounds_report.pdf. Accessed May 2014

  17. Power JD, Scott KR, Gardner EA, Curran McAteer BM, O’Brien JE, Brehon M, Talbot B, Kavanagh PV (2014) The syntheses, characterization and in vitro metabolism of nitracaine, methoxypiperamide and mephtetramine. Drug Test Anal. doi:10.1002/dta.1616

    Google Scholar 

  18. Nakachi N, Kiuchi Y, Inagaki M, Inazu M, Yamazaki Y, Oguchi K (1995) Effects of various dopamine uptake inhibitors on striatal extracellular dopamine levels and behaviors in rats. Eur J Pharmacol 281:195–203

    Article  CAS  PubMed  Google Scholar 

  19. Berger ML, Schweifer A, Rebernik P, Hammerschmidt F (2009) NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds. Bioorg Med Chem 17:3456–3462

    Article  CAS  PubMed  Google Scholar 

  20. Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2014) Changes in the prevalence of new psychoactive substances before and after the introduction of the generic scheduling of synthetic cannabinoids in Japan. Drug Test Anal. doi:10.1002/dta.1584

    PubMed  Google Scholar 

Download references

Acknowledgments

Part of this work was supported by a Health and Labor Sciences Research Grant from the Ministry of Health, Labour, and Welfare, Japan.

Conflict of interest

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

Author information

Authors and Affiliations

  1. Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo, 158-8501, Japan

    Nahoko Uchiyama, Yoshihiko Shimokawa, Maiko Kawamura, Ruri Kikura-Hanajiri & Takashi Hakamatsuka

Authors
  1. Nahoko Uchiyama
    View author publications

    You can also search for this author inPubMed Google Scholar

  2. Yoshihiko Shimokawa
    View author publications

    You can also search for this author inPubMed Google Scholar

  3. Maiko Kawamura
    View author publications

    You can also search for this author inPubMed Google Scholar

  4. Ruri Kikura-Hanajiri
    View author publications

    You can also search for this author inPubMed Google Scholar

  5. Takashi Hakamatsuka
    View author publications

    You can also search for this author inPubMed Google Scholar

Corresponding author

Correspondence to Nahoko Uchiyama.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 204 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Uchiyama, N., Shimokawa, Y., Kawamura, M. et al. Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products. Forensic Toxicol 32, 266–281 (2014). https://doi.org/10.1007/s11419-014-0238-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11419-014-0238-5

Keywords