Skip to main content
Springer Nature Link
Log in

Identification of six tryptamine derivatives as designer drugs in illegal products

  • Short Communication
  • Published:

Abstract

Purpose

To prevent the abuse of new designer drugs, Japan has declared 2385 substances and two plants as "Designated Substances" as of March 2020. Although the distribution of these substances has decreased over the past 5 years, newly detected designer drugs are still being found. We have detected six designer drugs in six powdery products between February of 2017 and April of 2019.

Methods

The structures of the compounds were determined by gas chromatography mass spectrometry (GC–MS), liquid chromatography mass spectrometry (LC–MS), liquid chromatography with hybrid quadrupole time-of-flight mass spectrometry (LC-Q-TOF–MS) and nuclear magnetic resonance (NMR) spectroscopy.

Results

Six tryptamine derivatives (4-acetoxy-N,N-dipropyltryptamine, 4-hydroxy-N,N-dipropyltryptamine, 4-hydroxy-N-methyl-N-propyltryptamine, N-ethyl-N-propyltryptamine, 4-hydroxy-N-ethyl-N-propyltryptamine (4OH-EPT), and 4-hydroxy-N-methyl-N-cyclopropyltryptamine (4OH-McPT) were identified. Among these, 4OH-EPT and 4OH-McPT were identified as newly distributed designer drugs.

Conclusions

The continuous provisional monitoring of newly detected compounds in illicit products will largely prevent the distribution of these products.

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

Access this article

Subscribe and save

Springer+
from 17,985円 /Month
  • Starting from 10 chapters or articles per month
  • Access and download chapters and articles from more than 300k books and 2,500 journals
  • Cancel anytime
View plans

Buy Now

Price includes VAT (Japan)

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Discover the latest articles, books and news in related subjects, suggested using machine learning.

References

  1. EMCDDA (2016) EMCDDA–Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA. EMCDDA-Europol, Lisbon, July 2017. http://www.emcdda.europa.eu/system/files/publications/4724/TDAN17001ENN_PDFWEB.pdf. Accessed Nov 2018

  2. EMCDDA (2017) EMCDDA–Europol 2017 Annual Report on the implementation of Council Decision 2005/387/JHA. EMCDDA-Europol, Lisbon, February 2018. http://www.emcdda.europa.eu/system/files/publications/9282/20183924_TDAN18001ENN_PDF.pdf. Accessed Nov 2018

  3. Araújo AM, Carvalho F, Bastos ML, Pinho PG, Carvalho M (2015) The hallucinogenic world of tryptamines: an updated review. Arch Toxicol 89:1151–1173

    Article Google Scholar

  4. Glennon RA, Gessner PK (1979) Serotonin receptor binding affinities of tryptamine analogues. J Med Chem 22(4):428–432

    Article CAS Google Scholar

  5. 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 Google Scholar

  6. Repke DB, Ferguson WJ, Bates DK (1977) Synthesis of 3-[2-(dialkylamino)ethyl]-and 3-[2- (cycloalkylamino)ethyl]indol-4-ols. J Heterocyclic Chem 14:71–74

    Article CAS Google Scholar

  7. Repke DB, Ferguson WJ, Bates DK (1981) Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2- (N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols. J Heterocyclic Chem 18:175–179

    Article CAS Google Scholar

  8. Brandt SD, Freeman S, Fleet IA, McGagh P, Alder JF (2005) Analytical chemistry of synthetic routes to psychoactive tryptamines Part II. Characterization of the Speeter and Anthony synthetic route to N, N-dialkylated tryptamines using GC-EI-ITMS. ESI-TQ-MS-MS and NMR. Analyst 130:330–344

    CAS PubMed Google Scholar

  9. Kikura-Hanajiri R, Uchiyama N, Kawamura M, Ogata J, Goda Y (2013) Prevalence of new designer drugs and heir legal status in Japan. Yakugaku Zasshi 133:31–40

    Article CAS Google Scholar

Download references

Acknowledgements

A portion of this work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Health, Welfare, and Labor of Japan.

Author information

Authors and Affiliations

  1. Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, 3-25-26, Tonomachi, Kawasaki-ku, Kawasaki, Kanagawa, 210-9501, Japan

    Rie Tanaka, Maiko Kawamura, Takashi Hakamatsuka & Ruri Kikura-Hanajiri

Authors
  1. Rie Tanaka
  2. Maiko Kawamura
  3. Takashi Hakamatsuka
  4. Ruri Kikura-Hanajiri

Corresponding author

Correspondence to Rie Tanaka.

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

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

About this article

Cite this article

Tanaka, R., Kawamura, M., Hakamatsuka, T. et al. Identification of six tryptamine derivatives as designer drugs in illegal products. Forensic Toxicol 39, 248–258 (2021). https://doi.org/10.1007/s11419-020-00556-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Version of record:

  • Issue date:

  • DOI: https://doi.org/10.1007/s11419-020-00556-5

Keywords

AltStyle によって変換されたページ (->オリジナル) /