Skip to main content
Top
Published in: Forensic Toxicology 1/2021

01-01-2021 | Short Communication

Identification of six tryptamine derivatives as designer drugs in illegal products

Authors: Rie Tanaka, Maiko Kawamura, Takashi Hakamatsuka, Ruri Kikura-Hanajiri

Published in: Forensic Toxicology | Issue 1/2021

Login to get access

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.
Literature
3.
go back to reference Araújo AM, Carvalho F, Bastos ML, Pinho PG, Carvalho M (2015) The hallucinogenic world of tryptamines: an updated review. Arch Toxicol 89:1151–1173CrossRef Araújo AM, Carvalho F, Bastos ML, Pinho PG, Carvalho M (2015) The hallucinogenic world of tryptamines: an updated review. Arch Toxicol 89:1151–1173CrossRef
4.
go back to reference Glennon RA, Gessner PK (1979) Serotonin receptor binding affinities of tryptamine analogues. J Med Chem 22(4):428–432CrossRef Glennon RA, Gessner PK (1979) Serotonin receptor binding affinities of tryptamine analogues. J Med Chem 22(4):428–432CrossRef
5.
go back to reference 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 227:21–32CrossRef 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 227:21–32CrossRef
6.
go back to reference Repke DB, Ferguson WJ, Bates DK (1977) Synthesis of 3-[2-(dialkylamino)ethyl]-and 3-[2- (cycloalkylamino)ethyl]indol-4-ols. J Heterocyclic Chem 14:71–74CrossRef Repke DB, Ferguson WJ, Bates DK (1977) Synthesis of 3-[2-(dialkylamino)ethyl]-and 3-[2- (cycloalkylamino)ethyl]indol-4-ols. J Heterocyclic Chem 14:71–74CrossRef
7.
go back to reference 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 18:175–179CrossRef 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 18:175–179CrossRef
8.
go back to reference 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 130:330–344PubMed 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 130:330–344PubMed
9.
go back to reference 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 133:31–40CrossRef 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 133:31–40CrossRef
Metadata
Title
Identification of six tryptamine derivatives as designer drugs in illegal products
Authors
Rie Tanaka
Maiko Kawamura
Takashi Hakamatsuka
Ruri Kikura-Hanajiri
Publication date
01-01-2021
Publisher
Springer Singapore
Published in
Forensic Toxicology / Issue 1/2021
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-020-00556-5

Other articles of this Issue 1/2021

Forensic Toxicology 1/2021 Go to the issue