Forensic toxicology
July 1, 2023
Rie Tanaka, Maiko Kawamura, Sakumi Mizutani et al.
18 citations
Three new analogs of LSD have been identified in paper sheet products sold as designer drugs in Japan. Using mass spectrometry and nuclear magnetic resonance spectroscopy, the compounds were determined to be 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD, and LSZ. Compared to LSD, 1cP-AL-LAD is modified at two positions (N1 and N6), and 1cP-MIPLA at N1 and N18. The metabolic pathways and biological activities of 1cP-AL-LAD and 1cP-MIPLA are not yet reported. This is the first report of LSD analogs with multiple structural modifications detected in sheet products in Japan, raising concerns about future distribution and highlighting the need for continued monitoring.
Journal of Pharmaceutical and Biomedical Analysis
July 21, 2020
Izumi Morita, Hiroyuki Oyama, Yuki Kiguchi et al.
17 citations
Two independent monoclonal antibodies were generated against psilocybin and its dephosphorylated metabolite psilocin, the psychoactive compounds in hallucinogenic mushrooms. Novel immunogenic conjugates were prepared by modifying the side chains of these molecules and linking them to carrier proteins. Mice were immunized, and hybridoma clones secreting the specific antibodies were established. Competitive enzyme-linked immunosorbent assays (ELISAs) using these antibodies enabled detection of psilocybin and psilocin at ranges of approximately 0.20–20 μg/assay and 0.040–2.0 μg/assay, respectively, with low cross-reactivity between the two compounds. In dried Psilocybe cubensis powder, psilocybin and psilocin contents were 0.39% and 0.32% by weight. These ELISAs offer a promising tool for identifying illegal hallucinogenic mushrooms.
YAKUGAKU ZASSHI
October 31, 2020
Rie Tanaka, Maiko Kawamura, Takashi Hakamatsuka et al.
15 citations
Three new LSD-like designer drugs were identified in paper sheet products seized in Japan between September 2019 and March 2020. Using methanol extraction followed by LC-MS, high-resolution MS, GC-MS, and NMR analyses, the compounds were identified as 1cP-LSD, MIPLA, and 1B-LSD. Like other N1-acylated LSD derivatives, 1cP-LSD and 1B-LSD easily break down into LSD during GC-MS analysis, requiring caution when testing.
YAKUGAKU ZASSHI
April 30, 2020
Rie Tanaka, Maiko Kawamura, Takashi Hakamatsuka et al.
15 citations
From 2014 to 2017 in Japan, four lysergic acid diethylamide (LSD) derivatives were detected in paper sheet products sold as designer drugs. The compounds were identified as ALD-52, ETH-LAD, AL-LAD, and 1P-LSD using GC-MS, LC-MS, LC-Q-TOF-MS, and NMR analyses. Extraction methods and analytical conditions for GC-MS, LC-MS, and LC-FL were studied. As of September 2019, 2372 substances and two plants are controlled as "Designated Substances" under Japanese law. Only 1P-LSD was already regulated since April 2016; pharmacological evaluation of the other derivatives is ongoing to inform future legislation.
Drug testing and analysis
May 1, 2024
Rie Tanaka, Maiko Kawamura, Sakumi Mizutani et al.
11 citations
A paper-sheet product sold as containing the LSD analog 1D-LSD actually contained a different, previously unreported compound: 1-thiophenoyl LSD (1T-LSD). Using mass spectrometry and nuclear magnetic resonance spectroscopy, the compound was identified as having a thiophene-2-carbonyl group instead of the claimed 1,2-dimethylcyclobutane-carbonyl group. Each unit of the sheet contained 87–100 μg of 1T-LSD free base. The compound slowly converted to LSD in methanol-d4 during analysis. Its UV spectrum differed from other LSD analogs, and its fluorescence was much lower. The authors recommend continued monitoring of sheet products for new LSD analogs.
Forensic toxicology
April 3, 2025
Rie Tanaka, Maiko Kawamura, Michiho Ito et al.
3 citations
Two new LSD analogs, 1S-LSD and 1T-AL-LAD, were identified in sheet products sold in Japan. Their structures were determined using gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and nuclear magnetic resonance. A trace amount of iso-1S-LSD, a C8-epimerization product, was also suggested in one product. This is the first report of these compounds in sheet products in Japan. The metabolic pathways and biological activities of 1S-LSD and 1T-AL-LAD remain unexplored, and further investigation into their possible in vivo deacylation and conversion into LSD or AL-LAD is needed.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
January 1, 2022
Rie Tanaka, Maiko Kawamura, Sakumi Mizutani et al.
3 citations
Three new derivatives of the dissociative drug methoxetamine (MXE) were identified in illegal products in Japan: methoxpropamine (MXPr), methoxisopropamine (MXiPr), and deoxymethoxetamine (DMXE). MXE itself, an analog of the anesthetic ketamine, is already controlled as a narcotic in Japan, and its overdoses have caused health problems. All arylcyclohexylamines, including these new substances, act as antagonists of the NMDA receptor. The findings highlight the ongoing emergence of novel psychoactive substances designed to evade legal controls.
Analytical methods : advancing methods and applications
September 16, 2021
Izumi Morita, Yuki Kiguchi, Hiroyuki Oyama et al.
3 citations
A new test detects psilocin, the main psychoactive compound in hallucinogenic mushrooms, with much higher sensitivity than before. The method first converts psilocin into a heavier chemical form (TBS/Psi), then uses an antibody that binds strongly to this modified compound. The antibody showed 69-fold higher affinity than an earlier version, and the test's detection midpoint was over 100-fold lower than the previous assay, reaching the desired low-picomole sensitivity. When applied to dried Psilocybe cubensis mushroom powder, the test gave positive signals indicating expected psilocin levels, while four edible mushroom species produced no detectable response.
Drug Testing and Analysis
February 18, 2026
Rie Tanaka, Maiko Kawamura, Michiho Ito et al.
Two new lysergic acid diethylamide (LSD) analogs, 1Bz-LSD and 1-TMSBz-LSD, were identified in tablet and paper sheet products sold in Japan. Using gas chromatography-mass spectrometry, liquid chromatography-photodiode array-mass spectrometry, liquid chromatography with hybrid quadrupole time-of-flight mass spectrometry, and nuclear magnetic resonance, the structures of the compounds were determined. 1Bz-LSD was found in a tablet product, and 1-TMSBz-LSD was found in a paper sheet product. This is the first report of these specific analogs being detected in such products in Japan.