Forensic science international
December 17, 2003
Kenji Tsujikawa, Tatsuyuki Kanamori, Yuko Iwata et al.
79 citations
Hallucinogenic mushrooms circulating in Japan were analyzed using scanning electron microscopy and high-performance liquid chromatography. Psilocybe cubensis contained psilocin (0.14–0.42%) and psilocybin (0.37–1.30%) in the whole mushroom, with higher concentrations in the cap than the stem. Copelandia species contained psilocin (0.43–0.76%) and psilocybin (0.08–0.22%) in the whole mushroom, again with more alkaloid in the cap. Psilocybe cubensis is psilocybin-rich, while Copelandia is psilocin-rich. The combination of SEM and optical microscopy was effective for observing characteristic fungal tissues such as basidiomycetes, spores, cystidia, and basidia.
Journal of analytical toxicology
March 1, 2002
Tatsuyuki Kanamori, Hiroyuki Inoue, Yuko Iwata et al.
61 citations
In rats, the psychoactive compound 2C-B is broken down into at least six distinct breakdown products through two main metabolic pathways. One pathway converts 2C-B into an aldehyde, which is then further processed into an alcohol and a carboxylic acid. The other pathway produces metabolites where a methyl group is removed from either the 2- or 5-position of the molecule, followed by acetylation of the amino group. These findings indicate that the body metabolizes 2C-B through multiple chemical changes, resulting in a variety of metabolites that are excreted in urine.
Journal of forensic sciences
January 1, 2013
Tatsuyuki Kanamori, Kyoko Nagasawa, Kenji Kuwayama et al.
20 citations
The main breakdown product of the hallucinogenic drug 2C-B in human urine is 4-bromo-2,5-dimethoxyphenylacetic acid, accounting for 73% of detected metabolites. Two other metabolites, 4-bromo-2-hydroxy-5-methoxyphenylacetic acid and 4-bromo-2,5-dimethoxyphenylethyl alcohol, made up 13% and 4.5% respectively. In contrast, the primary metabolites reported in rat urine were different compounds and appeared only in small amounts in humans, indicating species-specific differences in how 2C-B is processed. The most abundant human metabolite likely forms through deamination by monoamine oxidase (MAO) followed by oxidation, suggesting MAO plays a crucial role in human 2C-B metabolism.
Xenobiotica
November 3, 2008
Tatsuyuki Kanamori, Kenji Kuwayama, Kenji Tsujikawa et al.
11 citations
Alpha-methyltryptamine (AMT), a psychoactive tryptamine analogue, is metabolized in rats into at least four distinct compounds. After oral administration of 10 mg/kg to male Wistar rats, urine collected over 24 hours was enzymatically hydrolyzed, extracted, and analyzed by gas chromatography/mass spectrometry. The detected metabolites were 2-oxo-AMT, 6-hydroxy-AMT, 7-hydroxy-AMT, and 1'-hydroxy-AMT. These findings identify specific metabolic pathways for AMT, which may inform understanding of its pharmacological effects and duration of action.
Journal of forensic sciences
September 1, 2011
Tatsuyuki Kanamori, Kenji Kuwayama, Kenji Tsujikawa et al.
10 citations
After oral administration to rats, the drug 2C-I is broken down into several metabolites through O-demethylation, N-acetylation, and deamination followed by oxidation to carboxylic acid. Five of these metabolites were synthesized in the lab and identified using gas chromatography/mass spectrometry. The findings will aid forensic analysis of 2C-I and its metabolites in biological samples.
Forensic toxicology
January 1, 2024
Yuki Okada, Kazuki Ueno, Noriko Nishiwaki et al.
8 citations
Blotter paper labeled "1D-LSD" was seized and analyzed. Although the label suggested the compound was 1-(1,2-dimethylcyclobutane-1-carbonyl)-LSD, chemical analysis using GC/MS, LC/MS, high-resolution mass spectrometry, and NMR spectroscopy revealed the actual substance to be 1-(thiophene-2-carbonyl)-LSD, a different lysergamide. This is the first reported seizure of this compound and the first LSD analog where an aromatic carboxylic acid was condensed to LSD. The finding highlights that drug-infused blotter paper may contain substances inconsistent with their labeling, and authorities should remain vigilant for newly emerging lysergamides.
Drug testing and analysis
April 1, 2025
Yuki Okada, Hiroki Segawa, Tadashi Yamamuro et al.
6 citations
Since late 2023, a substance sold as "1D-AL-LAD" has appeared online, but chemical analysis suggests it is actually 1-(2-thienoyl)-6-allyl-nor-LSD (1T-AL-LAD), not the claimed 1-(1,2-dimethylcyclobutanecarbonyl)-6-allyl-nor-LSD. To aid forensic identification, researchers synthesized 1T-AL-LAD and characterized it with nuclear magnetic resonance spectroscopy, Fourier transform-infrared spectroscopy, liquid chromatography/high-resolution mass spectrometry, and gas chromatography/mass spectrometry. The compound was easily distinguished from previously reported lysergamides. Detectability differences in GC/MS and fragmentation patterns in LC/HRMS were noted and explained. This information will help identify the substance in seized materials should it emerge on the market.
Journal of forensic sciences
March 1, 2017
Tatsuyuki Kanamori, Tadashi Yamamuro, Kenji Kuwayama et al.
4 citations
Two glucuronic acid-conjugated metabolites of the psychoactive phenethylamine 2C-B were chemically synthesized for the first time, and a method to analyze them in urine was developed. The β-D-glucuronide of 4-bromo-2,5-dimethoxyphenylethylalcohol was synthesized using a glucuronyl donor and a Lewis acid catalyst; the β-D-glucuronide of 4-bromo-2,5-dimethoxyphenylacetic acid was produced by condensation followed by catalytic hydrogenation. Direct liquid chromatography/mass spectrometry of diluted urine allowed qualitative and semiquantitative evaluation of these metabolites. The simple method is expected to aid studies of 2C-B's metabolic fate.
Biological & pharmaceutical bulletin
January 1, 2016
Tatsuyuki Kanamori, Kenji Kuwayama, Kenji Tsujikawa et al.
1 citation
In rats, the urinary metabolic profiles of three hallucinogenic compounds—2C-T-2, 2C-T-4, and 2C-T-7—differed after oral administration. The major metabolite for 2C-T-7 was a β-hydroxylated-N-acetylated-sulfoxide, while for 2C-T-2 it was the N-acetylated-sulfoxide, and for 2C-T-4 the S-methylated-N-acetylated-sulfoxide predominated. These distinct metabolic patterns suggest that each analog undergoes unique biotransformation pathways.