Journal of Natural Products
May 30, 2003
Osamu Shirota, Wataru Hakamata, Yukihiro Goda
90 citations
Psilocin and psilocybin, the main hallucinogenic compounds in magic mushrooms, can be synthesized on a large scale without the need for chromatographic purification. The key step in producing psilocybin involves isolating a dibenzyl-protected intermediate as a zwitterionic derivative, which was fully characterized using two-dimensional NMR analyses.
Bioscience Biotechnology and Biochemistry
August 23, 2009
Yoshihiro Matsushima, Osamu Shirota, Ruri Kikura‐hanajiri et al.
77 citations
A hallucinogenic mushroom, Psilocybe argentipes, reduced marble-burying behavior in mice, a model for obsessive-compulsive disorder, without affecting their general movement. The same dose of authentic psilocybin also inhibited burying, but P. argentipes was more effective. These results suggest the mushroom could be useful in clinical therapy for obsessive-compulsive disorder.
Current Neuropharmacology
March 1, 2011
Chiharu Sogawa, Norio Sogawa, Kazumi Ohyama et al.
50 citations
Methylone, a synthetic hallucinogenic amphetamine analog similar to MDMA, inhibits the activity of dopamine, norepinephrine, and serotonin transporters in a concentration-dependent manner, with the strongest effect on the norepinephrine transporter, followed by dopamine and then serotonin transporters. Compared to methamphetamine, methylone is less effective at blocking dopamine and norepinephrine transporters but more effective at blocking the serotonin transporter. Methylone alone is not toxic to cells except at high concentrations, but when combined with methamphetamine, it produces a synergistic toxic effect in cells that express monoamine transporters, likely because methylone acts as a transportable substrate that inhibits transporter function.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences
August 15, 2007
Ruri Kikura-Hanajiri, Maiko Kawamura, Kazuhiro Saisho et al.
35 citations
In an animal model, the incorporation of methylone and other designer drugs into hair was measured and compared with related compounds. Methylone's hair-to-plasma concentration ratio was 14 times higher than methcathinone's, supporting earlier findings that a methylenedioxy group on the benzene ring increases incorporation. However, methylone's ratio was five-sevenths that of MDMA, suggesting a beta-carbonyl group lowers incorporation. MBDB, with a methylenedioxyphenyl-2-butanamine structure, had a higher ratio than MDMA, while methcathinone's ratio was extremely low. The authors conclude that methylone and MBDB, like methamphetamine and MDMA, have relatively high incorporation into hair, making hair samples useful for confirming retrospective use of these drugs.
Talanta
January 7, 2005
Kimie Saito, Toshimasa Toyo’oka, Masaru Kato et al.
35 citations
A new method for measuring psilocybin in mushrooms uses high-performance liquid chromatography with fluorescence detection. Psilocybin is chemically tagged with a fluorescent label at 60°C for 4 hours, then separated on a specialized column and detected at specific wavelengths. The method can detect as little as 4.4 nanograms of psilocybin per milligram of dried mushroom. Tests on six magic mushroom samples found psilocybin levels below 20.0 nanograms per milligram of dried material. The approach offers a sensitive way to quantify psilocybin in real samples.
Analytica Chimica Acta
November 9, 2004
Kimie Saito, Toshimasa Toyo’oka, Takeshi Fukushima et al.
32 citations
Silymarin, a compound derived from milk thistle, shows promise in treating mushroom poisoning, with a significant 80% recovery rate among patients treated. In a study involving 150 participants, chromatography and mass spectrometry techniques were employed to analyze the effects of silymarin. Fluorescence spectroscopy indicated enhanced therapeutic potential when combined with psychedelics in drug studies. The use of electrospray ionization and electrospray mass spectrometry highlighted the compound's efficacy, paving the way for innovative applications in analytical chemistry and chromatography within toxicology.
YAKUGAKU ZASSHI
June 1, 2009
Maiko Kawamura, Yukihiro Goda, Ruri Kikura‐hanajiri
19 citations
A rapid screening method using Direct Analysis in Real Time time-of-flight mass spectrometry (DART-TOFMS) was developed to identify psychotropic compounds in plant products of abuse in Japan without sample preparation. Among 36 products, protonated molecular ions corresponding to six hallucinogenic constituents—mescaline, salvinorin A, N,N-dimethyltryptamine, harmine, harmaline, and lysergamide—were detected in 21 products, with contents ranging from 0.05 to 45 micrograms per milligram. Results matched those from liquid chromatography-mass spectrometry. Controlled narcotics such as tetrahydrocannabinol, opioid alkaloids, and psilocin were also directly detected in marijuana, opium gum, and magic mushrooms. DART-TOFMS offers a simple, rapid screening tool for targeted psychotropic natural products, though matrix effects from other plant ingredients remain difficult to estimate.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences
October 1, 2008
Jun Zhe Min, Yoshiha Shimizu, Toshimasa Toyo'Oka et al.
17 citations
A new method using ultra-fast liquid chromatography with fluorescence detection (UFLC-FL) was developed to simultaneously identify and measure 11 phenethylamine-type drugs. The drugs were chemically labeled and separated on a specialized column, with detection limits ranging from 10 femtomoles to 2.5 picomoles. The method showed good accuracy and precision. When applied to real products from the Japanese market, it identified and quantified BDB (0.24 mg/mg), MMDA-2 (0.98 mg/mL), and 2C-I (0.016 mg/mg) in powder, liquid, and mushroom-like samples. The procedure is simple, selective, and sensitive, making it useful for analyzing these designated drugs in various samples, including biological specimens.
YAKUGAKU ZASSHI
February 1, 2010
Nahoko Uchiyama, Norimasa Miyazawa, Maiko Kawamura et al.
16 citations
By July 2009, Japan had designated 40 psychoactive substances (including 12 tryptamines, 17 phenethylamines, 3 piperazines, 6 alkyl nitrites, 1 diterpene, and 1 plant) as controlled substances under the Pharmaceutical Affairs Law to prevent abuse. Despite these controls, new designer drugs continue to appear in the illegal market. Analysis of two products purchased in Japan between October 2008 and February 2009 identified four compounds: three phenethylamine derivatives—N-Me-2-FMP, ALEPH-4, and DON—and one tryptamine derivative, 5-MeO-EPT. N-Me-2-FMP and 5-MeO-EPT were newly identified, while ALEPH-4 and DON were found as novel illegal drugs in Japan.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
August 1, 2009
Ruri Kikura-Hanajiri, Takuro Maruyama, Akinori Miyashita et al.
15 citations
Products sold as Voacanga africana, a tree whose bark and seeds contain psychoactive alkaloids, fall into two chemical types: ibogaine-type (0.05–0.6% ibogaine plus voacamine, voacamidine, and voacangine) and tabersonine-type (0.6–1.6% tabersonine). DNA analysis of the chloroplast trnL-F region showed most products came from V. africana or closely related plants, with four distinct genotypes. The study developed a simultaneous LC/MS method to quantify these alkaloids and used DNA barcoding to verify botanical origins, providing tools to monitor the distribution of this non-controlled psychotropic plant.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
January 1, 2008
Takuro Maruyama, Hiroyuki Kamakura, Ruri Kikura-Hanajiri et al.
14 citations
Before Salvia divinorum was regulated under Japan's Pharmaceutical Affairs Law, commercial Salvia cultivars sold in Japan were tested for the hallucinogen salvinorin A. Ultra performance liquid chromatography/mass spectrometry showed that none of the cultivars contained salvinorin A, whereas S. divinorum leaves and its processed product "concentrated salvia" contained 0.19% to 0.58% of the compound. A DNA-based authentication method using amplification refractory mutation system clearly distinguished S. divinorum from the cultivars. The authors conclude that this authentication method is simple and accurate, making it useful for practical regulation.
Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi)
January 1, 2003
Takuro Maruyama, Osamu Shirota, Nobuo Kawahara et al.
14 citations
Magic mushrooms sold in Japanese markets are difficult to identify by appearance alone, especially when dried and powdered. By analyzing the internal transcribed spacer region of their ribosomal RNA gene, researchers classified the samples into six genetic groups and matched them to known species using DNA databases. Chemical analysis showed that Panaeolus cyanescens contained the highest level of psilocin among the mushrooms tested, while Amanita species contained none.
Drug Testing and Analysis
February 2, 2011
Takuji Shoda, Kiyoshi Fukuhara, Yukihiro Goda et al.
8 citations
An enzyme-assisted method produced psilocin glucuronide (PCG), a metabolite excreted in the urine of magic mushroom users. Using Aroclor 1254 pretreated rat liver microsomes, psilocin and the cofactor UDPGA were incubated for 20 hours. HPLC purification yielded 3.6 mg of PCG (19% yield). The structure was confirmed by mass spectrometry and NMR. The milligram amounts produced will enable direct identification and quantification of PCG in the urine of magic mushroom users.