Bioactive Alkaloids of Hallucinogenic Mushrooms

Wieczorek, Piotr; Witkowska, Danuta; Jasicka-Misiak, Izabela; Poliwoda, Anna; Oterman, Milena; Zielińska, Katarzyna

doi:10.1016/b978-0-444-63462-7.00005-1

Cited by 18 publications

(14 citation statements)

References 118 publications

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“…Muscimol structure in the gas phase and solution. M A N U S C R I P T ACCEPTED MANUSCRIPT 8 We will start our discussion with a presentation of selected B3LYP/6-311++G(3df,2pd) calculated structural parameters of the three studied molecular forms of muscimol in the gas phase and solution (Table 1). To show the numerical impact of solvent polarity we also performed structural optimization in three solvents including chloroform.…”

Section: Resultsmentioning

confidence: 99%

Theoretical and experimental NMR studies on muscimol from fly agaric mushroom (Amanita muscaria)

Kupka

Wieczorek

2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Section: Resultsmentioning

confidence: 99%

Theoretical and experimental NMR studies on muscimol from fly agaric mushroom (Amanita muscaria)

Kupka

Wieczorek

2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…This technique was also used to identify unknown compounds in natural products, e.g. herbs, natural medicines and polyphenols [14][15][16], drugs [17][18][19][20], and enzymology [21,22]. Carbohydrates and other related compounds, which are difficult to detect with high sensitivity using other analytical instruments, have been subjected to LC-MS analysis [13,[23][24][25][26][27].…”

Section: Applications Of Lc-msmentioning

confidence: 99%

Hydrophilic Interaction Liquid Chromatography for LC-MS

Hanai¹

2018

Mass Spectrom Purif Tech

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The retention mechanisms in hydrophilic interaction liquid chromatography (HILIC) are quantitatively described in in silico analysis. Among a variety of polar bonded-phase silica gels, hexylamine-bonded silica gel is stable and can be used in both aqueous HILIC and ion-exchange liquid chromatography with high reproducibility. Hexynyl and phenylhexyl bonded silica gels are also used in HILIC with high reproducibility. The retention mechanisms in aqueous hydrophilic and non-aqueous hydrophilic (normal-phase) liquid chromatography are similar. Both hydrogenbonding and weak electrostatic interaction contributes to retention. Furthermore, strong electrostatic interaction is dominant in ion-exchange liquid chromatography. A suitable liquid chromatographic system for liquid chromatography (LC)-mass spectrophotometer (MS) is proposed.

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“…Generally, 100 g of dried Amanita muscaria contains about 150 mg of MUS and 30 mg of IBO; therefore, 10 g of dried mushrooms can evoke a psychedelic effect. The toxicity of MUS-LD 50 values in mice is 2.5 mg/kg [4]. Their psychotropic properties result from their ability to activate the N-methyl-d-aspartate glutamate and GABA receptors [5].…”

Section: Introductionmentioning

confidence: 99%

Direct Analysis of Psilocin and Muscimol in Urine Samples Using Single Drop Microextraction Technique In-Line with Capillary Electrophoresis

2020

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The fully automated system of single drop microextraction coupled with capillary electrophoresis (SDME-CE) was developed for in-line preconcentration and determination of muscimol (MUS) and psilocin (PSC) from urine samples. Those two analytes are characteristic active metabolites of Amanita and Psilocybe mushrooms, evoking visual and auditory hallucinations. Study analytes were selectively extracted from the donor phase (urine samples, pH 4) into the organic phase (a drop of octanol layer), and re-extracted to the acidic acceptor (background electrolyte, BGE), consisting of 25 mM phosphate buffer (pH 3). The optimized conditions for the extraction procedure of a 200 µL urine sample allowed us to obtain more than a 170-fold enrichment effect. The calibration curves were linear in the range of 0.05–50 mg L−1, with the correlation coefficients from 0.9911 to 0.9992. The limit of detections was determined by spiking blank urine samples with appropriate standards, i.e., 0.004 mg L−1 for PSC and 0.016 mg L−1 for MUS, respectively. The limits of quantification varied from 0.014 mg L−1 for PSC and 0.045 mg L−1 for MUS. The developed method practically eliminated the sample clean-up step, which was limited only to simple dilution (1:1, v/v) and pH adjustment.

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Bioactive Alkaloids of Hallucinogenic Mushrooms

Cited by 18 publications

References 118 publications

Theoretical and experimental NMR studies on muscimol from fly agaric mushroom (Amanita muscaria)

Theoretical and experimental NMR studies on muscimol from fly agaric mushroom (Amanita muscaria)

Hydrophilic Interaction Liquid Chromatography for LC-MS

Direct Analysis of Psilocin and Muscimol in Urine Samples Using Single Drop Microextraction Technique In-Line with Capillary Electrophoresis

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