SciCombinator

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Concept: Muscimol

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: Psychoactive drugs of fungal origin, psilocin, ibotenic acid, and muscimol among them have been proposed for recreational use and popularized since the 1960s, XX century. Despite their well-documented neurotoxicity, they reached reputation of being safe and nonaddictive. Scientific efforts to find any medical application for these hallucinogens in psychiatry, psychotherapy, and even for religious rituals support are highly controversial. Even if they show any healing potential, their usage in psychotherapy is in some cases inadequate and may additionally harm seriously suffering patients. Hallucinogens are thought to reduce cognitive functions. However, in case of indolealkylamines, such as psilocin, some recent findings suggest their ability to improve perception and mental skills, what would motivate the consumption of “magic mushrooms.” The present article offers an opportunity to find out what are the main symptoms of intoxication with mushrooms containing psilocybin/psilocin, muscimol, and ibotenic acid. The progress in analytical methods for detection of them in fungal material, food, and body fluids is reviewed. Findings on the mechanisms of their biologic activity are summarized. Additionally, therapeutic potential of these fungal psychoactive compounds and health risk associated with their abuse are discussed.

Concepts: Drug, Cognition, Psychoactive drug, Recreational drug use, Psychedelic drug, Amanita muscaria, Psilocybin, Muscimol

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In this article we report results of combined theoretical and experimental NMR studies on muscimol, the bioactive alkaloid from fly agaric mushroom (Amanita muscaria). The assignment of (1)H and (13)C NMR spectra of muscimol in DMSO-d6 was supported by additional two-dimensional heteronuclear correlated spectra (2D NMR) and gauge independent atomic orbital (GIAO) NMR calculations using density functional theory (DFT). The effect of solvent in theoretical calculations was included via polarized continuum model (PCM) and the hybrid three-parameter B3LYP density functional in combination with 6-311++G(3df,2pd) basis set enabled calculation of reliable structures of non-ionized (neutral) molecule and its NH and zwitterionic forms in the gas phase, chloroform, DMSO and water. GIAO NMR calculations, using equilibrium and rovibrationally averaged geometry, at B3LYP/6-31G* and B3LYP/aug-cc-pVTZ-J levels of theory provided muscimol nuclear magnetic shieldings. The theoretical proton and carbon chemical shifts were critically compared with experimental NMR spectra measured in DMSO. Our results provide useful information on its structure in solution. We believe that such data could improve the understanding of basic features of muscimol at atomistic level and provide another tool in studies related to GABA analogs.

Concepts: Fungus, Chemistry, Computational chemistry, Density functional theory, Quantum chemistry, Agaricales, Amanita muscaria, Muscimol

0

Fly control is necessary for maintaining good hygiene on farms. Because organic farmers are skeptical about chemical pesticides, alternative fly control remedies are being considered. Amanita muscaria is a widespread fungus that contains ibotenic acid and muscimol. This fungus has been used to catch flies for centuries, but traditional recipes are poorly described, documented and characterized.

Concepts: Fungus, Pesticide, Amanita muscaria, Amanita, Mushroom poisoning, Muscimol, Ibotenic acid, Muscazone

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Red fly agaric poisoning is rare. It can be consumed for suicidal purposes or its psychedelic effect. The paper describes the case of a young men, who fell into a coma after ingestion of the red toadstools. Quick identification of the poison, early use of gastric lavage and symptomatic treatment resulted in regression of symptoms and lead to the patient’s discharge from the hospital on the third day after intoxication. Authors discussing the poisonous alkaloids contained in the red toadtools: ibotenic acid, muscimol, muscasone and muscarine and theirs properties, responsible for the symptoms of intoxication.

Concepts: Fungus, Poison, Agaricales, Muscarine, Amanita muscaria, Gastric lavage, Muscimol, Ibotenic acid

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A. muscaria contains more excitatory ibotenic acid and less depressant muscimol compared to A. pantherina. In this study A. muscaria poisoned patients were more often confused (26/32, p=0.01) and agitated (20/32, p=0.03) compared to those poisoned with A. pantherina (8/17 and 5/17). Patients poisoned with A. pantherina were more commonly comatose (5/17) compared to those poisoned with A. muscaria (2/32) (p=0.03). In conclusion, the so-called ibotenic or pantherina-muscaria syndrome might be divided into two subtypes.

Concepts: Amanita muscaria, Amanita, Mushroom poisoning, Muscimol, Ibotenic acid, Muscazone

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The CE-ESI-MS/MS method for the identification, separation and determination of mushroom toxins, namely ibotenic acid, muscimol and muscarine, was developed. It proved to be sensitive and thus useful for the real sample analysis with omitting the labor and time consuming pretreatment step. The CE-ESI-MS/MS method was applied on the spiked human urine. The analytical characteristics of the proposed method, such as limits of detection, linearity and repeatability of the peak area and the migration time, were evaluated. The RSD of the migration time and peak area were from 0.93% to 1.60% and from 2.96% to 3.42%, respectively. The obtained LOD values were at the nanomolar concentration level, therefore the developed method is sufficient for the determination and quantification of studied toxins in human urine after mushroom intoxication.

Concepts: Ammonia, Mass spectrometry, Gel electrophoresis, Electrophoresis, Affinity electrophoresis, Tandem mass spectrometry, Amanita muscaria, Muscimol