Ibotenic Acid Decarboxylation to Muscimol: Dramatic Solvent and Radiolytic Rate Acceleration

Filer, Crist N.; Lacy, James M.; Peng, C. T.

doi:10.1081/scc-200051704

Cited by 13 publications

(7 citation statements)

References 5 publications

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“…180 Curiously, pure ibotenic acid is extremely unstable in solution and rapidly decomposes to muscimol without involvement of enzymes. 197 The addition of dimethyl sulfoxide to the water solution containing ibotenic acid reduces its stability. It was established that spontaneous decarboxylation of ibotenic acid is significantly accelerated in a mixture of dimethyl sulfoxide and 3 H 2 O or D 2 O.…”

Section: Methods Of Extractionmentioning

confidence: 99%

“…It was established that spontaneous decarboxylation of ibotenic acid is significantly accelerated in a mixture of dimethyl sulfoxide and 3 H 2 O or D 2 O. 197 Ibotenic acid and muscimol were determined in fresh, frozen, or freeze-dried mushrooms. [183][184][185] The following solvents are usually applied for extraction of ibotenic acid and muscimol:75% methanol in water or 50%-70% ethanol in water.…”

Section: Methods Of Extractionmentioning

confidence: 99%

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Fungal Hallucinogens Psilocin, Ibotenic Acid, and Muscimol

Stebelska

2013

Therapeutic Drug Monitoring

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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.

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Section: Methods Of Extractionmentioning

confidence: 99%

Section: Methods Of Extractionmentioning

confidence: 99%

Fungal Hallucinogens Psilocin, Ibotenic Acid, and Muscimol

Stebelska

2013

Therapeutic Drug Monitoring

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“…Interestingly, they discovered that low pH and extreme heating were required to promote any appreciable decarboxylation of ibotenic acid to muscimol in water alone. This unexpected result prompted our reinvestigation into the rate acceleration role of DMSO in this mild decarboxylation‐tritiation . Over 1400 published studies using [ 3 H]muscimol have documented the marked utility of this radioligand in the GABA receptor area …”

Section: Isoxazole and Pyrrole Alkaloidsmentioning

confidence: 99%

“…This unexpected result prompted our reinvestigation into the rate acceleration role of DMSO in this mild decarboxylation-tritiation. 108 Over 1400 published studies using [ 3 H]muscimol have documented the marked utility of this radioligand in the GABA receptor area. 109,110 Ryanodine is a pyrrole-containing alkaloid isolated from the bark of Ryania speciosa and has pronounced affinity for a class of intracellular calcium channels termed ryanodine receptors.…”

Section: Isoxazole and Pyrrole Alkaloidsmentioning

confidence: 99%

Tritium-labelled alkaloids: Synthesis and applications

Filer

2017

J. Label Compd. Radiopharm

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“…A proton‐decoupled tritium NMR (D 2 O) of 6 further revealed by a sharp resonance at 4.13 ppm that tritium had indeed been regiospecifically installed exclusively on the methylene group, the very site of decarboxylation. Later, we ourselves reinvestigated the process of both the deuteration and tritiation of 4 by this intriguing reaction, drawing conclusions as to the rate accelerating role of DMSO 17. Radioligand 6 has been valuably employed in many hundreds of receptor binding studies18–20 including photoaffinity labelling of the GABA A receptor 21–23.…”

Section: Gaba Receptor Agonistsmentioning

confidence: 99%