Muscimol decomposition?

[Ma_Huang]

Any muscimol chemists listening? My problem relates to the fact that my boiled-up fresh Amanita brews seem to be losing potency at a rapid rate, like within one week. The brews are mildly acidic courtesy of vinegar additions, and I guess some sort of oxidation (presumably of the hydroxyl) is always a possibility. Light doesn't seem to be implicated. Polymerisation or cyclisation could also be on the agenda. Anyone know whether commercial muscimol comes packaged with a stabiliser?

The next move will be to try an anti-oxidant like metabisulphite as a preservative, but I wanted to check with the assembled first. No, I don't want to go the dried shroom storage route, because I find that also reduces potency dramatically.

And if anyone has some tips for eliminating the nauseating substance(s) from fresh Amanita brews, that would be absolutely marvelous too

[Aurelius]

try vacuum sealing the package, adding a small portion of citric acid as an antioxidant, and keeping in the refrigerator for lower temperatures.

[Vitus_Verdegast]

Can't say for sure, but I always thought that the fresh Amanita muscaria's contained chiefly ibotenic acid (an amino acid), which is rapidly decomposed (decarboxylised) when drying of the mushroom, into muscimol. Perhaps that's why it decreases in potency?


Ibotenic acid is a potentiator of narcosis, it exhibits potent neuroexcitatory activity:
Johnston et al, Nature 248, 804 (1974).
Use as experimental neurotoxic agent:  A. Contestabile et al., Experientia 40, 524 (1984).

Patent BE665249

Patent US3459862

Muscimol is known as a potent CNS depressant and GABA agonist,
Theobald et al., Arzneimittel-Forsch. 18, 311 (1968) 
F. V. DeFeudis, Neurochem. Res. 5, 1047-1068 (1980)

Patent US3242190

Patent US3397209

[hest]

Mucimol is the fun part. Usual i dry my amantia, then all the ibotenic acid decarboxylate into mucimol wich is 10 times more potent.

[Aurelius]

Ibotenic acid converts to muscimole, true, but this should increase the potency of the sample.  (as muscimole is more active)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/muscimole.html

https://www.thevespiary.org/rhodium/Rhodium/chemistry/psychedelicchemistry/chapter6.html

The degradation of the muscimole at this point is what is probably causing the problems with decrease in potency.  Of course, there is the possibility that potency is decreased b/c in the orginal sample the two compounds potentiated each other and that is now not a possibility b/c there is *only muscimole.  *most of the ibotenic acid has decomposed to muscimole.

[Ma_Huang]

The brew gets at least 1 hour's boil under acidic conditions, so it is unlikely that there was too much ibotenic acid left in the first place. And the effects are definitely a strong downer, not excitatory. (Not the slightest shred of a hallucination, either). My test monkey is physically incapable of consuming enough of the dried shroom extract to get off.