[Ginkgo]

Hello,

I just found this forum, and looking forward to participate in the discussions. I am currently working on a theoretical tek for a crude extract of muscimol from Amanita muscaria. I've read the rules, and want to note that this is not an illicit drug, so I think this subject should be allowed here. It's an interesting subject from an organic chemistry perspective.

In a dream, well-dried Amanita muscaria were allowed to simmer in plain water. Both ibotenic acid and muscimol, the interesting compounds in this procedure, is water soluble. The heat should decarboxylate all the ibotenic acid into muscimol. The temperature was kept at max 60°C to prevent breakdown of muscimol, as it has a boiling point of 70°C. After an hour the mushrooms were filtered of, and the water was kept at a constant temperature of 60°C with a fan next to it for over two days, in order to reduce the solution to a resin.

Now, this resin is far from pure, and therefore I'm trying to find an easy way to clean it further. Muscimol has a pKa of 4.8, which means that at pH 2-3, 99.8-98.4% of the muscimol should be in salt form. By using 35% acetic acid, which have a pH of 2, the solution should be at pH ~2-3. Then one could pull with a non-polar, maybe heptane or perhaps d-limonene, which should pull the muscimol acetate. This could be basified and further cleaned if needed. Does this procedure seem correct? Will muscimol in fact become an acetate, and will it be pulled by a non-polar?

Perhaps I'm going at this the wrong way, maybe I should find a solvent that muscimol isn't soluble in, that will remove much of the other gunk? Maybe you have some other thoughts or theories? Please do share everything that comes to mind! Thanks in advance!

Additional bits of information: Muscimol is an extremely polar compound with a XLogP3 of -1.4. Muscimol is very soluble in water and methanol, slightly soluble in ethanol, DMSO and DMF.

[Arkcon]

We've discussed this molecule before: http://www.chemicalforums.com/index.php?topic=25596.0  There was a link in that old thread to synthesis, but its been lost now.  If you have a legitimate research application, you can probably purchase it.  Pricy, but that's the cost of research.  In general, your first plan, to extract pure compound is a better choice than find a solvent for "all other unknown" impurities.

[Ginkgo]

Thank you for your answer. This is just a 'hobby' project of mine, I love all kind of psychoactive plants and mushrooms, and extracting their compounds. So I'm not interested in buying muscimol, which is rather pricy anyway. I'm looking to do an extract that yield a product that isn't necessarily pure, but with less by-products than the resin I now have from water extract.

It would be great if someone could help me out here.

[Fluorine]

Hello Ginko,

This was discussed over at the Shroomery - I'm sure more than once. I couldn't find anything from a quick skim of J. Ott's Pharmacotheon regarding isolation but I remember seeing something in one of my books. I'll check when I get a chance. In the meantime here's some reading materia to give you a perspective of what the other constituents may be.

- A novel constituent of Amanita Muscaria, K. Bowden and A.O. Dryadale (1965)
- Amanita muscaria: chemistry, biology, toxicology, and ethnomycology
- Wirkstoffe aus amanita muscaria: ibotensaeure und muscazon (German), see Shroomery for translated excerpt
- The History and Chemistry of Muscarine

Remember, even though A. musciara and pantherina may have no recorded history of deaths it does not guarantee the same safety with the extracts. Be very careful.

[Ginkgo]

Thanks a lot for the answer! I will take a look at that reading material. I see that muscimol is a zwitterion, and therefore already in a salt form, does that mean that it isn't possible to make muscimol acetate by mixing muscimol with acetic acid?