Hypothetical Psilocybin extraction?

[Brennendes Wasser]

So I understand there is still no convenient route to isolate crystalline Psilocybin / Psilocin. So that's why this route here will probably also fail miserably. But I just had it in my mind and I currently cant see any dead end which would prevent this one to at least give a reasonably pure product:

1. Acidic cook of mushrooms in water at pH 3 (hopefully kills enzymes before they destroy alkaloids)
At this point you would probably convert all Psilocybin to Psilocin, which makes things easier

2. Adjust pH to 11 with sodium carbonate
At this point there are no zwitterions anymore and everything is freebased. The only ions could be tertiary amines (Bufotenidin-type in yellow amanita e.g.) which will not make it further here.

3. Defat with xylene
This will remove any non-phenolic alkaloid and also all fats. I guess psilocybin will not dissolve at RT, as (the pretty similar) Bufotenin needs boiling xylene.

4. Extract Psilocin with solvent of choice and evaporate

5. If that would indeed be pure enough maybe it can be recrystallized in boiling xylene like Bufotenin.



So is there any pitfall? When not having Psilocybin / Zwitterions I guess it makes stuff easier and step 3. would probably take away everything except Psilocin and it's siblings (Norspilocin, 4-OH-Tryptamin). Maybe those last 2 alone would prevent it from crystallizing, but except that it would be already fairly isolated if there is no bad surprise?

 

[Loveall]

I think psilocin will be destroyed in step 2 unfortunately.

 

[Loveall]

Here is another approach/idea.

So instead of using sodium carbonate in your step #2, use sodium bicarbonate to get to the isoelectric point for psilocin, skip the defat, then pull with EA and salt with an organic acid soluble in EA.

 

[Brennendes Wasser]

Ok that also looks interesting. And the clouding went into crystals or was it something not easy to be scraped up?

If I ever come across mushrooms again maybe I might try with that defat. I guess there will be pretty non-polar liquids that dont pull psilocin/-cybin. Probably a difficoulty of no real crystallization is having a too wild mixture and maybe the high polarity of psilocin could be exploited here.