Citric Acid and Mushrooms

[i_amnotted]

Hey I just ran into this on wikipedia and wanted to see if anybody could find me a study or some type of citation for it:

It is, however, true that mixing a juice containing citric acid (lemon juice, orange juice) may help extract the alkaloids from other drugs such as psychedelic mushrooms, or san pedro cactus (desert cucumber). When making mushroom tea, the addition of citric acid will help make the psilocybin a salt (psilocybin citrate). Salt forms of alkaloids are more soluble in water.

Link

 

[i_amnotted]

Can I get this moved to ADD, unless someone has something to add?

 

[Xorkoth]

Surely

 

[Jabberwocky]

Its part of the acid-base extraction technique (ie the acid part). The molecule is in its freebase form in the fungus matter and you 'unhook' that molecule from the freebase and add the citrate. Then you extract it with a solvent and then add a base (NaOH) to turn it back into a freebase, then add some more solvent and extract that by evaporation.

I think turning it into a citrate will change the choice of solvents you will have, but not sure, never done it that way (doesn't vinegar add a citrate to compounds (question mark)).

But, why would you do this with mushrooms(question mark). Just eat them.

 

[Coolio]

Vinegar is acetic acid, so it forms an acetate salt.

 

[vecktor]

I would be suprised if psilocybin was present as freebase in the mushroom, as it takes a pretty high pH to liberate it and the pH of the fungal cells is likely to always be in the range of 6-7.5 simply because most enzymes malfunction outside these limits.
the situation with psilocin and water solubility is more complex than say DMT because it can form a zwitterion. so that it is probably the case that psilocybin is most soluble in a very weakly acidic solution or where both the amine and the phosphate are charged, more acid and eventually the phosphate will be non charged the amine will still be charged but the more hydrophili charged groups the higher the solubility.
extraction of psilocybin and psilocin for quantitative analysis usually doesn't use acid just methanol. distilled water should be fine too without addition of acid.

V