Psilocybin chemistry question

[redeadnixon]

I was reading a thread over on drugs-forum about extraction of alkaloids from psilocybe mushrooms,
and my monkey got an idea..
He was wondering if psilocybin is a phosphate salt of psilocin? (Or is it an altogether differnt compound?)
If it's a salt, technically speaking doesn't this mean that psilocybin could be formed from psilocin via addition of phosphoric acid to an extracted solution of both alkaloids; without destroying the psilocybin.

The reason the monkey asks is that he was thinking of ways to improve shelf life of psilocybin,
He would also like to try fumarate salts of the alkaloids as used in spice extraction..

http://www.drugs-forum.com/forum/showthread.php?t=3768 - thread

 

[SnozzleBerry]

You can use acidic solutions to convert psilocybin to psilocin. The issue with extracted psilocin salt or freebase is the fact that it will oxidize very rapidly. It is unlikely to greatly improve the shelf life of the psilocin unless you store it in a tincture of sorts. I currently have some psilocin fb sitting in a small jar of naptha in my freezer. I have no intention of drying it until i'm about to bioassay it, as everything I've heard and talked to others about indicates that it will oxidize rapidly and lose potency. You could probably perform an acidified alcohol extraction and then reduce it to have a tincture. I would assume you could evap that tincture all the way to yield salt xtals as well.

 

[benzyme]

i'll answer this in a few, gotta switch OS's....

 

[benzyme]

one would probably think the phosphate would be hydrolytically cleaved at high/low pH
but by the calculations, at species 2 there's net -2 charge. 3 and 4 are pI species (the blue line overlaps the red line), species 5 has a net -1 charge, and species 1 has a net +1 charge.

(taken from a post i made at the shroomery)

i'd try to keep the pH in the range of the peak of the blue line, where it exists as a zwitterion (no net charge).
the other species may be inactive.

 

[redeadnixon]

So drawing from both of your replies + the df thread,
1) Acidify a methanol or ethanol solution to ~pH 4.5 with citric or fumaric
2) Add this to ground up shroom material and heat to 40-50C for half an hour with stirring.
3) Repeat 1+2 twice, then reduce liquid and store or evapourate fully.

Much thanks,
Peace.

 

[Global]

Alternatively, your body makes a very good "chemistry lab" to convert psilocybin to psilocin, as when you ingest psilocybin your body metabolizes the majority of it to psilocin. Also, as mentioned above, psilocin has a very short half life, and is not very stable.

 

[redeadnixon]

Alternatively, your body makes a very good "chemistry lab" to convert psilocybin to psilocin, as when you ingest psilocybin your body metabolizes the majority of it to psilocin. Also, as mentioned above, psilocin has a very short half life, and is not very stable.

My original question was about converting psilocin to psilocybin for increased shelf life,
As benzyme said, it does not work at increased/decreased pH, so cannot be converted via addition of phosphoric acid as i asked..
I must not have made myself clear, my fault.