Sep of 4hyrdoxylated tryp.

[meme]

OK, 4hodmt, 4hodet, 4hodpt, 4hodipt, 4hoamt, ect. can all be created by p.cubensis through the addition of the proper precursor into the substrate of the mushroom.  The problem lies in the seperation of these, as they are all very polar in the freebase.

Since polar molecules align to an electrical field, wouldn't get electrophoresis be ideal for seperating these?

OK, more specific questions.  All the references I've found so far online seem pre-occupied with isolation of proteins, but I remember from Bio I that the size of the molecule determines the type of gel matrix used.  Any ideas on a gel applicable for use with molecules of this size?

Also, how much electricity is enough/too much? SWIM is cheep and poor . . .

Also, can anyone think of an indicator/dye that might be used to seperate these?  Or would one simply have to do tests (which would imply that chromatography might be a better choice).
Today is opposites day.  Everything I say, I mean the opposite.

[Lilienthal]

> The problem lies in the seperation of these, as they are all very polar in the freebase.

No, the hydroxys are very unpolar. The phosphorylated analogs are more polar and more difficult to isolate.

> Since polar molecules align to an electrical field, wouldn't get electrophoresis be ideal for seperating these?

Only charged molecules like the psilocybin analogs are moving in an electrical field. Higher alkyl analogs of psilocybin can be separated on silica very easily. But yes, it is indeed possible to isolate psylocybin by gel electrophoresis.

[terbium]

OK, 4hodmt, 4hodet, 4hodpt, 4hodipt, 4hoamt, ect. can all be created by p.cubensis through the addition of the proper precursor into the substrate of the mushroom.
You mean by adding the non-hydroxylated tryptamine and having the fungus do the hydroxylation? Has this pathway ever been demonstrated, or is it pure speculation?

The problem lies in the seperation of these, as they are all very polar in the freebase.
Separation from what? If from each other, why not just add one substrate at a time?

[meme]

From Tihkal
Some fascinating studies have been done in Germany where the metabolically active mycelium of some Psilocybe species have been administered diethyltryptamine as a potential diet component. Normally, this mushroom species dutifully converts N,N-dimethyltryptamine (DMT) to psilocin, by introducing a 4-hydroxyl group into the molecule by something that is probably called an indole 4-hydroxylase by the biochemists. You put DMT in, and you get 4-hydroxy-DMT out, and this is psilocin. Maybe if you put Mickey Mouse in, you would get 4-hydroxy-Mickey Mouse out. It is as if the mushroom psyche didn't really care what it was working with, it was simply compelled to do its sacred duty to 4-hydroxylate any tryptamine it came across. It was observed that if you put N,N-diethyltryptamine (DET, not a material found in nature) into the growing process, the dutiful and ignorant enzymes would hydroxylate it to 4-hydroxy-N,N-diethyltryptamine (4-HO-DET) a potent drug also not known in nature. This is the title drug of this commentary. What a beautiful burr to thrust into the natural versus synthetic controversy. If a plant (a mushroom mycelium in this case) is given a man-made chemical, and this plant converts it, using its natural capabilities, into a product that had never before been known in nature, is that product natural? What is natural? This is the stuff of many long and pointless essays.

If you want, I can proabably ind some more documentation


Today is opposites day.  Everything I say, I mean the opposite.

[meme]

--No, the hydroxys are very unpolar. The phosphorylated analogs are more polar and more difficult to isolate.

OK, I'm not sure why I didn't see this before, that the C-O cancels out the O-H.  So if SWIM was to extract using an acid, which would convert psilocybin to psilocin, then an A/B would work, albeit yielding psillocin, and not psilocybin . . . OK, I'm trying to catch up to the race.

So I guess all those shroomers making tea are simply consuming (mostly) psillocybin, and not psillocin.  That's kind of interesting, if one considers the popular thoughts of the two methods of administration, oral and tea.

On a slightly different note, does anyone know what psillocin oxidises to?

Today is opposites day.  Everything I say, I mean the opposite.

[Lilienthal]

Simply dissolving in acid will not hydrolyze psilocybin. But It will protonate psilocin to it's salt whereby making it highly polar.

[Lilienthal]

And if you use the search engine you will find answers for most of your questions.

[meme]

Thank you, Lilenthal, you have been quite helpful.
The acid thing was a mid-remeberence (what a cool word) of:

Journal of Basic Microbiology
Vol 34, 1994; 17-22
by Jochen Gartz



--------------------------------------------------------------------------------

The occurence and extraction of indole derivatives in six species from four genera of higher fungi were investigated. By using pure methanol for extraction of the mushrooms analysis revealed the highest concentrations of psilocybin and baeocystin. The psilocin content of the species was higher by using aqueous solutions of alcohols than with methanol alone but was an artificial phenomenon caused by enzymatic destruction of psilocybin. The extraction with dilute acetic acid yielded better results than with the water containing alcohols. The simlpe one-step procedure with methanol for the quantitative extraction is still the safest method to obtain the genuine alkaloids from funghal biomass.




Today is opposites day.  Everything I say, I mean the opposite.