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Tamadragon said:
hey is there a way to deoxygenize water? bubbling c02 in it? chemical reaction? maybe a filter would work. you can filter out minerals. maybe 02 as well. i'll work on that. got to be info out there on the web

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yeah.  boil it.

water's capacity to hold dissolved gasses decreases as temp increases.  by the time you reach boiling point you've driven off any free oxygen (or at least the vast majority).  of course it will diffuse back into the liquid as it cools.  part of me has always suspected this is why tea works so well with mushrooms and why the heat doesn't seem to have detrimental effects...

or think the lemon juice methods... lemon juice is high in antioxidants.  somebody posted in cult a ways back some pictures of mushrooms that they coated in "fruit-fresh" stuff designed to preserve fruit and prevent it from turning brown (which is basically sugar and abscorbic acid - aka vitamin c)... and it not only prevented mushrooms from blueing, but took the blueing away and they turned back to the normal color!  not sure what was going on there... surprised nobody with more knowledge on the subject picked up on it and offered any theories... (well besides the obvious... antioxidants prevent oxidation   just odd that they might reverse it which doesn't completely make sense to me...)  but just an idea to toy with...

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wiggles said:
Well, there is always the inefficient everclear extraction. For crude experimentation that should work somewhat. Also, you could try to use Naptha, but I'm not sure if it'd be the correct polarity/nonpolarity for the extraction.

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Pinback said:
I think you are confusing the concepts. A base (in the Lewis sense) is a chemical species that can form a bond by donating an electron pair. It is not closely related to redox reactions. Also, if a species were to lose a single electron to the psilocin, the psilocin would be reduced, not oxidized.

Do you have any reference for the oxidized psilocin structure? I've only seen speculations as to what it is (o-quinoid structure), not any isolation or spectral data. I really doubt (because of the color!) that it would have lost its aromaticity. 

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Thanks for your comment.  I've had some good fun thinking about the problem because of it.  I've realized that I've confused one point, but as far as the concept I think I'm right on.

I've confused things by referring to the oxidation as being via a reaction with a base.  The point of confusion is because I've referred several times to the base as being a lewis base (electron donor), when in fact it would be a Bronsted-Lowry base (proton acceptor).  I guess thinking about redox reactions made me think of electrons.

You're taking an inorganic point of view whereas I take more of a o-chem/biochem viewpoint.  Oxidation is technically defined as loss of electrons, whereas I usually think of it in the biochem terms of a gain of oxygen or bonds to oxygen.

So anyways, in biochem terms the psilocin gets the H (proton) stripped off the 4-hydroxyl by a base (proton acceptor).  This results in the free electron on oxygen creating a double bond to the benzene ring.  There is no transfer of electrons at all, but it is still an oxidation reaction because the psilocin electron density is increased because of the loss of the proton.  Or you could say the psilocin oxidation state (or formal charge) is increased by one.

Sorry to throw you off by the talk of electrons and lewis bases.  You are right in that if it was a lewis base it would donate an electron pair and it would be a reduction, but this is not the case.


I don't have any reference to the structure of oxidized psilocin.  I've come up with a proposed structure that I've dubbed "psilocybeen".  A long while ago I was focused on finding a o-quinoid structure for the oxidation product.  I make a couple posts on it, but it generated no discussion.  Later I went back to those posts and studied the structure and decided that I was overcomplicating things and simply adding another bond to the oxygen was the most elegant solution to finding the oxidation product.  Thus I came up with the diagram and proposed structure posted above.

My proposed structure seems quite simple and intuitive, so I've favored it ever since.  I haven't really looked at in in great depth, or really thought about it's (non)aromatic nature.  Aromaticity hurts my brain.  If I had more free time I would look more closely at it.

I guess I'm satisfied with my conclusion.  I encourage you to look more closely at it if you have the time.  I couldn't come up with an oxidized structure that preserves it's aromaticity anyway.  Can you?

I'm not even sure if the proposed structure is aromatic or not, it's been too long since that o-chem chapter.


-FF

P.S.  There's an error or two in my diagram.  5 shrooms if you can point them out.

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fastfred said:
Sublingual administration sounds like an interesting idea. Has anyone tried it? It would be nice to confirm that it can be absorbed.

As far as all the inert atmosphere setups... That sounds like more work than it's worth. Just vacuum desiccate, vacuum distill, or rotovap the solvent. The easiest way to get rid of the oxygen is simply to pump it away with a vacuum pump. It's probably cheaper than a tank of gas anyway and it will also get rid of the solvent a lot faster.

All this talk about getting rid of the oxygen also ignores the fact that the oxygen that gets oxidized is already present in the psilocybin. All that's needed is a base (electron donor) to oxidize the psilocin.

I'm not sure that oxygen is involved in the oxidation at all. Psilocybin is mostly dephosphorylated to psilocin by enzymes and then oxidized to psilocybeen, often by a base.

> somebody posted in cult a ways back some pictures of mushrooms that they coated in "fruit-fresh"

That seemed to turn them a quite nasty color. I wouldn't use fruit-fresh because of the sugar in it. Better to use plain ascorbic acid since it's easily available.

> surprised nobody with more knowledge on the subject picked up on it and offered any theories...

I've posted many times on the subject. Nobody seems to know anything more about it of have any better theories. I've been interested in testing to see if the psilocybeen is converted back into psilocin by ascorbic acid for a long time, but nobody seemed willing to do any bioassay experiments.




-FF

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fastfred said:
Aqueous ethanol extraction is not inefficient. In fact, it is the most efficient extraction currently known.

Don't derail this thread by suggesting random solvents when you obviously have no idea what you're talking about. Naptha is non-polar and won't dissolve any of the actives at all. Suggesting it also really makes you sound like a meth cook.

-FF

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