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Invisiblefastfred
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Psilocin Oxidation/ Vitamin C Experiment Proposal * 1
    #3129834 - 09/13/04 03:48 PM (12 years, 2 months ago)

Background:
In the late 90s, while working on preservatives and antioxidant preparations to enhance the storage of mushrooms, I found that when mushrooms are placed in an aqueous solution the water turns blue over a period of several hours. Then the interesting part happened, I discovered that by adding ascorbic acid (vitamin C) the solution would return to a crystal clear color.

Hypothesis:
Psilocybin is readily and rapidly dephosphorylated into psilocin. The psilocin then further undergoes oxidation to an, as yet undetermined, compound. This oxidation is associated, although may not totally account for, the formation of a blue product. This blue product is completely destroyed or altered into a non-blue product by the addition of ascorbic acid. The psilocin in the solution, which may or may not actually be the blue product, is either reduced back into psilocin or decomposes into other non-psychoactive reaction products.

Proposal:
Without access to complicated and expensive analytical equipment, the most reasonable way to determine weather the oxidized psilocin is converted back into psilocin would be to ingest a quantity of the substance and note any increase in psychoactive effects relative to the oxidized solution.

Methods:
Dried mushroom powder is placed into aqueous solution (adjusted to a pH of 4 using acetic acid) and allowed to stand for at least 1 hour. The solution is then heated in a boiling water bath for 8 to 10 minutes, or until the solution reaches about 70?C, to convert most of the psilocybin into psilocin. [1] The solution is then cooled (optionally using running water) and filtered to remove the mushroom sediment. Next the solution is basified to a pH of 7-8 and allowed to stand until the solution is blue and no further darkening is observed. This step may be hastened by bubbling air through it. Once the solution's color has stabilized it is divided into two equal amounts. Half of the solution is consumed immediately and any effects noted. If this solution produces noticeable effects the remaining solution is stored for around one week under refrigeration so that any tolerance will dissipate. Prior to consumption, ascorbic acid is added to the second part of the solution until a clear color is obtained. The solution is then consumed and any effects noted, paying particular attention to the relative strength of effect compared to the first solution.

Alternate method:
Fresh or dried mushrooms are placed in water and allowed to stand for at least 1 hour with occasional or constant stirring. The solution is then filtered to remove mushroom debris and allowed to stand until the water develops a blue color. When no further darkening is observed the solution is divided in half and the first half is consumed. Effects are noted for a period of at least several hours. After any tolerance dissipates, ascorbic acid is added to the second solution until any blue color disappears and the solution is consumed. Effects are noted and compared to the first solution.

Results:
Any increase in the potency of the solution after addition of ascorbic acid would indicate that at least some of the oxidized psilocin was converted back into psilocin.

Discussion:
I will be attempting this experiment at some time in the future. I'm looking for collaborators to also perform this experiment due to the subjective nature of psychoactive effects. I'm also interested in hearing any comments or discussion on this proposal.

References:
[1] J. F. Casale "An Aqueous-Organic Extraction Method for the Isolation and Identification of Psilocin from Hallucinogenic Mushrooms"
J. Forens. Sci. 30(1), 247-250 (1985)
Link


-FF


Edited by fastfred (09/14/04 03:44 AM)


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OfflineShroomCat
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Re: Psilocin Oxidation/ Vitamin C Experiment Proposal [Re: fastfred]
    #3132983 - 09/14/04 03:28 AM (12 years, 2 months ago)

Awesome experiment, very scientifically laid out. Currently, I am not in posession of any mushrooms, or I would definitely partake. I am interested to see the results. . . they would have an impact on shroomers everywhere, I'd imagine. You'd get a five shroom rating, but apparently I don't have enough posts to rate people yet.


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Invisibleutopianglory
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Re: Psilocin Oxidation/ Vitamin C Experiment Proposal [Re: fastfred]
    #3132988 - 09/14/04 03:33 AM (12 years, 2 months ago)

This is going to be interesting :smile:


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InvisiblePinback
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Re: Psilocin Oxidation/ Vitamin C Experiment Proposal [Re: fastfred]
    #3133072 - 09/14/04 04:23 AM (12 years, 2 months ago)

I would definitely suggest a double-blind test if possible, preferably a number of them. It's very easy to fool oneself, especially since the substance affects the judgement, and also because that there is (subconsciously) an expected or wanted result. For this to be done, the solvents would of course have to be evaporated, and the residue put into opaque capsules or similar.

The test will also not show whether the blue substance is reduced to psilocin, but rather if it is converted to any psychoactive substance. If the oxidized psilocin is o-quinoid, as proposed by the paper in the other thread, this is not impossible. But I suppose that if the potency remains, this would be enough for most people.


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Invisiblefastfred
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Re: Psilocin Oxidation/ Vitamin C Experiment Proposal [Re: Pinback]
    #3134647 - 09/14/04 04:07 PM (12 years, 2 months ago)

>I would definitely suggest a double-blind test if possible

That might be kind of hard since one solution will be clear and the other blue. I suppose you could add some food coloring to the clear one. It would still involve an extra person though.

>For this to be done, the solvents would of course have to be evaporated

The solvents are non-toxic (vinegar and water) so you could just dring them down. Vinegar might not taste very good, but some people claim that drinking it has health benefits.

>The test will also not show whether the blue substance is reduced to psilocin, but rather if it is converted to any psychoactive substance.

That's a good point, but like you said, to most people that would be splitting hairs.

Weather the oxidized substance can be converted back into psilocin might depend somewhat on the extent of the oxidation. e.g. The first oxidation product might further oxidize into a second and third product.

Thanks for the comments.


-FF


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InvisiblePinback
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Re: Psilocin Oxidation/ Vitamin C Experiment Proposal [Re: fastfred]
    #3134811 - 09/14/04 04:44 PM (12 years, 2 months ago)

I guess I was a bit unclear; what I meant was that in order to make a (double-)blind test, the solvents would have to be evaporated and the appearance of the residue hidden.


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Re: Psilocin Oxidation/ Vitamin C Experiment Proposal [Re: fastfred]
    #3494041 - 12/13/04 10:13 PM (11 years, 11 months ago)

Any updates?


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Invisibleryan
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Re: Psilocin Oxidation/ Vitamin C Experiment Proposal [Re: Pinback]
    #3496343 - 12/14/04 10:51 AM (11 years, 11 months ago)

The blue is not the psilocin/psilocybin. Its not know what it is. A better test would be to see if adding any acid makes the blue go away - is the blue simply a pH reaction?


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Offlinetriptamine
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Re: Psilocin Oxidation/ Vitamin C Experiment Proposal [Re: ryan]
    #3556503 - 12/29/04 10:04 AM (11 years, 11 months ago)

The blue color reaction is indeed from psilocin. If pure psilocin crystals are left at room temperature for about a month, a nice blue color develops and the crystals loose some of their activity. It is interesting that what psilocin decomposes into is not known (or at least not in the literature), but it is postulated to be a quinone of some kind.

Triptamine


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Offlinetregar
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Re: Psilocin Oxidation/ Vitamin C Experiment Proposal [Re: triptamine]
    #15918907 - 03/08/12 12:52 PM (4 years, 8 months ago)

Great thread.

Done some experiments in dreams turning 4-aco-dmt into 4-ho-dmt:

http://www.shroomery.org/forums/showflat.php/Number/15914988

I also used crushed ascorbic acid to preserve the psilocin at the stage where it turned dark blue, then stuck vial in freezer.


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