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Invisiblefastfred
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Re: Psilocybin oxidation product? [Re: UrbanistiC]
    #12705820 - 06/07/10 09:23 PM (13 years, 9 months ago)

Quote:

UrbanistiC said:
Im stumped! I cant find what it oxidizes to either!




I'm fairly certain that the 4-hydroxyl oxidizes to a double bond to oxygen.

As much as I've looked into the subject there is no evidence to suggest that psilocin doesn't oxidize the same way serotonin does.


-FF

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OfflinePrimalSoup
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Re: Psilocybin oxidation product? [Re: Shmoppy McGillicuddy]
    #12706087 - 06/07/10 10:06 PM (13 years, 9 months ago)

Quote:

Also we had been discussing this in another thread, because FF had discovered the bluing disappears when ascorbic acid (vitamin C) is applied to bruised dried pieces of mushroom (oxidized psilocin) and that sort of led to the wondering if the bluing went away did it reconstitute some psilocin (leading to more potency) or did it just break the oxygenated form of psilocin into other non-blue compounds?


 

Adding citric acid crystals(cheap and easy) achieves the same effect in making tea and acid-adjusted water extracts psilocin effectively according to this source... 

I mention this a lot but it's become my standard technique for good reasons... :awecid:

Quote:

However, the bluing reaction may be caused by a chemical created in the same process as psilocybin/cin in cubensis and other bluing species, and could thus serve as an indicator as to how potent they are.




Always worked for me. :lol:

Peace
-PS


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

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Primal's simple tested teks and projects: :awesomenod: Wheat Prep 2.0  Acidic Tea Tek  Potency Project! 

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OfflineUrbanistiC
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Re: Psilocybin oxidation product? [Re: PrimalSoup]
    #12767837 - 06/19/10 05:33 AM (13 years, 9 months ago)

Still stumped!! Shitty! I hate that!! Okay, busting out the adderall now... HAHA!


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Offlinesashiva
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Re: Psilocybin oxidation product? [Re: UrbanistiC]
    #12773674 - 06/20/10 01:55 PM (13 years, 9 months ago)

Quote:

UrbanistiC said:
Still stumped!! Shitty! I hate that!! Okay, busting out the adderall now... HAHA!




alcohols (re: hydroxyl groups) oxidize to carbonyls ie aldehydes/ketones and if its an aldehyde then it can continue to oxidize into a carboxylate group. if the hydroxyl group is attached to a carbon with no hydrogen then no oxidation with occur


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"Video games don't affect kids. If Pacman had affected us as kids, we'd all be running around in darkened rooms munching on magic pills and listening to repetitive electronic music" -CEO of Nintendo

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Invisiblefastfred
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Re: Psilocybin oxidation product? [Re: UrbanistiC]
    #12773775 - 06/20/10 02:13 PM (13 years, 9 months ago)



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It drinks the alcohol and abstains from the weed or else it gets the hose again. -Chemy

The difference between the substances doesn't matter. This is a war on consciousness, on our right to the very essence of what we are. With no control over that, we have no need to speak of freedom or a free society. -fireseed

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Offlinemellowparty
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Re: Psilocybin oxidation product? [Re: fastfred]
    #12775248 - 06/20/10 07:01 PM (13 years, 9 months ago)

A piece of gill tissue turns blue in contact with air:



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Offlined-Dex-25
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Re: Psilocybin oxidation product? [Re: UrbanistiC]
    #13335247 - 10/14/10 10:49 AM (13 years, 5 months ago)

Hello,

As a new beginner and by that i mean i once grow out some casings a long time ago ohh about 10 years but perhaps because of my dislike for Psilocybin/Psilocin and the work versus reward was why i quit and so looked else where for bulk products. However ive always been into psychedelics especially after my first REAL BAD TRIP so ive been around including this forum which under a different name ive been around since 2000 when i first started out.

Anyways due to a recent trip in which i finally reached a TRUE spiritual experience although having believed i had experienced many before ive been reawakened so to speak...



This is how I believe along with many others is the cause for the blueing it just makes too much sense cause look at the facts and say im wrong!!!


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OfflineSolipsis
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Re: Psilocybin oxidation product? [Re: d-Dex-25]
    #23960032 - 12/27/16 09:20 AM (7 years, 2 months ago)

But psilocybes don't really have orange sort of colors like boletes have and also don't have an effect on cyp P450 enzymes as far as I know?

I think the fact that many tryptamines like psilocin indeed to turn blue and then even brown to black, even synthetic products like the research chemical psychedelics.. tells us that it may partially be psilocin oxidizing we are seeing, but at the same time I would think that it's certainly not the only such compound oxidizing to staining conjugated systems (some of which sort of dimerized).

So it's still probably not a reliable indicator but an indicator nonetheless since we know psilocin turns blue.

I doubt that brown-black discoloration from much more progressed solutions of tryptamines are just from a higher concentration of blue compounds. Also, just blue discolored tryptamines apparently do not lose potency initially. More likely the brown/black is from further degradation which DOES eventually wreck your potency.

So yeah imo there is a fair chance an antioxidant like ascorbic acid halts this further degradation and reverts the pH / redox dependent first step bluing reaction or at least changes the electronic charge / ionization. What removes the color may also improve stability because ionizing compounds are a bad step in the direction of degradation.

But more data is needed to confirm things like these.

On the one hand, knowing that tryptamines including psilocin turn blue is helpful, but on the other hand, what experiment would be better proof of anything? To show that you can isolate bluing compounds from psilocybes that are not psilocin?

Please someone do some chromatography xD

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Offlinealkap555
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Re: Psilocybin oxidation product? [Re: Solipsis]
    #23963626 - 12/28/16 07:14 PM (7 years, 2 months ago)

Based on the reactivity of 4-hydroxyindole, the oxidation of Psilocin (4-hydroxy-N,N-dimethyltryptamine) and Psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) should afford a mixture of the ortho- and para-quinones based on the indole-4,5-dione and indole-4,7-dione scaffolds, respectively.

At equilibrium, the thermodynamically favored 4,7-dione (para-quinone) should be the major oxidation product. Additionally, oxidation of 4-hydroxyindoles with Fremy's Salt (potassium nitrosodisulfonate) has been shown to proceed via formation of the 4,7-dione.

 



Sources:

http://onlinelibrary.wiley.com/doi/10.1002/jsfa.2740470206/abstract

https://books.google.com/books?id=YFqOVaLh90EC&pg=PA40&lpg=PA40&dq=oxidation+4-Hydroxyindole&source=bl&ots=RSFbjL_8rH&sig=cSG9ptcWes8u-LMTuRDpcggmdJU&hl=en&sa=X&ved=0ahUKEwjwsebXlJjRAhXC6iYKHWCSCNIQ6AEITDAJ#v=onepage&q=oxidation%204-Hydroxyindole&f=false
(see pg 39)

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OfflinePsilosophy328
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Re: Psilocybin oxidation product? [Re: alkap555]
    #24011884 - 01/15/17 11:03 AM (7 years, 2 months ago)

I like that explanation, given that wiki has this to say about why indigo gives its blue color (look at pictures of indigo and compare them to the bluing of psilocybes - very similar hue/saturation):

"The molecule absorbs light in the orange part of the spectrum (λmax = 613 nm).[16] The compound owes its deep color to the conjugation of the double bonds, i.e. the double bonds within the molecule are adjacent and the molecule is planar. In indigo white, the conjugation is interrupted because the molecule is nonplanar."

Granted, that is a rather simple explanation without any technical chemistry language to back it up (so then all planar molecules with two adjacent/conjugated double bonds are blue in color? I doubt it, but maybe).

What about reduction of pure aqueous psilocin oxide, and looking for new compounds? Might this be a reversible oxidation/reduction reaction?

Also, as others have pointed out - insight could be gleaned from the color of pure psilocin extracts. However, it would depend upon how they are prepared.  For instance, the conjugation of LSD with tatrate to stabilize it, whereas oxidation would likely occur without tartrate conjugate. In any case, I would imagine early chemists would have noted when/whether psilocin/oxide would turn blue.

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