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Why magic mushrooms turn blue solved!


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#1 Boebs

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Posted 08 July 2020 - 05:26 PM

The pigment, as it turns out, is not just a single compound but a complex mixture of linked psilocybin oxidation products. Most of them are quinoid psilocyl oligomers – compounds not unlike indigo, a deep blue pigment used to dye jeans. ‘[The blue compounds and indigo] share structural similarities in the indole core, and in both the basis for the colour is a quinoid,’ says the study’s lead author Claudius Lenz.

All of the six mushroom pigments the team identified are products of a cascade reaction starting with psilocybin. A phosphatase enzyme takes off its phosphate group, converting it into psilocin. An oxidising laccase then creates psilocyl radicals, which combine to form C-5 coupled subunits and then further polymerise via C-7. ‘I think they did a beautiful job of showing the cascade reaction,’ says Jaclyn Winter, who studies natural product biosynthesis in bacteria and fungi at the University of Utah, US.

More of the article here-->>


https://www.chemistr...4010870.article
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#2 HrVanker

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Posted 08 July 2020 - 05:30 PM

I always thought that the blue hue looked a lot like Indigo. Definitely interesting info. I wonder if we can find away to de-oxidize/re-phosphoralate the psilocin/psilocybin w/ this research.

It is possible to extract Indigo and re-use it as dye. I would think that a similar situation could happen w/ psilocybin. But would be most useful if working with pure psilocybin, not whole shrooms...

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#3 Psilosophie

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Posted 08 July 2020 - 09:51 PM

Aahhh I bet they had lots of fun studying "the pigmentation properties" of psilocybin. I wonder how tightly a study like that is scrutinized for a few missing mushrooms? Haha i can just imagine the excitement of the students who got to be part of the growing!

Thanks for sharing. Pretty interesting. So if their hypothesis is true [no evidence yet], psilocybin just serves as a precursor to these reactive oxygen species (free radicals?)

And here we psychonauts are putting it on this pedestal as if it's the center of the insecticide show. Or worse yet, an evolutionary adaptation to signal to humans how to reliably identify an ambassador species capable of sharing the Gaian collective unconscious thereby entering a biospheric symbiosis and saving the planet from our own worst enemy - ourselves.

Fascinating either way!
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#4 p2p

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Posted 08 July 2020 - 09:55 PM

Aahhh I bet they had lots of fun studying "the pigmentation properties" of psilocybin. I wonder how tightly a study like that is scrutinized for a few missing mushrooms? Haha i can just imagine the excitement of the students who got to be part of the growing!

 

 

There is always an allowance for "breakage" :smile: :smile:


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#5 TVCasualty

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Posted 09 July 2020 - 09:12 AM

Now I'm REALLY curious about what was going on when I noticed that dissolving citric acid crystals in water that had turned blue from soaking some fungi in it made the water turn back to clear. Did it revert to psilocin and would therefore be active or does it end up as some other, unidentified  (and inactive) substance?


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#6 Ferather

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Posted 09 July 2020 - 10:28 AM

Active mycelium:

Baeocystin:  [C11]--[H15]--[N2]--[O4]--[P]
Norbaeocystin: [C10]--[H13]--[N2]--[O4]--[P]
Psilocybin:  [C12]--[H17]--[N2]--[O4]--[P]
Psilocin:  [C12]--[H16]--[N2]--[O]

From above links:
 
"Psilocybin is a tryptamine compound with a chemical structure containing an indole ring linked to an ethylamine substituent. It is chemically related to the amino acid tryptophan, and is structurally similar to serotonin."
"Psilocybin is a member of the tryptophan-based compounds that originally functioned as antioxidants in earlier life forms before assuming more complex functions in multicellular organisms."
 
"Psilocin is relatively unstable in solution due to its phenolic hydroxy (-OH) group. In the presence of oxygen it readily forms bluish and dark black degradation products"
"Most species of psilocybin-containing mushrooms bruise blue when handled or damaged due to the oxidization of phenolic compounds"
 
"Psilocin is broken down by the enzyme monoamine oxidase. Some psilocin is not broken down, and forms a glucuronide"

Notes:
 
Nor-baeocystin are analogs of psilocybin, meaning single or various elements are added or removed.
It appears they can be phosphorylated or dephosphorylated (cleaved, added, a cycle?).
All four compounds contain carbon, hydrogen, nitrogen and oxygen.
 
Serotonin:  [C10]--[H12]--[N2]--[O]

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#7 FunG

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Posted 09 July 2020 - 02:10 PM

So psilocin is actively present in mushroom tissue? Pffft shows what I know.
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#8 Boebs

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Posted 09 July 2020 - 04:54 PM

Figured everyone would like the study:)
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#9 clumsy

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Posted 09 July 2020 - 05:10 PM

Others, elsewhere here, have noted that bluing is also present in non-psychoactive mushrooms. That would be in interesting follow-up study.


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#10 Boebs

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Posted 09 July 2020 - 05:28 PM

Yea it was mentioned in the article, not in detail tho

#11 HrVanker

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Posted 09 July 2020 - 05:31 PM

Now I'm REALLY curious about what was going on when I noticed that dissolving citric acid crystals in water that had turned blue from soaking some fungi in it made the water turn back to clear. Did it revert to psilocin and would therefore be active or does it end up as some other, unidentified (and inactive) substance?

Was the citric acid crystal experiment from an old thread about "blue honey"? I remember a thread from years ago where they were reducing mushroom tea to mix into honey. IIRC, the plan was to reduce the honey further, back to its original volume.

If the bluing molecules were reverted back to psilocin, would lemon tek have a similar effect? I'm not well versed in the finer differences between ascorbic and citric acid. Perhaps lemon tek reverts oxidized psilocin, rather than de-phosphorylating the psilocybin. I've seen that claim debated back and forth.

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#12 PJammer24

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Posted 09 July 2020 - 06:30 PM

So psilocin is actively present in mushroom tissue? Pffft shows what I know.

 

psilocin is present when the mushrooms are fruiting and when first harvested. The psilocin present in the mushroom oxidizes much more quickly that the psilocybin. So unless you eat them fresh, the amount of psilocin you ingest is minimal and insignificant. People have been trying to isolate and store psilocin in things like honey to avoid oxidation but there haven't been any convincing successes that I have read. 

 

Your body converts psilocybin into psilocin when digested.


Edited by PJammer24, 09 July 2020 - 07:25 PM.

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#13 PJammer24

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Posted 09 July 2020 - 07:27 PM

Now I'm REALLY curious about what was going on when I noticed that dissolving citric acid crystals in water that had turned blue from soaking some fungi in it made the water turn back to clear. Did it revert to psilocin and would therefore be active or does it end up as some other, unidentified  (and inactive) substance?

 

This is interesting when you consider that psilocybin is converted to psilocin during the digestion process where it is interacting with your stomach acids... hmmm?


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#14 TVCasualty

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Posted 10 July 2020 - 11:30 AM

 

Now I'm REALLY curious about what was going on when I noticed that dissolving citric acid crystals in water that had turned blue from soaking some fungi in it made the water turn back to clear. Did it revert to psilocin and would therefore be active or does it end up as some other, unidentified (and inactive) substance?

Was the citric acid crystal experiment from an old thread about "blue honey"? I remember a thread from years ago where they were reducing mushroom tea to mix into honey. IIRC, the plan was to reduce the honey further, back to its original volume.

If the bluing molecules were reverted back to psilocin, would lemon tek have a similar effect? I'm not well versed in the finer differences between ascorbic and citric acid. Perhaps lemon tek reverts oxidized psilocin, rather than de-phosphorylating the psilocybin. I've seen that claim debated back and forth.

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It wasn't an experiment, it was an accident I happened to notice. Some powdered fungi had gotten wet on my kitchen counter and the puddle of water had turned blue. I don't remember at this point how the citric acid got mixed with the blue water (I either spilled dry crystals on it or a few drops of a citric acid solution) but as soon as it did it turned instantly clear.

 

I did the lime juice soak using a saturated solution of citric acid instead to test if it worked the same as the juice and it did, so as far as I can tell the key to how the pre-soak works is the antioxidant properties of the citric acid combined with the pH being low enough to induce dephosphorylation of the psilocybin in vitro. I tried a pre-soak with grapefruit juice and it did not provide the same results. Grapefruit juice has a lot of Vitamin-C/ascorbic acid but doesn't have as much citric acid as lemon or lime juice, which supports the hypothesis that the way a lemon or lime juice soak works is a function of pH and/or citric acid.


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#15 HrVanker

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Posted 10 July 2020 - 11:58 AM



It wasn't an experiment, it was an accident I happened to notice. Some powdered fungi had gotten wet on my kitchen counter and the puddle of water had turned blue. I don't remember at this point how the citric acid got mixed with the blue water (I either spilled dry crystals on it or a few drops of a citric acid solution) but as soon as it did it turned instantly clear.

I did the lime juice soak using a saturated solution of citric acid instead to test if it worked the same as the juice and it did, so as far as I can tell the key to how the pre-soak works is the antioxidant properties of the citric acid combined with the pH being low enough to induce dephosphorylation of the psilocybin in vitro. I tried a pre-soak with grapefruit juice and it did not provide the same results. Grapefruit juice has a lot of Vitamin-C/ascorbic acid but doesn't have as much citric acid as lemon or lime juice, which supports the hypothesis that the way a lemon or lime juice soak works is a function of pH and/or citric acid.


Ok, then that must have been another thread. Did a little looking, but I cannot find the source. I don't recall if they used citric or ascorbic acid... but they had a dark blue tea, added the acid and poof, clear water (video was attached).

Over on Reddit I have seen a couple people, who appear more knowledgeable than myself, post about the ineffectiveness of lemon tek. IIRC, they stated that the pKa of ascorbic acid is not high enough to cause dephosphorylation. But perhaps it is strong enough to separate the oxygen from the oxidized psilocin?

Presumably the psilocin loses a molecule or two when it oxidizes. Would the psilocin want to re-form in solution, or would it require another reaction?

I need to learn more chemistry...

#16 Jrotten

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Posted 10 July 2020 - 11:43 PM

Now I'm REALLY curious about what was going on when I noticed that dissolving citric acid crystals in water that had turned blue from soaking some fungi in it made the water turn back to clear. Did it revert to psilocin and would therefore be active or does it end up as some other, unidentified (and inactive) substance?

when I make tea I squeeze a fresh lemon during the steep and I’ve had the water go back from blue also. I thought I was doing some good, but maybe less so now. If the water has lemon from the start it never blues.

Edited by Jrotten, 10 July 2020 - 11:46 PM.

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#17 TVCasualty

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Posted 11 July 2020 - 01:38 PM


Over on Reddit I have seen a couple people, who appear more knowledgeable than myself, post about the ineffectiveness of lemon tek. IIRC, they stated that the pKa of ascorbic acid is not high enough to cause dephosphorylation. But perhaps it is strong enough to separate the oxygen from the oxidized psilocin?

 

Did anyone have anything to say about the citric acid content of the lemons?

 

And when they were discussing the lemon/lime tek as being ineffective were they referring to a theoretical chemical analysis based on a pKa chart or the result of a disappointing bioassay?



#18 HrVanker

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Posted 11 July 2020 - 01:48 PM

Did anyone have anything to say about the citric acid content of the lemons?

And when they were discussing the lemon/lime tek as being ineffective were they referring to a theoretical chemical analysis based on a pKa chart or the result of a disappointing bioassay?

So I found one of the posts I've seen on the matter, here is a link to the start of that comment thread.

They are speaking scientifically, but grad students have been known to go a little Dunning-Kruger. I don't have the information to check their claims, currently trying to find the average pKa of stomach acid.

And I'm still grappling w/ the concept of pKa itself. As I understand it now, it's essentially the number of H ions per molecule of acid in solution...?

Edit: though u/TheDrugsLoveMe also said that Psilocin is pretty stable... perhaps the psilocin-citrate he mentioned is more stable?

Psilocin and -cybin are pretty stable. You could probably trust the tea to stay potent for the next month to maybe 6 weeks? But that's just a guess, at best.

Really, I don't have any good stability data to go on. Not that I wouldn't love to conduct a study...


Edited by HrVanker, 11 July 2020 - 01:59 PM.

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#19 TVCasualty

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Posted 11 July 2020 - 02:11 PM

I'm not the person to ask to explain pKa.

 

Granted, it's not been definitively proven by chemical analysis that citric acid or maybe the low pH of a solution of it is what causes the noticeable and consistent changes to the qualitative effects of a given dose of fungi. But it's the explanation that makes the most sense with the info we have, which doesn't mean it's correct. Still, soaking fungi in strongly acidic juice or a citric acid solution results in trips that are consistently reported to be different in several ways (peak intensity, duration, body load) than those lacking a pre-soak (to a degree that seems unlikely to be entirely placebo).

 

So while I can't say for sure what's happening with these soaks, I can say as confidently as I can say anything that SOMEthing is happening, and that I like it a lot more than when it doesn't happen.


Edited by TVCasualty, 11 July 2020 - 02:11 PM.

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#20 Ferather

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Posted 12 July 2020 - 10:13 AM

Psilocin citrate (see here), I also found citrate‐phosphate + alcohol is better, but obviously citric acid is easier and cheaper.






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