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Psilocybin Degradation


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#1 Norman

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Posted 09 August 2020 - 02:30 AM

It’s fairly common knowledge and my experience that psilocin and psilocybin degrade relatively rapidly in stored mushrooms. Even a sample carefully dried, vacuum packed, and frozen will be noticeably weaker after a year.
I’d never thought to ask - what does it break down into? DMT is pretty stable, does that HO group cause the entire molecule to become unstable and break down or does it just break off and leave a DMT molecule behind?
Could old mushrooms still be loaded with DMT and just orally inactive without an MAOI?
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#2 ElrikEriksson

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Posted 09 August 2020 - 11:44 AM

I've never seen an analysis of the dry degradation products of psilocin/psilocybin but, yes, its certainly centered on that phenol group.

The bluing reaction of fresh mushrooms is also based on that phenol and atmospheric oxygen, in that case forming short polymers some of which are blue.

The dry oxidation products are likely similar in the location of reactions, just without the blue compounds as products.

 

It's not something that mainstream science has an interest in studying.



#3 clumsy

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Posted 09 August 2020 - 02:55 PM

It has long been known that psilocin is highly unstable vs. psilocybin: https://www.zamnesia...ifferences-n767, but there is no mention of the breakdown products. Others here have remarked about the surprising lifetime of dried shrooms.



#4 Norman

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Posted 10 August 2020 - 03:06 PM

So odd that it’s so unstable yet it holds up to MAO better than DMT.
It’s reportedly near impossible to extract too making me wonder if a standard A/B is yielding unrecognized DMT.
Have also heard that aya brews using phosphoric acid are stronger. Could the DMT starting out as a phosphate salt be more resistant to MAO breakdown like psilocybin is?
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#5 Norman

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Posted 25 August 2020 - 06:21 PM

Okay spurred by recent discussion of precipitation and boredom I’m bumping this dud.

Has anyone ever thought about precipitating the fumaric acid salt of mushroom alks?
As in a saturated acetone or methanol solution precipitated by adding a saturated fumaric acid solution dropwise.

#6 pharmer

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Posted 25 August 2020 - 08:59 PM

Would an MSGC of a sample of fresh fruits and then another MSGC of the very same sample which had been dried and aged 1 or 2 years give us the answer?

 

Would the degraded product/s show up in the second MSGC?


Edited by pharmer, 25 August 2020 - 09:00 PM.


#7 coorsmikey

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Posted 25 August 2020 - 09:08 PM

Generally yes if you could measure how much was used during the first MSGC then subtract the from what degrades from the second:)

Edited by coorsmikey, 25 September 2020 - 08:37 PM.


#8 NardDogOverdrive

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Posted 25 August 2020 - 09:16 PM

I have never held mushrooms long enough for them to degrade except for once.  I stumbled across a jar of horse poo wild cubes that I harvested in a field about 3 years ago.  Stumbled across the jar 1 month ago and totally forgot about them.  I took 3 grams, my normal dose, it was stronger than any 3 grams I have ever had.  All mushrooms I have had prior were homegrown.  So yeah, I can't attest to mushrooms losing potency in my one experience.


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#9 ilikethings

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Posted 25 September 2020 - 05:29 PM

I have never held mushrooms long enough for them to degrade except for once.  I stumbled across a jar of horse poo wild cubes that I harvested in a field about 3 years ago.  Stumbled across the jar 1 month ago and totally forgot about them.  I took 3 grams, my normal dose, it was stronger than any 3 grams I have ever had.  All mushrooms I have had prior were homegrown.  So yeah, I can't attest to mushrooms losing potency in my one experience.

I have stored fruits for about 1 year (they were dried and vacuum sealed) and I did not notice any drop in potency either.  Unlike some of the folk above (based on their comments), I'm not a trained chemist but just wanted to add my experience.  I wish there was "go to" tek for a basic extraction other than the typical A/B aka bi-polar methods commonly discussed. 


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#10 pharmer

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Posted 28 September 2020 - 08:06 AM

Generally yes if you could measure how much was used during the first MSGC then subtract the from what degrades from the second:)

Even better, I hope, is that the MSGC would show exactly which components had degraded and what they were changed into.

 

But this is waaaaaaay above my pay grade



#11 Misfit

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Posted 08 October 2020 - 12:08 AM

It’s not a question of pay grade it’s a question of who has access to one?

#12 Phineas_Carmichael

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Posted 13 January 2021 - 02:33 AM

It's been a hot minute since I've done this kind of chemistry, so take everything I say with a hefty grain of salt.  I had to dig out some of my old textbooks;  they were holding up the broken bedframe in the guest room!

It’s fairly common knowledge and my experience that psilocin and psilocybin degrade relatively rapidly in stored mushrooms. Even a sample carefully dried, vacuum packed, and frozen will be noticeably weaker after a year.
I’d never thought to ask - what does it break down into? DMT is pretty stable, does that HO group cause the entire molecule to become unstable and break down or does it just break off and leave a DMT molecule behind?
Could old mushrooms still be loaded with DMT and just orally inactive without an MAOI?

My first thought here was to look into what the body breaks psilocybin and psilocin down into, so I looked into what metabolites human drug tests look for when testing for mushroom use.  Come to find out that specific urine tests for mushroom use just straight up look for psilocin!  Your body immediately breaks psilocybin into psilocin, which binds to serotonin receptors for a few hours, before being filtered out by the kidneys and excreted in urine.  

 

That -OH group on psilocin is real susceptible to oxidation, as are the amines in the indole ring & at the end of the carbon tail.  Likely the phenol group is converted to a carbonyl in atmospheric oxidation.  The terminal amine on serotonin is coverted to a carboxylic acid group in vivo to form 5-HIAA, it's possible that this happens to psilocin in the body as well, and potentially could be what hair tests for mushroom use look for, but I think less likely as the dimethyl groups make the amine more stable than serotonin's...

 

As for old mushrooms being loaded with DMT and inactive without an MAO inhibitor, it's a hypothesis worth testing.  If anyone's holding on to a bunch of old mushrooms that don't have the same kick they used to I could see eating them with some harmala alkaloids & seeing if the trip is like pharmahuasca... 

 

I've never seen an analysis of the dry degradation products of psilocin/psilocybin but, yes, its certainly centered on that phenol group.

The bluing reaction of fresh mushrooms is also based on that phenol and atmospheric oxygen, in that case forming short polymers some of which are blue.

The dry oxidation products are likely similar in the location of reactions, just without the blue compounds as products.

 

It's not something that mainstream science has an interest in studying.

 

The bluing of fresh mushrooms acting on phenol group on the psilocin makes perfect sense.  Lots of indole compounds are in the blue to purple range.  Psilocybin, the chief compound in dried mushrooms has a big old dihydrogen phosphate instead of the phenol, which is subject to a different sort of oxidation, as well as the amine in the ring.  Without a bunch more study I'm afraid I'm a little too rusty to speculate on what kind of breakdown products we'd get from atmospheric oxygen, my apologies.

So odd that it’s so unstable yet it holds up to MAO better than DMT.
It’s reportedly near impossible to extract too making me wonder if a standard A/B is yielding unrecognized DMT.
Have also heard that aya brews using phosphoric acid are stronger. Could the DMT starting out as a phosphate salt be more resistant to MAO breakdown like psilocybin is?

 

Now, enzymatic breakdown is a completely different animal than atmospheric oxidation.  I've never been a biochemist so I can't speak to how, but enzymes are big huge proteins that surround and attack our simple little molecules.  If DMT is a foot soldier & MAO is a man-trap, that -OH group is some kind exoskeleton that makes it so psilocin (our foot-soldier wearing armor) doesn't fit in the trap and just slides right by.

 

I can't speak to aya & the acids used, but the salt is an ionic bond, easily broken by water.  The DMT salts in our body are constantly being broken apart by all the water we're made of & recombined, giving MAO a chance to attack the freebase every time it bounces... It's possible that phosphoric, being a diprotonic acid keeps the DMT a salt more often, but it's always been my understanding that the HCl in stomach acid renders that question moot.  I suspect this might be placebo (and would love to see a double-blind study!), but again I am not and never have been a biochemist.

Okay spurred by recent discussion of precipitation and boredom I’m bumping this dud.

Has anyone ever thought about precipitating the fumaric acid salt of mushroom alks?
As in a saturated acetone or methanol solution precipitated by adding a saturated fumaric acid solution dropwise.

 

I have never seen, in the Scientific Literature or Clandestine Reports, stable psilocybin or psilocin salts of any kind.  I suspect that the reactive functional group on the benzene portion of the indole ring might make this impossible. I'm sorry it's been such a long time since i've done this kind of chemistry...

 

Generally yes if you could measure how much was used during the first MSGC then subtract the from what degrades from the second:)

Even better, I hope, is that the MSGC would show exactly which components had degraded and what they were changed into.

 

But this is waaaaaaay above my pay grade

 

Only if the degradation products elute through the gas phase in sufficiently different time ranges. And especially only if the software package that came with the instrument has these weird psilocybin & psilocin degradation products in its analysis library.  And that the MS portion breaks them down into recognizible ions and not just ghost images of the parent molecule.......

 

You could potentially "do it live" by analyzing the raw data, but that kind of thing is waaaaaaay above my pay grade too. :laugh:

 

It’s not a question of pay grade it’s a question of who has access to one?

 

The lab 2 doors down from  mine has one & the dude who works there on my shift is cool.  Problem is, everything analyzed is saved & there's no way to "clear the browser history" as it were, much to our chagrin.   :mad:


Edited by Phineas_Carmichael, 13 January 2021 - 02:40 AM.

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#13 Norman

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Posted 13 January 2021 - 03:26 AM

Thanks Phin!
I knew you could shed some light!




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