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Invisiblefastfred
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Psilocin oxidation product? * 1
    #3121442 - 09/11/04 06:52 AM (12 years, 6 months ago)

I've been looking around, for awhile now, to find out what product(s) psilocin oxidizes into. There doesn't seem to be much info available so I started speculating based on how serotonin and indole rings oxidize. This led me to two possibilities. My o-chem is pretty rusty, so could someone help me out?



This is what I have so far... Hopefully there are some chemistry wizards here who can tell me what's up.


-FF


Edited by fastfred (09/12/04 10:40 AM)


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OfflineAnnoA
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Re: Psilocybin oxidation product? [Re: fastfred]
    #3121445 - 09/11/04 07:02 AM (12 years, 6 months ago)

Hmm...here is some information about this:
http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=2680


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OfflineRed
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Re: Psilocybin oxidation product? [Re: Anno]
    #3121475 - 09/11/04 07:59 AM (12 years, 6 months ago)

If I read that right, mixing pottasium cyanide with an extracted product would greatly extend its life?

Assuming one wanted to er, uh.. kill all their friends. ;P


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Invisiblefastfred
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Re: Psilocybin oxidation product? [Re: Red]
    #3121514 - 09/11/04 08:37 AM (12 years, 6 months ago)

Thanks for the link Anno. It seems like the authors of the paper don't exactly know what it is either...
"The nature of this oxidation product is unknown." "The authors suggested that the final product might be of an o-quinoid structure."

"o-quinoid structure"... I'm lost... Anyone know what that means?

Here are some other references that I haven't had time to look at yet...

Blaschko, H. & W.G. Levine (1960)a Biochemical Pharmacology 3: 168-169. ?Enzymatic Oxidation of Psilocine and other Hydroxyindoles.?

Blaschko, H. & W.G. Levine (1960)b British Journal of Pharmacology 15: 625-633. ?A Comparative Study of Hydroxyindole Oxidases.?

Bocks, Sheila M. (1967) Phytochemistry 6: 1629-1631. ?Fungal Metabolism - IV. The Oxidation of Psilocin by p-Diphenol oxidase (Laccase).?

Bocks, Sheila M. (1968) Biochemical Journal 106: 12P-13P. ?The Metabolism of Psilocin and Psilocybin by Fungal Enzymes.?

LEVINE W. G., 1967 - Formation of Blue Oxidation Product from Psilocybin. Nature, 215: 1292-3.

Hortia A. and L. J. Weber. 1961. The Enzymic Dephosphorylation and Oxidation of Psilocybin and Psilocin by Mammalian Tissue Homogenates. Biochemical Pharmacology. 7:47-54.

Horita, A. and L. J. Weber. 1963. Oxidation of 4- and 5-hydroxyindole derivatives by mammalian cytochrome oxidase. Life Sciences. 1:44-49.

Here is another pic of some stuff I've been looking at...



-FF


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Offlineshirley knott
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Re: Psilocybin oxidation product? [Re: fastfred]
    #3122437 - 09/11/04 03:22 PM (12 years, 6 months ago)

um.. why do you worry about this?



also wrong forum, btw  :wink:


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Invisiblefastfred
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Re: Psilocybin oxidation product? [Re: shirley knott]
    #3125079 - 09/12/04 05:04 AM (12 years, 6 months ago)

I'm not worried about it per se. It just seems to be an area where the science is lacking.

Also, once the oxidation product is identified it can be given a common name which would make discussions about it a little easier.

I posted it here because this seems to be where extractions, psilocin, oxidation, and chemistry are talked about.


-FF


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OfflineSpudz76
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Re: Psilocybin oxidation product? [Re: fastfred]
    #3125099 - 09/12/04 05:19 AM (12 years, 6 months ago)

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?  And if that didn't do it, how could blued psilocin be turned back into psilocin or even better back into psylocybin.  Some extractions have covered the conversion of psilocin back to psilocybin, but if the addition of a oxygen scavenger like ascorbic acid protects the psilocin then maybe it would be worth using somehow in an extraction method as a buffer to increase yield/strength.

That is why he is studying it.  Quite cool I think.

Also of note is there is no other "mushroom chemistry" or "mushroom preservation" forum here that I know of, and thus this falls best under advanced cultivation (since part of cultivation is harvesting, and drying, and this is just a possible extension of that).  So I'd say it is in the right place.  Sure it could go in general discussion but who goes there? :smile:


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InvisibleShmoppy McGillicuddy
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Re: Psilocybin oxidation product? [Re: Spudz76]
    #3125716 - 09/12/04 01:16 PM (12 years, 6 months ago)

Its been said that the bluing is not actually psilocin oxidizing, but instead an enzyme action that exists in cubensis, that may or may not have anything to do with psilocybin/cin. Erowid has referenced three papers that mention this, and it has to be said that some other psychoactive species which contain psilocin and psilocybin do not bruise blue.

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.

The papers are in German, but here they are:

2. GARTZ J., 1991- Quantitative Bestimmung der Indolderivate von Psilocybe semilanceata (Fr.) Kumm. Biochem. Physiol. Pflanzen 181: 113-128.

3. GARTZ J., 1987- Variation der Alkaloidmengen in Fruchtk?rpern von Inocybe aeruginascens. Planta Med. 48: 539-541.

4. GARTZ J., 1989- Analyse der Indolderivate in Fruchtk?rpern und Myzelien von Panaeolus subalteatus (Berk. & Br.) Sacc. Biochem. Physiol. Pflanzen 184: 171-178.


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


Edited by Shmoppy McGillicuddy (09/12/04 01:19 PM)


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Offlinehyphae
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Re: Psilocybin oxidation product? [Re: Spudz76]
    #3125726 - 09/12/04 01:19 PM (12 years, 6 months ago)

The same reaction should occur most likely with lemon juice also. In cooking they rinse sliced bananas, apples, etc; to keep them from oxidizing and turning brown now in our case it would be blue oxidation but in either case it seems to prevent oxidation on the surface which of course would be the most likely the place for it to occur! :wink: I'm sure if theres any info's on this oxidation in cooking it may shed some light on what actually occurs during this reaction. GL FF


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Re: Psilocybin oxidation product? [Re: hyphae]
    #3125924 - 09/12/04 02:35 PM (12 years, 6 months ago)

We had discussed that in the other thread. The thing most interesting is that ascorbic acid gets rid of the blue bruising/staining and so it was wondered if it just further decomposes the oxidized psilocin to get rid of the blue, or if it might somehow actually be restoring the psilocin back from the oxidized form. I think it's probably unlikely, mostly because it seems too simple. But something useful to check out anyway, just in case.


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InvisiblePinback
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Re: Psilocybin oxidation product? [Re: fastfred]
    #3126190 - 09/12/04 04:34 PM (12 years, 6 months ago)

This is what o-benzoquinone looks like:

So probably, the o-quinoid structure that they refer to looks something like this:


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Re: Psilocybin oxidation product? [Re: fastfred]
    #3127035 - 09/12/04 10:02 PM (12 years, 6 months ago)

Well, this could bring up may interesting questions besides "what exactly is it".


I personally do not believe that the bluing reaction is directly the result of oxidized psilocybin/psilocin. I believe Shulgin noted this when he synthesized them. An enzyme acting upon the psilocin, could be the reason. Other species that have the same "active" chemicals that do not turn blue leads me to believe otherwise unless the catalyst enzyme is missing in those species. Even species absent of psilocin/psilocybin can bruise blue.

I think the most interesting thing is that ascorbic acid removed this coloration. A better way to preserve the actives could be developed...

Provided it actually prevents or slows the decomposition of alkaloids... Who knows, psilocin could oxidize into a potent anti-cancer drug or something else beneficial. RED FLAG - illegal substance, forget about research on these...


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Invisibleutopianglory
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Re: Psilocybin oxidation product? [Re: fastfred]
    #3128431 - 09/13/04 04:53 AM (12 years, 6 months ago)

It might help in explaining why many feel that vitamin C aids in digestion of the mushroom matter at the very least.


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Invisiblefastfred
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Re: Psilocybin oxidation product? [Re: utopianglory]
    #3128800 - 09/13/04 10:51 AM (12 years, 6 months ago)

ATWAR and Shmoppy, I don't feel that there is another substance involved in the bluing. While there certainly may be certain enzymes involved in oxidizing the psilocin and hence the bluing, I still think it is actually oxidized psilocin.

While some authors have speculated the involvement of unrelated bluing compounds, I have found the evidence of this lacking. Other authors have speculated that it IS the psilocin oxidizing. It is true that some non-active mushrooms bruise blue, but there are many compounds that oxidize to a darker color. That is, in fact, the general rule for oxidizations.

It is also known that psilocin oxidizes to a bluish color, so I see no reason to believe that just because other compounds oxidize blue that the blue oxidization when psilocin is present would be from another compound. Perhaps even in the non-psilocybin mushrooms the bluing agent is actually psilocin and is simply oxidized by enzymes before it can be analyzed. Perhaps these mushrooms produce only psilocin with no psilocybin. Psilocin oxidizes so quickly in the presence of oxidizers and oxidizing enzymes that they would have to analyze the sample extract within minutes or hours to get a reliable reading. It is also possible that the psilocin would oxidize during the extraction process because of certain enzymes which might be soluble in the extraction medium.

Simply put, when asked to explain a bluing reaction I choose to look at known compounds that have been found to be present in the sample, rather than try to explain it with unknown compounds which are present in unrelated samples from other species.

ATWAR mentions that some other psilocybin species do not bruise blue. I would be curious to hear more information on that. I would be interested to see what their psilocybin/psilocin ratio is. If you could post a link to Shulgin's conclusions it would be much appreciated.


-FF


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Re: Psilocybin oxidation product? [Re: fastfred]
    #3133213 - 09/14/04 06:35 AM (12 years, 6 months ago)

Alexander Shulgin
Here's a link to his bio on his site, which links to his papers, and also perhaps you could ask him your questions directly before he dies or forgets (he looks pretty old!). He knows alot about all sorts of psychoactive compounds.


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Re: Psilocybin oxidation product? [Re: Spudz76]
    #3133716 - 09/14/04 11:44 AM (12 years, 6 months ago)

Interesting topic.

I would just like to add the I know for a FACT that Ps. Semilanceata DOES bruise blue. Albeit it does not always do it, nor does the blueing occur immediately as with other species. Also, I have found more that natural location/temperature where they are grown have the greatest effect on this 'blueing'. (from brown/orangish/grey/blue) I know of locations where a 1m sq. area will almost certainly have the blue liberty caps. The most potent experience I have ever had on this species was the bluest liberty caps you have ever seen that were literally picked under snow. OEV for at least 2 hours. A very intense (and very pleasurable) experience... and one that I was never able to replicate. Sorry that this is somewhat offtopic. But I had to reply to the blueing comment as I have read this elsewhere before.

More mushroom research!!!


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Re: Psilocybin oxidation product? [Re: PSemilanceata]
    #12702139 - 06/07/10 11:18 AM (6 years, 9 months ago)

Im stumped! I cant find what it oxidizes to either! Have you seen this site? http://isomerdesign.com/PiHKAL/index.php?domain=tk

I bet the conclusion is somewhere in there... maybe?

And I posted on a different thread explaining the bluing. Here is a copy paste of it...

(Blue Mycelial Paradox thread)

Now the bluing I know is related to several compounds... not having to do with potency at all. But when Psilocin hits oxygen, it turns blue....


The Swiss chemist Albert Hofmann and the laboratory assistant Hans Tscherter from Sandoz Laboratories isolated psilocin and its phosphate ester psilocybin from Psilocybe mushrooms in 1959, guided by self-administration.

Psilocin can be obtained by dephosphorylation of natural psilocybin under strongly acidic or under alkaline conditions (hydrolysis). Another synthetic route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole.

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. Similar products are also formed under acidic conditions in the presence of oxygen and Fe3+ ions (Keller's reagent).

And the verdict is that the bluing is not only a breakdown of alkaloids, but Variegatic Acid hitting oxygen as well.. which is why we have the following color changing mushrooms with no psilocin derivative or product, most common being the Boletus that bruises blue just like Psilocybes....

    *  Agaricus bisporus (white button mushroom) - Usually bruises pinkish. Stick your thumb into a grocery store-bought one to test.
    * Boletus campestris - Bruises blue or blue-green. Many yellow-pored boletes bruise blue.
    * Psilocybe cubensis - The stems bruise blue or blue-green. This is a hallucinogenic mushroom, but note that not all hallucinogenic mushrooms bruise blue.
    * Russula rubescens - Bruises reddish, and then slowly turns to black.
    * Mycena haematopus - Bleeds purplish.
    * Lactarius helvus (maple syrup milky cap) - Bleeds colorless latex that smells like maple syrup.
    * Lactarius chrysorrheus - Bleeds white latex that dries to a deeper yellow.

Or the Gyroporus Cyanescens that has a high amount of Variegatic Acid...




Bottom line... its not a paradox! This explains it quite clear...

Psilocybin is a naturally occurring compound found in varying concentrations in over 200 species of Basidiomycota  mushrooms, distributed amongst the following genera: Psilocybe  (116 species), Gymnopilus (14), Panaeolus  (13), Copelandia (12), Hypholoma  (6), Pluteus  (6) Inocybe  (6), Conocybe (4), Panaeolina  (4), Gerronema (2) and Agrocybe, Galerina  and Mycena  (1 species each).[9]  The spores  of these mushrooms do not contain psilocybin or psilocin. Mushroom caps tend to contain more of the psychoactive compounds than the stems.[10][11][12]  The total potency varies greatly between species and even between specimens of one species in the same batch.[13]  Younger, smaller mushrooms have a higher concentration of alkaloids and have a milder taste than larger, mature mushrooms. In general, the psilocybin content of mushrooms is quite variable (approximately 0.5–2% dry weight) and depends on species, growth and drying conditions, and mushroom size.[14]  Mature mycelium contains some psilocybin, while young mycelium (recently germinated from spores) does not contain appreciable amounts of alkaloids.[15]  Many species of mushrooms containing psilocybin also contain small amounts of the psilocybin analogs baeocystin  and norbaeocystin.[16][17][18]  Most species of psilocybin-containing mushrooms bruise blue when handled or damaged[19]  due to the oxidization of phenolic compounds. This reaction, however, is not a definitive method of identification or determining a mushroom's potency. Source: http://en.wikipedia.org/wiki/Psilocybin

Side note... phenolic compounds give grapes and berries and mushies and plums and red cabbage and, tea, chocolate, etc their color :smile: In fact, some polyphenols cure tumors, and are strong anti-oxidants as well.. that's why they say a glass of wine is good for you... beneficial phenolic compounds! Whats cool about that is that the anti-tumor Resveratrol phytoalexin is produced by plants when fungi attack it... imagine that :smile:

Back to the Psilocybin...

The intensity and duration of entheogenic effects of psilocybin mushrooms are highly variable, depending on species or cultivar of mushrooms, dosage, individual physiology, and set and setting. Source: http://en.wikipedia.org/wiki/Psilocybin

Your mileage may vary when it comes to your trip... so there is no clear way to define weak or strong on a broad basis. Psilocin is mystifying like that, hence the title magic mushrooms :wink:


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

SO there you go, hope that helps :smile: Im too tired this morning to research anymore, but I will check back this afternoon and help find the answer if you havent by then :smile:


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OfflineUrbanistiC
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Re: Psilocybin oxidation product? [Re: UrbanistiC]
    #12702168 - 06/07/10 11:27 AM (6 years, 9 months ago)

Read this... about the oxidization... http://www.erowid.org/archive/rhodium/chemistry/psilocin.extraction.html

And then check this out...

"Psilocybin: a pharmacological profile." American Journal of Pharmacy  146: 91-95 (1974). I cant find the doc, but I bet its in there.

And I bet you 20 bucks the answer is in here... http://www.erowid.org/archive/rhodium/pdf/psilocybin.und.psilocin.pdf ; but its in german? Shitty. Thats the person who first extracted/synthed the stuff.

And a list of studies with one in particular... http://www.maps.org/w3pb/new/2005/2005_Carter_22621_1.pdf

Here is the list... http://www.maps.org/research/index.html#PSILOCYBIN


Okay, off for some sleep. Hope those links help.. its where I would start looking.


But, maybe it just turns into a phenolic compound?


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Invisiblenooneman
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Re: Psilocybin oxidation product? [Re: fastfred]
    #12703487 - 06/07/10 04:33 PM (6 years, 9 months ago)

It would be interesting to know if any of the chemicals that psilocin oxidizes into are active on their own.


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OfflineUrbanistiC
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Re: Psilocybin oxidation product? [Re: nooneman]
    #12704365 - 06/07/10 06:50 PM (6 years, 9 months ago)

Well now, lets find out! Im working on an answer now. I have the feeling its more simple than I am anticipating!

I am so impressed with the level of study being put into Psilocin as of late... a drastic increase since 2000-2002 when I first starting paying attention to the beneficial properties of this amazing substance. Yet, its still such a young research subject! Hofmann opened the science communities eyes to it in 56 by naming it psilocin and psilocybin.  Yet at present, a useful aqueous extraction procedure has not been reported for psilocin and psilocybin.


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Keep it ReaL.


Edited by UrbanistiC (06/07/10 06:54 PM)


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