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Invisibledeeptraveller
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Re: psilocybin / psilocin extraction. [Re: deeptraveller]
    #6202077 - 10/23/06 04:37 PM (15 years, 1 month ago)

forgive me that I have tried to confuse you...I have made it not specially :^)

after re-read I have understood that insolubility psilocybin / psilocin in 190 proof is well (and it has no anything the common with efficiency of extraction)


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we makes only that we makes...... this is very amusing idea if you under mushrooms_try this if you are not afraid
I have told it or have thought?


Edited by deeptraveller (11/05/06 03:12 PM)


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Invisiblefastfred
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Re: psilocybin / psilocin extraction. [Re: deeptraveller]
    #6206130 - 10/24/06 02:56 PM (15 years, 1 month ago)

> very pity that later then 13 years after first extraction the efficiency of solvent is subject to doubt...

Yes, it is a shame that there is still so much confusion on the subject.

> Probably, all already saw this information....

Yes. It's a good paper. I think everyone is pretty much in agreement with them. Acetic acid and aqueous ethanol are the best solvents to use. Methanol takes much longer and is poisonous. I also believe that the solubility is lower and therefore would require more volume of solvent.

Both acetic acid and aqueous ethanol solutions suffer from two problems... enzymatic dephosphorylation of psilocybin to psilocin by phosphatase and oxidation of psilocin.

I've proposed solutions to both problems. Use ascorbic acid to prevent oxidation, and use EDTA to chelate the metallic ions which inactivates the phosphatase.

Both ascorbic acid and EDTA are cheap preservatives in wide use and are completely safe to consume. I would like to thank the poster who initially suggested EDTA, he actually deserves the credit for that idea.

I'm hoping someone will try one or both of these ideas and compare them with regular extracts.


> tell me why it precipitated bigstyle all at once when i combined the two extraction fluids.

It's called crashing out the solute. It's a very cool chemistry trick and can be very useful. When you changed the concentration of the solvent it caused the solubilities of the solute to change and the excess "crashed out" of solution.

For example, if you take something that's soluble in acetone and insoluble in water and dissolve it in acetone... then add water to the solution (acetone and H2O are miscible) the solubility of the solute will quickly drop to zero as you add the water and the solute will come crashing out. i.e. it precipitates from the solution almost instantly.

So what you had was two aqueous ethanol solutions that were both fully saturated. When you mixed them the effect was to lower the ethanol concentration, which caused some of the solutes to come crashing out.

Now, as to what exactly it is... it's hard to say. I would guess that most of the psilocybin is still in solution, but some of the psilocin might have crashed out. I'd guess it's mostly bio-gunk though.

I would filter out the precipitate and test it. You could probably redissolve it by adding some concentrated ethanol to bring it back up to a higher ethanol concentration. Bio-gunk sometime likes to coagulate and undergo condensation reactions that from messes that won't redissolve. I would test that also to see if it will redissolve, if it doesn't then you've just come up with a good way to purify the solution.

There's been discussion of acid-base extractions for purification. I don't think those will work well for a number of reasons. But other ways of manipulating the solubility might work well. You could add acetone to the solution which should precipitate some sugars. You could lower the alcohol content, which it seems would precipitate some bio-crap. Interesting stuff.


-FF


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Invisiblefastfred
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Re: (psilocybin / psilocin extraction) - sediment tested: can be discarded [Re: shirley knott]
    #6206174 - 10/24/06 03:05 PM (15 years, 1 month ago)

Quote:

shirley knott said:
i filtered and bioassayed the sediment - nothing good was contained in it. therefore the liquid will be filtered and the orange goop discarded before reducing the volume in a double boiler. i'll be sure to take pics.




Cool! I just posted what I wrote yesterday and then saw your results. So it seems that crashing the solution with some water is a good way to remove a bunch of bio-gunk.

From the amount of bio-gunk that precipitated vs. the amount of actives that I would assume to be present it looks like you've greatly cleaned it up. That should do wonders for the final purity.

Maybe you could weigh the precipitated bio-gunk to see how much it was. If you have time I would also be interested to see if it can be redissolved in ethanol or if it's coagulated into insoluble bio-crud.

Also, did the bioassay show any nausea or other negative effects from the bio-gunk?


-FF


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Offlineshirley knott
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Re: (psilocybin / psilocin extraction) - sediment tested: can be discarded [Re: fastfred]
    #6206193 - 10/24/06 03:09 PM (15 years, 1 month ago)

biogunk was an entirely pointless experience both times.

sediment was again filtered out and discarded. see the other thread in PE for details and pics, i'll save this thread for summary info, like final results.

latest quality:


Edited by shirley knott (10/28/06 01:00 PM)


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Invisibledeeptraveller
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Re: (psilocybin / psilocin extraction) - sediment tested: can be discarded [Re: shirley knott]
    #6206825 - 10/24/06 05:24 PM (15 years, 1 month ago)

What does it mean: EDTA?

fastfred when you suggest to add an ascorbic acid? Prior to the beginning of process of extraction or after the end of it...only for storing longer?

From conversation with the Russian chemist in 2003:
Ascorbic it is necessary to add up to pH=3...4.

The citation:
by the way, would be very valuable to hear an explanation of the chemist why, say, n,n,-DMT, as against psilocybin, it is taken with good efficiency and without antioxidants...
Answer:
psilocybin is oxidized faster DMT owing to taking place in 4-th position indol's hydroxil groups. As everyone other phenolic(i.e. hydroxil at an aromatic nucleus) group it tends to oxidation, is especial in the alkaline environment.
There is one more nuance - psilocin amfoteric(dual structure) substance, i.e. in alkaline enough solution it will be ionized due to phenolic group and to gasoline at extraction will not go - it is necessary to select optimum ðÍ. Difficulties, difficulties...

p\s\ the word 'hydroxil' means OH group.
p\p\s\ it would be possible to invite here the chemist of the honours pupil for that that he has helped to solve this problem of times and on always? I think what enough to ask advice of the student of the fourth year of university.


--------------------
we makes only that we makes...... this is very amusing idea if you under mushrooms_try this if you are not afraid
I have told it or have thought?


Edited by deeptraveller (10/25/06 06:37 PM)


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Invisiblefastfred
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Re: (psilocybin / psilocin extraction) - sediment tested: can be discarded [Re: deeptraveller]
    #6212948 - 10/26/06 04:21 AM (15 years, 1 month ago)

EDTA is ethylenediaminetetraacetic acid. It is a common food preservative. It binds metal ions and removes them from solution.
Look here...
http://en.wikipedia.org/wiki/EDTA

> fastfred when you suggest to add an ascorbic acid?

I suggest adding it to the solvent before beginning the extraction.

In my opinion, as soon as the psilocin enters solution it begins to be oxidized fairly quickly.

One other note... EDTA needs to be used in a pH range of 4-8 for it to be effective. It is a good buffer, so that should never really be a problem.


-FF


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Invisibledeeptraveller
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Re: (psilocybin / psilocin extraction) - sediment tested: can be discarded [Re: fastfred]
    #6214385 - 10/26/06 04:10 PM (15 years, 1 month ago)

thanks for a link....very interestingly(I shall read...it is new to me)

How you consider? does exists an additive to solvent which can transform psilocybin in psilocin during boiling solvent?


--------------------
we makes only that we makes...... this is very amusing idea if you under mushrooms_try this if you are not afraid
I have told it or have thought?


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OfflineRGDL
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Other modes of action for ascorbic acid [Re: fastfred]
    #6224159 - 10/29/06 04:44 PM (15 years, 1 month ago)

Maybe the ascorbic acid causes some of the active ingredients to get converted into their salt form. Solubility in water increases and you get a better extraction (similar to the way a simple DMT extraction works). After all, the published literature has reports of acetic acid being just as effective as methanol for extraction, and there are anecdotal reports of cranberry juice working as well.


--------------------
Roof Gnome Discovery League


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OfflineBabo911
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Re: Other modes of action for ascorbic acid [Re: RGDL]
    #6225415 - 10/29/06 11:18 PM (15 years, 1 month ago)

Now RR said this was best for people who have alot of mushrooms and would like to condense them.... Well I have ALOT of sclerotia..... would this work in the same respect?

Got about 100 qt jars of sclerotia on the way.... (long story) that will be ready next month and was wondering if I could condense it?


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Invisiblefastfred
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Re: Other modes of action for ascorbic acid [Re: Babo911]
    #6226857 - 10/30/06 04:26 PM (15 years, 1 month ago)

> does exists an additive to solvent which can transform psilocybin in psilocin during boiling solvent?

There are already water soluble phosphatase enzymes present that will dephosphorylate psilocybin to psilocin. They are quite effective. I've read reports that complete conversion will happen in about 90 min at 90C. Actually boiling the solvent would probably denature the enzymes, so I wouldn't go over 90-95C.

> Maybe the ascorbic acid causes some of the active ingredients to get converted into their salt form.

The actives are zwitterions. They are their own salt. In order to form a salt they would have to have a positive charge, which is not the case.

The solubility of anything is mainly a function of pH, temp., polarity, and hydrogen bonding.

As for sclerotia I don't see why a standard extraction wouldn't work well. They might be a little tougher to grind up, but otherwise it should work the same.


A note about EDTA... I must have been looking at the wrong diagram, but you wouldn't want to have a pH as low as 4. It actually works best at alkaline pH. So a pH closer to 7 would be better. So you would want to use a minimum of ascorbic acid. Otherwise you could use ascorbic acid with some sort of weak buffer. A touch of gypsum might work well. Otherwise you could just use a bit more EDTA.

Ascorbic acid is a very effective antioxidant, so I think it would be effective in amounts small enough not to swing the pH too much. Otherwise EDTA is a good preservative itself, so you might not even need the ascorbic acid if you used EDTA.

I would love to have a HPLC handy to figure all this out and find the optimal extraction procedure. An alternative might be to use pDMAB and a spectrophotometer to figure things out, but you couldn't get a psilocin/psilocybin ratio that way. You would just get a reading of total indole alkaloid concentration.


-FF


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OfflineRGDL
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Re: Other modes of action for ascorbic acid [Re: fastfred]
    #6228664 - 10/30/06 11:09 PM (15 years, 1 month ago)

Are both psilocin and psilocybin zwitterions? What about when you raise the pH?

Casale (J. Forens. Sci. 30(1), 247-250 (1985) performs what looks like an acid/base extraction, on psilocin. (Apparently psilocybin can't be extracted with organic solvents no matter what the pH). He ends up with green crystals -- probably some product loss to oxidation -- as a crude product, but with something to reduce the oxidation (either EDTA or ascorbic acid), that might be fairly simple procedure to end up with a reasonably pure product.

And if you sealed it up well, you might be able to store it for quite a while.

Link to casale article
[http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/psilocin.extraction.html]


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Invisibledeeptraveller
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Re: Other modes of action for ascorbic acid [Re: RGDL]
    #6230483 - 10/31/06 12:46 PM (15 years, 1 month ago)

I have not correctly written!... I wanted to write the following:
How you consider? does exists an additive to solvent which can transform psilocin in psilocybin during boiling solvent?

It would be very good, isn't it?

fastfred
all that you writeing about EDTA is very interestingly to me.

As you think what quantity EDTA in grammes it is necessary to add in 100ml of C2H5OH (or there are no such data and EDTA its necessary to add up to achievement of a level ph=7)?

where to search this substance in Russia?...I would like to try to apply it

RGDL your information is interesting..... I should spend some time to translate it for russian


--------------------
we makes only that we makes...... this is very amusing idea if you under mushrooms_try this if you are not afraid
I have told it or have thought?


Edited by deeptraveller (11/07/06 04:06 PM)


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OfflineWhAcKeD
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Re: all you need to know about psilocybin / psilocin extraction. [Re: hIgHdRoLoVeR]
    #6234485 - 11/01/06 12:03 PM (15 years, 1 month ago)

nm


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Invisibledeeptraveller
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Re: all you need to know about psilocybin / psilocin extraction. [Re: WhAcKeD]
    #6238008 - 11/02/06 07:08 AM (15 years, 1 month ago)

RGDL
It is very difficult and hardly probable a necessary way of extraction. The basic purpose is to get rid of chitinous fabrics of mushrooms, but thus to keep all active substances. Cleanliness of the received substances is a minor question. Very few people is interested in extraction clean psilocin, I can assume that all interests complex extraction psilocybin + psilocin, and as to achieve stability of this extraction.


That me has interested it is only one thing substantiation about application for extraction of an acetic acid (I till now do not know what better to use 190proof or acetic acid). 190proof more attractive solvent from the food point of view. Strong concentration of vinegar can damage to a stomach...It is required to carry out additional chemical transition about which I didn't think yet..


--------------------
we makes only that we makes...... this is very amusing idea if you under mushrooms_try this if you are not afraid
I have told it or have thought?


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Invisiblefastfred
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Re: all you need to know about psilocybin / psilocin extraction. [Re: WhAcKeD]
    #6248004 - 11/04/06 08:02 PM (15 years, 29 days ago)

> Are both psilocin and psilocybin zwitterions?

I guess that's debatable. I wouldn't put formal charges on psilocin's structure, but I'm sure it has some dipole moment. The thing is that the secondary amine is always going to have basic character. You might look at the hydroxyl group and figure it has some acidic character. So you probably wouldn't call it a zwitterion, but you would probably say it's amphoteric.

> What about when you raise the pH?

Psilocin decomposes or is oxidized quickly at higher pH. I assume it gives up it's H from the hydroxyl group, which would then probably form a salt.

So if you look at psilocybin it's definitely a zwitterion, so it's not going to form any salt. I don't see how psilocin would form any sort of salt. Nitrogen likes to have 2 bonds and 2 lone pairs. If you put a positive charge on it then it will just act as a base and pick up a hydrogen. So if you did it in a basic solution it might form some kind of salt, but at basic pH it's unstable and the hydroxyl group is probably more vulnerable reaction than the amino group.

As far as the acid-base extraction, sure it will work and give you a pretty pure product. But do you really need that much additional purity, is it the best way to get that level of purity, is it worth the added complexity and solvents, and can you afford the inevitably greater loss of product?

Psilocin isn't very stable, but there are plenty of substances that aren't normally very stable. There are plenty of products that would never work without a preservative, but when you use one they become quite viable. That might be the case with psilocin.


-FF


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Invisibledeeptraveller
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Re: all you need to know about / psilocin extraction. [Re: fastfred]
    #6250151 - 11/05/06 03:24 PM (15 years, 28 days ago)

How you consider? Whether ph=8 represents some danger to a mucous membrane of a human body?


One of these days I shall offer a new way of psiloc(yb)in extraction.

fastfred I very much would want to read your opinion of that I shall write


--------------------
we makes only that we makes...... this is very amusing idea if you under mushrooms_try this if you are not afraid
I have told it or have thought?


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Offlineshirley knott
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Re: (psilocybin / psilocin extraction) - potion complete [Re: shirley knott]
    #6250307 - 11/05/06 04:24 PM (15 years, 28 days ago)



:pirate:  :teleport:  :scrambled:  :zoom:

so i finished my potion - that last 30ml looks pretty tasty for next time  :crazy2:


--------------------
buh


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Re: (psilocybin / psilocin extraction) - potion complete [Re: shirley knott]
    #6250342 - 11/05/06 04:38 PM (15 years, 28 days ago)

so did it finally end up being potent ?
i remember lots of failure


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Offlineshirley knott
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Re: (psilocybin / psilocin extraction) - potion complete [Re: ohmatic]
    #6250386 - 11/05/06 04:51 PM (15 years, 28 days ago)

the powder was over 2 years old, and the final elixir is indeed potent  :crazy2:


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buh


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Invisibledeeptraveller
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Re: (psilocybin / psilocin extraction) - potion complete [Re: shirley knott]
    #6253856 - 11/06/06 04:38 PM (15 years, 27 days ago)

excellently!

how you consider it is possible to evaporating more solvent (would be cool to transform a potentiality of 30ml in 15ml) or it is a limit?


--------------------
we makes only that we makes...... this is very amusing idea if you under mushrooms_try this if you are not afraid
I have told it or have thought?


Edited by deeptraveller (11/06/06 04:53 PM)


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