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OfflineChuangTzu
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Notes from a failed psilocin extraction (update: 2nd attempt)
    #4084169 - 04/22/05 09:56 AM (11 years, 7 months ago)

Today I attempted to extract psilocin from some mushrooms without success. The process I used was based on this article: Extraction Method for the Isolation and Identification of Psilocin; Casale, J. F., J. Forens. Sci. 30(1), 247-250 (1985). There were to be 2 substitutions made, namely petroleum distillates for ether and hexane. Here are my notes:
  • 12.5g dried mushrooms were ground to a fine powder in a blender.
  • 12.1g of this powder (~0.4g were lost in grinding) was transferred to a 3/4l flask to which was added a 5% aqueous acetic acid solution. Solution capped and mixed by swirling resulting in a green/grey sludge with pH between 3 and 4, probably being closer to 4. This was left to sit in a dark place.
  • Solution mixed each 10 minutes for a total of 7 more times (total time since adding acid, 70mins). NOTE: I added 10 minutes to the extraction time because it should probably be stirred constantly.
  • For the last 5 minutes the solution was swirled continuously while I waited for a pot of water to boil.
  • The flask was set onto a thick rag in a boiling water bath for 8 minutes with the lid open swirling occasionally and then cooled under running, cold water (~5 mins.) NOTE: During the heating, the muck started to turn a dark blue, from its original green/grey. This was noticed on the surface before shaking.
  • The muck was scraped out of the flask and into a conical coffee filter and allowed to drip for 5 minutes after which the remaining liquid was squeezed out. (80ml grey/white cloudy liquid was recovered)
  • 20% aqueous NaOH was added to bring the solution up to pH 8 (not sure exactly how much but definitely less than 10ml). A very dark, opaque blue solution resulted. NOTE: This should be done carefully, yet quickly. Carefully because the change is not linear--15 drops might produce no change in one region of the pH scale and 2 drops might bring you from pH7-pH8. Quickly because basic conditions + air = rapid amine destruction.
  • NOTE: Here is where everything starts to go wrong...
  • 50ml petroleum distillates added. On pouring I noticed that this was a much higher boiling fraction of petroleum distillates than I thought, it was obvious that it probably wasn't extracting anything from the aqueous phase.
  • I blitzed down to the gas station and bought some naphtha, came back, separated the two phases with a plastic bag sep. funnel and added 50ml of naphtha to the aqueous phase. This also seemed to be a terrible choice.
  • Again separated off the aqueous phase and tried the only other solvent I had on hand, chloroform. This formed a nasty emulsion which I tried, unsuccessfully, to break with salt.
  • By this time the aqueous layer was an impenetrable navy blue, almost black and I was out of solvents to try so I gave up.

Possible conclusions:
  • High boiling petroleum distillates are probably not very good solvents for psilocin.
  • Chloroform is also probably not a very good solvent for psilocin and is probably also not good for extracting aqueous solutions due to its tendency to form shitty, un-bustable emulsions.

Discussion:

I made the judgments of good solvent/bad solvent on the basis of color change alone. This is based on my experience with doing extractions of colored solutions and the fact that Casale obtained crude psilocin as a greenish residue. My experience is that if the product is colored and the solution being extracted is colored, then the extract will also be colored. This isn't necessarily true in all cases though for a variety of reasons. However, I didn't have the motivation to continue with the procedure of evaporating all those nasty solvents if I wasn't pretty sure it was working. I'll be trying this again in the next few days with the "proper" solvents. [Edit: oh yeah, and chloroform eats the hell out of plastic. But maybe only when mixed with a little water and naphtha?]

UPDATE: ROUND 2


This extraction was to go as previously with the following modifications:
  • 1. Extract the aqueous phase with several small portions of chloroform instead of ether.
  • 2. Recrystallize from methanol.

Everything else would be the same as above and as in the article with the exception that I wouldn't be drying the extract under nitrogen, just plain wet air.

  • The actual procedure went as planned except the jar in which the mush was soaked cracked in the boiling water bath after only about 2-3 minutes. The working volume of water was now about 3-fold and the temperature of the liquid was now possibly above 70C (as called for in the article) but I didn't have a thermometer so I didn't check. This made it harder to filter and also necessitated the use of much more chloroform than I would have liked.

  • The basified aqueous layer was extracted 5x with a total volume of about 200ml chloroform. It remained totally clear and the aqueous phase remained a deep blue. The chloroform was poured into a shallow aluminum baking tray and set outside under a fan for 1 hour.

  • At the end of this time, the pan contained a small amount of white residue and a few drops of green oil which was spread out on the pan and allowed to dry under then fan for another 20 minutes or so. The remaining greenish residue was scraped off with a scalpel and put into the bottom of a test tube. It was noticed that a lot of dust was stuck in the drying residue (use filtered air in the future?).

  • Boiling methanol was added to the residue with shaking forming a greyish solution but the dust made it difficult to see when/if all of the residue dissolved.

  • The test tube was capped and put in a freezer for 2 days.

  • As of now, there are no crystals, only dust, in the liquid.


More possible conclusions:
  • A thicker insulating layer should be placed under a flask in a boiling water bath when using crappy non-Pyrex equipment.
  • Always have a thermometer handy.
  • Air might be as bad for psilocin as we thought (when someone says psilocin is unstable, it's left unclear what they're comparing it to--compared to graphite, or compared to nitroglycerin? LSD is also somewhat unstable but it manages to hold itself intact for at least a few months in ambient conditions....)
  • That blue stuff (whether it is the breakdown products of psilocin or not) isn't soluble in non-polar solvents. This is at least congruent with it being an oxidation product and suggests that there is either significant functionalization, or complete breakdown of at least one of the rings.
  • My experience with color carrying through in all parts of the reaction is countered by the case of psilocin extractions.


Questions remaining:
  • Exactly what are the oxidation products of psilocin. Does anybody have a reference to an article which discusses this? For that matter, what are the metabolites of psilocin in humans?
  • Why is psilocin so much more unstable than DMT or any of the 5-substituted DMTs?
  • By what mechanism does the oxidation take place? It's fairly certain that it occurs at the 4-position and not at the amine since this behavior is not seen in DMT itself (except at high pH when all amines are easily oxidized. An interesting note, however, is that the blue color isn't seen in this case until the solution is basified, indicating that (if the blue is in fact oxidized psilocin) psilocin is actually stabilized in acid (a fact which is also alluded to by the Casale article).


Edited by ChuangTzu (06/26/05 09:37 AM)


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OfflineIGnosticAbhorI
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Re: Notes from a failed psilocin extraction [Re: ChuangTzu]
    #4084189 - 04/22/05 10:06 AM (11 years, 7 months ago)

Throw this in adv. cult....They'll eat it up :wink:

Sorry to hear that it didn't work, not exactly understanding all of that steps (still reading about P_extraction).....But it sounds intriguing...

Gl for next time :thumbup:

-Gnostic


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Offlinepyronicx
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Re: Notes from a failed psilocin extraction [Re: IGnosticAbhorI]
    #4084268 - 04/22/05 10:46 AM (11 years, 7 months ago)

Damn too bad it didn't work out.
Get some other chemicals and try again i will do the same =]
good luck


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Offlinedjsigma
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Re: Notes from a failed psilocin extraction [Re: pyronicx]
    #4084727 - 04/22/05 01:32 PM (11 years, 7 months ago)

It sounds to me that at the elevated temperatures you used, the psilocin was oxidized. it says in the link you provided that the oxidized version of psilocin is blueish in color. Tis really isn't all that much of a surprise, seeing as how acidic solutions are oxidizing in nature, and elevated temperatures just increase this. It seems to me that the extractions you've been doing aren't all that neccessary, however. I have read a few things here regarding extraction into alcohol solutions (methanol and ethanol). I would think these polar solvents would be better at solubilizing the psilocin anyway, given its structure. Try looking here if you want to keep trying the extractions.

http://www.shroomery.org/forums/showflat.php/Cat/0/Number/4019092/page//fpart/1/vc/1

And chloroform is actually a great solvent for extracting aqueous solutions, provided there isn't any crap in the aqueous layer that would make the two form an emulsion (pure water and chloroform do not mix in any proportions or form any sort of emulsions).


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OfflineChuangTzu
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Re: Notes from a failed psilocin extraction [Re: djsigma]
    #4084931 - 04/22/05 02:25 PM (11 years, 7 months ago)

Quote:

djsigma said:
It sounds to me that at the elevated temperatures you used, the psilocin was oxidized.




Yes, probably somewhat, but the heating was intentional--not for the extraction but to convert the psilocybin to psilocin, which is necessary to get any kind of extended crystals to form.

Quote:


it says in the link you provided that the oxidized version of psilocin is blueish in color. Tis really isn't all that much of a surprise, seeing as how acidic solutions are oxidizing in nature, and elevated temperatures just increase this.




Acidic solutions aren't inherently oxidizing or reducing, it depends on the exact nature of the dissolved species. In fact, psilocin is actually much more stable in acidic media than basic.

Quote:


It seems to me that the extractions you've been doing aren't all that neccessary, however.




Who cares?

Quote:


I have read a few things here regarding extraction into alcohol solutions (methanol and ethanol).




Me too.

Quote:


I would think these polar solvents would be better at solubilizing the psilocin anyway, given its structure.




They are plenty soluble in acetic acid. According to this article, Extraction and analysis of indole derivatives from fungal biomass; Gartz J, Journal of Basic Microbiology 34, 1994 there isn't a significant difference in the total amount of extracted alkaloids from cubensis with any of the various solvents--all are around 0.7%. Furthermore, alcohol also extracts a host of other crap from the mushrooms from which the alkaloids can't be extracted without first converting the psilocybin to psilocin bringing us right back to acetic acid.

Quote:


Try looking here if you want to keep trying the extractions.

http://www.shroomery.org/forums/showflat.php/Cat/0/Number/4019092/page//fpart/1/vc/1




That tells me nothing. I do not want a 25-50% mixture of psilocin and psilocybin. I want pure crystals. Needles if possible.

Quote:


And chloroform is actually a great solvent for extracting aqueous solutions, provided there isn't any crap in the aqueous layer that would make the two form an emulsion (pure water and chloroform do not mix in any proportions or form any sort of emulsions).



There is crap in the aqueous layer. Why would I be extracting pure water?


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Re: Notes from a failed psilocin extraction [Re: ChuangTzu]
    #4085217 - 04/22/05 04:04 PM (11 years, 7 months ago)


Quote:


Acidic solutions aren't inherently oxidizing or reducing, it depends on the exact nature of the dissolved species. In fact, psilocin is actually much more stable in acidic media than basic.





I was under the impression that things like perchloric acid and nitric acid were very strong oxidizing agents, hence why they dissolve metals so readily. The perchloric acid, in particular, is explosively oxidizing when it comes in contact with organic matter.

Quote:


There is crap in the aqueous layer. Why would I be extracting pure water?




You wouldn't want to extract pure water. I was simply stating that because you have emulsification agents in your water layer, you're not going to be able to separate the two layers. Without that crap in there, however, chloroform makes a wonderful extraction solvent. But take from that what you will, what do I know except you shouldn't listen to everything you read on the internet. Happy experimenting.


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InvisibleSoopaX
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Re: Notes from a failed psilocin extraction [Re: ChuangTzu]
    #4085231 - 04/22/05 04:09 PM (11 years, 7 months ago)

Where have you seen that heat turns psilocybin into psilocin?


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OfflineChuangTzu
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Re: Notes from a failed psilocin extraction [Re: djsigma]
    #4085331 - 04/22/05 04:33 PM (11 years, 7 months ago)

Quote:

djsigma said:

Quote:


Acidic solutions aren't inherently oxidizing or reducing, it depends on the exact nature of the dissolved species. In fact, psilocin is actually much more stable in acidic media than basic.





I was under the impression that things like perchloric acid and nitric acid were very strong oxidizing agents, hence why they dissolve metals so readily. The perchloric acid, in particular, is explosively oxidizing when it comes in contact with organic matter.




Yeah, and sulfurous acid is a reducing agent....

Quote:

But take from that what you will, what do I know except you shouldn't listen to everything you read on the internet.



Do I seem like some kind of amateur to you? Where do you think I got the chloroform?

Quote:


Happy experimenting.




Thanks.


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OfflineChuangTzu
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Re: Notes from a failed psilocin extraction [Re: SoopaX]
    #4085355 - 04/22/05 04:43 PM (11 years, 7 months ago)

Quote:

SoopaX said:
Where have you seen that heat turns psilocybin into psilocin?




In that article that I posted, they heat the acidic mush to 70C. They claim that this dephosphorylates the psilocybin but don't give a reference. This doesn't mean that heat turns psilocybin into psilocin under all conditions.


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OfflineHambo
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Re: Notes from a failed psilocin extraction [Re: ChuangTzu]
    #4085380 - 04/22/05 04:53 PM (11 years, 7 months ago)

Quote:

ChuangTzu said:

Do I seem like some kind of amateur to you?  Where do you think I got the chloroform?





You're a kidnapper? :smile:

I did degree level chemy too fella.. Too hard for me, but I also couldn't resist playing with chloroform. Mind you I couldn't resist sniffing fuming HCL either.. fook that hurts.. for ages... I'm glad I got thru in one piece as it happens.

Keep doing what you're doing, and posting your findings.. As you know I'm particularly interested in this side of things :smile:


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OfflineChuangTzu
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Re: Notes from a failed psilocin extraction [Re: Hambo]
    #4085417 - 04/22/05 05:08 PM (11 years, 7 months ago)

Quote:

Hambo said:
Quote:

ChuangTzu said:

Do I seem like some kind of amateur to you?  Where do you think I got the chloroform?





You're a kidnapper? :smile:





Who me? :whistling:


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Re: Notes from a failed psilocin extraction [Re: ChuangTzu]
    #4085447 - 04/22/05 05:16 PM (11 years, 7 months ago)

Far be it from me to question anyone's professionalism. Like Hambo said, I've done my fair share of sniffing ether and playing with chemicals I probably shouldn't have. I was just trying to analyze what may have happened, so that the technique can improve. As Hambo also said, I think a lot of us find this type of thing facinating, so anyone who actively experiments with it is ok in my book.


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OfflineJuan_del_Pueblo
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Re: Notes from a failed psilocin extraction [Re: djsigma]
    #4085507 - 04/22/05 05:36 PM (11 years, 7 months ago)

You guys seem like you know what your talking about. I'm just a simple uncle fester guy myself. I did get crystals this weekend. Not as clear as I wanted, but I got'em(thnx Hambo). My process was less tech then yours(just everclear). I try to work with simplicity.
I would like to hear about your continued research on the topic. Converting psilocybin into psilocin? A more pure Crystal? I can't wait...


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Offlinedr0mni
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Re: Notes from a failed psilocin extraction [Re: Juan_del_Pueblo]
    #4085724 - 04/22/05 06:43 PM (11 years, 7 months ago)

I haven't tried anything but a crude extraction that worked, but very shitily. I've read teks saying that to reduce useless crap in your solution you do as follows:

1)Soak powdered shrooms in ethanol or methanol for 12-24 hours.

2)Filter alcohol and evaporate on a dish.

3)Scrape up goop from plate (when I used feild cubes the goop was black/purple, when I used cultivated cubes it was the color of honey)

4)Disolve ball of goop into acidic solution (HCL would work well because NaCl is the only byproduct of neutralization).

5)filter this solution using vacuum filtration.

6)continue to basify, mix, and separate...

Never tried it but it sounds like it would work well.

Or if you want crystals you might be able to put the filtered acidic solution in the freezer and drop the temp so the crystals become insoluble, then filter again.

I'm just guessing here...


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InvisibleSoopaX
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Re: Notes from a failed psilocin extraction [Re: dr0mni]
    #4085753 - 04/22/05 06:49 PM (11 years, 7 months ago)

Where does the sodium come from for the NaCl formation?


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OfflineChuangTzu
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Re: Notes from a failed psilocin extraction [Re: SoopaX]
    #4088600 - 04/23/05 03:39 PM (11 years, 7 months ago)

Quote:

SoopaX said:
Where does the sodium come from for the NaCl formation?



I think he was assuming you'd use sodium hydroxide or sodium bicarbonate in the basification step.


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OfflineChuangTzu
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Re: Notes from a failed psilocin extraction (update: 2nd attempt) [Re: ChuangTzu]
    #4094404 - 04/25/05 10:12 AM (11 years, 7 months ago)

If any mod wants to slide this over to the advanced forum, that's fine by me....


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Re: Notes from a failed psilocin extraction (update: 2nd attempt) [Re: ChuangTzu]
    #4102865 - 04/27/05 03:37 PM (11 years, 7 months ago)

The write-up for the second attempt was appended to the end of my original post. Don't know if anyone saw that... And sorry for being a dick before.


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OfflineOmEgAx1
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Re: Notes from a failed psilocin extraction (update: 2nd attempt) [Re: ChuangTzu]
    #4151634 - 05/08/05 11:50 PM (11 years, 6 months ago)

I dont understand why you are trying to convert psilocybin into psilocin. Psilocybin is the stable form of the crystal, Psilocin breaks down in the presence of oxygen...


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Re: Notes from a failed psilocin extraction (update: 2nd attempt) [Re: OmEgAx1]
    #4159588 - 05/10/05 11:21 PM (11 years, 6 months ago)

I think I may have found some answers. First, to answer Om's question: Conversion to psilocin does make for a more unstable compound, but it allows you to use an acid/base extraction to effectively isolate the pure compount. I can offer some suggestions to CT: Heat the mush and acetic only up to 70 degrees C. Even 60 degrees should be ok. Heat up to this temperature quickly (by immersing in boiling water) and after reaching this temp, cool vessel under running water to quickly reduce the temperature. At high temperatures, psilocin will break down quickly. If you have the capability, it is best to do this in an inert gas enviroment, but yields can be good even without this method. Use dilute NaoH to basify (10% is ok, but add dropwise with stirring) to a pH of 8. Try not to overshoot this, as too strong of a base will breakdown psilocin. It is also critical to basify slowly for one of the reasons already pointed out here (non-linear scale). Immediately add suitable solvent (chloroform is good, naptha does not have good solubility for psilocin, DCM should be ok too, but this has not been tried to my knowledge) and GENTLY mix for about 2 minutes. Evaporate choloform (again, preferably under N2 or argon, but ok at atmosphere) to yield yellow xtals. These are ususally not very pure (say 50-70% pure) and can be crystallized in a mixture of chloroform/heptane (1:3) to yield slighly yellow transparent psilocin xtals which will turn green after a few weeks at room temp.

Triptamine


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