Extraction of Psilocin (2 methods to discuss)

[egbert]

SWIM will be getting a lot of mushrooms soon, and because of this SWIM is interested in finding a proper extraction process. From what he has researched, it is very hard to obtain an extremely pure product without the aid of chromatography.

The two processes that he is interested in are the Soxhlet procedure and the one highlighted below. Can anyone comment on the Soxhlet extraction procedure? I did a little research on the Soxhlet apparatus, and it seems that it is not hard to operate, plus SWIM has chemistry experience at the University level.

Today I came across this method, and was wondering if anyone out there has actually tried this procedure:

Experimental

A representative sample of 2 to 10g of dried mushrooms is ground to a fine powder by mortar and pestle. The powder is mixed with 100 mL of dilute acetic acid in a 250-mL beaker. The pH is readjusted to pH 4 with glacial acetic acid. After standing 1 h, the beaker is placed in a boiling water bath for 8 to 10 min or until the internal temperature of the acid mixture reaches 70°C. The beaker is removed and cooled to room temperature under running water. The acid mixture is separated from the mushroom powder by suction filtration using glass wool. The filtrate is brought to pH 8 with concentrated ammonium hydroxide and quickly extracted with two 50-mL portions of diethyl ether. Gentle mixing instead of shaking should be used to prevent an emulsion. The ether is dried over sodium sulfate, filtered, and evaporated under nitrogen with no applied heat.

Crude psilocin will appear as a greenish residue. Recrystallization from chloroform/heptane (1:3) yields white crystals. The resulting powder can then be submitted to infrared and mass spectral analyses.

I can't find the link to the site right now; however, I remember reading that heating up the acid mixture to 70C converts the 'cybin to the 'cin. Also, the less time you spend between the addition of Ammonium Hydroxide and the Diethyl Ether, the better, as the psilocin will break down at that Ph level. Can anyone explain how you would go about evaporating the anhydrous ether under nitrogen?

I'm familiar with A/B extractions, and since this is evaporated in ether, then what you're left with is the freebase, right? SWIM want to eventually eat as much fresh at first, and then perform some type of extraction for long terms storage. SWIM realizes that psilocin breaks down easily in the presence of light and air, but the proper precautions would be taken. Amber bottle + C02 could be a possible storage route? Like the ones that hold the crystal LSD. How would you go about making such a container? If it is airtight, then would the small of amount of air that gets trapped in the vial oxidize the product?

Maybe there's someone out there that has tried both these methods? The Soxhlet apparatus is within SWIM's price range, and therefore that is always an option for him; however, he is more interested in the latter procedure because he has those all that equipment + chemicals readily available.

I apologize in advance if there is a thread out there like this. I'm still browsing the forums.

PEACE
-D

[Hippie3]

cf. http://forums.mycotopia.net/feasts-f...ion-study.html (Psilocybin Extraction Study)
?

[slaphappyjacko]

The best kitchen chemistry xtraction that can be done is with acetic acid. According to articles I have read, this is the solvent of choice even in a lab setting. It is more selective than alcohols, which also pull compounds which convert -bin to -cin (-cin being significantly less stable).

You will not be able to isolate any individual compound without analytical tools and the use of chromatography. Remember that what most people on call DMT or mescaline are actually alkaloid mixtures. I have yet to see FTIR, GC/MS, or NMR performed on any home brew extract.

There is no need for the soxhlet. It is useful, but in this case its use will not result in a product any more pure or in higher yield than that obtained using other methods (i.e. ground mushrooms soaked and agitated in vinegar, or reflux)

Evaporating ether under nitrogen could be performed by using a three necked round bottom flask. One neck is for a condenser, one for a thermometer, and one for the nitrogen. The nitrogen would need to be coming in from a large tank, as is standard in most chem labs. On a smaller scale, A balloon filled with CO2 or nitrogen can be attached to a needle from a syringe and then poked through a septum covering one neck of the flask. I don't recommend doing any of this.

BTW- Merck index says psilocin is unstable in solution, especially in alkaline solutions.

Therefore I don't recommend an a/b extraction.

If you are still in school, see if you have access to scifinder. I was able to locate a couple of papers on the subject. I believe it was Gartz who concluded acetic acid was the solvent of choice. Also, don't be afraid of the librarians. They can get you hard copies of pretty much anything (journal wise). If they ask me, I tell them the truth: I study biochemistry. I did a paper on clandestine methamphetamine production, and didn't raise a single eyebrow with the librarians.

Good luck. Don't be afraid to experiment.

PS- remember when reading papers to keep in mind the intent of the scientists who put it together. A paper may tell you how to get a "pure" isolated sample, but at a yield that is impractical for anything more than analytical chemistry. If you dipped a needle in a pile of alkaloid, the amount that you pull out would likely be sufficient for current analytical tools. On the other hand, a 90% yield extract of mixed alkaloids and crud is worthless for preparing standards (the first step to quantitative analysis) but great for pushing the envelope in psychedelia.

PPS- If you get your hands onPan cyan/trop and still need stronger, I don't know what to tell you

[righteous]

Another word on inert storage:

You may be able to find at a large beer/wine brewing supply store, a product which comes in a pressurized can with a spray-straw thing sticking off it that is pure argon,
This product is made for displacing the air in the headspace of an opened bottle of fine wine, such that it's degradation might be prevented (Sometimes that oxidative aging is exactly what you're going for, but some folks like a tart, new-tasting wine)

Argon is more expensive than nitrogen any way you go, but it also quite a bit heavier than air and more likely to form a nice protective 'blanket' over your product....

You may also find it cheaper to rent a helium tank than a nitrogen tank such as you might find at a party supply store..... What ever gas you use, if you really want to get all the oxygen out, you'll need to bubble it through your liquids before creating the solution of psilocin in order to displace dissolved/trapped air in the mix.

Cheers

[slaphappyjacko]

Found this today. It pretty much contradicts what I posted before, but I have read the article he sites. I won't contradict The Man, but I still recall Gartz saying otherwise (not to use alcohol). I have a BUNCH of misc articles on topics relevant both to this forum and to this thread. I will dig through them and find what I have.

SWIM has been collecting fungus "trash" for this very purpose. he/she doesn't find it interesting so much for consumption, but rather for bragging rights.

A few years ago, SWIM performed a crude MeOH extract on fungus, and upon evaporation, was able to see a few tiny crystals in a film of sweet smelling brown scum. The xtract was not consumed, so its activity is unknown.

[slaphappyjacko]

I re-read the paper from Gartz, and I was mistaken.

While acetic acid can be used, anhydrous MeOH was the solvent of interest.

It is concluded in the paper that if there is water present in the alcohol, most of the psilocybin is converted to -cin. This is because the compounds responsible for the conversion are water soluble and not so much in the MeOH.

He also found that ~12hrs @ room temp was required for total extraction with methanol. Less at elevated temperatures (of course)

A reflux apparatus is relatively safe/cheap/easy, and would be very useful if one is unwilling to just soak-n-shake. It is not necessary.

I don't know how clean an extract like this would be (not very), but it is possible that a series of recrystallizations could yield a pretty pure extract.