yinga (Hive Bee)
03-13-03 22:31
No 416689
      Ask Dr. Shulgin on Psilocybe Mushroom Extractions  Bookmark   

Ask Dr. Shulgin Online

ARCHIVE:  March 5, 2003

Psilocybe Mushroom Extractions

Dear Dr. Shulgin:

A friend of mine performed a Soxhlet extraction of 12 grams of powdered Psilocybe cubensis, using 95% ethanol. When the 60 mL of extract cooled to room temperature, many small transparent, colorless crystals had formed on the bottom of the container and did not redissolve on agitation. Do you know what these crystals are? -- Journeyman

Dear Journeyman:

There is a fascinating report in the literature that gives a quantitative measurement of the efficiency of extraction of both psilocybin and psilocin from the mushroom Psilocybe bohemica. The citation to the article is Kysilka, R. and Wurst, M., Planta Med. Vol. 56 pp. 327-328 (1990). These Czechoslovakian scientists studied the efficiency of both methanol and ethanol as solvents, each containing varying amounts of water. The results were, to me, both unexpected and most provocative.

The isolation of psilocybin seemed to be quite reasonable. This alkaloid is reasonably soluble in boiling water from which it can be nicely crystallized. It is less soluble in boiling methanol, and almost insoluble in boiling ethanol. And the extraction efficiency is optimum with methanol and almost as good with ethanol. With both, the less water present, the better. The compound is, after all, a perfect example of a zwitterion, the internal salt of a phosphoric acid and an amine base.

But the numbers with psilocin are strange. With aqueous ethanol, the optimum extraction was with a 70% ethanol concentration, and the extraction efficiency dropped almost to zero when there was no water present. But methanol was extremely inefficient regardless of the amount of water present in it. These researchers were apparently surprised by these findings, as they explored further and uncovered other clues. Time is a factor. Psilocin is extracted at a much slower rate than is psilocybin because it is contained intracellularly in the plant, and thus slower to be gotten out. They conclude that many of the low psilocin assays of mushrooms are due to this difficulty of getting the alkaloid out of the plant and into the extracting solvent. Using this information they determined that the levels of psilocybin and psilocin are substantially the same in Psilocybe bohemica, in conflict with the published literature values where very small amounts of psilocin were observed.

Efficient extraction apparently requires patience.

As to the identity of the crystals that were drifting around in the cooled Soxhlet receiver, from their being insoluble in ethanol, and white, and transparent, I would guess that you are seeing pure psilocybin.

-- Dr. Shulgin

(Hive Addict)
03-13-03 22:55
No 416700
      Old news  Bookmark   

This has been posted before... UTFSE!

Accept No Imitations, There Can Only Bee One; www.the-hive.ws
(Hive Bee)
03-13-03 23:18
No 416709
      Whoops, my bad. The date said march 5 so I...  Bookmark   

Whoops, my bad.  The date said march 5 so I made an assumption..
(Hive Bee)
03-18-03 02:09
No 418236
      but anyway...  Bookmark   

this is great information for psilly bees, and that post slipped way down quite quickly, this one's still quite high up.

I once did an extraction ethanol and I was looking at it when it got quite low with all these crystally things floating around and it occurred to me that it might be worth catching them in a filter.

I didn't, I tried to dry the whole mess down, and the bad news is that urea is the main other chemical that comes through. dark golden brown smells like wee. hygroscopic too it seems, and I wasn't willing to heat it to get it out, afraid of oxidising the psilocybin.


worst of all is the local 'methylated spirits' contains fluorescin (my guess due to it's seeming UV activity though not properly verified with a blacklight) becomes quite concentrated and the whole mix is *really* hard to drink, bitter as fuck.

so once the crystals form, perhaps let it sit in a fridge for a week to let the crystals grow bigger then filter and dry and scrape them off for later use. perhaps store with an equal amount of ascorbic acid to slow down decomposition, as well as keeping in the freezer.

Or maybe do a simple water extraction and boil down then crash out with ethanol or acetone...

SWIU's gotta get his thai cube spores going then, double quick. SWIU hates eating fresh or dried mushrooms.

It means buckle your seatbelts dorothy, because kansas ... is going bye bye
(Hive Bee)
03-29-03 13:37
No 422249
      This is faster  Bookmark   

Urushibara I do like your posts. But I don't like that you don't recognize the value in mine. Or perhaps you have missed the following ultrafast write-up to obtain pure crystal psilly and to separate it from urea:

1 extract the mushrooms powder in 140 proof or 70 percent alcohol

2. Filter the liquid as fine as possible (0.2 um syringe filters are nice

3. evaporate to 1/10 of the volume,

4a remove undesired components with pet ether (twice)
4b acetone (twice) and
4c. 95 percent alcohol (cold)

5. then extract the remaining dark stuff in 95 percent ethanol (boiling),

6. separate the liquid from the dark granules (gravity, decanting)

7. cool the ethanol until white crystals form.

(Hive Bee)
03-29-03 13:46
No 422251
      yachaj  Bookmark   

The disregard of your other post was unintentional, I was merely responding to a thread that was much higher up the list.

Since, as mr shulgin says, psilocybin is not very soluble in ethanol, wouldn't it be better not to boil it down and simply freeze the extract solution, this would drive the psilocybin out of the water and it would then have to crystallise, which could be easily caught in a filter. I boiled some down once and it was still insoluble enough to crystallise, but I don't think it is neccessary to boil it down as this would act to decrease the ethanol proportion, and as shulgin says it is less soluble in ethanol. At -20 to -40 it is probably damn near completely insoluble.

just a thought, after seeing that the psilocybin crystals precipitated out pretty much within a few hours of placing the extract on a dish.

swim hasn't got any psilos to play with in this sort of way at the moment...

It means buckle your seatbelts dorothy, because kansas ... is going bye bye
(Hive Bee)
03-29-03 15:20
No 422267
      No boiling down  Bookmark   

Urushibara wrote:
>The disregard of your other post was unintentional, I was >merely responding to a thread that was much higher up the >list.


>wouldn't it be better not to boil it down and simply >freeze the extract solution

I have my doubts since it is really handy to use 140 proof ethanol for the initial extraction. Am I correct in that you propose to simply soak the mushroom powder in alcohol, filter, evaporate, freeze and catch the first white crystals which precipitate (urea stays in solution)?

At the very least you will need to evaporate most of the liquid. Psilocybin may be poorly soluble in pure water and -ethanol, but that does not mean insoluble (the proof is in mushroom tea - a cup of water may still hold a few grams of psilly in solution!).

Other problem besides the urea is that the mushrooms contain fatty resins and alcohols as well: the mushroom 'perfume'. When most of the 140 proof is evaporated the mushroom alcohols stay behind and may keep the crystals oily. But they can be removed with acetone.

The final boiling/cooling step which I mentioned takes just a few minutes (place the vial with cleaned up insoluble stuff and 190 proof ethanol in boiling water). This shouldn't hurt the alkaloids too much. The only purpose of this step is to re-dissolve the alkaloids for recrystallization of the psilocybin.