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Thread: Extracting psilocybin from mushrooms without ethyl alcohol?

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    #26
    Have you seen grape alcohol?
    There are others too *no sources for consumables of any kind please*
    Last edited by Solipsis; 03-06-2013 at 05:15.
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    #27
    Quote Originally Posted by lcrlover View Post
    Have you seen grape alcohol?
    There are others too *snip*
    Its illegal to order alcohol online in PA. Liquor is government controlled, not privatized.
    Last edited by Solipsis; 03-06-2013 at 05:16.
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    #28
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    Methanol is not controlled in the same way ethanol is - you can't drink methanol, it will just blind you.
    No worries if you're under 18, or it's Sunday in a state with blue laws....
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    #29
    @ Solipsis

    I'm not understanding all of the chemistry talk, but what kind of psilocybin salt would the extraction yield then?
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    #30
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    Is there any particular reason ISO alcohol shouldn't be used?


    it's what I have on hand... I have an eighth of mushrooms I've been saving for like a year, maybe even more lol... I haven't wanted to take them because I hate the taste and they give me gut rot. If I could extract them that would be cool, though... I'm sure it would store better too. They aren't that important to me, as I have a good stash of 4-AcO-DMT too, but I don't want to waste them obviously
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    #31
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    Boom

    http://www.fanaticus.com/mycoalki.htm

    Shred the Monkey states
    "My monkey's brother ground up 48 grams of dry mushies and put them in a quart jar, covered the mushies with 153 proof grain alcohol (best he can find in these parts) and put it in a double boiler situation. After a half hour of letting the alcohol boil (without letting the water boil), the whole mess was filtered with 5 micron filter paper in a Buchner filter system using a vacuum cleaner for the vacuum source. The liquid was put aside, and the dry filtrate was put back in the jar, covered with alcohol again and boiled for another half hour. Repeated filtration. Mixed the two extract liquids together.

    The wife and I did a bioassay. She said her trip felt about equivalent to a 30 gram freshie trip. I felt about somewhere between 40 to 45 grams fresh. It was weird that from dry mushies that definitely have a distinct feel from fresh, the extract felt more like fresh and THERE WAS ABSOLUTELY NO TUMMY UPSET!! This was about the strongest dose I can take and not end up talking to the goddess at the peak."


    I would imagine Bacardi 151 is legal in Pennsylvania

    Also for Folley:

    "Behold, cystals - little white snowflakes - just using 99% isopropyl---"
    Last edited by EarthBounded; 04-06-2013 at 21:57.
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    #32
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    Quote Originally Posted by Folley View Post
    Is there any particular reason ISO alcohol shouldn't be used?


    it's what I have on hand... I have an eighth of mushrooms I've been saving for like a year, maybe even more lol... I haven't wanted to take them because I hate the taste and they give me gut rot. If I could extract them that would be cool, though... I'm sure it would store better too. They aren't that important to me, as I have a good stash of 4-AcO-DMT too, but I don't want to waste them obviously
    Yeah I have IPA on hand as well but no other alcohols. I think sekio already hinted at the reasons: anhydrous methanol is just superior for selective extraction of the alkaloids. Other solvents like acetic acid, water or other alcohols than methanol can extract sugars along with it and other impurities, but worse yet: those enzymes.

    I'm actually not sure if the only issue is with phosphatases that would yield psilocin (which is of course still nice) or if there is general catalysis of degrading reactions. Heat *might* destroy enzymes but it destroys alkaloids as well over time. Then again a lot of recrystallisations are from boiling solvent which can't be good either for that reason.

    So the main answer for relatively pure extraction is methanol and another subsequent main question is how to leave behind enzymes and keeping the alkaloids without too much loss. A/B workup?
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    #33
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    Quote Originally Posted by Solipsis View Post
    but worse yet: those enzymes.
    Solipsis, I am curious what do you mean by those Enzymes? Are you referring to what induces nausea?
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    #34
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    By the enzymes I mean at least the phosphatases and maybe other esterases, they can cleave phosphate groups and ester groups off of molecules hence the names.

    Psilocybin is the phosphate ester of psilocin. A phosphatase could therefore turn psilocybin into psilocin. The mushrooms apparently contain such enzymes and if they get extracted along with the alkaloids, you isolate them and put them together... which would make that conversion reaction happen faster since they are all in contact, not stuck anymore in (dried) mushroom tissue.

    My question is if these are the only enzymes that are present that might get extracted. If there are also other types that oxidize / metabolize indoles then there is a problem.
    Psilocybin conversion to psilocin is not that bad, it depends what you want. But oxidation is of course bad because we don't want to lose the alkaloids.

    If extracts are sometimes unexpectedly weak, there can be a few reasons (that I can think of): it can be inefficient extraction, it can be that a psilocybin with psilocin mix causes more dramatic psychological effects*, or it can be that oxidation or other degradation occurs, yielding oxides or rubbish. (* there are some people who suspect that compared to synthetic psilocin it seems psilocybin causes quite the headfuck which might account for at least part of the observation that mushrooms seem to produce effects that can be more difficult. Which can be problematic for some, but also potentially more of a lesson).

    So that is what I was wondering about.

    About the nausea, I believe that it is mostly the indigestive nature of mushroom tissue that causes it. Other than that there always remains the possibility of nausea with serotonergics because of 5-HT3 activation for example but no more than seen with synthetic tryptamine analogues.
    My experiences with Copelandia Cyanescens for example (which are very potent and comprise very little mushroom tissue in total for a dose) is consistent with this and I think that mushroom tea also often solves this. Then again, people often eat the pulp residue of the tea filtration / extraction, which would defeat the purpose of avoiding eating the mushroom tissue.
    Also there may be variation between fresh mushrooms, dried mushrooms, dried and reconsistuted / rehydrated mushrooms and boiled and strained mushrooms. Some forms may be more fibrous than others.

    I don't know those things for a fact but at least this is my theory.
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    #35
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    Quote Originally Posted by Solipsis View Post
    By the enzymes I mean at least the phosphatases and maybe other esterases, they can cleave phosphate groups and ester groups off of molecules hence the names.

    Psilocybin is the phosphate ester of psilocin. A phosphatase could therefore turn psilocybin into psilocin. The mushrooms apparently contain such enzymes and if they get extracted along with the alkaloids, you isolate them and put them together... which would make that conversion reaction happen faster since they are all in contact, not stuck anymore in (dried) mushroom tissue.
    Thank you for the response, I am putting that down in my notebook it helps me understand a few other things.

    The OP wasn't 100% clear on what he was trying to achieve, crystallization or similar results, or more of a tincture where the active alkaloids are suspended in Alcohol...

    From personal experience I have made 10-15 different mushroom tinctures in my day, grain alcohol is illegal in my state as well, I simply substitute 151 proof liquor which is legal everywhere in the USA.

    I mix the alcohol with the dry cubensis in a mason jar, tape in black duct tape put in the freezer shake twice a day for 4 days , untape, strain, then evaporate as much excess alcohol as possible. this turns a 1/4 ounce dry into 1/2 shot glass full of tincture, I pour 1/4 ounce by volume in a glass of red wine and drink so this is equivalent to 3.5g dried and all I can say is this is one of the most incredible trips, it hits within 5 minutes and last a shorter duration, more similar to DMT, I believe this is the safest way to extract all alkaloids correctly and would work better with fresh mushrooms because some of the psilocin and psilocybin content is lost during drying.

    I would be skeptical if going for crystallization could achieve these " perfect " effects. I feel like something will be lost along the way unless done by a chemist. However I could be wrong.

    I appreciate the info Solipsis
    Last edited by EarthBounded; 05-06-2013 at 19:07.
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    #36
    Quote Originally Posted by Bagseed View Post
    @ Solipsis

    I'm not understanding all of the chemistry talk, but what kind of psilocybin salt would the extraction yield then?
    i'm still wondering
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    #37
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    Quote Originally Posted by Anon610 View Post
    Well its 90% Ethanol and 10% Methanol. That should be fine correct? I heard ISO doesn't work as well. Now will this turn it into a tincture or crystals?
    I really don't want to go blind. Lol. But I need the best alternative. I'd like to make it a crystal/powder base but tincture is fine too. Lotta guides require 190 proof alcohol, which I need a special permit for.
    I didn't see this before my post above, to answer your question 151 proof is your " safest " most realistic option to obtain all alkaloids and leave the tissue behind. Just buy Bacardi 151 and let it soak an extra day and shake it ALOT, this works just fine, I have had some of my best responses from people who know there psychedelics with this exact Bacardi 151 / mushroom tincture, we actually call it getting tinct'd now because we had such a blast. It is very easy to ruin a project using IPA or Methanol if you are not experienced with alkaloid extracts.

    Quote Originally Posted by Bagseed View Post
    i'm still wondering
    It would be a full spectrum alkaloid powder I believe consisting of psilocin and psilocybin. Could B wrong

    A very good extraction would look like this:

    http://www.shroomology.com/topic/359...50-extraction/
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    #38
    yeah i supposed that it would yield more than one alkaloid, but i was wondering what form of salt they would be in (eg. fumarat, hcl,...) because solipsis said that it would not yield the freebase.
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    #39
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    Quote Originally Posted by Bagseed View Post
    yeah i supposed that it would yield more than one alkaloid, but i was wondering what form of salt they would be in (eg. fumarat, hcl,...) because solipsis said that it would not yield the freebase.
    I see, well I believe it is very complicated to convert plain mushrooms to a Fumarate or HCL Salt, I don't think Just Methanol or IPA could accomplish that possibly A/B?

    Solipsis? Now im curious also what kind of salts could come from an A/B mushroom extraction, someone has had to try it.

    I would guess most simple ethyl, IPA or Methanol Alkaloid extracts just yield a alkaloid powder not defined as a Fumarate, HCL or free base. So what would they be defined as? Visually I believe they resemble Fumarate salts but wouldn't be considered a Fumarate. Thats just my guess.

    Clarification from the pros?

    I would be curious to know what kind of salt is pictured in this tek:
    http://www.fanaticus.com/mycoalki.htm
    Last edited by EarthBounded; 05-06-2013 at 22:58.
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    #40
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    Quote Originally Posted by Bagseed View Post
    @ Solipsis

    I'm not understanding all of the chemistry talk, but what kind of psilocybin salt would the extraction yield then?
    Sorry, must have missed your question until you "followed it up" yourself

    I think that the salt forms yielded from extraction is a mix, I figure it would be made up by the minerals (better said the positive ions that are typically metals such as sodium and potassium) that you would typically find if you analyse the fungal cells. But not all of them, some don't seem to combine well such as calcium which would yield an insoluble salt, if calcium is no good perhaps magnesium doesn't work either.
    Like I said earlier: in 'neutral' conditions psilocybin has a net negative charge so the counterion it combines with would be positively charged. The fumarate that was suggested is an example of a negative ion.

    For psilocin it is different. I mentioned earlier that it has a pKa of 8.47 which means that at an acidity level (pH) of 8.47 half of it is protonated and the other half in freebase form. If the pH is about 7 there would be a lot more of the protonated form which would be positively charged and the counterion would be negative. I am guessing that less than 10% would be freebase but I could be way off. Again the rest might be extracted as a rich mix of salts of whatever kind of negative ions are around. Citrate, chloride you name it.

    I am thinking that it doesn't matter so much what kind of form (freebase or protonated) of alkaloid it dissolves preferably. Because if dry mushroom tissue is used there is no more equilibrium in the solution of fungal cells. Sorry I really cannot make this any less technical.

    Quote Originally Posted by EarthBounded View Post
    Thank you for the response, I am putting that down in my notebook it helps me understand a few other things.

    The OP wasn't 100% clear on what he was trying to achieve, crystallization or similar results, or more of a tincture where the active alkaloids are suspended in Alcohol...

    From personal experience I have made 10-15 different mushroom tinctures in my day, grain alcohol is illegal in my state as well, I simply substitute 151 proof liquor which is legal everywhere in the USA.

    I mix the alcohol with the dry cubensis in a mason jar, tape in black duct tape put in the freezer shake twice a day for 4 days , untape, strain, then evaporate as much excess alcohol as possible. this turns a 1/4 ounce dry into 1/2 shot glass full of tincture, I pour 1/4 ounce by volume in a glass of red wine and drink so this is equivalent to 3.5g dried and all I can say is this is one of the most incredible trips, it hits within 5 minutes and last a shorter duration, more similar to DMT, I believe this is the safest way to extract all alkaloids correctly and would work better with fresh mushrooms because some of the psilocin and psilocybin content is lost during drying.

    I would be skeptical if going for crystallization could achieve these " perfect " effects. I feel like something will be lost along the way unless done by a chemist. However I could be wrong.

    I appreciate the info Solipsis
    You are certainly entitled to your beliefs just like I am entitled to mine.

    The claim was not really that crystallisation yields perfect effects but a product superior for storage. Whether it is better to have an impure extract containing weird-ass secondary alkaloids or to have a pure extract containing virtually nothing besides psilocybin and psilocin is up for debate. We simply don't know. It could be that the only thing other alkaloids do is potentiate psilocin and psilocybin by serving as substrates for MAO - sacrificing themselves so that less primary alkaloids are metabolized.

    I guess your experience counts for something, but the value is limited if you have no experience with methanolic extractions as well. The researcher Gartz did compare them and found that methanol was best for alkaloid extraction. I don't know how far he went comparing how effective it is for secondary alkaloids such as baeocystin. But I think that alkaloid makeup was determined using that solvent, if the solvent would be selective only for psilocin / psilocybin that would have certainly skewed the results.
    Honestly I don't believe it, because things like baeocystin are TOO similar to psilocybin.

    Quote Originally Posted by EarthBounded View Post
    It is very easy to ruin a project using IPA or Methanol if you are not experienced with alkaloid extracts.
    Why? The procedure is not really *that* different. You can extract with methanol, evaporate the methanol and then add vodka or everclear or something like that.

    That you found your projects a success is not an argument that it cannot be improved.

    Quote Originally Posted by EarthBounded View Post
    I see, well I believe it is very complicated to convert plain mushrooms to a Fumarate or HCL Salt, I don't think Just Methanol or IPA could accomplish that possibly A/B?

    Solipsis? Now im curious also what kind of salts could come from an A/B mushroom extraction, someone has had to try it.

    I would guess most simple ethyl, IPA or Methanol Alkaloid extracts just yield a alkaloid powder not defined as a Fumarate, HCL or free base. So what would they be defined as? Visually I believe they resemble Fumarate salts but wouldn't be considered a Fumarate. Thats just my guess.

    Clarification from the pros?

    I would be curious to know what kind of salt is pictured in this tek:
    http://www.fanaticus.com/mycoalki.htm
    What is the big deal with salt forms? Is it that fumarate salts are more stable? If so, yes it would take an A/B extraction a la DMT. First you freebase the alkaloids, then you salt with fumaric acid.
    What salts can come from a workup like that? It depends on what acid you use in the process. Fumaric acid yields the fumarate, citric acid the citrate, vinegar the acetate, etc.

    The kind of salt depicted there could be the mix I was talking about. It depends on why it crystallized / what procedure was used. Assuming that no A/B extraction was done it would be a mix of naturally occuring forms.


    I'd like to be peer reviewed by ADD type folks.
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    #41
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    @ Solipsis -----> U r the Man bro, and I appreciate all your advice.

    I was simply letting the OP know if you are a beginner and want to make some sort of a mushroom extract a simple 151 proof alcohol is the easiest, safest best first step In my opinion. I feel a mask and eye protection along with proper ventilation is a necessity if working with Methanol or IPA, plus evaporation precaution. I definitely wasn't insulting your opinion and appreciate the clarification on salts.
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    #42
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    No problem, I didn't take it that way. And yes if you don't want to get complicated, using plain alcohol in the form of highest % spirits available is definitely the way to go.

    I was wondering about all this and about mushrooms that I might have extra of to experiment with that I want to turn into a crystalline product in the best possible way... but this kind of thing always irks me: if you do an acid/base extraction with something like 4-HO tryptamines (the goal being to clean it up and create some kind of salt) and your polar phase is water based, then that mix seems like a no-no because it often yields black goo and you need to evaporate the water at some point.

    So what about adding a few drops of concentrated sulfuric acid during an alcoholic extraction - after filtration to be precise (I will probably try to get methanol, which isn't so hard to acquire) ? Is that asking for oxidation or will the right amount yield sulphates than can be crystallized ?
    Do you then crystallize by making a saturated boiling solution that you gently cool all the way to -20 (Then evaporating the methanol to recover the rest as powder) ?
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    #43
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    I'd use dilute sulfuric not concentrated.
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    #44
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    http://www.fanaticus.com/mycoalki.htm

    the information here is priceless.
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    #45
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    Oh yes, I meant mostly that I would not use aqueous sulfuric acid but a dilution is indeed wise, I would dilute it in more methanol and it is possible I might dry the solution during the process using a desiccant.

    And that fanaticus site, which is mentioned by a lot of people here and over at the shroomery is great because it confirms a lot of extraction theory from the Gartz paper and also some ideas about possible reasons why an extraction might be superior to raw mushrooms. One reason that is as good as certain is avoiding the fibrous mushroom tissues that can cause indigestion apparently, and another reason that is bound to remain subjective is less mindfuck and more of the bliss-type stuff that I imagine to be a bit more in the direction of synthetic psilocin.
    By the way I agree with what you said earlier MGS, psilocin is very special, I find it more akin to DMT but it has the advantage of not being such a rocket ride because of the different ROA, and generally being different anyway.
    It is definitely one of the reasons why I plan on experimenting with these extractions.

    I'll try to make crystals in part, a special extra pure fraction that has more novelty of course, and with the rest I guess I will make a solution with added anti-oxidants. Both meant for storage in deepfreeze.

    Unfortunately I don't know a way to test if I will be successful in making sulphates... I'd basically assume that crystallizing from a low pH solution causes more indolol alkaloids to be cationic.

    Thanks for the help. I'll return here if I have results.

    One last thing though: I wonder what this means for my plans:

    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
    It would be very cool to isolate some psilocybin as crystals separately
    Last edited by Solipsis; 20-06-2013 at 02:20.
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    #46
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    I have like 3g left from a year ago I don't really plan on taking for a long time still. I'll probably just soak them in 99% ISO for a while, filter out and evaporate off. Perhaps repeating if I think it's necessary to clean it up.


    Will be taking that all at once, and since it's only 3g to begin with it shouldn't be a hell of a dose.
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    #47
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    If you start off with an average dose (about 3 grams though that can indeed be strong) and use a process that is less than efficient - ISO is not ideal for starters - then you run the risk of getting less than a satisfactory dose in the end, even if you take it all.
    But I would still do what you are planning because it is awesome to do experiments like this and you can get a qualitative improvement if all goes well. Good luck!
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    #48
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    Yeah, I'll just have to expect a light trip or take 10mg of 4-AcO-DMT with it if I want something heavier. These things hit pretty hard at 3g, though the stomach pains often distracted from the trips.


    I've made hash oil with that exact process, so this should be much harder.
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    #49
    So I have 91% ISO alcohol. Will this work? Can someone instruct me on how to do it basically, or link me. I've checked but nothing solid really for ISO extraction.
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    #50
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    Yes it should work, just not exactly as well as MeOH or EtOH.

    A problem could be that if you use an alcohol that is not really meant to be ingested (although IPA is not really toxic) that also contains water you will need to evaporate the solvent after extraction, and re-dissolving it is then optional.
    Ethyl alcohol does not have that problem, you can just drink it after extraction. And methanol without water should evaporate with less of a problem.
    To be honest I don't know if the extracted solution will make a brown goo or how fast. Remember that it is a risk and you may want to start with a small extraction first.

    Here's how I think I would do it:

    - You start by drying your mushrooms (if they are not dry yet), then grinding them as much as you possibly can. Maybe an electric coffee grinder is appropriate, I don't know if mortar and pestle work.
    - Put the mushroom powder in a glass container, an adequate size seems to me to have it filled up for 1/3 to 1/2 part.
    - Add enough solvent to cover the powder plus a little bit more so that you can stir it and still leave it covered.
    - Close the container and set it aside for maybe like a day or so.
    - Filter it using a coffee filter or a tea sock
    - Put the liquid in another container ideally with a large surface area opened up. For example if there is little liquid left a watchglass has an ideal shape.
    - If you have a fan, let it gently produce an airflow over the opened container with liquid. You can consider using the airflow coming out of your computer for this.
    - Take the mushroom pulp out of the filter and put it back again in the first container.
    - You can repeat the process the same way a second and even third time, or heat and simmer the mushroom/alcohol mix for maybe 1-3 hours (I think) by double-boiling. Be careful that you set up your gear so that your container does not fall over from the water vapor bubbling up and so that you don't get an insane amount of condensation dripping into it. Also make sure that you don't boil it dry. Use a limited exposed surface area, an erlenmeyer flask for example has an ideal shape here.
    - Filter the alcohol when hot (watch your hands, wear protection) and let it cool, if you can slowly.
    - In case you see powder or crystals forming out of the cooling alcohol solution, close the container and set it in the fridge, then after some hours set it in the freezer, some more hours or like overnight.
    - Hopefully this will produce nice crystals that you can quickly filter when it is still cold.
    - It's up to you if you want to pool your 2 or 3 batches or keep them separately. If you are able to crystallize some of it nicely, it can be a reason to keep it separate. Titrate your doses, initially treating that crystal as pure psilocin or psilocybin.

    The powder or crystals or solid with gunky texture that you yield can be stored and administered in different ways: in solid form or redissolved in something like everclear alcohol. You might want to add an anti-oxidant like ascorbic acid (vitamin C).
    Equal the resulting volume of liquid or mass of solid in strenght with the amount of mushrooms you made it from. Assume you had 100% efficiency, that way you cannot overdose, apart from misjudging the potency of your mushrooms to begin with.
    If you split your batches you will need some new kind of calculation.

    __________________________________________________ _________________

    Apparently psilocin exists mostly intracellularly, so it is trapped. I wonder if doing a freeze-thaw cycle on wet mushroom tissue can allow you to extract the psilocin better. My guess is that having to mess with the gooey stuff is not worth that little bit extra, but who knows. I have had problems before with cactus snot, no idea how you can break something like that down to pull a properly filtered solution from it. Maybe with a Soxhlet.

    Now that I think about it, getting a goo may have something to do with sugars. Mushroom cell walls are made of chitin, a polymer made of sugars. A known problem with extracting mushrooms using a solvent that contains water is that sugars may be extracted along with the alkaloids. Freeze-thawing mushrooms causes cell lysis. Busted cell walls may also mean sugar derivates interacting with water. Maybe it is something like making jelly or agar-agar.

    So my question is: what is a known method to deal with this? Maybe you can dry the goo with fans and storing it with a desiccant for a while, then perhaps it is possible to grind it so that it may be extracted with an anhydrous alcohol?
    Last edited by Solipsis; 27-06-2013 at 22:25.
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