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Extracting psilocybin from mushrooms without ethyl alcohol?

The benefit is in having an easily measured dose form of psilocin, so instead of guessing at potency you can just take 10mg of psilocin and be done with it.

According to Erowid, complete extraction of the psilocin was achieved in 24h@room temp or 1 hour @ 45C.
 
True, that is an advantage, but extracted psilocin / psilocybin is reported to be quite unstable after evaporation for some reason although I am not sure if those who reported this used different solvents and accidentally extracted enzymes along with it that degrade the alkaloids.
In any case, an alcoholic solution is reported to be the best way to store it. Mushroom extract apparently just isn't the same as synthetic psilocin regarding stability. Again if you are going to ingest it, make sure you use something like vodka and not methanol.

FYI, if you homogenize your mushroom batch by powdering / crumbling as fine as possible and mixing it - you also have consistent potency. Disadvantage is you still need to titrate your dose with every batch.

If methanol is as effective as you say I might consider the extract near pure for all intents and purposes, in other cases you possibly still have to adjust your dosage according to purity just like with crude cactus extracts.

I have started again with cultivation (like in the past Cubensis, but I will also start with Panaeolus Cyanescens and medicinal / gourmet mushrooms soon), when I start building up a surplus I intend to do extraction and maybe even recrystallisation experiments. Even if the crystal is unstable, it's fun isn't it? ;)
 
^ could it be that the methanol extraction would yield the freebase compound? if that's the case, converting into a salt would be good, right?
 
Nah I just checked, the pKa of psilocin's amine is 8.47 and psilocybin is negatively charged above a pH of 4. If I am not mistaken both point to them existing primarily as salts in the tissue and I don't believe methanol would convert them into freebase form.

Furthermore Jochen Gartz wrote that there is significant enzyme activity of the phosphatase type with aqueous / acidic extractions.

Ethyl alcohol is reported to work but methyl alcohol is superior. Apparently as we are used to with these indolols extracts have the tendency to turn into goo, but I am not sure if this is mostly due to residual water from improperly dehydrated and/or low grade solvent.
In any case it sounds like the psilocybin is readily dephosphorylated and the alkaloids easily further degraded / oxidated / hydrated. So best is to extract with dried methanol absolute and immediately recrystallise from boiling water, unfortunately I don't know if you can only do that with psilocybin or with psilocin or a mix as well. Obviously you would lose some there but it could possibly kill any residual enzymes.

Still not sure if you can really yield high quality psilocin or alkaloid mix this way.
 
Methyl hydrate. Go to an automotive shop and ask for it, they use it for air brake antifreeze.
Although if alcohol is illegal where you live I'm guessing its a middle eastern country, they may have no need for air brake antifreeze

No, I live in Pennsylvania. I need to get a permit for anything stronger than 151 proof alcohol.
So things like Everclear are illegal here. Thus I need a safe substitute for grain alcohol.
 
Have you seen grape alcohol?
There are others too *no sources for consumables of any kind please*
 
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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....
 
@ Solipsis

I'm not understanding all of the chemistry talk, but what kind of psilocybin salt would the extraction yield then?
 
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
 
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---"
 
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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

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?
 
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.
 
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
 
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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.

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-crystal-of-the-gods-5050-extraction/
 
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.
 
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
 
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@ 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.

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.

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.

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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