i'm glad you're undertaking this experiment user_7,
we'll all learn something..

benz is definitely the man, and i cant handle the internet much a.t.m. let alone shroomery,
so i'm not sure what's being said there, but it should be remembered that acetone with even 1% water
will act differently..

the Hofmann technique (and anne) emphasise the success of the procedure is dependant on how dry
the mushrooms are, and powdered...like anne said, or similar: dry dry, dry.... (and see merck lol)
it was over 12 years ago, but i can assure you that chloroform took out absolutely no actives
(it took out the nauseous inducing aroma concentrated)..dcm should much the same..
the more thorough the washes, the cleaner the end result will be, as crude alks

also, protonation (complexing to an acid) will not produce the same form of alkaloid as the Hofmann (crude/chroma),
meaning it may not be vaporisable (i'd say it probably isn't) and it may have slightly different metabolic properties (which may or may not be desirable) ..so i don't discount that experiment either..as well as taking the pH up...god knows what that does...

I'm not too worried about losing a little of the alks, I've got more than I need in theory. But I might keep the DCM and acetone in case the methanol extract lacks potency; should indicate it's still in the acetone or DCM. Sounds like I may need to dry my cheap eBay "99.6%" acetone though.

The thought of vaping it does sound appealing. Do you reckon it'll work in glycerine in a little vape pen?

definitely worth keeping and evaporating the chloroform (or dcm etc) and acetone fractions, especially in a first attempt,
one because it's quite interesting smelling and pondering what they pull out, and also it will be of interest to
those following the thread i'm sure..

it was actually more like 18 years ago now that i think about it...i'm not sure about glycerine, maybe, but a range of vaping methods will work..the reason i keep emphasising vaporization of this semi-purfied alkaloid result (at exactly the pH the fungi had it too) is that it's really interesting, and, isn't as potentially 'too much' as the oral route can be (echoing pitubo and downwardsfromzero), in part because of the duration..it also doesn't exhibit the potential physical symptoms..
large dose psilocybin can be rough on a mammalian system...maybe plant too...

.

{edit: re some of the symptoms reported by pitubo and downwardsfromzero -
my instinct (with no actual theoretical basis) tells me not to try and store in ethanol..
maybe trace water content..? i'm not familiar with quite as extreme symptoms as that..though heartrate (real or perceived) is a psilocybin high dose one..and the post adrenaline response negating it.. but back in the late 90s (and we never had a lot) it was airtight in the freezer...we thought about the tartrate..thanks for those reports}

if you protonate the alks, the amine carries a positive charge, the alkaloid will not be soluble in nonpolars. dcm is slightly polar, but not so much that you'd see any significant loss of alks in the protonated state. traditionally, ethyl ether was used, and it's slightly more polar than dcm, but highly volatile and flammable. toluene would be another acceptable nonpolar solvent.

If you decide to do chrom, or deprotonate, I suggest dilute ammonia in ethyl acetate (with a third solvent, n-butanol, for chromatographic separation). try to keep the pH in the 9-10 region, and work quickly.

There are easy workarounds for otc inert atmospheres. Think welding shop and brew mart.

And if I don't protonate them, will I then lose significant alks in the non-polars?

depends on the solvent. hexane, no. dcm, yes.

but isn't it already to an extent protonated in the fungal body...?

(but an arbitrary change of acid and pH may change the extracted result..no?)

it's possible that dcm will behave differently to chloroform...hence we'll all learn something..

in the fungal body, it's likely zwitterionic...in this form, it will be bound to ribosomal proteins. yes, a change in pH will dislodge it from said proteins.. of course, proteins are large molecules, so separation against a stationary phase (chromatography) is suggested. small molecules, such as alkaloids, will elute first.

dcm has some miscibility with water, so it can pull a small amount of charged species. chloroform will pull less

Hmm... Now I'm not so sure about it. I don't have access to chloroform and don't really want to get involved making it. Sounds like I will lose my alks in the solvents.

Thinking of going for Willsolvem's A/B method as outlined here on the Shroomery, minus chromatography.

"
Dry mushrooms (ideally freeze dried) and grind to a powder

Extract with either 2% tartaric/sulfuric acid solution, dilute galactic acid, or vinegar over 4hrs and filter mushroom material

Basify to 8.5-9 with aqueous ammonium hydroxide solution, potassium hydroxide solution, or a 10% sodium hydroxide solution (least preferred)

Extract with chloroform, dichloromethane, or pet ether 3x

Combine extracts

Dry with MgSO4

Reduce volume under vacuum, or strip solvent completely under a inert atmosphere
"

Apparently the inert atmosphere isn't essential.

Any thoughts?

i would have thought not huge loss with dcm at the natural pH of the fungus..people defat with it..psilocybin is insoluble in NP solvents generally (ether, butane etc) ...its just that dcm is slightly more polar than chloroform, hexane etc..hmm

the a/b you mention does not have the step of washing sugars and additional proteins with acetone,and I'm not sure it's end result as the Hofmann technique..if there are more reports of it working (i.e. producing near pure crude alkaloids) then fine...it's just that we know the Hofmann method works..rather than an 'extraction' it is a cleaning away of everything not needed other than the alkaloids..

edit: the method you posted above is actually based on J.F. Casale, J. Forens. Sci. 1985..which involves the dephosphorylation of psilocybin to the phosphate ester of psilocin..but also uses a chloroform/heptane kind of chroma/re-x as the last stage...i am not entirely convinced the end product will behave the same as the 'Hofmann' crude product, which, in my mind, is 'closer' to what was in the fungal body (prior to any decomposition)

A lot of the language in this thread goes over my head, so forgive me for being slow... I was under the impression benzyme was suggesting that DCM wasn't a suitable alternative to chloroform.

So I'll just go ahead with the Hoffman then and keep my wash solvents in case my alkaloids got pulled at any stage. Got some Epsom salts to dry my acetone. Can I use them on the DCM too?

Do you think I should do acetone and DCM wash at low temperature to minimise loss?

Should I add water to my methanol to increase pulling power and what's a good balanced percentage to avoid taking too much crap with it?

Cheers

i'm not a chemist either

also, it comes down to also whether you want psilocybin+psilocin+ (the mushroom alkaloids)
or just psilocin (which the psilocybin breaks down into)

i guess i'm steadfastly sticking to the Hofmann method, as it's known to work...and if he's not a reliable source i don't know who is...i'm assuming that at the pH in the dried mushroom it's not very soluble in dcm (in chloroform it's not), and should work, though perhaps lose a small amount..but other solvents are a bit more efficent..this applies to all extractions, different non-polar solvents (even though all used) have different efficiencies..
that other method you posted is aiming to convert to psilocin and is aimed more at drug lab analytical purposes..so i don't know if it's 'the same' kind of resulting thing as the Hofmann result which has multiple bioassays..

the method benzyme suggested sounds interesting though, and is different again

the chloroform (dcm) and acetone washes are done at room temperature in the Hofmann method, i would suggest vigorous agitation and at least an hour each..the more thorough the better..and the material is dried again between washes..

given time, agitation, and maybe a few washes, it should be soluble enough in methanol, i don't know that water will help, and it would be deviating from the 'tek'..

good luck in this much anticipated experiment user_7 !

Cool. Yeah psilocybin seems more appealing as it's more stable so will stick with Hoffman. Was just worried DCM wasn't a suitable alternative. I prefer the simplicity of this method anyway.

Been away from home over this week, but should be back tomorrow to begin soon.

DCM is a suitable alternative. It is not at all that different from chloroform, its hard even to say definitively which solvent is more polar, it depends on what you are relating its polarity to.
Chloroform has a larger dipole than DCM, so chloroform is more polar. DCM has a bigger dielectric constant than chloroform, so DCM is more polar.
None of these by themselves are accurate descriptions of what we understand as polarity.
DCM is slightly more soluble in water than chloroform, a difference of 4mL per LITER of water. So I`m guessing this is what we are basing it off of? The chlorinated solvents are severely limited compared to ethers and of course alcohols, without an oxygen atom to act as a strong hydrogen bond acceptor.

I wouldn't worry too much about polarity of non-polar solvents, way overthinking this. Perhaps DCM might yield you some losses, but it would be negligible. If they are not negligible however, that could suggest it is extracting the proteins with the psilocybin still bound to them?

If you are really concerned about that though, why not skip the step altogether? Do a simple methanol extraction straight on the dried fungus. Benzyme has done this and posted it on the forum, it yields you a potent protein laden psilocybin goo, and I doubt a little protien will cause you nausea, the methanol extraction removes >95% of the plant material

..i’ve kept on this thread because i’ve seen so many ‘psilocybin extraction’ threads go nowhere, or fail to grasp it..yes i agree with MindIllusion that we’re getting too finicky about NP solvents…most will work..
but if one was going to to just do a methanol soak one may as well avoid the toxicity and just do an ethanol/water extraction, and we’re back to square one either way - full spectrum gunk as opposed to almost entirely alkaloids goo ..and the fungal material is always filtered out, whatever method..

it was a long time ago, but the Hofmann procedure did/does the following, to recap:

firstly, the non-polar solvent removes primarily the fats and i’d guess some aged proteins..
when the chloroform was evaporated it left a waxy ball of ‘fat’ putty which was instantly recognisable as the nausea inducing aroma of mushrooms (to a few people)…with no alkaloids

secondly, the acetone removes presumably the structural proteins and sugars..when evaporated it resulted in a dark brown hard tar-like residue with a ‘burnt sugar’/‘almost coffee/cocoa aroma..no activity..acetone is used to extract structural proteins in places..

leaving then mostly just the fungal material (which is filtered), and alkaloids which go into the methanol..

this is pretty much just the crude alkaloids (not a full spectrum gunk)…what really surprises people who’ve done this is how few people have tried this…jim de korne said similar..he got a 'grey/blue' soft crystal

the way most of these psilocybin extraction threads go, maybe this will just remain something known to a few ‘elite’ who’ve done it…it can even just be smoked in a joint with herbal material for a milder effect..
i never had access to a lot of it, but always wanted to explore it further one day..

i’ve seen the consequences of information, but the fact the mushrooms are so easily cultivated makes this safer information (for the environment) than for instance acacias..the main consequence here is what are people ready for? ..and psilocybin is a very unusual molecule in the world, indeed..as McKenna wildly speculated on..

people..why do so few few know about this? (i realise having sufficient quantities is a factor) ..and yes, if too much is taken (particularly orally) it may temporarily psychologically disturb the more sensitive...but this is the dmt nexus!
(meaning that we would ask people to research dosage and be responsible and thoughtful in any endeavour)

orally it has a clarity of ‘direct access’ not often experienced with mushrooms on their own, or tinctures..and vaped it is ‘similar’ but different to DMT…different ‘personality’, ‘mode’ and ‘agenda’…

the big intelligence galactic voice inside the head Logos beheld alien veiled thing..

like User_7 noted, the method is very simple…it’s like there’s almost some kind of subconscious field keeping people away from this…perceptual filter…interesting..

So what kind of quantities are we talking for a worthwhile extraction here? I see it keeps getting mentioned that sufficient quantity is needed but that's kind of a broad statement, no one has mentioned at what amount of fungus would be needed.
Say I have a QP of shrooms would that be enough to do an extraction? Just curious.

I'd say a 1/4 oz. or more, to make it worth the effort.

Cleansing has begun. My powdered mushrooms have been washed in acetone, filtered and are currently soaking in DCM. Acetone came out cloudy with a greenish tinge. Pictures and detailed write up to come when I have time.

Just a question on smoking. It appeals to me to test the product by this route as I may not have time for a full experience for a little while. But rolling in a joint seems inefficient. Does anyone have any ideas on a more practical way to smoke it. I still like the thought of vaping in glycerine/propyl glycol, but don't know if I'm on the right track with that.

Just the same as DMT? Or would light bulb style be better as psilocybin is more delicate?

Can't wait to see the write up