New Coffee Recipe (Magic extraction and stabilization)

[greenmeanie]

I've been lurking quite a bit in the vaults, reading up on various teks for extraction. One that caught my eye was So Blue it was Black (So blue it was black). In this thread, Dr_T mentions he has an espresso machine. I also read a thread in which someone suggested to use nearly boiling water to extract mushrooms, because that could denature the phosphatase enzyme found in the fruiting bodies, which helps quickly convert the stable 4-PO4H2 (cybin) into the unstable 4-OH (cin).

I recently had a dream that combined several ideas. Allow me to give some background. I'm currently working on a Chemistry degree, so I'll try to be precise with my terminology. If anything is unclear, feel free to wikipedia or ask me for clarification.

Psilocybin is the phosphate ester of psilocin. An ester is a chemical combination of an alcohol (ROH) and an organic acid (HO2R). Phosphoric acid is the acid, and the 4-OH group on psilocin is the alcohol. Psilocybin exists as a stable zwitterion, in which one basic end (the tryptamine) is protonated to the alkyl dimethyl ammonium ion (RNHCH3CH3)+ while the other acidic end (the phosphoric acid) is deprotonated to the phosphate ion (RPO4H)-. The amine is positively charged, and the phosphate is negatively charged. Take note to remember that the phosphate group is attached via an oxygen, not the phosphorus. Because the entire molecule is highly charged, it is very soluble in H2O or CH3OH and not very soluble in organic solvents like hexane, xylene, or ether.

According to this paper, it is widely accepted that the biologically active form of the chemical is the one in which the phosphate group has been removed by enzymes in the digestive tract, forming psilocin (4-OH-DMT). This is because the highly-charged ion form is less likely to cross the blood-brain barrier which is primarily made of non-polar (charge-disliking) lipid or fat membranes. Unfortunately, the free 4-OH psilocin is unstable in solution, quckily oxidizing to a "blue product" of unknown composition, but likely a quinone or imine.

So the chemist's goal in the preparation of magic extracts: the "locking up" of that pesky 4-OH group so it does not oxidize while in storage. The gods already took care of that by giving the mushrooms an enzyme to attach phosphoric acid to the 4-OH, but that only remains stable inside the cell walls and when the fruit bodies are dried. Once we try to dissolve the active compounds in water, the chemical equilibrium shifts toward the right, in which phosphate is liberated and water is re-attached to the 4-position.

4-(PO4H)-DMT + H2O --> 4-(OH)-DMT + PO4H2

Also according to the paper above, the phosphatase enzyme is more active at higher basic (~9) pH. By reducing the pH to acidic levels, loss of phosphate in solution can be slowed. But it can still leave the molecule even with no enzyme, just in the presence of water. Combining the knowledge of teks like lime juice or other acidic formulas with the fact that 4-AcO-DMT is a known and potent analog of psilocin, I would like to propose that any extracts of active compounds should have a multi-facet approach.

1. Extraction must be done using purified H2O, de-gassed to remove any dissolved oxygen.
2. Extraction should be performed only on recently prepared finely-ground dry specimens. If ground and stored with air, all cell walls are destroyed and chemicals begin to oxidize immediately. Unground bodies have intact cell walls, allowing less penetration by the H2O. Fresh (moist) specimens are difficult to pulverize without introducing a high level of air into the cells (blending).
3. Extraction should be performed as quickly as possible, so high heat should be involved. It should be clear now that the major destruction of active chemicals is not from heat itself, but oxygen and instability in solution.
4. During extraction, free psilocin should be surrounded with an abundance of organic acids. Viable candidates are acetic acid (vinegar), citric acid (lime/lemon), ascorbic acid (vitamin C), tartaric acid (wine sour), or malic acid (Mega Warheads). In addition to inhibiting the action of phosphatase, these acids will readily form esters of the 4-OH alcohol, stabilizing the molecule against oxidation in storage.
5. Immediately following extraction, the result should be quickly filtered under vacuum and quickly cooled, then stored in an amber vessel under an inert atmosphere.

In order to perform such an extraction, a gnome could hit several faeries with one philosopher's stone by utilizing the most amazing chemical apparatus found in the kitchen: the common espresso machine. This device can quickly heat water to just below boiling, then force it at high pressure through a fine mesh screen to contain any particulates.

Step 1: Boil water on the stove. This will de-gas it. Cover and cool.
2: After water has cooled to room temp, add to espresso machine reservoir.
3: Finely grind your cracker-dry beans to a powder, using a coffee grinder. One shot (1oz/30mL) of espresso takes about 7g of ground coffee beans.
4: Measure out an equal proportion 1:1 of beans and ascorbic acid powder. Vitamin C can be found at any drugstore. This acid is also an anti-oxidant preservative.
5: Following the instructions provided with the espresso machine, brew your coffee. The initial 30mL should be more than 80% effective in strength.
6: Crush up an amount of dry ice into your storage container, and pour your coffee over it. Observe the cloud of vapours.
7: Subsequent brewings can be made with the same beans, until the coffee runs clear. Seal the storage container when CO2 gas evolution stops, or you could get a nice glass explosion.
8: Store your coffee in the fridge until thirsty, and compost the spent beans.


Benefits of this method include the instant preservation of actives by hot acid, instant filtering of any solids, and tiny volume of coffee that must be drank in order to achieve an effect. It is also likely that the quick-cooling action of the solid CO2 would cause some chemicals to fall out of solution, without any need for evaporation (opportunity for oxidation).

Any comments or thoughts on my dream?

And in case you were wondering, there should be no caffeine in this brew

[Dr_T]

So, in your dream- you actually tried this?

[golly]

Sounds like your really enjoying your Chem class..heh...

It's worth a test run..The O2 deprivation idea agrees with my experience - that it's not so much the heat but exposure to air that's the killer..
I would be very interested to know, how well a water based extract can keep..
Only drawback if it works, is access to dry ice with every use..

[retack]

fumaric acid was preferred for long term storage/stability, as psilocin fumarate is hydrophobic compared to other salts (as with most/all fumarates).

[greenmeanie]

Originally Posted by retack

fumaric acid was preferred for long term storage/stability, as psilocin fumarate is hydrophobic compared to other salts (as with most/all fumarates).

No, I have not attempted this method. It still hasn't rained enough in the area...

As this is proposed to be a water storage technique, I would think that hydrophobia is an undesirable trait. I believe that Vitamin C would provide ample antioxidative properties to the solution.

Upon further dreaming, I have a hunch that this exact method could yield some potentially comatose Papaver tea...

[Subbalteatus]

well let us know when you do try it greanmeanie : )

Looks like My old dried powder in a shotglass with key lime juice has some substantaility here..

Peace,
Subbal

[retack]

oh i didn't realise you were leaving it in solution. i don't know of any data regarding long-term deoxygenated aqueous stability, acidified or not. if pure, it should be a very long time.

if you have not completely destroyed the enzymes responsible for degrading psilocybin/psilocin, your solution will most definitely degrade over time, even in deoxygenated acidic water.

[purefficiency]

How'd this go?

I was thinking about making some "magic" chardonnay.