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defat cactus - when?


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#1 pharmer

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Posted 27 June 2018 - 04:12 PM

defat as a tea?

 

or in acid phase?

 

other?



#2 Phineas_Carmichael

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Posted 27 June 2018 - 11:39 PM

If you want to defat cactus you'l need to extract it into an acid first.  Defat the acid, then basify to extract the freebase with a non-polar solvent, and salt that solvent with an acid to obtain a crystalline product. Basically an A/B DMT extraction but instead of freeze precipitation or evaporating the solvent you salt or gas it as in a normal mescaline extraction.

 

See here for a rough (albeit with potentially confusing results on the 2nd attempt) outline:

https://mycotopia.ne...ine-extraction/



#3 Norman

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Posted 27 June 2018 - 11:47 PM

In short, tea is the acid phase.

Has anyone tried evaporating the solvent down until just freebase is left and then converting it to a salt? Would seem easier than salting from the solvent.

Edited by Norman, 27 June 2018 - 11:52 PM.

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#4 pharmer

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Posted 28 June 2018 - 02:06 PM

If I understand this correctly

 

A tea of cactus (in tap or distilled water) is naturally acidic because the native state of the molecule in live cactus is M Hcl  therefore the tea is acidic

 

If that is correct and the molecule is sequestered in the acidic water -  a defat of tea without more acid added will not result in losses  of the target molecule? Only fat  and crud will be taken away by a non polar solvent?


Edited by pharmer, 28 June 2018 - 02:07 PM.

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#5 CatsAndBats

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Posted 28 June 2018 - 02:31 PM

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#6 Norman

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Posted 28 June 2018 - 08:21 PM

Yes plants are generally somewhat acidic so the tea is acidic and the alkaloids are in the form of a salt which is water (polar) soluble and insoluble in non polar solvent (xylene). So when you defat an acidulated solution the alkaloid salts stay in the water phase and the fats and oils mix with the np and go away. The reason acid is usually added in extractions is to ensure that all of the alkaloids are converted.
If you’re looking to defat a tea that you intend to drink, I’d suggest adding a small amount of food grade acid first .

Edited by Norman, 28 June 2018 - 08:31 PM.

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#7 pharmer

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Posted 28 June 2018 - 08:58 PM

domo arigato, Senseis

 

I'm having a discussion elsewhere that had me doubting what I thought I knew.


Edited by pharmer, 28 June 2018 - 09:55 PM.

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#8 Norman

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Posted 28 June 2018 - 11:44 PM

I think I’m going to have to give that drying down idea a go.
There’s a Tupperware full of cactus glop in the freezer so I’m thinking I’ll defat it thoroughly, base it, extract with xylene and then let the xylene evaporate completely. Freebase mescaline is supposed to be a caustic oil so I’ll cover it with water and add sulfuric acid drop by drop. When the freebase oil dissolves into the water solution, all of the freebase should be converted into sulfate since freebase wouldn’t be soluble in water and sulfate salt would. Drying that down should yield mescaline sulfate, no?
It works with DMT anyway.

Phin - in that procedure you linked to you use toluene then toluene/xylene then xylene. Is there a reason for that or did you just run out of toluene? The defat for what I’m talking about will have to be really thorough since fats will never go into the aqueous solution no matter how much acid is added.
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#9 Phineas_Carmichael

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Posted 29 June 2018 - 02:21 AM

If I understand this correctly

 

A tea of cactus (in tap or distilled water) is naturally acidic because the native state of the molecule in live cactus is M Hcl  therefore the tea is acidic

 

If that is correct and the molecule is sequestered in the acidic water -  a defat of tea without more acid added will not result in losses  of the target molecule? Only fat  and crud will be taken away by a non polar solvent?

Mescaline's pKa is 9.56, so as long as the pH of the tea is less than 7.56 then 99% of the target molecule will be a water-soluble salt. pH 6.56 means 99.9% is the salt mathematically speaking.

 

I don't know what the pH of a cactus tea is from personal experience, so I would advise you to measure before trying to defat a straight tea and add acid if the pH is too high.  Sorry, I'm a science nerd; I like my measurements...

 

...

Phin - in that procedure you linked to you use toluene then toluene/xylene then xylene. Is there a reason for that or did you just run out of toluene? The defat for what I’m talking about will have to be really thorough since fats will never go into the aqueous solution no matter how much acid is added.

We really had no reason for the mixed-solvent system.  7 years ago (has it really been that long?!) my buddy Freddy and I were just starting to get into the clandestine chemistry game and had access to both xylene and toluene.  We figured that using both would be better than using either alone, so why not use both?  I am not sure if one or the other is better for defatting; xylene is just toluene with a couple extra methyl groups in various positions on the benzene ring & I have no idea how they affect the solubility of "fats" & "tannins" from the plant.  Sorry for my ignorance. 

 


I think I’m going to have to give that drying down idea a go.
There’s a Tupperware full of cactus glop in the freezer so I’m thinking I’ll defat it thoroughly, base it, extract with xylene and then let the xylene evaporate completely. Freebase mescaline is supposed to be a caustic oil so I’ll cover it with water and add sulfuric acid drop by drop. When the freebase oil dissolves into the water solution, all of the freebase should be converted into sulfate since freebase wouldn’t be soluble in water and sulfate salt would. Drying that down should yield mescaline sulfate, no?
It works with DMT anyway.

 

...

DO IT!!!!!  I'm mad curious to see what happens, and chemically speaking this is a solid protocol!

 

My only concern is what might happen to the freebase oil while the the xylene is evaporating.  Freebases are prone to oxidation.  Plus to that, it might be hard to tell when the xylene is fully evaporated out of the oil (think BHO cannabis extracts)

 

However...

 

The boiling point of freebase mescaline is 180*C

The boiling point of xylene is ~140*C

The boiling point of toluene is 111*C

 

Just spitballing here, but a gentle steam bath (as long as we don't get close to 180*C) might evap the non-polar solvent quickly enough to yield the oil without long exposure to oxygen...

 

----

 

Once you have the oil I think covering it in water and adding acid dropwise until the oil dissolves is fucking brilliant!  A nice slow evap of the sulfuric water should yield pretty silver needles.

 

Test it and keep us posted?  Please?


Edited by Phineas_Carmichael, 29 June 2018 - 02:50 AM.


#10 pharmer

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Posted 29 June 2018 - 06:18 AM

I don't know what the pH of a cactus tea is from personal experience, so I would advise you to measure before trying to defat a straight tea and add acid if the pH is too high.  Sorry, I'm a science nerd; I like my measurements...

 

I have a fancy new electronic pH meter so I'll do exactly that and report back here.

 

Norman, I'd suggest starting a new searchable thread for your experiment. Should make it easier to find than plugging it into here.

 

 

Mescaline's pKa is 9.56, so as long as the pH of the tea is less than 7.56 then 99% of the target molecule will be a water-soluble salt.

 

Alright, as long as non-chemists are asking chemistry questions and smarter people are answering them, WHY, WHAT IS HAPPENING in the range between 9.56 and 7.56 that guarantees water soluble salt?


Edited by pharmer, 29 June 2018 - 09:30 AM.

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#11 Norman

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Posted 29 June 2018 - 10:14 PM

The only difference I’ve noticed in using toluene vs xylene is that toluene evaporates faster and stinks a little less. I was just wondering if you knew something (else) that I didn’t.
Yes I think I’ll give it a go and start a thread once I’m less busy at work and done with the DMT and LSA projects I have going.
Thanks for the heads up about oxidation, I hadn’t thought of that. Steam sounds like a good idea and I wouldn’t mind not having to wait the eternity it takes xylene to evaporate. If I could get DCM or chloroform I’d use that. I think they’d be broad enough spectrum and evaporate really quickly.
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#12 Phineas_Carmichael

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Posted 30 June 2018 - 03:01 AM

...

Steam sounds like a good idea and I wouldn’t mind not having to wait the eternity it takes xylene to evaporate. If I could get DCM or chloroform I’d use that. I think they’d be broad enough spectrum and evaporate really quickly.

Both would be excellent choices, but slightly difficult to lay your hands on.  DCM though is easy enough to find; I know there's a paint stripper at your local hardware store that's at least 60%, and with such a low boiling point it is really easy to distill out.

 

Chloroform is an easy(ish) synthesis from household chemicals, but we don't talk about that here.  :ph34r:

 

Mescaline's pKa is 9.56, so as long as the pH of the tea is less than 7.56 then 99% of the target molecule will be a water-soluble salt.

 

Alright, as long as non-chemists are asking chemistry questions and smarter people are answering them, WHY, WHAT IS HAPPENING in the range between 9.56 and 7.56 that guarantees water soluble salt?

Okay.  There are 3 basic chemical equations we have to hold in our heads, and the first one is the hardest:

 

1) H2O <---> H+ + OH-

 

Dig it?  Water is not just a static compound.  The molecules are always banging & crashing into each other and knocking little bits off then the bits recombine into water again.  That's an oversimplification, but it works for our purposes.  So, when we dissolve our target molecule in an aqueous solution it has both H+ & OHions that it can interact with.  We add more of one or the other to force our molecule to be in the form we want.

 

2) HCl <--aq--> H+ + Cl-

 

HCl is a "strong acid," meaning that it completely breaks apart in water, so that it vastly increases the concentration of H+ ions that our target molecule can react with.

 

3) NaOH <--aq--> Na+ + OH-

 

NaOH is a "strong base" that vastly increases the concentration of OH- ions that our target molecule can react with.

 

Now, for what we are doing to mescaline the alkaloid, specifically:

Alkaloid States.jpg

(Wow, please excuse my horrible penmanship.  I was at work & only had sharpies & paper to work with :blush: )

 

Mescaline in it's botanical state (the alkaloid) is in the middle at the top.  Branching off down and to the left is what happens when it reacts with HCl.  The H+ ion first bonds with the lone pair of electrons on the nitrogen, making the nitrogen positively charged (protonated), then the Cl- ion bonds ionically with that hydrogen to form the hydrochloride salt.  Again, an oversimplification, but good enough for our purposes here.

 

Branching off down and to the right is what happens when mescaline reacts with the OH- ion.  The OH-  breaks the bond with one of the nitrogen's hydrogen atoms to create water, leaving the nitrogen negatively charged (deprotonated) and giving us freebase mescaline.

 

======

Everybody with me so far? :confused:

======

 

Now the magic of the pKa values that I cite so often...

 

When the pH of a solution is equal to the pKa of the target molecule (9.56 for mescaline), this 3-way equation is in equilibrium.  Meaning the target molecule is in a state of constant flux between the salt, the alkaloid, and the freebase.  It's essentially a 50/50 mix of salt and freebase in solution because the mixture is so chaotic.  Molecules are banging and smashing into each other, knocking bits off & recombining just like H2O <---> H+ + OH-

 

By changing the pH we are adding H+ or OH- ions and that pushes the reaction in one direction or the other.  If there are more H+ ions, more of the target molecules will react with them instead of the OH- & we end up with the salt in solution.  The same is true in reverse for the freebase and OH- ions.

 

Now just a little math, bear with me, we won't actually be doing any calculations.  Remember that the formula for calculating the pH of a solution is pH = -log[H+]  That is to say the pH of a solution is the negative logarithm of the concentration of H+ ions in that solution.  Because pH is a logarithmic function, for every 1 point down on the pH scale there are 10 times more H+ ions in the solution.  The same is true in the reverse, for every one point up, there are 10 times fewer H+ ions & 10 times more OH- ions.

 

So, for mescaline, when the pH is 7.56 there are 100 times more H+ ions for the alkaloid (target molecule) to react with than at the pKa value and this pushes the equilibrium to 99% hydrochloride salt. pH 6.56 --->1000x more H+ & 99.9% hydrochloride, pH 5.56--->10,000x more H& 99.99% salt et cetera.  Same goes for the other direction.  pH 11.56--->99% freebase, pH 12.56--->99.9% freebase, you get the idea.

 

======

And now for a ramble I am not sure is completely necessary...

======

 

"But wait, Phineas," you say, "doesn't that mean we don't need to acidify beyond pH 7.5 to defat mescaline?  Why would I want to add an acid if the pH of the tea is below 7.5?"

 

Excellent insight.  :wink:  While at pH 7.5 99% of your mescaline is in the salt form and insoluble in non-polar solvents, there's also an awful lot of fats, oils, tannins, and garbage in solution as well.  This garbage tends to form an emulsion (mixture of the aqueous phase & non-polar phase) between the liquids & prevents clean separation.  So, if you're trying to defat at pH 7.56 you could end up with an emulsion layer that is full of garbage that won't transfer into the non-polar, but also full of mescaline too because it is a mixture of the 2 phases.

 

This is why we typically acidify and basify more strongly that pKa +/- 2 in our extractions.  The presence of the excess H+ or OH- ions in the aqueous phase makes it "more polar" and as such separates from the non-polar phase faster and more thoroughly.  

 

======

Ramble over

======

 

All of that make sense to everyone?  I always get to the end of posts like this and wonder if I went too deep into the chemistry and potentially lost someone.  If something doesn't make sense, please let me know; it's sometimes hard to explain this stuff with words on the page instead of diagrams on the blackboard...  :wacko:


Edited by Phineas_Carmichael, 30 June 2018 - 03:53 AM.

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#13 pharmer

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Posted 30 June 2018 - 08:00 AM

Oh! It's a beautiful thing.

 

Will assimilate and apply   :)

 

Well done.


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#14 Norman

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Posted 30 June 2018 - 02:45 PM

Damn Phin, Im going to print that and put it in a binder!
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#15 Cuboid

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Posted 30 June 2018 - 03:10 PM

Thanks Phineas, good explanation, I found the Wikipedia Acid Base Reactions page useful for further understanding these A/B extraction discussions.
https://en.m.wikiped...d–base_reaction
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#16 Phineas_Carmichael

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Posted 30 June 2018 - 05:24 PM

Thanks Phineas, good explanation, I found the Wikipedia Acid Base Reactions page useful for further understanding these A/B extraction discussions.
https://en.m.wikiped...d–base_reaction

That is a good read.  Lots of excellent info for home chemists.

 

I would be remiss if I didn't include some of the Wikipedia articles I read to compose this explanation.  Wouldn't want you all to think I just keep this stuff in my head all the time now!

 

https://en.wikipedia.org/wiki/Alkaloid

https://en.wikipedia.../wiki/Free_base

https://en.wikipedia...cid–base_theory

https://en.wikipedia...iation_constant

https://en.wikipedia.../Conjugate_acid


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#17 Cuboid

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Posted 01 July 2018 - 06:20 AM

^^^^ That's tonight's bedtime reading sorted then ^^^^^

#18 pharmer

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Posted 01 July 2018 - 08:22 AM

WTF? Why does Phineas not have an apartment building sized pile of awards under his avatar?


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#19 coorsmikey

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Posted 01 July 2018 - 03:55 PM

WTF? Why does Phineas not have an apartment building sized pile of awards under his avatar?

YEAH WTF? Will have to fix that! As soon as I get home from my trip consider it done!

#20 pharmer

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Posted 01 July 2018 - 05:00 PM

I recommend a new award. The Almost As Good Looking As Pharmer. Solid Platinum Bunsen Burner






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