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Ethyl acetate approach [CIELO] Options
 
downwardsfromzero
#381 Posted : 7/6/2021 7:21:44 PM

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Loveall wrote:
Then we would see the pH paper turning green I guess.

Update: There was no pH change in fresh EA after 12 hours of magnetic stirring. Whatever salt is forming doesn't change and is inert in EA once it crashes, which makes sense.

The water pH in water as mentioned before is 3.55, so it is likely the product is a hydrogen salt, 62% to 81% less potent than MescalineHCl depending on if it is the dihydrogen or hydrogen form respectively (the old naive assumption was that we had mescaline citrate fully reacted which would have been 90% as strong as MescalineHCl).
I raised the example of dissociation of the tribasic mescaline citrate as a potential outcome in the titrated aliquots experiment that I outlined. If freebase mescaline in EA were to be mixed with one third of its molar equivalent of citric acid and the solvent then be allowed to evaporate a solid that is theoretically the tribasic citrate would be produced. I would predict that washing the resulting solid(? - see below) with fresh EA would result in mescaline freebase being washed out of the solid material, especially perhaps if the solvent was a bit damp.

A similar question is whether dibasic mescaline citrate behaves similarly. The outcomes of these two experiments would help us to home in on the stoichiometry. And a 3:2 ratio of mescaline to citric acid subjected to the same regimen would, hopefully, act to bolster the evidence.

This make me think the stoichiometry could be a factor behind the necessary loading of citric acid required for the crystals to start forming. Trimescaline citrate and/or/mixed with bimescaline citrate could possibly be room temperature liquid eutectics or something similar. This potentially renders one or both of them soluble in the EA [This figures, in my view, because the material is proportionally mostly mescaline, if that makes sense]. Thus, precipitation only starts once sufficient citric acid is present in the solution at a ratio in considerable excess of one mole of citric acid per two moles of mescaline, up to at least a one to one ratio - and, as has been found, more if a higher level of plant impurities is present.




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Loveall
#382 Posted : 7/8/2021 2:58:54 PM

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Thanks DWFZ.

Thinking about all this, I like shroombee's idea of the simple conversion to HCl salt. I missed that HCl is a negative azeotrope and will tend towards 20% HCl in solution as it evaporates. Starting with a mescaline citrate mass (m1), after dissolving in water, adding HCl, and evaporating, I think only mescaline HCl (m2) and citric acid (mc) will be left:

(MesH)nH3-nCit*xH2O + nHCl -> nMesHCl + H3Cit*H2O + (x-1)H2O

Where I assume citric monohydrate forms during evaporation. Also added the possibility of the starting mescaline salt being a hydrate.

We should be able to separate the citric acid mass (mc) with ethyl acetate. The ratio of MesHCl mass (m2) to citric acid mass (mc) gives n.

For each mol:

m2 ~ 247n
mc ~ 210

Taking the ratio:

n = (210/247)(m2/mc) = 0.85(m2/mc)

Where I've assumed citric acid remains as the monohydrate during ethyl acetate separation (could be wrong).

Knowing n would also tell us x since:

For each mol:

m1 ~ 211n+192+18x
mc ~ 210

Taking the ratio:

x = (1/18 ) (210*(m1/mc) -211n - 192)

So shroombee's suggestion may allow us to fully characterize the mescaline citrate salt form. If after measuring m1, m2, and mc we experimentally get integers for n and x confidence would be high.

I started testing this but made the mistake of using heat to speed up evaporation. Turns out that citric acid breaks down with heat (175C) and started to make a mess. Gonna try again with slow room temp evap (will take a few days).

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Homo Trypens
#383 Posted : 7/18/2021 12:03:50 PM

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TL;DR

If you get goo instead of crystals, separate it, don't throw it away, and let the EA sit for several days. There just might be some crystallisation over time.

---

So, i gave the CIELO a try last weekend. Two actually, each with 100g of dried san pedro powder, 25g of lime, 300g of water, slightly below 1L of EA.

On the first one, i had an accident in the microwave. It boiled over, and then i broke the beaker. So i did not complete the microwaving, and i did not cold pull. I had lost about 100g of the 200g water i wanted to lose. As a consequence, my EA was pretty green. Other than that, everything seemed to be looking good. I dropped about 7g of citric and walked away.

The next day however, i did not have any crystals. Instead, i had a clear-ish goo layer below the EA.

So i started another one. Used a plastic container for the microwaving this time. I evaporated 220g of the 300g water, and i did a mini variant of the cold pulls (3h in the freezer/fridge as opposed to 24h). I used fresh EA to avoid problems coming from the used one. The color was much nicer this time, and again after dropping 5.00g of citric there was nice clouding. After an hour or two, the clouds had sunken a few cm. It looked very promising.

But this time again, next day there were no crystals. Again that goo.

I combined the goos, redissolved them in water - nothing was insoluble. I evaporated most of the water, and continued air drying it for maybe two days. At that point, it was a trippy looking beautiful amber goo, not dry or hard but also not runny anymore. It was 4.25g of this goo. I redissolved that goo in water, based with lye, pulled with limonene, salted with sulfuric acid, and i'm still evapping that now.

But that's a story for when it's done. Here, i wanna report what happened with the used EA while it was sitting in a jar, waiting to be freezer treated to remove the water it had pulled from the cactus paste.

My freezer is tiny, and not empty. There is no way i can fit a 2L container in there. So i did the freezer treatment in portions. after 2 small dishes, i got me a bigger one that can hold 1L and wanted to pour the rest in there. When i grabbed the jar from the shelf, i noticed some crystals swimming in the bottom of the jar.

So there had been mesc still in the EA , and it did precipitate as crystals slowly!

I poured through a coffee filter, and i let the residual EA evaporate. I got 420mg of nice needles (not washed yet, might do that later on) plus a yet unknown amount that was not scrapable from the glass, which i dissolved with some water and am evapping now.

I have also collected the ice crystals from freezing the used EA, and will evaporate that water to see if some more is hiding in there.
Homo Trypens attached the following image(s):
HT-CIELO-goo.jpg (3,175kb) downloaded 389 time(s).
precipitation-after-goo-gone.jpg (92kb) downloaded 385 time(s).
citrate-scraped.jpg (93kb) downloaded 386 time(s).
 
Loveall
#384 Posted : 7/18/2021 3:29:47 PM

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Thanks for the ongoing work and report so far Homo Trypens.

I wonder why you got goo first instead of a more solid precipitate. Did you let the EA settle for a while before adding citric acid? Sometimes some "drops" form on the glass walls and can be easily decanted off. These drops could be a little bit of excess water in the EA from the pulls (but I'm not sure) that take time to settle out and could be one possibility why you got layers. Another option if this layer keeps on forming is to chemichally dry the EA with CaCl2 (deicer pellets), decant, and then salt with citric. That has been tested, but is not in the TEK because it seems like it is not needed (no change/improvement), but if you keep on having this layer issue it may be worth a try.

Edit: Did you move the paste that was microwaved in plastic to glass before pulling with EA?
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Homo Trypens
#385 Posted : 7/18/2021 5:43:00 PM

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i did not let it settle for any length of time, no. There was absolutely no visible droplets or debris, so i didn't think it was necessary. Gonna do that next time.

Thanks for the tip with the CaCl2, i'll try that too if this keeps happening. Magnesium sulfate wouldn't work? Because i have some of that handy.

Yes, i did transfer from the plastic to a glass beaker before pulling, and coffee filtered the EA on it's way into the jar.

Another thing i was wondering is if there might be water already in the fresh EA? The one i got is sold as a cleaning product, so they might not see water as a problem... I think i'll freeze a portion to see if there are ice crystals forming.
 
Loveall
#386 Posted : 7/18/2021 8:19:19 PM

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Homo Trypens wrote:
i did not let it settle for any length of time, no. There was absolutely no visible droplets or debris, so i didn't think it was necessary. Gonna do that next time.

Thanks for the tip with the CaCl2, i'll try that too if this keeps happening. Magnesium sulfate wouldn't work? Because i have some of that handy.

Yes, i did transfer from the plastic to a glass beaker before pulling, and coffee filtered the EA on it's way into the jar.

Another thing i was wondering is if there might be water already in the fresh EA? The one i got is sold as a cleaning product, so they might not see water as a problem... I think i'll freeze a portion to see if there are ice crystals forming.


Sometimes it takes a while for the droplets to form. If you do see them show up over time, that could be a place where we may need to add details in the TEK.

Since the EA will absorb some water from the paste, it may not need to be dry to begin with I believe.
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Homo Trypens
#387 Posted : 7/18/2021 8:53:09 PM

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So, i was not inactive this weekend either Smile

I did a cactus paste along the lines of what ACY recommended, 200g cactus powder, 400g of water, a ton of lime and two tons of magsulf. Had that on a little warming for 3 days. I split it into 3 parts, each of them for a different approach.

One i pulled with d-limonene and salted with acetic. This worked without any hiccups, one pull is already evaporated and gave a nice bit of acetate.

One i pulled with acetone and then added sulfuric. I expected clouding, but none happened, so i'm not sure what's going on there, no time anymore to figure it out this weekend. This one is on hold for now.

The third one was reserved for EA and citric. I split that one in half now, too. The first half i just pulled with fresh EA from the can, gonna check for water in the morning. If there is, i'll separate before adding the citric. So far it looks as the other two did, without any drops or floating solids.
The other half i'm gonna pull tomorrow with some fresh EA that i put in the freezer over night.

We'll see what happens. If both crystallise without goo, great. If one has goo and the other doesn't, also great. Both results would point into some direction for further experimentation.

If both still have the goo, my next try will be with a paste that i dry completely. I know that bears the risk of lime making it into the EA, but i'm willing to take that risk once just to get to the bottom of my goo problem.
 
Homo Trypens
#388 Posted : 7/19/2021 8:30:16 AM

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The fresh EA does not produce ice crystals in the freezer.

The paste portion i pulled with fresh nonfrozen EA, i let it sit for a few hours before adding citric, no water sank to the bottom, and it did not produce goo. There is visible crystallisation already, after a few hours.

So it must be something about my paste preparation (or this particular powder).

Next weekend, i'm gonna try to make goo again. And then play with degrees of dryness and amounts of lime.

I hope it wasn't the magnesium sulfate in this weekend's paste that did the trick, because i used pretty much all i had and funds are too low to order anything at the moment Smile
 
Loveall
#389 Posted : 7/19/2021 1:53:50 PM

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Homo Trypens wrote:
The paste portion i pulled with fresh nonfrozen EA, i let it sit for a few hours before adding citric, no water sank to the bottom, and it did not produce goo. There is visible crystallisation already, after a few hours.


This makes sense, congrats on the xtals. The chilled EA may have absorbed some moisture and maybe that extra water saturated the EA and caused the goo. Once you decanted the goo, xtalization finished as it normally would. I think that as long as you do the rest for a few hours + droplet check and remove any drops, xtals should reliability form 🤞

I have seen these drops before, so it can happen. Last time I got them, I had squeezed a bit too hard with the french press. They decanted easily before salting and caused no issues.

A note about resting, cold EA holds less water I believe, so resting in the fridge to check for droplets may be more robust.

Let's see what you get, but I think that we need to add more details around the check for droplets between pulling and salting in this TEK. It could be very important since the TEK doesn't chemichally dry the solvent before salting.

Edit: I observed that acetone was not very efficient at pulling mescaline from a very dry paste, which I think matches your observation. Interesting that you are finding that EA is more efficient, I believe that someblackguy also observed the same thing as you. Also interesting that you did not get dry lime clouds in the EA after drying with magnesium sulfate.
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Homo Trypens
#390 Posted : 7/19/2021 6:21:12 PM

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Loveall wrote:
Also interesting that you did not get dry lime clouds in the EA after drying with magnesium sulfate.


Yeah it was interesting, after adding the magnesium sulfate the paste actually got softer. I kept adding absurd amounts - more than half a kilo for a paste from 200g cactus and 400g water. It took days for it to almost dry, even with some heating (maybe 30-40°C). It was not fully dry when i pulled. Pulling did grab some small particles, probably some lime as well as some magsulf, but this was easily separated from by settling then carefully pouring through a coffee filter.
 
_Trip_
#391 Posted : 7/22/2021 1:43:25 AM

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Decided to give this TEK a go. Just thought I would share what I found.

I used the microwave and cold extract option.

However I screwed up a little, when i first added the ethyl acetate i noticed the cacti material absorbed almost the entire amount of ethyl acetate. I should have just continued to do repeat pulls but instead I stupidly added bit of water to moisten the material, in the hope the ethyl acetate would be easier to pull.

Long story short I did 6 pulls and didn't notice a water layer in the ethyl acetate but assumed some did get absorbed.

Regardless I added the citric acid and waited 36hours and no crystals formed I added excess 15 mg per gram, still only a tiny few crystals formed.

I figured there's too much water in the ethyl acetate so I froze it overnight, the next day I checked it and it was full of floating ice crystals (nothing else). I filtered the ice crystals and evaporated them (some ethyl acetate made it in with the ice crystals, it left green/ yellow oily goo. The goo was bitter and completely dissolved in acetone. There were a few particles that didn't dissolve and therefore may have contained some mescaline citrate (or another alkaloid that doesn't dissolve in acetone).

Anyway left the jar aside hoping mescaline citrate would crash out, it did not. So I froze the ethyl acetate (for a few hours) and again more ice crystals floated at the top, however, this time there was a white layer on the bottom. So after pouring out the ethyl acetate amd filtering the ice crystals I collected the frozen white layer at the bottom of the jar with water. Then separated it for evaporation and then put the ethyl acetate back in the original jar.

I repeated this again, froze it at -20 degrees (-4f), i got the ice floating crystals again (so more water was in there) and the white frozen layer at the bottom. Again I filtered, separated, collected the bottom white layer (separated that) then evaporated etc.

The 2 white layers I pulled with water evaporated in the one pan (with a heat fan), it left a couple little crystals and a clear layer of resin. The resin was scrapped up and hardened as it cooled. I scrapped it up into a slightly off white crystal like powder and it came to 700mg (from 50g of powdered bridgesii). This was pretty much on par with and A/B I did with the same bridgesii powder previously.


I tasted the off white powder. It tasted similar to HCL mescaline and was quite bitter (a little of a sour tang). But it was not sour like citric acid. I put 40mg aside and covered it with acetone, very little dissolved.

Hopefully I'll be able to test it soon. But i believe it is mescaline citrate.

It appears I was able to crash it out in the freezer once enough water was removed.

I believe shroombee had a similar experience.


***Tried freezing a third time no white layer at the bottom, so I don't believe it is excess citric acid crashing out and freezing.


Disclaimer: All my posts are of total fiction.

 
Homo Trypens
#392 Posted : 7/24/2021 12:56:31 PM

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So, i have done some more experimenting.

First, i cold pulled the other sixth of last weekend's paste (the one with a lot of magnesium sulfate). The fresh EA was in the freezer for 24h+, the paste was in the fridge for the same length of time. I did 1min pulls and i got nothing at all. Little discoloration in the EA, no crystals 48h after adding the citric, no water ice crystals when freezing the EA for next use. Very strange, my hypothesis is that the paste was too dry, the magsulf and lime somehow hardened to something that was basically impenetrable for the EA.

Then during last week, i made another paste. I did it like this:
- mixed 200g cactus powder with 400ml of water and 10g of citric. Mixed well. Placed the paste on heating, maybe 45°C. I believe this is as effective in destroying chlorophyll as microwaving, it takes more time but is zero work and has no potential for accidents.
- the next day, added 10g of lye and kneaded it in wearing thick rubber gloves.
- another day later, kneaded in an unmeasured amount of lime, probably around 150g.
- spread it out a bit so it would air dry a little. Let it sit for 2 days, kneading and spreading it a bit twice per day, for more even drying.
- it had a rubbery consistency after that.

Yesterday i divided this paste into two halves. I pulled both at room temperature (1min stirring, 2min settling per pull), but for one i reused EA from earlier attempts, for the other one i used fresh EA. There was some lime coming along when decanting, so i had to pour through a coffee filter which removed all of it.

Both produced no goo, both are crystallising nicely now (left is reused, right is fresh). Pics are at the 12h mark.

The fresh EA was clear after filtering. Quite a lot of lime was in the coffee filter. I let the EA sit for a few hours to see if there was any lime still in it, but that was not the case. I dropped 5g of citric, upon which nice clouding started. In the pic, it looks cloudy but not crystally. There absolutely is crystallisation happening in the bottom zone though (see second pic).

The reused EA was already cloudy when it came through the coffee filter. It got even more cloudy when i added 5g of citric. So there must be some citric left from the last use, makes sense. Note how it is producing crystals all over the place.

---

So, i still don't know which aspect of paste preparation caused my trouble, but i'm fairly certain now that it was the paste. My next experiment will be a paste using 100g cactus, 25g lime, and the microwaving again, to see if i can reproduce the goo. If not, the mesc spirit was just messing with me!
Homo Trypens attached the following image(s):
weekend_3.2.jpg (71kb) downloaded 195 time(s).
bottom_zone.jpg (29kb) downloaded 196 time(s).
 
Loveall
#393 Posted : 7/24/2021 5:53:48 PM

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Thanks for the updates and congrats on the xtals ✨🤩✨

Hopefully the next repeat without adding any extra water simply works.

One question/comment on the reused ehtyl acetate, after the sodium carbonate wash, it is possible to us pH paper to verify it is no longer acidic. Did you try this? If not it may be worth a try. Simply keep on shaking with sodium carbonate saturated water to wash until the pH paper is neutral.


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Homo Trypens
#394 Posted : 7/24/2021 7:04:10 PM

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Hmm, i did not wash the EA at all. I only froze it and filtered out the water ice crystals.

But from the looks of it, it doesn't hurt to have the citric still in there. I guess the 2-3min contact of the mesc with the citric aren't enough to grow crystals that don't get through the coffee filter. It leads to faster crystallisation and more places they stick to ont he glass walls, it seems.

This pic is at 18h after dropping the citric, still left is reused and right is fresh EA
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Loveall
#395 Posted : 7/24/2021 11:03:59 PM

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Well, that explains why the reused ethyl acetate was cloudy. To reuse it in a "classic" extraction the citric acid is washed so free base mescaline can go into the solvent.

I guess you did two steps at once (pull and start to crash). That's kind of out of the ordinary but interesting that it sort of works(?).
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_Trip_
#396 Posted : 7/25/2021 4:29:18 AM

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Been experimenting with this Tek 3 times now all using microwave and cold pull options.

Last attempt I got a 3.4% pull from 70grams of dried Bridgesii. (slight off white crystals).

This doesn't seem right, yet it was very bitter tasting not sour like citric acid.
I have pulled 1-1.3% HCL before from the same bridgesii.
However the powder used for this EA attempt was from a Bridgesii that sat in the dark for a couple months to increase the mescaline content before it was powderising. Like I always have, I took out the spines, wax layer and inner white core but 3.4% seems too high. Unless citrate is 60% as strong as HCl by weight that would bring it down to 1.5% (equivalent to HCL) or am i butchering the chemistry mathematics here?

Disclaimer: All my posts are of total fiction.

 
Homo Trypens
#397 Posted : 7/25/2021 9:58:45 AM

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Yes it did sort of work, but it was a bad idea.

It leads to contamination by something that isn't citric acid or lime. My guess is Calcium citrate. I'm gonna have to play with solvents to clean it up... Good thing i kept the products from the two jars separate Razz

I'll wash the EA from now on.
 
Loveall
#398 Posted : 7/25/2021 12:59:30 PM

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_Trip_ wrote:
Been experimenting with this Tek 3 times now all using microwave and cold pull options.

Last attempt I got a 3.4% pull from 70grams of dried Bridgesii. (slight off white crystals).

This doesn't seem right, yet it was very bitter tasting not sour like citric acid.
I have pulled 1-1.3% HCL before from the same bridgesii.
However the powder used for this EA attempt was from a Bridgesii that sat in the dark for a couple months to increase the mescaline content before it was powderising. Like I always have, I took out the spines, wax layer and inner white core but 3.4% seems too high. Unless citrate is 60% as strong as HCl by weight that would bring it down to 1.5% (equivalent to HCL) or am i butchering the chemistry mathematics here?



We don't know the salt form. As you may have read from the the TEK:

"During crystallization, citric acid (H3Cit) reacts with free base mescaline (Mes) to form to form a mescaline citrate salt. The number of mescaline molecules (n) that react with one molecule of citric acid and precipitate is unknown:

nMes(↑) + H3Cit(↑) ⇒ (MesH)nH3-nCit(↓)

Where n could be 1, 2, or 3. The resulting mescaline citrate salt's strength relative to mescaline HCl is 62%, 81%, and 90% respectively."

The mass spec result gave very clean mescaline, that is likely what you have by following the TEK, we just don't know the precise salt form.

It would be very interesting if you converted the mescaline citrate you got to HCl. I've been trying by simply adding HCl and evaporating (with plans to remove citric with EA later), but I got a brown byproduct from what I think is HCl reacting with citric acid while I heated the mix so it would evaporate faster. This byproduct does not dissolve cleanly in EA, making a mess of things.

Dissolving the 3.4% mescaline citrate candidate in a small amount of water, basing, pulling with xylene, and salting with HCl should work and could give us an answer.


PS: there could also be a hydrate form, lowering the % a little more
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_Trip_
#399 Posted : 7/25/2021 1:30:03 PM

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Yeah I saw your post previously. I'm just thinking going off previous (A/B) Teks with the same powder I'm thinking 62% sound about right comparing previous and current yields. However this observation is just that I could be completely wrong, comparing yields of different Teks is in no way accurate.

I was literally thinking about doing something along those lines.

I have a 4th run I may do tomorrow if I have time or I'll just sacrifice 400mg or 500mg of stuff I already have.
After my first attempt (that I stuffed up, sort of) getting excess moisture out via the microwave i think is a good way to go. I found a massive difference in yield between 1st and 3rd attempt on the same powder. Only difference between the two attempts was water content. So drier seems to be better and as you pointed out is better for solvent reuse.

I'll go again in the next couple days regardless.

As for the conversion.
i'm thinking dissolve about 500mg in 50ml of water add caustic soda until I have a PH of say 12 and then pull with 20ml xylene and salt it out with say 20ml water+HCL. Does that sound about right?



Regardless, Loveall I must say best mescaline TEK I've ever done, fastest, easiest, cleanest and probably purest tek out there. So hats off to everyone who contributed.

Don't know why you named it CIELO TEK should be the Ultimate Fucken Mescaline TEK.

Disclaimer: All my posts are of total fiction.

 
shroombee
#400 Posted : 7/25/2021 8:19:52 PM

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_Trip_ wrote:
However I screwed up a little, when i first added the ethyl acetate i noticed the cacti material absorbed almost the entire amount of ethyl acetate. I should have just continued to do repeat pulls but instead I stupidly added bit of water to moisten the material, in the hope the ethyl acetate would be easier to pull.

Thanks for sharing this mistake. I added a note to the TEK to not add water to the paste, and to just add more ethyl acetate if the paste absorbs it all.

_Trip_ wrote:
It appears I was able to crash it out in the freezer once enough water was removed.

I believe shroombee had a similar experience.

Right, I found in some earlier experiments that removing water ice seemed to facilitate xtal formation. However, those experiments gave me less yield than the current tek where I get xtals immediately upon adding citric with the magnetic stirrer.

Since the simple tek works so well for me as a repeatable baseline, I should follow up with variations like adding a little water before salting, removing water through freezing, microwaving, etc. Might be illuminating.

Loveall wrote:
It would be very interesting if you converted the mescaline citrate you got to HCl. I've been trying by simply adding HCl and evaporating (with plans to remove citric with EA later), but I got a brown byproduct from what I think is HCl reacting with citric acid while I heated the mix so it would evaporate faster. This byproduct does not dissolve cleanly in EA, making a mess of things.

I was wondering what happened to the HCl conversion experiment. So it didn't work? I thought you were trying a slow evaporation?
 
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