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Ethyl Acetate Approach for Harmala Options
 
Loveall
#21 Posted : 9/2/2021 11:58:14 AM

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_Trip_ wrote:
Weird that you had trouble crashing the harmala citrate until you added water. I had no issue when I converted the FB harmala too citrate. Could this have something to do with FB harmala being hydrated or something? (excuse my poor chemistry understanding).

Not sure, perhaps the EA could have some water, especially if the can has spent some time open (or it comes with some water already from the hardware store). I can say that if drying well right before salting I'm observing that citric acid needs a little water to react with and crash out harmala candidate.


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_Trip_
#22 Posted : 9/2/2021 12:09:16 PM

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The EA was bought as 100% EA so it should be dry. Maybe ya right it may have drawn moisture from being open who knows. I did have to shake it a lot to get it to precipitate.

Either way a bit of water helps citrate crash. Citric acid does crystalize nicely from goo if left but fumaric acid seems like a quicker better alternative. It is however harder to come by where I'm from.

How clean did the FB harmala come out when based from the harmala fumarate?
And did it crash faster when shaken or have you left it to slowly crash out?
Disclaimer: All my posts are of total fiction.



 
Loveall
#23 Posted : 9/2/2021 1:20:18 PM

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_Trip_ wrote:
The EA was bought as 100% EA so it should be dry. Maybe ya right it may have drawn moisture from being open who knows. I did have to shake it a lot to get it to precipitate.

Either way a bit of water helps citrate crash. Citric acid does crystalize nicely from goo if left but fumaric acid seems like a quicker better alternative. It is however harder to come by where I'm from.

How clean did the FB harmala come out when based from the harmala fumarate?
And did it crash faster when shaken or have you left it to slowly crash out?


I slowly crashed out fumarates. Haven't finished FB harmala conversions, I got several tests going on during the salting steps right now, including fully drying the ground seeds (that's looking very promising so far, and seems super fast - I dare say faster and much cleaner than crude water pulls + basing - we will see).
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_Trip_
#24 Posted : 9/2/2021 10:59:31 PM

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Awesome work. I think you'll end up with a much cleaner product than i got. Fingers crossed anyway.
Disclaimer: All my posts are of total fiction.



 
Loveall
#25 Posted : 9/4/2021 1:11:29 AM

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The fully dry Tek doesn't quite work as well as I had hoped. Some water seems to be needed for good xtalization - even for Fumaric.

From my all my tests, the red oil after pulling from wet paste and salting with citric seems best so far.

πŸ’šπŸŒ΅πŸ’š Mescaline CIELO TEK πŸ’šπŸŒ΅πŸ’š
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_Trip_
#26 Posted : 9/4/2021 2:42:23 AM

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Hmm very surprising, I thought drying it fully would facilitate a cleaner higher yielding pull but good to know going forward. I still don't understand how I had no issue convert harmala FB to citrate in clean dry EA i must of had water in my EA.

Even though the fully dry tek didn't work as planned, did it pull a decent yield and cleaner product still? Because a little distilled water could always be added later for xtalization and it may facilitate a purer product. So would you deem fully drying still worth investigating?


I did have good results reducing the the water content down to 1/3 rd with a microwave as per other 'dry' teks and inline with the Cielo tek. I might be wrong but microwaving facilitates cell lysis which could help release more harmala. It is also a quick method. So this may be a good way to go if fully drying isn't worth investigating. In addition one can always chemically dry with CaCl2 after the pulls. Less water may mean less impurities, but it is also becoming evident a little water may be needed.

Your thoughts?
Disclaimer: All my posts are of total fiction.



 
Loveall
#27 Posted : 9/4/2021 3:06:41 PM

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_Trip_ wrote:
Hmm very surprising, I thought drying it fully would facilitate a cleaner higher yielding pull but good to know going forward. I still don't understand how I had no issue convert harmala FB to citrate in clean dry EA i must of had water in my EA.

Even though the fully dry tek didn't work as planned, did it pull a decent yield and cleaner product still? Because a little distilled water could always be added later for xtalization and it may facilitate a purer product. So would you deem fully drying still worth investigating?


I did have good results reducing the the water content down to 1/3 rd with a microwave as per other 'dry' teks and inline with the Cielo tek. I might be wrong but microwaving facilitates cell lysis which could help release more harmala. It is also a quick method. So this may be a good way to go if fully drying isn't worth investigating. In addition one can always chemically dry with CaCl2 after the pulls. Less water may mean less impurities, but it is also becoming evident a little water may be needed.

Your thoughts?


I agree. Can't explain your result with fresh EA, but I can say that when everything is super dry in my case (which means CaCl2 has been used), xtalization is not occurring very well. When I add water clouds show up, and red stuff crashes, not an oil, but still reddish and a little sticky. It does not seem different enough vs the red oil you get with less effort to justify the chemical drying steps.

I think your process is good _Trip_. The the alkaline wet microwaved paste is easy to make, the warm EA pulls seem efficient and separate easily. I feel like overall it is less work compared water water pulls and more selective to harmalas (less junk to fight later if wanting a pure product) - although I have no hard data to confirm, could be wrong.

I have one more thing I want to try: Do pulls with EA on microwaved paste like you discovered, but then add water that has citric acid and 15% NaCl and form a water layer. Harmalas have nowhere to go and should precipitate as a citrate salt, while a lot of contaminants should stay in the water and ethyl acetate. Then continue with your process: decant, dissolve in fresh water, and base to recover the FB. So same process you did originally, but instead of using citric acid granules for crashing harmala citrate, use a 15% NaCl + citric acid solution so fewer contaminants crash thanks to the water layer. I'll report back.
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Loveall
#28 Posted : 9/5/2021 4:43:43 AM

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I tested the following:

- Made alkaline wet paste with 1:1.2 ground rue:20% Na2CO3 water solution. No microwave, just mixed for 10 minutes as a test. Started with 75g of rue.
- Pulled with ~2 parts room temp EA twice stirring for a few minutes until EA got very dark. Clear EA decanted very easily - no filtering.
- Added 1 part water to combined EA pulls to form a separate layer, EA is alkaline on pH paper and water is yellow at this point (first picture).
- Titrated with citric acid until pH paper is acidic in EA. Any EA cloudiness quickly disappears and water turns a very dark red, and fluorescent under a picture flash (second picture). Harmalas should be in the water at this point.
- Shaked in 18% NaCl by water volume. Water becomes orange/red as what should be Harmala HCl begins to clump up. No signs of red oil (3rd picture).
- Crashing Harmala HCl put in fridge where it appears to be settling (4th picture). Will catch in filter tomorrow and measure yields of first two pulls (4th picture).

So far this is less than an hour of work with no filtering, no long pulls, and no heating. Orange harmala HCl looks pretty good, will need to measure yields and check purity.
Loveall attached the following image(s):
IMG_20210904_211336438.jpg (721kb) downloaded 206 time(s).
IMG_20210904_211733904.jpg (762kb) downloaded 204 time(s).
IMG_20210904_212333906.jpg (764kb) downloaded 206 time(s).
IMG_20210904_232228361.jpg (813kb) downloaded 204 time(s).
πŸ’šπŸŒ΅πŸ’š Mescaline CIELO TEK πŸ’šπŸŒ΅πŸ’š
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πŸ’šπŸƒπŸ’š Salvinorin Chilled Acetone with IPA and Naphtha re-X TEKπŸ’šπŸƒπŸ’š
 
_Trip_
#29 Posted : 9/5/2021 5:06:18 AM

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Awesome work Loveall,
Adding in a manske like step might be the way to go for a purer end result. If purity and yield is good this could be a simple and quick as it needs to be.

As I'm sure you're already thinking you may have to do a few runs on the original material to work out yield potential.

From there we will just need to work out ratios to get the most out of it.

The only possible downside I could see is there may be a small chance EA re-use might be harder as it may be loaded with more gunk. However this may not be the case or even matter once it is cleaned.

Are you going to redissolve in vinegar and water to then freebase with sodium carbonate?
If so my only observational input would be to consider using more water rather than less. This helped achieve better purity (going off what my results got in the third run).

I also want to add, I have kept all the sodium carbonated saturated water to see what crashes out when left for a few days. And what i have noticed is the harmala is a lot 'dirtier' when left over longer periods to precipitate. That information may or may not help.
Disclaimer: All my posts are of total fiction.



 
Loveall
#30 Posted : 9/5/2021 5:22:25 AM

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_Trip_ wrote:
Weird that you had trouble crashing the harmala citrate until you added water. I had no issue when I converted the FB harmala too citrate. Could this have something to do with FB harmala being hydrated or something?


Not sure, but we did follow two different paths. I dried with CaCl2 right before salting. I don't think you've tried that yet, but curious to see what you get.
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_Trip_
#31 Posted : 9/5/2021 5:34:13 AM

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Yeah I think next extraction I'll stick to what I have already done and go down the 'dry' tek path again but add in CaCl2 step before salting. It may remove more impurities. I could decant add water then salt with NaCl, filter, redissolve in vinegar and water then base. The decanting of EA while redissolving citrate and then adding NaCl step (manske) may facilitate a cleaner product. I'll have to see what the end result looks like.

We'll have to compare notes on yield and 'appearance' of purity. This may help to determine if a dry style tek is necessary or a wet tek is better. Of-course, since we are both using seeds from different vendors we will likely get different results. We may have to eventually try each others methods.
Disclaimer: All my posts are of total fiction.



 
Loveall
#32 Posted : 9/5/2021 7:59:59 PM

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Loveall wrote:
I tested the following:

- Made alkaline wet paste with 1:1.2 ground rue:20% Na2CO3 water solution. No microwave, just mixed for 10 minutes as a test. Started with 75g of rue.
- Pulled with ~2 parts room temp EA twice stirring for a few minutes until EA got very dark. Clear EA decanted very easily - no filtering.
- Added 1 part water to combined EA pulls to form a separate layer, EA is alkaline on pH paper and water is yellow at this point (first picture).
- Titrated with citric acid until pH paper is acidic in EA. Any EA cloudiness quickly disappears and water turns a very dark red, and fluorescent under a picture flash (second picture). Harmalas should be in the water at this point.
- Shaked in 18% NaCl by water volume. Water becomes orange/red as what should be Harmala HCl begins to clump up. No signs of red oil (3rd picture).
- Crashing Harmala HCl put in fridge where it appears to be settling (4th picture). WΜΆiΜΆlΜΆlΜΆ ΜΆcΜΆaΜΆtΜΆcΜΆhΜΆ ΜΆiΜΆnΜΆ ΜΆfΜΆiΜΆlΜΆtΜΆeΜΆrΜΆ ΜΆtΜΆoΜΆmΜΆoΜΆrΜΆrΜΆoΜΆwΜΆ ΜΆaΜΆnΜΆdΜΆ ΜΆmΜΆeΜΆaΜΆsΜΆuΜΆrΜΆeΜΆ ΜΆyΜΆiΜΆeΜΆlΜΆdΜΆsΜΆ ΜΆoΜΆfΜΆ ΜΆfΜΆiΜΆrΜΆsΜΆtΜΆ ΜΆtΜΆwΜΆoΜΆ ΜΆpΜΆuΜΆlΜΆlΜΆsΜΆ ΜΆ(ΜΆ4ΜΆtΜΆhΜΆ ΜΆpΜΆiΜΆcΜΆtΜΆuΜΆrΜΆeΜΆ)ΜΆ.ΜΆ

So far this is less than an hour of work with no filtering, no long pulls, and no heating. Orange harmala HCl looks pretty good, will need to measure yields and check purity.


I did two more pulls and added them to the jar in the last picture. For the 4th pull I heated the extract in a water bath and boiled the EA. Clouds formed in the acidic EA, and they cleared up into the salty water where more yellow precipitate appeared.

I added another 75ml of water to have more room for (hopefully) manske xtals, and set the salt concentration to 10%. Then, I heated the salted jar in a hot water bath, all the yellow/orange precipitate dissolved when the water was hot (something I've seen manske do before). This left two clear layers (first picture).

Moved that to the fridge to slowly cool.

I'm seeing "large" shiny crystals forming 🀩. I hope they are relatively pure harmine and harmaline HCl (last 3 pictures, finding it difficult to show the xtals in a picture xtals because extract is still dark).

So, we have been able to get xtals directly out of the ethyl acetate FB extract by salting with citric and the "trick" of adding a salty water layer also. I think the salty water forms harmala HCl because of the common ion (manske) effect, and keeps impurities dissolved (or dissolved enough for xtals to crash).

Definitely worthy of more investigation. _Tips_'s idea to do STB on rue with EA could be a practical alternative to the acidic water pulls approach. Perhaps even less work, and EA should be reusable after a simple sodium carbonate wash (done directly after decanting harmala HCl off).

Edit: added a 5th picture after decanting
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IMG_20210905_145117870.jpg (715kb) downloaded 178 time(s).
IMG_20210905_145020631.jpg (836kb) downloaded 175 time(s).
IMG_20210905_151717852.jpg (721kb) downloaded 166 time(s).
IMG_20210906_091427581.jpg (5,372kb) downloaded 130 time(s).
πŸ’šπŸŒ΅πŸ’š Mescaline CIELO TEK πŸ’šπŸŒ΅πŸ’š
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_Trip_
#33 Posted : 9/5/2021 11:05:01 PM

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Amazing work as always Loveall, I'm looking forward to your end FB result.

Edit:
Decided to do a fourth run on the original 66g. This time I decided to do CaCl2 filter to dry the solvent. I added citric acid, a bit of shaking and very quickly this formed. So it would appear if the solvent is dried goo doesn't form.

So unless calcium chloride got in to the solvent this should be xtalized harmala citrate. I can't find anything on ethyl acetate absorbing calcium chloride. I hope someone can confirm this though.





Drying the solvent maybe a step towards a purer end result.

I have decanted and then manske this with NaCl and distilled water to see if a purer product will result. Forgot how long it takes to form.
Disclaimer: All my posts are of total fiction.



 
Loveall
#34 Posted : 9/6/2021 1:25:45 PM

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Calcium Chloride does not go into ethyl acetate.

How exactly did you dry the solvent? When I dried everything it wasn't that yellow. I had to add a lot of CaCl2 (~5% +) and give it time to absorb the water. Before enough CaCl2 is added a separate water layer formed during drying.

Manske HCl xtals should form overnight in the fridge, if not sooner.
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Loveall
#35 Posted : 9/6/2021 2:37:55 PM

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Quick note on the "in-situ" manske approach. I've learned that 22% salt in the water layer pushes out the red oil (10% NaCl does not). The resulting manske xtals are yellow instead of red (I think this means a lot cleaner).

There is a tiny chance the red oil pushed out by the 22% NaCl water layer contains harmalol HCl, something to figure out later.

I'm starting a new run (simple microwaved wet paste, and hot EA pulls) where I salt EA with vinegar that has 22% salt and remove the red oil that I think will form between the EA and vinegar layers before manske starts. I hope that is a quick path to orange and relatively pure harmala HCl (red is not as pure I believe). After that will FB and hope for a high yielding white harmala FB product with little effort 🀞.
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_Trip_
#36 Posted : 9/6/2021 11:38:07 PM

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Loveall wrote:
Calcium Chloride does not go into ethyl acetate.


Yeah I didn't think it did.

So to dry the solvent I get my collect EA after pulling from the based seed mix, I had about 400ml of EA. I got a 120ml beaker filled it with CaCl2 pellets dumped it into the EA. Gave it a quick shake only twice over 10 minutes then proceeded to the the first filter. So I really added a lot of CaCl2. Like your previous results Loveall, I too found the Cacl2 yellowed and pullout some gunk.
Let's not forget I'm microwaving 2/3rds of the water content away and after the 4th run there would have been little water contamination left. So I believe it was dried thoroughly. And the citrate appeared to form nicely.


Loveall wrote:

I'm starting a new run (simple microwaved wet paste, and hot EA pulls) where I salt EA with vinegar that has 22% salt and remove the red oil that I think will form between the EA and vinegar layers before manske starts. I hope that is a quick path to orange and relatively pure harmala HCl (red is not as pure I believe). After that will FB and hope for a high yielding white harmala FB product with little effort 🀞.


Yeah fingers crossed.

I'll keep you updated if my harmala FB comes out any cleaner via drying the solvent and adding a manske step.


I'm also wondering Loveall since the end result has been fairly clean anyway (even using the initial method i did), i was thinking maybe a mini A/B at the end might be a good way to clean it up some more.
-Redissolve FB harmala in clean EA
-Salt it out
-FB again in distilled water sodium carbonate
-Filter and dry
A mini A/B could be done very quickly with this method. This may or may not be as effective as adding a manske step but if it is it'll be less time to wait for it to crash out(so one might not need to manske or chemically dry).
Disclaimer: All my posts are of total fiction.



 
_Trip_
#37 Posted : 9/7/2021 4:57:53 AM

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Just thought i would share here's the following image.


On the left is the final result from an A/B manske extraction that was repeated 3 times. The middle vial and vial on the right are from the ethyl acetate approach.
The middle vial was done as per my original approach (first 3 pulls on the 66g). No manske nothing special just decant EA, add warm (tap) water base with sodium carbonate filter and dry.
The vial on the right was the 4th pull from the original 66g, solvent was chemically dried, citrate was separated dried and then a manske was preformed all with distilled water then filtered to get harmala HCL,this was then based; I can't explain how it ended up so dark. I would have thought it would have come out cleaner. Color doesn't necessarily mean its purer but it is a good indicator. Could the NaCl be dragging in impurities? I had the water looking so much clearer in each step???




The original run may be a good blue print.


***On a side note if you look at my picture from the 3rd run of the EA approach:


The final result was quite dark compared to the first 2 runs in the vial, this was due to using far less water when dissolving the citrate and then basing. The 3rd run was cleaned up with a mini A/B by dissolving in EA, salting again with citric acid and basing with sodium carbonate. It worked well and came out looking exactly like the yield in the vial.

I don't have access to ammonia to wash the end result with but i think it looks fairly good.
Disclaimer: All my posts are of total fiction.



 
Loveall
#38 Posted : 9/7/2021 7:24:16 AM

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Looks good _Trip_.

I think your original process is great. That white freebase looks very clean to me, the red oil cleans up very nicely during FB precipitation. Congrats.

When I based the ground seeds with sodium carbonate I did not need to filter the EA, it decants clear - FYI.

I think it is time to analyze the product with your process, see if it is pure and does not contain unwanted alkaloids. Also, you can wash the free base with 0.5% sodium carbonate. To paraphrase your process which I plan to repeat as is:

Microwave water/ground seeds/sodium carbonate to a fluffy paste, extract with hot EA 5x, precipitate with citric acid, dissolve in water, add sodium carb, collect precipitate/wash/dry



Setting your great experimental TEK aside, I'm trying to get "clean" xtals during the salting stage. It seems to be working using 22% NaCl vinegar, but there are also red clumps that crash with the xtals. The manske xtals can be re-dissolved with heat, while the red gunk remains and can be filtered out, then I add +1/3 more water layer and large manske xtals slowly grow. I'm interested in the red isolated gunk, I wonder if it has harmalol HCl. It dissolves in water and is very fluorescent. If the product in your original approach is pure and the red clumps don't have harmalol, then I think there is no practical point to this approach.

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_Trip_
#39 Posted : 9/7/2021 12:11:39 PM

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Yeah Loveall, that looks about right. I make sure i microwave two thirds of the water out before doing the pulls and I've been using calcium hydroxide for basing. Also adding more water when dissolving the citrate seems to decrease the concentration of impurities when basing with sodium carbonate.

And yes I should be washing with .5% sodium carbonate.

We just need to figure out the optimal ratios of EA and water etc.

My thinking is (which is influenced by other teks)

100g of rue=300ml of water and 25g of calcium hydroxide
EA I'm thinking minimum 1lt-1.25lt (200ml-250ml per pull)

As for dissolving citrate 500ml min of water.
(I still want to confirm if adding vinegar at this stage helps clean up the end result before freebasing) as previously discussed I doubt it.

Your thoughts on these values?



That is interesting about the harmalol. But I think as you've mentioned an analysis of alkaloids will help determine exactly what is going on.

This process could be seeing vasicine and vasicinone in the end result. There has been much debate on these two alkaloids and i do believe after reading a few posts they do have a few health benefits (unless your pregnant). This may or may not be a factor to people if deciding to do this tek.

But i can say that one should be able to get 5% pulls easily (even if it takes a couple runs).
Disclaimer: All my posts are of total fiction.



 
Loveall
#40 Posted : 9/7/2021 2:46:51 PM

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Values seem good overall. I think one can use less EA and make it hot, I'm using about 75% of what you are and heating it in a warm water bath (no open flame).

One comment is that you filtered the EA (looked cloudy) from a ground rue/water/Ca(OH)2 paste. When I use a paste made with sodium carbonate (instead of Ca(OH)2) the EA is clear and does not need filtration.

Are you still filtering your EA? I don't find this necessary with sodium carbonate.

Yes, vasicine and vasicinone may be present in the simple Tek. Not sure though.

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