First I really really wanted to thank you Jees for helping me on my first steps. Seriously!

It seems now really, that in the 2nd extraction there's nothing in it???
Now even after 1.5 days there's nothing more precipped.
The funny thing is, that after I filtered the first Manske (one night after salting), I just put the liquid away to see if after 2 more days more would precipitate out. This it did indeed, but such a tiny amount, that I simply discarded it. But that was even more, than did precipitate out now from my 2nd extraction...

I really wonder if the fact that I used quite a high water to seed ratio (30:1) and that I made the water 3% acetic (which is much more than the usual recommended dash of vinegar), resulted in basically almost all alkaloids extracted in the first run. Another explanation would be that the amount of alkaloids dissolved is just too small for the big amount of water, so that all stays in solution.

Will add tomorrow another 100g/l to get to 250g/l in total and see if this changes anything.

BTW: The FB from the first extraction is really very potent. Bioassayed 150mg, which 1h later was joined by some 30mg "vapor", and it worked perfectly.

Thanks for the compliment, yet I did read you wrong about the 2nd run: I thought this was a 2nd manske on same extract, but now I realize it is the second run on the seeds

1 gr out of 20 gr seeds is 5% and is already a success on 1 run only, so no wonder your seeds aren't giving much anymore. So you had a lot of water with little alks in, meaning a very low concentration. Such demands max salt to obtain anything meaningful, so you had it right pumping up the salt.

OK, I will try. So then I will go for a concentration of 300g/l, to see what difference that makes.

BTW:
I use 3% acetic acid, because that was the number from the original Hasenfratz tek.
All Nexus-teks only use a dash of vinegar except the cold caapi tek, which as I saw also uses 3% acetic acid.
Why do the boiling teks don't use more acetic acid? Because of the smell, or because it doesn't make a difference in the extraction yield?

I personally find it very strange, that it seems that basically most of my yield is from just one extraction, and am now wondering, why?
That's especially puzzling, as I only syphoned off after the first extract, so there was still quite some water remaining on and in the mush. I wonder how it would have looked like if I would really have pressed out everything completely from the first run.

In the VDS protocol they did use also about that concentration but they used it on whole seeds. IMHO that's a real pity. So I cannot really compare results.
I grind my seeds always with a pepper grinder.

VDS did not make fine from the beginning, only after 4 runs he did it:
I guess that makes it equally with grinded from the start. I like that hybrid idea actually.

I've always had good results with grinded seeds too, but found that pressed whole seeds reaches the same yield. It is not easier on the filter though.

I was just wondering how their yields for the specific extractions would have been, if they would have ground the seeds from the beginning.

One question: If I have the HCl salts. Am I right, that I first have to FB it, before I can make a citrate or acetate out of it, because the Cl-ions bind stronger?

I was just wondering, because in the Fritzsche article it is stated, that you can also get FB, by making the acetate and simply evaporating it.
There seems to be even a possibility of a separation tek by this, as Harmine FB will be built by cold evaporation, whereas Harmaline FB needs heat on evaporation. So in theory you could let it cold evaporate, then put water on it again, an the FB Harmine stays solid, whereas the Harmaline-Acetate will again dissolve.
The problem will probably be, that the Harmaline-Acetate is first a gunk, then crystals, so I would think that it encloses the Harmine, so that it cannot completely evaporate properly.


Lol, it really looks like Fritzsche was the one first discovering these Alkaloids. He even gave them their names.
Also interesting IMHO that only Harmaline can convert to "Harmala Red", but not Harmine.


Edit: Read further in old books, and now it's not clear to me, if Goebel or Fritzsche gave them their names. Or if Goebel named Harmaline and Fritzsche Harmine.
There was also quite a discussion among them and other scientists if "Harmala Red" was formed due to oxidation from Harmaline. Goebel said yes, Fritzsche no.
Goebel discovered a method to completely transform the Harmaline to "Harmala Red" in a very short time. But he only sold this tek in secrecy for money.
The usual method of Ethanol soaking needed quite some time for complete transformation. So IMHO it is still unclear if "Harmala Red" is active or not. As I would think tests that have been done on the Nexus didn't fully convert it. Just by ethanol, it needs weeks to months for full conversion. So I would think with all the teks we used, probably only a very small amount has been converted. So if it is then still active, doesn't say much, as it is mainly still Harmaline.

Edit2:
IMHO also interesting that Goebel wrote, that the alkaloids in the plant are in the phosphoric acid salt form.

Edit3:
Here a few links to some of the articles (all in german):
http://www.samorini.it/doc1/alt_aut/ek/fritzsche-untersuchungen-uber-die-samen-von-peganum-harmala-1.pdf
http://www.samorini.it/doc1/alt_aut/ek/fritzsche-untersuchungen-uber-die-samen-von-peganum-harmala-2.pdf
http://www.samorini.it/doc1/alt_aut/ek/fritzsche-untersuchungen-uber-die-samen-von-peganum-harmala-3.pdf
http://www.samorini.it/doc1/alt_aut/ek/fritzsche-untersuchungen-uber-die-samen-von-peganum-harmala-4.pdf
http://www.samorini.it/doc1/alt_aut/ek/fritzsche-untersuchungen-uber-die-samen-von-peganum-harmala-5.pdf
http://www.samorini.it/doc1/alt_aut/ek/fritzsche-untersuchungen-uber-die-samen-von-peganum-harmala-6.pdf
http://www.samorini.it/doc1/alt_aut/ek/goebel-ueber-das-harmalin-.pdf
dokument.tips_ueber-das-harmalaroth.pdf

Wow Aum_Shanti, this is very interesting history! Thanks for sharing, nice work.

I didn't know the alks are present as phosphates! Pure coincidence: my most succesful Rue extraction was a 'Tao of Rue' variation using Phosphoric Acid for the primary seed extraction - only because it's totally non-volatile and odourless.

Exotic knowledge Aum_S

Stop wondering

50 mg FB harmine + drops standard vinegar + 10 ml water, all dissolved nicely, had it evaporated, added 50 ml demin water, pH went 5.75, added 200 ml tap water --> pH upped to 6.8
Let it stand for hours, filter, dry, got back 20 mg FB from original 50 is only 40% yield return. Too low for many kitchen birds.
There was no complication of harmaline involved, I guess that would make yield even worse.
So there is some truth in there (concerning harmine alone as far as this test goes) and that is an interesting fact, I thought it all would re-dissolve again by re hydration, but there seems to be no practical use beyond 'interesting'.

I would think because some FB dissolves in the water.
Everywhere it is stated that a bit FB dissolves. But AFAIK we have no numbers how much FB dissolves in plain water.

I would have planned to use 0.5% sodium carbonate solution for "washing" after the evaporation instead of dist or tap water.

^^^ I read your point yet my A/B transitions + filtering + washing + drying give me a very consistent 97 % yield.

Edit:
will redo the same experiment but will add sodcarbonated water this time.

Your are usually also just FB washing with normal water?

OK, then I think my theory that this was the problem is probably wrong.

I do wash with sodcarbed water, or far diluted ammonia, that's why I'll redo the experiment, you had a point there. When I saw that pH 5.75 I did became afraid to loose harmine FB into the water, but the water stayed clear nevertheless so I thought no dissolving.

Without acetates for harmine: plain water works, the water stays clear. For harmaline not so as it turns the water colored which indicate some FB going into the water. So your theory is certainly valid for harmaline. Then again it is to see how much and I have no idea about that.

The acetates are drying as we speak.

A short update about my extractions.

Nothing relevant precipitated out of the 2nd cold extraction by Manske even with fully saturated NaCl.

The third cold extraction didn't color the water anymore, even after 4 days. So I then did a heavy boil on it for 45 Mins. This colored the water a bit.
Will do a Manske on it, to see if there is anything relevant from this boil.

Edit:
If not, then this cold extraction is IMHO way easier for extraction than the current boiling teks. Also as it only needs one extraction.
I'm curious why my yield was so high for just one cold extraction. IMHO either because I used a lot of (acidic) water, or because I extracted quite acidic (3% acetic acid).

Yes that 5% yield on 1 wash is amazing but cool actually

So I did that acetates drying trick again, then washed the dry-rest with sodcarbed water instead of demin/tap water. So pH could never drop this time. Out of 50 mg starting FB I got 23 mg recovered FB after the trick. Quite the same as the 20 mg when using demin/tap water.
Too low recuperation imho for making it a separation tek.

Very nice from you that you tested it.
Would have been too easy if it worked, I guess ...

As next I will also do a cold extraction with less water and then with less acid. I'm really curious, when and where there is a difference in result.

Just as an update:

After the Manske of the boiled rest extraction, I only got some strange looking stuff in it. Didn't look like the nice crystals from my 1st cold extraction.
After vacuum filtration, it only yielded a little bit of brown stuff.
No comparison to the very nice pure looking yellow residue from the 1st cold extraction Manske.
It seems like due to boiling some things get into the water which make it through the Manske also???
Also the Manske filtering was a pain in the ***, compared to the 1st Manske filtering.
The stuff seems to plug the pores of the filter much quicker.

Don't know if I really wanna see how much real alkaloids are in there. As it is really just a tiny amount (but why it did then still plug the filter that much is beyond me), and I would probably have to go through several purification steps, as currently I cannot even tell if there's any good stuff in it. It totally doesn't look like that.

I really wanna do the further tests I indicated. But I'm currently a bit out of time. So be patient (lol, if anyone is interested at all...).

Edit:
But what I can say for now: It seems, this one cold extraction really did get basically all alkaloids out. The remains seem insignificant to justify any further extraction. Even heavy boiling for 45Mins didn't get any additional significant amount (just strange unwanted stuff).

Now I'm just at the 1st Manske of my next experiment. This time with only a small dash of vinegar (20ml of 5%) added to 600ml Water and 20g Rue (again 30:1 water/rue ratio).

Interestingly the Manske looks completely different. Last time I got many many small crystals clinging together in all of the flask developed over time, which would not settle to the bottom even if shaken vigorously.
This time immediately upon adding NaCl, some "fine powder" fell out. Now after a night, it seems all the powder settled to the bottom, leaving the rest of the flask without any solid.

Why this strong difference?

I could think, because I only added a small amount of acetic acid, most Harmala Alkaloids did stay as phosphats and didnt' convert to acetats. And maybe the phosphats react differently when adding NaCl?

Anyone another idea, of possible explanations?

Nope, I've been using phosphoric acid plenty of times instead of acetic acid all together, resulting in just the same needles forming. It's something else then.

OK thanks for the info!

Hmm, the only other difference I can say, is that this time I used a magnetic stirrer.
The salt was in the container, then the (cold) filtered extract was added and stirrer on. Then also the heatplate was switched on. But the NaCl disappeared so fast, that I soon could again switch the heat off. The liquid just got a bit warm.

Before, I made it almost the same way, but there I stirred manually, and it needed much longer to dissolve, so also the liquid got warmer.

Hmm, OK, that could be the culprit. Due to being still quite cold and due to the fast dissolving of the NaCl maybe much fell out so fast, that crystals couldn't build up.
Also that the liquid was this time barely acidic compared to last time could be a reason. As the NaCl reaction works worse the more acidic the liquid is.

Now I did the basing of this stuff. Unfortunately it seems I kinda wanted to make it too quick.
(all is done on magnetic stirrer)
I dissolved my yellow Harmala HCL powder in 50ml water.It didn't dissolve and I didn't heat to do it. I just thought, when I add the Sodium Carbonate it will anyways react.
So I added 0.5g Sodium Carbonate powder, as this is what I calculated would have been needed for about 1g Harmala alkaloids. It immediately fizzed, changed color, fizzed further, changed color again, and that was it. Also some strange bigger darker blocks formed, which never formed before.
What exactly happened here???
I now have some FB (0.617g dried at 200°C), but it is way less than in my first experiment. Unfortunately I'm not sure if this is because I used the mentioned (faulty?) procedures for extraction, or if way less material did get out of the seeds due to much less acetic acid. Darn!
Unfortunately I discarded the seeds, as I anyways just wanted to know if the one extraction only, also would work if only a dash of vinegar is used.
Do I have to repeat this experiment now???

Any suggestions?

Edit:
BTW:
It's really astonishing how much water the FB can hold. First I just dried it with a hair dryer: Then it weighed 0.843g and looked dry. But already visually I could tell, that this can never be that much, as it only seems roughly half of my previous yield. Then after drying at 200°C the weight decreased to 0.617g.

Edit2:
Now wanted to purify this FB with the method I linked earlier. But it didn't work at all.
See https://www.dmt-nexus.me...&m=790859#post790859