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Harmine, harmaline and THH from Syrian Rue. Verification and finetuning of the VDS-protocols Options
 
Jees
#281 Posted : 12/21/2016 7:34:40 PM

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After filtering out the solids of Harmine, the coffee filter got flushed with sodium carbonated water until all yellow was out, as the sodcarb elevated the pH of the flushed liquid it started to precipitate partly. I wanted to know if there was any harmine or solely harmaline in this flush water, I could only see harmaline which makes sense actually. It is the form of how the harmaline pellets are build while they still cling onto each other. Once it breaks up you have the classic Harmaline pellets.
So I could add the flush water to the pot.
Jees attached the following image(s):
dhh.inthemake.jpg (45kb) downloaded 402 time(s).
 

Live plants. Sustainable, ethically sourced, native American owned.
 
Jees
#282 Posted : 12/21/2016 7:53:42 PM

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The pot got further based (all with ammonia BTW) to meet the second pH depression around 8.35 and worked trough it's dip up to 8.7
By this time I was definitely sure I was trough the complete second pH depression, but the liquid was still some nice yellow.
After filtering out all solids, the yellow liquid got further based with lye to 12.5
It was clear that between 10 and 11 there was still transition between yellow and white.
Filtered of this beyond-pH-depression material (we used to call this nexine) and dried and got these in-situ crystallization which scream out loud: Harmaline.

It tells me the pH depressions do not take down all. I must admit that the volumes and concentrations differed from VDS ones. But it illustrates a vulnerability in the separation system, though I believe it is the best kitchen method around for the moment being.

How much did the second pH depression fail to precipitate? 5%
Near 4 gr of the total DHH was caught by the 2nd pH depression, and 200mg retrieved DHH after that due extra basing. The pic (in-situ) is of that particular 200mg. Clear DHH if you ask me (debunked nexine again)

For DHH I don't mind, but what if the first pH depression also misses out some? It means Harmine to end up in the Harmaline. For this I will re-treat my Harmaline to see if I can knock out some Harmine.


Jees attached the following image(s):
dhh.01.jpg (43kb) downloaded 398 time(s).
dhh.02.jpg (49kb) downloaded 399 time(s).
 
Jees
#283 Posted : 12/23/2016 1:13:14 PM

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So above I did some pH depression separations at concentrations 3 x less than VDS. It was for a practical reason trial: to avoid alkaloids sticking to walls and ph probe and the trick for that by lowering concentration worked flawless.

This "sticking" here is not like the goo spook, I think the sticking is a prelude of the goo like in not-yet-goo. VDS had this too btw:
Page 5 & 6: ...Because crystals attached themselves to the sides of the reaction vessel, it was rinsed with vinegar after filtration and the freebase was precipitated from the washing solution with an excess ammonia and the dried residue added to the main filtered fraction...

Can one lessens concentration at will without compromising the pH depressions indicator? I found: no.
The 3 x lesser concentration I used had already an impact on lesser deep pH depressions. In examples of far too low concentration I got no pH depressions at all. Yet basing does lead to milk + fall out, but no real pH depressions, and everything seems to happen at noticeable higher pH levels.

.

I took all DHH from previous posts (meaning the DHH during 2nd pH depression + all the DHH that came by hard basing the filtrate afterwards) and re-dissolved and put in a concentration equal to VDS ( = 24mg/ml)
I based first to 7.8 with ammonia to see if any harmine sneaked into my DHH and it did, but very low. There was a mist and some fluffy dot at the bottom, but too little to examine (I tried). Cotton filter made the DHH perfectly clear at 7.8, in situ check = optimal.

Basing to find the (only) pH depression to start at 8.40 and rolled back to 7.50 even touching a full 1 pH drop Shocked
This is the most crisp and deep pH depression met for DHH. And it makes sense because the moment VDS started on his 2nd pH depression, he already precipitated 50% of alkaloids weight on harmine, this subtracts from the liquid concentration, while in my case its all harmaline all in liquid. So my alkaloid concentration is now actually double of VDS, hence my deeper pH depression. I went on to pH 9 which should mean all of DHH should be caught according to VDS. He says to find nothing in basing further, I still have some yellow left and will extra base that to see whats in it.


So it looks like the system of pH depressions, their magnitude (and separation quality?) is related too concentration after all. Once more a friendly finger toward VDS why he generalized his approach too easily and discarded others as "wrong".

On the other side he managed to use optimum concentration of a good balance between the start of sticking-alkaloids and the depressions obtained.

It is now also clear why the second pH depression in VDS papers is smaller than the first. After the first then 50% of alkaloids is no more liquid (and contingently filtered out as harmine), after which his concentration in the liquid dropped by 50%. Lesser concentration means lesser pH depression. This I illustrated by performing a pH depression of DHH-only at the very same concentrations used in VDS paper 1st pH depression. Now the pH depression for DHH-only is just as big and clunky as VDS's first depression for harmine (in a harmine+DHH mix). No difference at all.

Puzzle pieces fall into place, and once more noticed that VDS paper is very well tuned already.

Since I have now my DHH precipitated done in double the concentration of {VDS 2nd pH depression}, it should in expectation catch max DHH. I'll have to filter and dry the portions to see the numbers. To be continued.

Chime in to add or think differently, all is welcome.
 
An1cca
#284 Posted : 12/23/2016 2:47:05 PM

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So the amount of pH depression is not a static chracteristic of the molecules, it's a function of their concentrations. Excellent research and a valuable addition to the article... Great job JeesThumbs up !

Would you use the same concentrations as VDS in the future, or do you prefer more concentrated/dilute solutions now?
 
Jees
#285 Posted : 12/23/2016 5:44:46 PM

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An1cca wrote:
So the amount of pH depression is not a static chracteristic of the molecules, it's a function of their concentrations. Excellent research and a valuable addition to the article... Great job JeesThumbs up !

Would you use the same concentrations as VDS in the future, or do you prefer more concentrated/dilute solutions now?

Yes pH depression is a sensitive thing I recon.

Interesting issue: how a less pronounced depression would lead to lesser accuracy? This is not clear now. Could we bargain diluting scot-free to lessen the 'sticking'?

Now: just one experiment that a washed, dried + redissolved + basing a former 3xdiluteVDS then a little cloud could be filtered out @ 7.6 long before DHH even began to precipitate @ 8.3 .
Was the first depression weaker due less concentration and did this lead to harmine in the DHH? Would a stronger depression (more concentrated) do better? Too much question marks.

This is the heart of the just born cleanup step: you came from a 3xdiluteVDS 2st pH-depression catch that now will be dissolved again but more concentrated = as per VDS 24mg/ml, fairly DHH only. That will make the eventual (traces) harmine fall out at 7.5 (let stand some hours), which it didn't at 3xdiluteVDS as there it was an alleged 'contamination'.
Before and after cotton filter, the transparency of filtrate differs a lot, meaning it means something meaningful. Filter dry rest is too small to bother.

So its about an extra step, redissolving your dry DHH at VDS concentration 25mg/ml, then basing -> 7.5, filter, basing, at the end at you might expect some sticking of DHH just like harmine did on its 1st pH depression. So maybe no escape from removing some un guilty sticking (but not goo-ing) powder. A little price to eliminate traces harmine for sure to visually degree when coming from 3xdiluteVDS.

Yet VDS's concentrations hit a remarkable middle spot therefore having a finger in both extremes negative effects, being plastering on the concentrated side (Harmine), and pH depression suffering on the diluted side (a weak DHH depression it has) but the first depression is there to work with and that counts for separating.

Sometimes I think the second depression does not have to be clear because the separation act has been done already and basing out is all there is to do. And enjoying that.

Bucket list: 2 x diluted VDS Laughing
Maybe the best of world?
Pleased
 
Jees
#286 Posted : 12/23/2016 7:57:09 PM

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So because I separated Harmine from DHH in 3xdiluteVDS I worried about selectivity.

a) The 1st pH depression leaked some Harmine into the 2nd depression but this Harmine got intercepted (filtered off at 7.5) by a following more concentrated pH rise cleanup step of the DHH.

b) was the 3xdilute also responsible for the 5% DHH that sneaked out of the 2nd pH depression? (Yet this DHH got intercepted by a further basing of the filtrate with lye.) Answer of the next test: YES

The cleanup step of a) ends with basing out of DHH trough it's huge pH depression (remember) to end at 9. VDS says all potential DHH is out by then, my liquid was still some yellow.

OK filtered DHH out at 9, washed with sodcarbed water, dried and gained 94.5% of all DHH that was started with in the 3xdiluteVDS 2nd pH depression catch, not bad considering that this 5.5% also incorporates the 'contaminating' Harmine that got filtered off, and some losses that are always part of transitions.

The yellow filtrate got based further with lye and stayed unchanged yellow until 10.5 and turned transparent over the course to 12.5
I do not know if I'm going to be able to catch this neglectable amount, it is this tiny, barely visible, a bit of drifting slime. I can safely consider a full catch of DHH at pH 9 in this case, meeting VDS fully here.

.

So yes working with 3xdiluteVDS leads to a 5% DHH loss in the DHH depression catch, while working under 25mg/ml (VDS level of concentration) catches much better to full.
If same logic went true for Harmine under 3xdiluteVDS, that might have been the cause of the harmine leak into the 2nd pH depression.

.

Thus concentration not only influences pH depressions in appearances but also in their selectivity performance. 3xdiluteVDS = 8mg/ml create losses. I did that but corrected with cleanup.
I think it is fair to head for best performance in selectivity, then higher concentrations would be most beneficial it seems, but the line is drawn where the sticking of powder is still manageable. A bit of it is no problem, as long as it does not become goo. I do think that VDS number meets that criteria nicely.

- For those aiming at 1 separation step and then go for reduction, use VDS advise.

- For those who know that they like an extra (re-concentrate + re-base) cleanup step for their DHH fraction anyway, they can as well lower concentration of their Harmine+DHH mix, it works a bit nicer that way, perhaps 2xdiluteVDS. Then do a 25mg/ml cleanup on your DHH fraction, a filter Harmine traces out at 7.5, further base to 9, done. Then go for reduction. Remember that this style of cleanup works under double the DHH concentration that VDS used, so it is much better in pushing out harmine at the low end (to filter away at 7.5) , and better in retaining DHH under pH 9 at the top end. Looking at a 95% yield, very attractive. Next experiments will be with 2xdiluteVDS for separating but still going for the extra DHH cleanup to see how well 2x is in selectivity. But I've material now to work with.

Jaja..
Razz
 
Jees
#287 Posted : 12/24/2016 8:16:49 PM

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An1cca wrote:
Love I wonder what recrystallized DHH looks like when viewed in this manner. Frozen jungle?
I did not forget your post #196: here is harmaline with top lightening Wink , sorry for the delay, it's token fresh today.
Looks like a Christmas scene right on time Pleased
Jees attached the following image(s):
featherfest.jpg (104kb) downloaded 330 time(s).
 
Jees
#288 Posted : 12/24/2016 8:24:02 PM

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For fun I mixed some near invisible amounts, estimated a bit 50/50, harmine + DHH in a drop of vinegar, diluted the drop with water, added 1 drop ammonia 12%, let stand for 10 minutes, and notice how DHH feathers try to become harmine sticks and vise verse.

Last two ones show the core middle cross of DHH that came trough and served as a Christmas bow tie Love
Jees attached the following image(s):
50perc.01.jpg (105kb) downloaded 326 time(s).
50perc.02.jpg (104kb) downloaded 325 time(s).
50perc.03.jpg (107kb) downloaded 323 time(s).
50perc.04.jpg (108kb) downloaded 322 time(s).
 
An1cca
#289 Posted : 12/25/2016 12:23:46 AM

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A-MA-ZING Shocked

Consider posting these pics on Erowid, archive/art material!

 
exquisitus
#290 Posted : 12/25/2016 6:45:38 AM
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Jees wrote:

Last two ones show the core middle cross of DHH that came trough and served as a Christmas bow tie Love

modern art Thumbs up
 
Jees
#291 Posted : 12/25/2016 10:45:36 AM

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Thanks for the kind words.

An1cca wrote:
...Consider posting these pics on Erowid, archive/art material!
I'll check out on that page, haven't been on that site for some time. But if so we better have LC-MS verified labeling which should be provided by the coming analyses.

Glad to see my 50/50 harmine/DHH pics are just like your 50/50 just before reduction "flying birds" post #169. The face of syrian rue before separation.


 
Jees
#292 Posted : 12/25/2016 11:17:18 AM

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Yesterday I made two times a pH depression precipitation (of Harmine) in half of VDS concentration, thus 12mg/ml. This is always referring to starting volume, as the ammonia adds to it a bit during basing.

There was still some sticking at that concentration, but just a bit less.
Depression depth was both times 0.7 pH
Compared to 24mg/ml the depressions there are 0.8 to max 1 pH as by VDS and myself.
So a little sacrifice on that but I believe that good separation was obtained nonetheless, as further basing of the filtrate gave no Harmine whatsoever, I mean not a trace to visually notice.

So for now I think it is a good/safe concentration to make Harmine pH depressions in.

.

Interesting note: if you really use the very least vinegar for dissolving, helped by some heat appliance, then when you start basing this drops the starting point of the pH depression. I was able to let the Harmine pH depression point start at 6.5 and with very slowly basing it rolled back to 5.8 Shocked (this was in 12mg/ml) It means all Harmine was in at 7.00 and further basing of filtrate gave no Harmine.
The times I used more vinegar, and some more base to compensate for that, pH depression starting points always ended up higher, at least 6.8 but usually 7. VDS recorded 7.2
Another example/proof of non static behavior.
This is good news actually, it reliefs pressure of pH-meter calibration accuracy because the form is the most important, not the absolute. As per VDS and myself, after wherever-it-situates ph depression start point, then going trough the dip, then ending at start point + 0.5 then generally the Harmine lute is safely in.
 
An1cca
#293 Posted : 12/25/2016 9:20:08 PM

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Jees wrote:
Glad to see my 50/50 harmine/DHH pics are just like your 50/50 just before reduction "flying birds" post #169. The face of syrian rue before separation.

...would love to see these birds (any caterpillars?) with top-lighting in your setup. Crystal porn addicted I guess...Embarrased


Another thing I noticed, related to the prevention of alkaloids sticking to the pH-probe or vessel walls, is that the quicker you run through the basification-step, the less attachment you get. In some experiments, I left the solution to stand for more than 12 hours to really define the lowest point the depression would go. Consequently, bigger and stickier crystals attached themselves to the vessel and the probe. Not like in sticky-goo though. These are hard and brittle and redissolve instantly in dilute acid. So yet another tip would be to 'surf along the depression line' until the drop after each increment becomes weaker and weaker, reduce the volumes of base you're adding, and stop at depression-starting-pH + 0,5 (this should most likely also be the point where depression stops). No need to wait for the depression to go all the way to the bottom, that's mere academic spielerei Pleased .

Like you observed Jees, other salts formed in situ inside the mother liquor (ammonium acetate) may act as buffers, skewing or raising the pH-curve. I totally share your conclusion that this is largely irrelevant if one 'surfs the curve'Cool .

Refining and refining...I feel like a solid tek is within reach, Nexians!

BTW, the samples arrived in a postal 'sorting depot' about 4 days ago (still in my country that is), no more tracking info since then...
 
downwardsfromzero
#294 Posted : 12/27/2016 1:57:49 AM

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Yoinks! Those pics are beautiful! This thread is magnificent. Season's greetings to you all. Love




“There is a way of manipulating matter and energy so as to produce what modern scientists call 'a field of force'. The field acts on the observer and puts him in a privileged position vis-à-vis the universe. From this position he has access to the realities which are ordinarily hidden from us by time and space, matter and energy. This is what we call the Great Work."
― Jacques Bergier, quoting Fulcanelli
 
Jees
#295 Posted : 12/27/2016 3:29:10 PM

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Thanks downwardsfromzero Love

An1cca wrote:
...Another thing I noticed, related to the prevention of alkaloids sticking to the pH-probe or vessel walls, is that the quicker you run through the basification-step, the less attachment you get. In some experiments, I left the solution to stand for more than 12 hours to really define the lowest point the depression would go. Consequently, bigger and stickier crystals attached themselves to the vessel and the probe. Not like in sticky-goo though...

Very cool we observe the same stickyness just as VDS, but a non guilty form (no goo) and easy to deal with. The usual way I deal with it is much less devious than VDS did, he redissolved the sticky stuff and re-based it. I remove it fully mechanically: put on a surgeon type glove and manually wipe the beaker and probe with some filtrate water, poor that in the coffee filter (which contains already most of the crystals), add again some filtrate water in the beaker, wipe it all over again with the plastic hand/fingers, add to coffee filter, no more than 3 times needed, takes 1 minute to complete and near no loss at all.

But what An1cca brings up here is quite interesting and a good moment in the thread to start talking about how to actually treat a pH depression. I usually went for the max dip (curve A) if only just for the porn of it, basing slow. So I never really noticed that basing faster (curve B) makes less sticky, very glad you mentioned this. So I checked this out and I agree. Then I added another possibility to base radically once the pH depression start point has been detected: curve C.

What I've found so far:
* Curve A: in VDS concentration and in 2xdiluteVDS: sticky, but some less in 2x
* Curve B: in VDS concentration -> a bit sticky, in 2x dilute no or almost none sticky !
* Curve C: in 2xVDS dilute: holy crap don't do this: a milk that looks like an emulsion that has a hard time crystallizing/settling. I went for a redissolve all of it and re-base like B.
With C the extra problem is you very easily overshoot your + 0.5 pH this way, so if this is a mixed batch of harmaline+DHH, then a very bad separation could follow if the 2nd pH depression got triggered accidentally. You would be forced to redissolve and start over again.

So it looks like the least (near none) sticky was found in curve B in a 2xdiluteVDS or 12mg/ml.
Keep dropping ammonia like 1 drop/sec, once a pH plateau or slight dip in pH is seen: increase drop rate to try holding on to the same pH. After like 50% has precipitated you will be amazed that your syringe needle will be pissing ammonia just to try to keep the pH steady. Then suddenly pH will start rise, stop at 0.5pH above start point. Your Harmine is in. For DHH precipitating you can easily go for pH 9 or 10 to stop.
I have no idea if there would be a selectivity difference between using A or B. Could be tested but best with TLC I guess.
Jees attached the following image(s):
curve.gif (21kb) downloaded 252 time(s).
 
DreaMTripper
#296 Posted : 1/5/2017 3:29:29 AM

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Good to see the thread still going great pictures and great work.Smile
 
An1cca
#297 Posted : 1/5/2017 9:59:20 AM

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Great news to start the year with: the samples were delivered on 28/12 at 5.40 pm Big grin ......

O Chromos,
mighty God of sacramental separation,
may you purify and provide to Spectros,
Angel of molecular insight and knowledge.
May you both free us from ignorance and doubt
bringing wisdom to the entheogenic cloud...

Sorry, that was still some Christmas in my stomach I thinkEmbarrased

On topic now: Jees, your graph is a very helpful representation of the actual process of 'surfing the curve'. We can now safely say that 1/2 VDS or 12mg/ml looks like the most practical dilution to start with. Just going with the flow, and indeed 'pissing' the base halfway the curve, makes for a quick (minutes), efficient (very high yielding >90%) and effective (exact separation) procedure. Tek-material. Thumbs up

What's the concentration of your ammonia?
 
Jees
#298 Posted : 1/5/2017 9:17:36 PM

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Thank you for the prayer Pleased
Nice to know they samples hit home Thumbs up Thumbs up

I think in practice people will be ending between path A and B and be very good with that.
If one is too focused to follow B then it's not unthinkable to overshoot the +0.5 pH point. If that happens between harmine and DHH during the aiming for a good separating point, then one has to start all over: redissolve, rebase. There will be more salt in the mix due the extra acid & base, so the pH points will be slightly higher. I've noticed the effect of salt many times, you can catapult your pH points with it.

When working with like 5 gr then I used to base with 12% ammonia.
Today played with 1 gr and based with 6% with great pleasure and joy. There's no handicap if one has a hard time finding 12%.

It was about 1.680 gr raw caapi FB extract. Only a fool would manske a caapi extract so I felt called for. It yielded 1.157 gr or 69% harmalaHCl. Dissolved, based, filtered, washed, dried: 0.904 gr or 78%-to-harmalaHCl or 53%-to-RawExtract.
Now that could be, since he tended 500mg of that rawExtract to ceremony, which would be like 53% = 265mg of harmala, that fits, yet quite potent, this dose.
The manske filtrate got based too, a firm amount of white slime settled nicely. No solids at all, so I opted to align the pot with the sewering and gravity transferred the content. Good ole grav. I digress, now I just know caapi raw extract have like 50% in true actives, in this case. I've always wondered how 'active' a raw caapi extract (only A/B's) is. Dunno what that other 50% in slime is, probably healthy caapi stuff but no harmalas I'm afraid.
 
Aum_Shanti
#299 Posted : 1/12/2017 5:56:55 PM
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Sorry if this question seems dumb:

What advantage is there after an extraction, to separate Harmin from Harmaline or to convert Harmaline to THH?

E.g. as I understood it THH, isn't an MAOI, so I don't really understand why one would like to convert it to THH.

Again sorry if this question seems dumb. But I'm really pondering about this, as there's some extraction to be done, and I just asked myself about these additional steps.
I claim not that this is the truth. As this is just what got manifested into my mind at the current position in time on this physical plane. So please feel not offended by anything I say.
 
Jees
#300 Posted : 1/13/2017 6:21:03 AM

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^^^
Harmaline has a body load factor that THH has not.
THH contributes as being a 'weak reuptake inhibitor' instead of a MAOI.
THH has a very long half life (slow elimination) making it an endurance component, far longer than harmine or harmaline.

You can experience the difference between harmine+harmaline and harmine+THH by comparing B Caapi vine tea with a syrian rue tea. I know it's not completely correct but from a practical point very much telling at least.

For a very good answer to your question we have to have more experiences with people sharing results. Only after rigorous ID'ing of the components (which is taking place I suppose) we can start speaking with the best confidence at hand. So the best is yet to come.
This has been a culprit for so long to have no reliable kitchen friendly THH extraction method. Now that we hope to have found one, this is only the start of getting to know THH better. Some ayahuasca purists claim to have a hold on the THH grail in their brews but they never experienced harmine, THH separately.
Some consider THH as an almost holy grail. Maybe the syrian rue dudes are going to know better what everyone is talking about Pleased

If its for having top notch experiences, one is not obliged to separate, then good ole syrian rue suffice as it comes.

One could separate and not convert DHH to THH at all, and keep the 2 for checking out individually. A good separation method is needed for such occasions.

Thanks for the interest!
 
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