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Harmine, harmaline and THH from Syrian Rue. Verification and finetuning of the VDS-protocols Options
 
Michel
#381 Posted : 7/3/2017 12:27:11 PM

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WoW Shocked I was not expecting that so fast !
Thank you Beautiful Travelers !
 

Psychedelic news, articles, interviews and art from the DMT-Nexus and other sources.
 
exquisitus
#382 Posted : 7/4/2017 4:43:55 AM
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a manske experiment i have been running for 4-5 weeks. seems relevant to the discussion here.

collect angel hair crystals, boil again in microwave (open glass, so evaporation happens!), put in fridge (open glass, so evaporation happens!).
repeat in a loop. until patience runs out.

just right now i have around 2-3mm liquid with angel hair crystals in it. diameter of glass vial around 3cm, so it seems like small amount of liquid to me. i am amazed i still get angel hair in such amount of liquid, but it's a fact. liquid keeps on giving. i ran out of patience, that's my last cycle for sure.

perhaps by doing this in a loop one can extract asymptotically all harmalas (exactly which?).

observation. if i boil and freeze with glass kept closed (nice contact, rubber and all, so evaporation is virtually eliminated from the equation) i don't get angel hair, no matter how long i wait, just the same ol yellow liquid.

 
An1cca
#383 Posted : 7/4/2017 6:11:31 AM

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Exquisitus, what is the NaCl-concentration you start with in your Manske?

It would be interesting to know (TLC?) if there is one of the harmala's that precipitates later than the others. I did not set up a comparative experiment, but had the impression that THH needs a higher salt-concentration to fall out of solution...
 
exquisitus
#384 Posted : 7/4/2017 7:01:33 AM
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An1cca wrote:
Exquisitus, what is the NaCl-concentration you start with in your Manske?


i don't remember exactly, was it 1/3, 0.3 or vds' 88/250... something similar, wayyyyyy more than 1/10 for sure.
still lots of experimentation ahead of me to a somewhat locally optimal ratio methinks, so i am not yet really concerned about that...
sakkadelic was using a similar ratio (35/100?) if memory serves...
 
Elrik
#385 Posted : 9/18/2017 12:15:03 AM

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Bicarbonate can precip THH!?

I just had a disturbing experience. Reading through this thread I came across the importance of breaking down carbonic acid when (bi)carbonate processes are used and the statement that VDS was likely using mechanical stirring even when no mention of stirring was made.
I had done a reduction of harmine+DHH with the (bi)carbonate fractionation into harmine and THH. My harmine fraction was half the gram weight of my THH fraction, a believable ratio. But I had done it without mechanical stirring, just occasional stirring with a stir rod so I decided to do a test on them both.
I followed the (bi)carbonate method harmine/DHH separation procedure on 2 grams of my harmine freebase. I added the bicarb solution without mechanical stirring and it took a full 2 minutes for any precipitate to form, after 15 minutes lots more had formed and I put it on a stir plate to drive off the carbonic acid. It fizzed for 30 minutes on the stir plate, when that finished I filtered it and returned the filtrate to the stir plate for 45 minutes. No new precipitate formed so I added the carbonate, and finally some 10% ammonia. Neither provoked precipitation. I ended up with as much harmine as I started with.
Next I did the procedure on the THH fraction. Here I went straight to mechanical stirring [a 3cm stir bar going at a good speed in a 250ml beaker]. Supposedly the bicarbonate stage would precipitate only harmine and some of any DHH that might remain. After 20 minutes of vigorous stirring I was happy to see a clear solution but knowing it would take at least 30 minutes for all CO2 to be driven off I left it going. When I came back at 40 minutes it looked like milk. After another 5 minutes I filtered it, obtaining what looked like all of my starting alkaloid, and I returned the filtrate to stirring for 45 minutes. There was no more precipitation. I added the sodium carbonate and stirred for 45 minutes, no precip, I added ammonia and let it mix for 5 minutes, no precip. The filtercake of solids looks like it will dry to the starting 2 grams.
Wut?
I must have reduced something. I did the reduction hot for 6 hours under vigorous stirring and my "THH" fraction did behave differently than my "Harmine" fraction. All (bi)carbonate work was done at room temperature, of course.
Is it the case that fully driving the carbon dioxide off from a bicarbonate basing will freebase all three alkaloids? If so how do we know when to filter to separate the alkaloids?
What of the (bi)carbonate fractionation of harmine/DHH? VDS seemed intentionally vague on how long his mixtures were stirred. If stirring to equilibria will base all the THH surely it would base all DHH.
An1cca, when you successfully separated harmine and DHH by this procedure how long did you leave it stirring to drive off CO2?

I'm working toward producing a lifetime supply so I want it separated well, it looks like I may have to resort to ammonia basing with microscopy to fully separate these alkaloids. Probably not in time for this coming weekend when I finally get time away from the family. I'll probably just assay these questionable fractions then Laughing
 
Jees
#386 Posted : 9/18/2017 2:08:34 PM

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Thank you for the experiment Thumbs up

Elrik wrote:
... Supposedly the bicarbonate stage would precipitate only harmine and some of any DHH that might remain...When I came back at 40 minutes it looked like milk.

Don't forget the Zn salts, these are typical to form "milk" effects. Harmalas never gave me much of milk appearance but rather dust looking.

Elrik wrote:
...Is it the case that fully driving the carbon dioxide off from a bicarbonate basing will freebase all three alkaloids? If so how do we know when to filter to separate the alkaloids?...

It would have been more indicating if you had pH checks between the stages, we're kind of blind now. A pH meter is quite cheap, and even if the absolute calibration is a tad off, they are good for indicating pH-differences.

Especially working with carbonates, it has shown before that close sticking to VDS is important, but you are right that he did not mention much about stirring times.

I have a fair trust in the reduction process.
To free your products from Zn-salts, redissolve them both separately in vinegar, base firm with ammonia only this time. Filter. You can wash them with a weak carbonate flush.

About bicarbonate taking out the THH, this is surprising indeed.
Microscopic checking of the crystals formed (best in situ) could reveal something. But if we have no pH-data nor these images nor any other kind of identification then it's hard to say something. The VDS protocols surely would not expect us to take out THH on bicarbonate, only partly DHH as you mentioned.
If bicarbonate would take out THH, then it surely would take out DHH fully, which is not the case as we know so far.
The only thing you did in particular is the long precipitations times, as you mention that might be a factor not included so far.

For me this is just another reason to stick to ammonia only (+ pH meter), carbonates only added fuzz. But I understand the no pH meter style of things. But if so, we should have a reliable workflow and we find us a bit uncomfy now isn't it.
Hope An1cca jumps in on his thoughts.

*

On another note, I'd never pharma further with Harmine-THH combo only, something is missing imho. Last time was 150 harmine + 50 DHH + 50 THH and that was much more wholesome blend. So I would always keep some DHH un-reacted.
Thumbs up


Disclaimer: all my posts are fiction.
 
Elrik
#387 Posted : 9/18/2017 7:39:14 PM

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Jees wrote:
It would have been more indicating if you had pH checks between the stages, we're kind of blind now. A pH meter is quite cheap, and even if the absolute calibration is a tad off, they are good for indicating pH-differences.
This occurred to me as well, but only in retrospect. I wasnt anticipating the ability of bicarbonate to base out THH. I have universal pH indicator liquid, so if I want I can make paper to test a couple drops at any time. I'd like a viable pH meter with a probe, but if I had the spare cash for one right now I'd instead buy half a kilo of MHRB while its still buyable Wink
Jees wrote:
To free your products from Zn-salts, redissolve them both separately in vinegar, base firm with ammonia only this time. Filter. You can wash them with a weak carbonate flush.
Oh, I'm confident my products are essentially zinc free. In work-up after the reduction I did basically what you suggested but I dissolved them in diluted vinegar with 5% ammonium sulfate before adding excess ammonia. A subsequent manske on each was clean and beautiful [I like to store them as hydrochlorides so they'll last intil I'm 85]
Jees wrote:
If bicarbonate would take out THH, then it surely would take out DHH fully, which is not the case as we know so far.
The only thing you did in particular is the long precipitations times, as you mention that might be a factor not included so far.
I hope this is all it was. When an1cca said to drive off all CO2 I took it literally, hence the long stir times. I'm hoping filtering after 20 minutes of stirring will separate the alks. Then, perhaps, the THH bearing filtrate could be returned to stirring and preciped in full without the need for sodium carbonate. Tho, in practice, I'd probably hit it with a slug of ammonia at the end just to be safe.
Jees wrote:
I'd never pharma further with Harmine-THH combo only, something is missing imho. Last time was 150 harmine + 50 DHH + 50 THH and that was much more wholesome blend. So I would always keep some DHH un-reacted.
Thumbs up
I really look forward to finding my own preference. Up to now I've only been using DHH+harmine, apparently in a 2:1 ratio, and at very high dose so it lasts as long as a mushroom trip. That always feels a bit harsh, though, so I'm aiming to fine tune it and go down to more reasonable doses. The trip duration being halved might not be so bad, when I trip I go for a balls-to-the-wall howling-at-the-moon trip which is something I can rarely do for 12 hours straight. Cutting that in half will give me more opportunities to partake.
Good point on keeping some DHH. Including the harmine in the zinc reduction cleaned it more than anything I've ever managed, my harmine.HCl is actually off-white now, if someone wanted to exploit that while still reserving some DHH for mixing the solution could be simple- save some of the starting DHH+harmine as the DHH source and gauge its ratio by that of the formed harmine and THH.
Its esfand harvest season here so I'll soon have a fresh ~1 kilo of seed to play with, good timing now that I have a slightly better understanding and more questions Smile
 
Elrik
#388 Posted : 9/19/2017 10:22:35 PM

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Well, the THH experiment is reproducible.
In order to get a clearer picture of what happened in my previous set of experiments I did two more.
To begin, I wanted first hand confirmation that prolonged vigorous stirring of a sodium bicarbonate solution will not cause a rise in pH at room temperature (its well known that involving heat will cause a rise in pH).
No such rise in pH was observed in the course of stirring vigorously for 60 minutes.
Next, as suggested, I wanted to establish the pH readings as I repeated the previous experiment of subjecting my THH product to the first round of VDS's [bi]carbonate method for harmine/DHH separation.
Again, there was a significant delay before any precipitation occurred with the solution still being perfectly clear after ten minutes of mixing. A depression in pH was noted following precipitation. After sixty minutes of vigorous stirring all of the starting alkaloid was recovered by filtration. Further stirring and basification produced no precipitate.
Lab minutiae:

A major limitation was the use of pH papers rather than a more accurate and continuous measurement but the depression of pH clearly followed, rather than preceded, precipitation. This raises the possibility that in THH precipitation by bicarbonate it is not the driving off of carbonic acid produced in the reaction that prompts precipitation but rather that the reaction is very slow to occur and carbonic acid is being produced as precipitation occurs. Bicarbonate is used in dramatic excess so the drop in bicarbonate concentration likely isnt the cause of significant drop in pH, moreover stirring the filtrate for 45 minutes raised the pH. This is likely when the CO2 was finally driven off.
It is also noteworthy that in neither THH experiment did the mixture fizz the way it did in the harmine experiment. Carbon dioxide was clearly generated much more quickly in the harmine experiment, allowing the mixture to become super saturated and fizz.

In these two experiments, and the prior two, all procedures were done at room temperature with distilled water.
 
An1cca
#389 Posted : 9/21/2017 8:25:58 PM

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Hmmm Elrik, I can't explain your results either. I've never had bicarbonate precipitate THH. However, I was quite unsettled when getting the GC/MS results back of my reactants. See post #332. The purer-looking harmine after reduction isn't pure at all in fact. The techniques I followed did manage to provide me with some pure THH.

I can totally confirm the bicarbonate-separation of HAR-DHH, it's just a lot of work compared to a pH-selective precipitation. Are you sure your bicarbonate hasn't been heated or otherwise contains any carbonate? If I look at your pH readings of an 8% solution, this seems improbable though. My guess would be that you don't really have what you think you have (in terms of purity of alkaloids that is). Microscopy can confirm or reject this. Somewhat after post #332, I posted a photographic study of the impure samples that were sent to Energy Control. I hope that will help...

Oh yes, as for time of stirring, I usually do all steps in a matter of minutes-1 hour max. My improvised stirrer didn't let me run it for a prolonged time.

After many experiments I must conclude, as does Jees, that ammonia is the safest and easiest way to go. If you're stashing up for a lifetime, the investment in a cheap pH-meter seems very much worth it!

And by the way, it's so nice to see more people doing research, thanks Elrik!
 
Elrik
#390 Posted : 9/21/2017 10:41:35 PM

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Thanks for the input Smile
Your almost certainly right that my fractions arent pure yet, and should be fixed if making a 50+ year supply [but I'm still irrationally thrilled by white harmine Laughing ]. Thankfully I do have two microscopes hidden under years of lab dust.
And you and Jees are also right that, if I'm really getting my home lab back into meaningful operation, I need to replace my ancient broken second-hand pH meter. A new 90 $USD unit is now on order Very happy I knew I would regret anything cheaper than that.
I still intend to eventually investigate just what was going on with this kitchen-tek bicarbonate work, though. My bicarb should be ok, its the same storebought stuff I brush my teeth with and its never felt soapy on my skin like sodium carbonate does, lol. Something tells me there may be an important clue operating behind the phenomena I observed and many people will not have pH meter or microscope access.

My stir plate was built from an old computer fan, magnets from an old computer hard drive, a 2 cm section of tree branch as a spacer, a 7 VDC power supply from a forgotten gadget, and a glass plate. Its functioned surprisingly well. I got the idea from a youtube video.
Elrik attached the following image(s):
100_7921.JPG (38kb) downloaded 134 time(s).
 
An1cca
#391 Posted : 9/22/2017 7:45:49 AM

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Is that your Harmine in that vial on the left? Sure looks white...
I still don't have a clue what the impurities are in the samples I presumed to be pure. Tens of percents while it seems that microscopically, not much else is present. If someone would dig into this, we might be able to selectively remove them...
 
Elrik
#392 Posted : 9/22/2017 6:35:02 PM

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Nah, those are just plant hormones from other projects.
Heres the 2 gram THH freebase block left over from the last experiment.
Elrik attached the following image(s):
100_7931.JPG (18kb) downloaded 113 time(s).
 
An1cca
#393 Posted : 9/22/2017 6:51:26 PM

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Aha, well THH was the only harmala alkaloid I managed to get 90+% pure. If you're really going for it, you can send your reactants to Energy Control for analysis. That way you will know your purity for future dosing and the community can learn from the techniques you followed. Happy experimenting!
Oh yes, if you're serious about harmala's, I really think it's worthwhile digging up those microscopes... Pure beauty!
 
moyshekapoyre
#394 Posted : 11/17/2017 5:07:12 AM
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Hey there, I'm a bit late to this but I was wondering if Mindlusion or anyone else has figured out how to easily oxidize harmaline into harmine. I'm no chemist but it seems just dissolving harmaline into a little alcohol and adding some H2O2 would oxidize it to harmine. However, I don't know how long that should take, or if there are any special concerns with this process.

The reason I'm interested is, for whatever reason, the seeds I've got lately are yielding mostly harmaline.
 
Elrik
#395 Posted : 11/17/2017 9:33:00 AM

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The easy way is outlined in TiHKAL. Basically in ethanolic solution harmaline is oxidized with concentrated nitric acid, using concentrated hydrochloric acid and heat to drive the reaction. This would not be safe for the large majority of people. Peroxide probably wouldnt work.
The easiest, safest, and most likely cheapest method of getting more harmine would be to buy more P. harmala. This time from a different vendor Pleased
 
An1cca
#396 Posted : 11/17/2017 9:50:53 AM

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moyshekapoyre wrote:
The reason I'm interested is, for whatever reason, the seeds I've got lately are yielding mostly harmaline.


Are you sure your separation is carried out well? What method do you use? Do you have access to a microscope for identification?

If you're OK with all that, then I totally agree with Elrik that extracting another batch would be the best option. Also, conversion of your DHH to THH is easy and effective (I got 91% purity), so you might as well do that instead....
 
tregar
#397 Posted : 11/17/2017 4:19:57 PM

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Good research you all have going here.
 
moyshekapoyre
#398 Posted : 11/18/2017 2:16:39 AM
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An1cca wrote:
moyshekapoyre wrote:
The reason I'm interested is, for whatever reason, the seeds I've got lately are yielding mostly harmaline.


Are you sure your separation is carried out well? What method do you use? Do you have access to a microscope for identification?

If you're OK with all that, then I totally agree with Elrik that extracting another batch would be the best option. Also, conversion of your DHH to THH is easy and effective (I got 91% purity), so you might as well do that instead....


The separation is using the same procedure as always, same vendor as always, but I don't know if there is some special thing to watch out for that would easily convert harmine to harmaline. Tried not using heat and not much vinegar but that didn't help. I guess during winter months the seeds tend to be more harmaline heavy.

I just bought a 60x microscope on ebay for $7. Hope that works. I have been converting to THH, but was just wondering if I could also convert some to harmine. Looks like that won't be doable in the kitchen, so thank y'all for saving me some wasted effort. Smile

Btw if I read this thread correctly, it seems THH has a short shelf-life, quickly oxidizing back to harmaline? Anything I can do about that?
 
Loveall
#399 Posted : 11/18/2017 6:02:27 AM




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moyshekapoyre wrote:
The reason I'm interested is, for whatever reason, the seeds I've got lately are yielding mostly harmaline.

What pH are you doing your extraction at? A lower pH may help pull more harmine. From this,



9/18 Edit: As stated in the referenced tread, the solubility plot is only an approximation calculated by a computer program demo. It does not account for temperature or for interactions between compounds. It should not be read as "pH needs to be 2.5 to extract harmine", instead it should be read as "to troubleshoot extract procedures with low harmine to harmaline content, try lowering the pH of the boil". This will not work if the seeds are the issue and is only a suggestion. Apologies that the text from the figure implies something else.
“... (a) psychedelic substance occasionally causes psychotic behaviour in people who have not taken it.”
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ijahdan
#400 Posted : 11/18/2017 10:05:54 AM

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moyshekapoyre wrote:


Btw if I read this thread correctly, it seems THH has a short shelf-life, quickly oxidizing back to harmaline? Anything I can do about that?



Im also worried about this. Jees recommends storing in a salt form but I never got round to doing that, and most of my thh is now infused in changa anyway, so has to remain freebase. Would be interesting to study this thh-harmaline oxidation process more.
 
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