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Harmine, harmaline and THH from Syrian Rue. Verification and finetuning of the VDS-protocols Options
 
An1cca
#541 Posted : 9/18/2019 6:01:46 AM

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Hi Doubledog,

I think in your case repeated precipitations as in paragraph 2.4 will provide you with (sufficiently) pure DHH for conversion. Just keep stirring to decompose all the carbonic acid that forms.

6-9 hours should be plenty for conversion. You don't have to wait until the bubbles stop forming.

For most purposes, it's not a problem that some harmine remains in the reaction products.

Good luck!
 

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Jees
#542 Posted : 9/18/2019 6:10:18 AM

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^^^ An1cca beat me by a minute, we posted simultaneously, but I leave my response unchanged Pleased

Hi dd,
doubledog wrote:
...Is production of small bubbles a sign of ongoing reaction? It is now 3 days from the start and bubbles are still there...
It is the reaction between vinegar and zinc that produces the bubbles, it does that even without harmalas. So you can't use the bubbling as a rating for harmala conversion. I suppose after 3 days that is overkill but then again that isn't a bad thing either. You might filter the remaining zinc out by now.

Did you overshoot or undershoot the separation between harmine and harmaline with sodbicarb?
Hard to say, we've found that fixed pH points for separation does not exist because of variables come into play. That is why using pH depressions as an indicator are more reliable to make the separation, yet some seem to have a hard time with that either. I've never found a problem with it personally, it worked always like in the VDS paper for me.

In earlier days we trusted in a fixed pH separation point of pH 8.75 (and sodbicarb fits that bill nicely) but in certain conditions the separation happens much earlier, some of us here were able to separate even at pH 7. VDS was right to point attention to this.

If you have a hard time separating correctly, mind that you can perform reduction on non-separated rue extract to end with a mixture of harmine (which doesn't convert) and THH (converted harmaline), and use that as a readily mix. Separation is actually only necessary for those who want just THH on it's own. But ime the mix of harmine + THH is just about perfect for entheogenic purposes.
 
doubledog
#543 Posted : 9/18/2019 6:29:08 PM

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Thank for your advice, I am going to separate zinc from the solution and then precipitate thh with ammonia.

I definitely overshooted sodbicarb, I added it in a small fractions to reach pH 8, but nothing started to precipitate, so I added bigger amount and put it in the fridge. After few hours, big amount of sticky brown precipitation appeared on the bottom of the jar. Remaining solution changed colour and after basifying with KOH produced low amount of precipitate (should be harmaline).

So I again dissolved the brown part in vinegar and repeated the separation, now with more carefull addition of sodbicarb.
But again, precipitation was not immediate and I was left with too high amount. I should say that I had no way to found out what is the ratio of harmine/harmaline in my rue, so I assumed 1:1 and just control it visually.

I then repeated separation for the 3rd time (only on first brown part) , and was able to capture pH depression around ph 7,5 (just estimated, but below 8 ) even with simple pH strips. What complicates the procedure is that at this low pH, precipitation occurs with time delay, not immediately.

So, my harmaline fraction is a product of 3 steps of separation of harmine, but I realized that issue is that my harmine fraction could be mixed with some harmaline. Hope that only with small amount.
My aim is to have mix of harmine and THH, with a few % of harmaline, as I believe that this mix would be ideal for entheogenesis and overal health benefits.

Also want to mention that my method of extraction of mixed harmaloids from Rue seeds was use of quick boils on grinded seeds. Just add vinegar, bring to boil, boil it for 1 minute or even less, let sit in hot water for another 5 minutes and decant. Did it 5 times, combined pulls and after whole cleaning procedure (including Manske salting) the yield was almost 6%.
 
Fruit is life
#544 Posted : 9/1/2020 12:36:46 AM

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Hello, does anybody find THH to be heavier then Harmaline/Harmine? E.g 100mg THH looks like alot less then 100mg Harmaline. I have just finished up a zinc reduction on 1g Harmaline and and after basing/drying my recovery is about 0.9g so ~10% loss. However, this is the first time I've had my hands on supposed THH and I notice that although it weighs 900mg is looks to be about only 300-400mg of Harmaline volume wise. Cannot find anybody else commenting on this, only other thing I can think of is that my conversion loss is actually somewhere around 50% and there are some zinc salt contaminants making it heavy?
The self that talks doesn't know, the self that knows doesn't talk.
 
An1cca
#545 Posted : 9/1/2020 5:35:59 AM

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THH crystal shape is clearly different from HAR or DHH. Perhaps the needle-like form makes them fluffier than the more round crystal shape of THH. Using ammonia as a base, I always got the same (GCMS 90+%) kind of precipitate. What you could do as an experiment is letting zinc and vinegar react for half a day without any DHH, filter the solution and then try to get some precipitate with ammonia. Do not use any other base. This simple experiment might answer your question. You can also dissolve your THH and apply a test-strip to the solution: https://www.simplexhealt...nc-50-strips-p-865.html

Let us know if anything comes out...
 
GordoTEK
#546 Posted : 9/1/2020 7:46:29 PM

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8:41 of my THH reduction video shows my starting harmine/harmaline mix and 20:34 shows the final harmine/THH output. There was 10% less total weight. But volume is hard to compare. I've never carefully measured that. It doesn't look like an extreme difference to me though just eyeballing it...

 
GordoTEK
#547 Posted : 9/1/2020 7:49:41 PM

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Wondering if anyone here knows anything about doing the THH reduction using magnesium instead of zinc? I have heard "through the grapevine" that this is a better, faster way to do it. The only seller of THH on amazon clearly is using magnesium based on the product description:
https://amzn.to/3lC7HLP
"minute impurities being food-grade harmine, harmaline, magnesium chloride and sodium chloride"
 
Elrik
#548 Posted : 9/2/2020 9:32:21 AM

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I wouldn't be 100% certain that an admission of possible magnesium chloride contamination means magnesium metal was used. Magnesium chloride could very likely work as well as salt to salt out ß-carbolines. If it worked the residual magnesium chloride could be mostly removed with a cold alcohol wash, unlike with salt.
You're likely right, though. Wink

I have a question. It's been a year or two since I read all 28 pages of this thread but I don't think this was mentioned. When doing pH metric separation of harmine-THH mix is there no pH depression?
When I did harmine-DHH separation I did get the expected pH depression behavior including a batch of harmine I could take in near gram doses with no side effects [I love pure harmine], a mixed fraction, and a DHH fraction. But the other day I ran the reduction nice and vigorously and followed it by doing the pH metric procedure with pretty much the same conditions as VDS and using a good quality freshly 3-point calibrated pH meter. I added 10% ammonia to the mechanically stirred solution in small portions using a burette so the meter could accurately track the progress. I basically replicated the process I used for harmine-DHH, just the alkaloid solution was a little more concentrated and the gram quantity was higher. The pH steadily raised with no depression. I got precip and overshot just a little, stopping at pH 7,7 and let it stir for a minute or two more to make sure it was really stable before vacuum filtering out the harmine base. The motherliquor was then put back to basing, I got a haze at 7,8 and filtered again for good measure and in a clean beaker began basing again. I got precip at 8,5 with no swings in pH, I then dumped in ammonia to pH 9,5 and filtered my THH fraction.
It just didn't act the same as before. It was easier Laughing But not what I was expecting.
 
An1cca
#549 Posted : 9/2/2020 10:10:13 AM

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Interesting observation Elrik Wut? . In the VDS paper, a pH depression is mentioned although not quantified. I never really looked much into this, because the pH-ranges for HAR and THH are sufficiently far apart for selective precipitation.
 
Elrik
#550 Posted : 9/2/2020 5:17:51 PM

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Thanks, that was what I was suspecting, far enough separated that they don't 'fight', I just never found a pKa for THH in the literature so I wasn't sure.
 
Jees
#551 Posted : 9/2/2020 8:21:34 PM

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Hi people,

THH separates 'easier' than harmaline from the harmine, The step is somewhat wider between THH and harmine than the step between harmaline and harmine.

p36 2.3 : excess sodium bicarbonate precipitates the full harmine and potentially also a part of the harmaline. Hence called a 'mixed fraction'. More efforts were needed to separate further.

p37 protocol 4 : using an excess of sodium bicarbonate only precipitates the harmine, no THH.

This could motivate one to make the reduction on a harmine+harmaline mix, because after reduction the sodium bicarbonate can make the distinction easier/profounder between harmine and THH. Personally I haven't gone that route though, so I can't testimony on the absence of a pH depression in that case, but I find it quite surprising there was none Elrik, I would have suspect one.

PS: use ammonia, carbonates are a hassle, but the above motivation remains on separating.

 
Elrik
#552 Posted : 9/3/2020 6:25:38 AM

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On my very first THH prep I used the carbonate method. It certainly was messy and awkward.
But I did get convincingly separated isolates. The whole pharma experience changed when I included the THH product as a predose. So if someone is stuck without a reasonable pH meter or a microscope, the carbonate method is functional.
 
GordoTEK
#553 Posted : 9/5/2020 4:40:55 PM

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GordoTEK wrote:
Wondering if anyone here knows anything about doing the THH reduction using magnesium instead of zinc? I have heard "through the grapevine" that this is a better, faster way to do it. The only seller of THH on amazon clearly is using magnesium based on the product description:
https://amzn.to/3lC7HLP
"minute impurities being food-grade harmine, harmaline, magnesium chloride and sodium chloride"


Just looking into this a bit more...
You can find lab grade, 99.95% purity magnesium on amazon for pretty cheap. And the reduction in acetic acid happens very rapidly, as little as 15 minutes (vs. 8 hours or overnight with zinc). You can see many examples of magnesium in vinegar vids on YouTube to get a sense of how rapidly free hydrogen is produced:

I know "faster" is not always "better" but again a trusted source tells me it works great for THH reduction and its the best way to go. I'm thinking this might also eliminate the concerns about trace amounts of lead and cadmium which are common in elemental zinc (I'm not actually sure if this is also common with elemental magnesium? But I can't find any info suggesting that it is after various online searches). Using magnesium ribbon also eliminates the nasty zinc powder residue that must be carefully filtered out when using zinc.
 
An1cca
#554 Posted : 9/6/2020 6:12:43 AM

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Thanks for digging into this, Gordotek! Only a small step away from checking if a DHH solution indeed turns blue in UV after such a short reduction period...
 
Jagube
#555 Posted : 9/6/2020 12:55:13 PM

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An1cca wrote:
Thanks for digging into this, Gordotek! Only a small step away from checking if a DHH solution indeed turns blue in UV after such a short reduction period...

I think that's a confusing test, because usually it just loses the green glow.
For it to glow blue, it would have to be very diluted, much more than in a typical DHH reduction. I've only seen a blue glow once and that was on a harmine fraction which I subjected to the DHH reduction conditions to remove the harmaline contamination.

When I did my first reductions, I couldn't see a blue glow and thought there was something wrong. It took me a while and a few Nexus posts to conclude the non-glow was the sign to look out for.

Even if it does glow, the glow is so weak it's nothing like the 'insane' green harmaline glow and can easily be missed if anything of the intensity of the latter is expected.

Yeah, this magnesium thing is intriguing! I've looked on an auction site and 'metallic magnesium' seems to be the search query to use. Most of the products seem to be coarse shavings rather than a powder though.
 
An1cca
#556 Posted : 9/6/2020 2:24:13 PM

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Microscopic examination would be ideal of course.

Personally, after reduction I get a clear and beautiful blue glow glow comparable to the one in the VDS document. After a while, the blue solution spontaneously changes to green again after filtering out the zinc. Partial oxidation by atmospheric oxygen I suppose. Because the blue is easily overpowered by the DHH-green, I thought it would already be informative to just shine some UV on the Mg-reduced reactants...
 
GordoTEK
#557 Posted : 9/6/2020 6:49:00 PM

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Jagube wrote:

Yeah, this magnesium thing is intriguing! I've looked on an auction site and 'metallic magnesium' seems to be the search query to use. Most of the products seem to be coarse shavings rather than a powder though.


I started my search with the same assumption, that I should be looking for powder, but I've since concluded that UN-like zinc, powder is not necessary with magnesium, and it's probably even a bad idea. The ribbon is perfect - unlike chunks of zinc, thin magnesium ribbon completely breaks down in acetic acid in just 15 to 20 minutes. When it's done, presumably your reduction is done. Again, I have not actually put this to the test yet personally, but I will certainly give it a try soon and I'm pretty confident it will work. I suppose you could break the ribbon up into a bunch of small bits pretty easily if you wanted to (it does easily break apart and can be torn by hand), which should speed things up even more, but I don't know that this would be an advantage, I'd probably let it magnetic stir for 30 minutes regardless.

Another advantage is that Mg has a molecular weight of just 24.305 vs. zinc at 65.39, that means you can use less than half the weight in Mg compared to zinc for the same reduction.
 
Fruit is life
#558 Posted : 9/23/2020 11:57:24 PM

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Yes conversing with the the person selling pure THH or the 2:1:1 mix regarding THH reduction this is what he had to say.

"The THH I sell is what Shulgin referred to as the D isomer, and it is a potent MAOi unlike the L isomer that some people say feels just like a little mood booster. Average dose: 200mg of the HCl salt. This D-THH is reduced from harmaline using magnesium in HCl."

He later corrected himself and mentioned that the THH was actually racemic, but was sure it was a potent MAOi which I don't believe.

He specifically mentioned using magnesium ribbon and hcl acid, and that the total reduction time was only 10 minutes, I think it would be worth a shot!
The self that talks doesn't know, the self that knows doesn't talk.
 
Jozeh
#559 Posted : 9/25/2020 11:58:02 AM

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I have given this a whirl.

The first shot didn't work too well. Trying to recover in basic phase dropped a lot of Mg salts/some kind of flocculent precipitate.

Second time round I had 2.3g of mixed Harmala HCL, that was pretty clean from a few runs of A/B and Manskes, in an acidic phase. More than a 3:1 mol weight excess of magnesium ribbon was introduced. Waited for the reaction to complete T < 1 hour. Mansked with a 10:100 salt to water ratio. Which produced some crystals that were recovered, notice the unusual crystal formation, 1.2g of even cleaner Harmine HCL, I am assuming.

However what is left is having trouble to Manske out.





 
Jagube
#560 Posted : 9/25/2020 12:13:49 PM

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Jozeh, did you manske the acidic reduction solution, without basing with ammonia first? I'd base it first, as that removes the metal salts (in the case of zinc anyway) and already gives a fairly pure product. A manske step is not necessary unless you want to convert to HCl salts specifically. And if manskeing straight away, I don't know if that will not interfere with the process. Can't think of a reason it would, but perhaps a chemist can chime in?

For one, when basing, you can see the pH depression points, which gives you an idea of what you have in there (harmine, THH, harmaline...).

If nothing else is manske'ing out, you can still crash it out with ammonia?
 
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