I recently came across information indicating that THH (tetrahydroharmine) is formed in-situ while B Caapi is boiled. It appears that THH is not present in the caapi vine. THH is formed by chemical reaction with the acids and antioxidants in the vine. Specifically, hydrogen atoms from the acids/antioxidants combine with harmaline (and harmine) to form THH.

THH has a reputation for mood enhancement during the trip. THH is a serotonin reuptake inhibitor, so a mood-enhancing effect is to be expected. THH appears to be highly desirable in ayahuasca.

In another thread on this website, data is presented showing that B caapi contains little THH. These analyses were done on methanol extracts, presumably without long duration oooking. I would expect that THH will not be produced by methanol extraction. https://www.dmt-nexus.me...aspx?g=posts&t=29967

I have done ayahuasca with both syrian rue and B caapi. The B caapi is far preferable. Its more pleasant, less negative, and is more healing. I think this might be because THH is formed during B caapi preparation, but not syrian rue preparation.

The times I did syrian rue, the seeds were brewed for a very short period of time (10 minutes or so). It just isnt necessary to boil syrian rue for a long period to extract the alkaloids. Without a long boiling I believe that THH will not be formed.

The times I did B caapi, the vine was boiled for many hours, because it takes this long to extract the alkaloids. Also, I added citric acid to improve alkaloid solubility.

I am wondering what might happen if syrian rue seeds are boiled for many hours with acid (citric acid) and antioxidants. My hypothesis is that the harmalas in syrian rue would be converted to THH. So it may be possible to make a good quality ayahuasca analog using syrian rue if its boiled long enough with acid and antioxidant.

Has anyone tried long duration cooking of syrian rue? With acids and antioxidants?

The attached paper mentions that THH is likely produced in situ during boiling of B Caapi. It states:

"In Situ Production of THH
The average ratio of THH to harmine in the vegetáis
was consistently near 1:1, from all sources (Table 2), while this ratio was closer to 1:5 in a large survey of source plant material (i.e., B. caapi, see Callaway, Brito & Neves 2005 in this issue). It is presently unclear whether harmine and harmaline are being chemically reduced to THH during the acidic process of decoction, or if THH is simply more stable than the other two harmala alkaloids, which maybe lost through decomposition, or a combination of both processes. Figure 1 illustrates a likely chemical pathway for the conversion of both harmine and harmaline to THH through reduction under acidic conditions."

In a new experiment, friends tried long boiling of caapi with a combination of citric acid, malic acid and ascorbic acid. The solution was highly acidified (ph of about 3.5). Ascorbic acid may cause significant conversion of harmaline and harmine into THH because its a pretty good reducing agent.

We found that this boiled caapi product did not fully activate dmt. We believe this is because almost all the harmine and harmaline was converted to THH, which is not an MAO inhibitor.

Has anyone else had a similar experience?

Its got me thinking about way to obtain a perfect blend of harmine and THH: Prepare two batches of rue: one boiled for a short time in water to provide harminee/harmaline, and another batch boiled for a long time with citric acid and ascorbate, to provide THH. The two batches are then combined to provide controlled amounts of both THH and harmine/harmaline.

there are antioxidants already in rue. I would suspect that long boils with rue will also cause THH to be formed. Im not an expert though..so dont take my word for it.

So maybe just a long boil with rue. I would expect that not enough antioxidants would be present, because alkaloids are quite concentrated in rue. The idea here would be to completely convert the beta carbolines into THH in one batch, so there would be no harm to adding excess antioxidants.

heres a thread on this very subject

https://www.dmt-nexus.me...aspx?g=posts&t=31699

Great thanks for the link. I think that prolonged boiling with vitamin C and acid will produce THH. So I am going to try this with syrian rue, and then do a bioassay. Will report results.

Please do, curious to hear. Please include exact steps of how much water, rue, acid and vitamin c you use
Are there additional psychoactive effects of THH?
I remember one time having just rue, without anything else, and tripping balls.
I believe it was acid boil with vinegar or citric acid, and then concentrated drink of disgustingness.
Since then, I have taken rue by swallowing in capsules.
The effects since have been nothing like that one time, and I have always been trying to find an explanation.
My usual effects are the stimulant effects and the brightened lights and semi sketchy trails.

Here is what im doing:

50 grams syrian rue
couple liters water (adding water regularly)

Added at beginning:
3 grams vitamin C + about 1000mg bioflavonoids
3 grams citric acid

After boiling for 5 hours, added another 3 grams vitamin C + 1000 mg bioflavonoids

Will boil for about 12 hours or so.

This was a topic of some limited discussion at the MAPS conference. It seems that even those who have published papers/been aware of some reporting of possible reduction reaction occuring via brewing are still fairly intrigued by the potential phenomenon.


In what sense do you mean? THH is a weak SSRI, fwiw.

..remember also there are two possible isomers of THH..
as mentioned here in the thread endlessness linked earlier..
.

DDanimal: anything to report yet?

According to wikipedia, ascorbic acid is only a mild reducing agent. I don't understand any of the chemistry of all this, but I was thinking of trying something similar to this using a mix of fumaric/ascorbic acid adding a few rooibos tea bags for antioxidants.

In the sense to explain my strange experience one time that differed from all previous Rue experiences.
Perhaps it was the ratio of harmala/harmaline in the seeds...who knows.

Okey, I think we've waited long enough.

How did things go with the c-vitamin rue brew?

I also vaguely recall an acidic brew made over many hours that turned out spectacular.

Updates brewers?

I recently noticed that brewing rue with ascorbic acid seemed to make it significantly more euphoric, but this anecdotal claim really ought to be backed up with some kind of analytical data which will follow in due course.

Any updates on this highly interesting issue? Do you remember the brewing time and approximate pH downwardsfromzero? I suspect that - if a conversion to THH really occurs - this should happen much faster than with caapi brews. Which would be awesome since the whole 3x3 brewing is just so damn energy wasting.

Hi MuteUSO! It now seems more reasonable to suspect that the harmol might be preserved by ascorbic acid in these brews and that's responsible for the difference in subjective effects, although reports do trickle in that hydrogen peroxide might act as a reductant for the harmaline → THH conversion. And some have suggested that ascorbic acid reacts with atmospheric oxygen to produce H2O2 in situ. Since the last post I made in this thread I've performed a larger set of PC cooks on 1kg rue seed with loads of ascorbic acid and again the resulting brews and crude extracts seemed quite smooth.

I've reported in the Ethyl acetate for harmalas thread (actually, here) regarding two separate fractions that were obtained by exploiting differential solubility of harmala freebase components in butyl acetate. One of them seems to have a special magic to it and I hope to report more on that in the upcoming weeks.

As far as brewing goes, it was still a bit energy intensive doing multiple 30 minute PC boils, and the waiting time for cooling off afterwards was the most tedious part. Solvent extraction of the seeds followed by a smaller ascorbic acid cook on the resulting alkaloids might help with the answer to this conundrum - although rue seed does also contain remarkable quantities of tocopherols (vitamin E derivatives) which are strong reducing agents as well. We'll just have to see.