Edit: To save those the trouble of reading through all of this (unless you want to), all my attempts to convert harmaline -> THH failed. Tried different antioxidants, acids, long boils, and many TLC plates on them. None showed significant THH increase. Should be my last post on this page where I explain what I think is going on. I think it's some enzyme only present in caapi evidenced by the big difference in results from methanol and cold water extracts of caapi among published scientific studies and on the nexus, and the difference in alkaloids between extracts of fresh/dried plants.

I'm interested in rue as a more abundant and cheaper source of harmalas, but I know it lacks THH/has too much harmaline causing many people to say they prefer caapi. These threads made me curious whether long boiling of rue would result in THH formation and a more caapi like brew:

https://www.dmt-nexus.me...aspx?g=posts&t=31699
https://www.dmt-nexus.me...aspx?g=posts&t=29967
https://www.dmt-nexus.me...aspx?g=posts&t=41623

I decided to do some tests of my own using the Bunk Police TLC separation kit. I grinded up my seeds in a blender and did 3 different extractions of 100g each:

-Cold water extraction left to sit for 16 hours, shaking occasionally. (this one I actually only did 50g of seeds)
-Boiling for 1 hour with plain water
-Boiling for 8+ hours in water along with vinegar and a bit of antioxidants (amla powder)

All these were filtered thoroughly through coffee filters. With half of each I did a crude manske (no A/B, just put 10-20g salt/100mL into their jars and left in the fridge overnight). I then tested the extracts both with TLC and on myself.

First off, I have some thoughts on the 'toxic' part of the seeds:

Before the manske of 1 hr tea- it felt quite speedy, as if i had a decent sized cup of coffee or tea. Similar harmala effects to caapi were felt, but the speedy effect was very prominent. I felt this effect was undesirable.
After the manske-
Not much if any noticeable stimulant type of effect that I was getting from the boiled/filtered tea. I think if someone really liked caffeine/stimulants they might enjoy the full spectrum rue but for people like me who don't like it, I will have to manske any time I am consuming rue. It may even be possible that someone might not feel the stimulant effects if they have a high natural or earned tolerance to stimulants like caffeine. For me it feels quite anxious and on edge, though maybe I am the odd one out because I don't even drink tea because even 1 cup of green tea can affect me like that. I could see how some people say it's impossible to have visionary experiences on rue alone, because before you get there, the toxicity takes over. I'm sure for many people that's the case. Even on a low dose I felt quite anxious as I said. But someone with a stimulant tolerance may be able to easily venture into visionary territory without feeling a stimulant overload. That is my initial thoughts on what may be happening based on the feeling of the effects.

I took a lot of the manske product to make sure I was feeling it more than the tea, and as others have said it does appear to me to remove this 'toxic' effect. But to me it feels much like caffeine or kratom.

Question- do the vasicine compounds have a stimulant effect? If so this could support my theory. I know endlessness has mentioned after manske the vasicine compounds were indeed removed.

1hr boiled tea manske VS 8hr boiled with vinegar and amla then manske'd-
Subjectively the 8 hr one seems to taste less bad. Slightly less bitter/numbing sensation in mouth and not as overpowering. Also the 8hr seems to be of a lighter color. Though i did add about 2x the amount of salt to the 8hr manske, so it could be salt contamination(?) or maybe a purer product. I believe this just to be a more pure harmala product based on appearance compared to this user's post: https://www.dmt-nexus.me...aspx?g=posts&t=67650 . I should do a 2nd round manske on my darker colored product to confirm it will turn the same color as my 2nd one. This 8hr more pure one also seems to be less stimulating than the first. Perhaps the stimulating compounds are the same ones which cause bittering. I know harmalas can taste like that, but caapi 30x extract just tastes like cough syrup to me and I have no problem eating tons of it plain. The rue extract tastes more offensive and numbs my mouth more. Could just be the higher harmaline levels too.

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Attached to this OP is my end yields from all the manskes. You will see #3, the long boil seems to have given the most pure product. I'm not sure if it was more pure because of the longer boiling, or because I used more salt or just the right amount. I used less salt in #2 so that could explain it. But the ratio of water to salt between #1 and #3 were quite similar so I lean towards thinking maybe the boil did some purification work.

TLC results:

Had some struggles getting my plates to separate correctly and I am still a novice at TLC. Not a chemist by any means. I am hoping I can get some advice on interpretation and also how to do these better next time. To make it less confusing I am going to opt to make multiple posts in this thread along with pictures attached so I can comment on each one.

The order I did the extracts in was first to make the 1 hr tea, then the long boil, then also decided to finally do a CWE. So my first TLC plate was a comparison of my initial 1 hr boiled tea plus a sample scooped right out of the pot midway through the boil. I see 4-5 different spots on these plates but after my later results I am wondering whether these were done incorrectly. At first I didn't realize you had to put lid on jar when waiting for the whisking up the plate to complete, just left it open so that could have affected it.

This was also a good thread to compare my results to: https://www.dmt-nexus.me...aspx?g=posts&t=67650 . I actually used the same bunk police kit that user did.
Please let me know if anyone else knows of a thread with harmala TLC results.

So first you have the 'no acid tea' and 'crude brew w/ acid' comparison plate. I saw 4 distinct spots on here but in my later ones after just a manske I just see 3 so I'm wondering if something weird happened. At the very top in dark blue what I think I have is harmine. It seemed to separate into two and even moreso after the boil so I thought it could have been harmol or some breakdown product of harmine. At the bottom I believe I have a lot of harmaline. Looking at the other user's THH results, his harmaline had a distinct light blue glow even in small amounts the matches mine. The THH appeared to be a clearly darker shade.

Question- is it possible his THH was in freebase or something which changed the color it glowed? Or can I assume his compounds will glow exactly the same as mine no matter what form they are in? If that is the case I may re-evaluate my results. But for now, I will go on assuming his results are an accurate reference I can use to compare to mine.

So I think I can clearly identify the harmaline present by its distinct light blue hue in small amounts and the brownish color it seems to develop into when more concentrated. That being said, there appears to be 2 spots but the bottom one does not look like his THH, which had none of that light blue hue. It looks similar to harmaline to me. So I am unsure whether there is much THH there.

There is also actually one more spot, which can hardly be seen in the first TLC plate. It is a bright yellow spot that looks like the color of a yellow highlighter. I attached another picture of a later plate that this yellow spot is more visible in. Interestingly, this yellow spot is hardly visible on that plate, or any of the plates anymore. It seems to slowly dissipate and go away over maybe 30 mins or maybe longer after drying. Perhaps it could be an oily substance can still disperse through the paper after the solvent is dried? These spots didn't seem to go away or change in visibility after a manske so I don't think they are vasicines as I first thought.

Edit: The yellow spot could also be a compound which glows better when the paper is coated in solvent. Realizing that all the compounds seem to glow better when the paper is wet.

And the plate with 'slanted' in the filename is a mistake I made of doing the TLC on a non level surface. I then realized this causes the results to appear 'slanted' as when the water creeps up it will do so unevenly if it isn't perfectly level. So the vertical positions of the compounds are skewed.

This may be of help if you haven't seen yet:
https://www.dmt-nexus.me...aspx?g=posts&t=35984

The top spot is dark blue spot is harmine, the bottom spot that is yellowish and sometimes seems hard to see is THH, the one above it that is light blue (with dark center if very concentrated) is harmaline.. Seems indeed you kinda screwed the separation in the first plate by leaving the top off..

Im not sure if there's any sign of vasicine/vasicinone/deoxyvasicine in any of the plates, there aren't other clear spots but we also did not yet test with a reference standard containin those to be sure they dont co-chromatograph with harmalas or for some reason dont appear in the TLC clearly (maybe they are just in too small quantities?)

Just on top of the harmaline in your last plate, there is a darker spot, Id like to see if maybe that isnt another substance, maybe if you drop a reagent carefully on top so it doesnt also touch the harmaline, you might be able to see if it reacts in any different way. Not sure what reagent would be the best in this case but do a few different just to experiment.

You can also play around with different concentrations of the samples you are loading on the plate, for example have a more diluted solution of same sample on a lane next to it, see if you can see things a bit better. Sometimes when a sample is too concentrated and spot is too large, it hides behind it some other substance that ends up co-chromatographing. That might not be the case now but its good to experiment and see if you can get more answers or eliminate more errors/uncertainties.

Do you by any chance have a normal UV light, like 365nm? It helps seeing harmalas too.

BTW, congrats on running your first TLC plates, with experience you'll learn a lot And thanks for sharing!

Finally here are the TLC results from my manskes done on the filtered brews/teas. Here is where I started to have some problems with the compounds separating or showing oddly on my plates. They started to go in V shapes (even though everything appeared to be level) and looked a lot different than my first ones. Though as I said I am wondering if my first ones may have been wrong, these ones I did more 'properly' I think according to the directions- kept the lid on when waiting for them to develop.

First I have the still wet with solvent plate where you can see those yellow spots. Next you can see the same plate after it dried. If you look closely you can see some darker spots that those yellow ones appeared to turn into as it dried. It seems to me they just glow a different color when wet but I can't say for 100% sure. The spots that are left appear to be in a similar position to this user's https://www.dmt-nexus.me...aspx?g=posts&t=67650 THH TLC results. It's hard to tell exactly what color it is because there is a smaller amount but it looks like it could be a similar blue, indicating THH.

On the last plate I added more product so it would glow brighter and I could see better. On this plate you can see the bottom spot better, but it did this weird mixing blobbing together thing despite being on a flat surface and done (as far as I can tell) properly. It's hard to tell on that plate so I'm looking at the lower concentration plate for determining the ratio...

If that is indeed THH, it appears to be in a small amount. But then again, judging by this thread where he converted harmaline to THH https://www.dmt-nexus.me...aspx?g=posts&t=67650 it looked like almost all of his harmaline was converted to THH, but it appears far more faint than when in its harmaline state. Perhaps THH just glows under a blacklight more faintly than the other harmalas. I will soon test some caapi manske and compare it with my extract to see what a real high THH manske result looks like.

The wikipedia article states only a very small amount (~0.1%) of THH was found by dried weight in rue seeds. It doesn't look like the THH content changed much by boiling and didn't seem to vary between extracts. Even being generous and saying that maybe it doubled or tripled, that would only bump it up to ~0.3% which is very low when compared to any other of the primary alkaloids of the seeds. I doubt I created any sizable amount of THH here by long boiling.

So assuming my assessment is correct and not much THH was created, this raises a few questions. It was thought that boiling may cause some conversions to happen between the harmala alkaloids. But this doesn't seem to be the case to me (again I am a novice but would love to hear more opinions). Is it something that only happens with caapi maybe? Is it something that only happens with a DMT plant added (read tryptamines may convert to beta carbolines somewhere) in the brew? Is there another explanation for the THH content differences people have found between the raw plant and the brews?

This would seem to dispel that instability theory where THH is the most stable and so the others break down leaving a higher THH content. A very long boil with a ton of vinegar didn't seem to cause many changes in ratios at all.

And finally- Is there anything else I could try to generate THH in a brew like what appears to happen with caapi? I know there is the zinc conversion method but I am curious if you could do it with a simple brew. It seems not. Maybe there are some chemicals in the caapi that specially react only when boiled and cause THH creation? Maybe there is something you could add in a rue brew to cause this as well?

You're fast!! Haha was still typing out some of my results. Awesome didn't see that thread. It looks similar to my THH, but were those plates wet? When mine dried they looked quite different. I see the one guy replied there that fats fluoresce green so I am thinking of dipping my plates back in and see if the THH fluoresces green again or perhaps if it was some sort of fat/oil that dissipated as I thought initially.


Yeah the tea's plates which felt totally different and had that stimulant effect looked very similar in terms of major glowing alkaloids that were clearly distinguishable. Of course it looked more pure and clear after manske but you're right I don't see any despite the clear difference in effects which I think was maybe due to the vasicines.


Absolutely can do that. I'm curious also. I am not 100% sure if I botched that plate but I know all the ones today I remembered to close that lid. I wonder if that is another substance. Interesting that it only would seem to appear in the cold water extraction. Perhaps it is very unstable. It also didn't appear to fall out in the manske if it is another substance. Though maybe it could have been hidden mixed in with the harmaline in all my manske plates?

Edit: Attached is the marquis test which seemed to be the only one clear enough to use. Other 2 reacted with very similar dark colors/no reaction for all. But judging by the quantity and similar very faint glow to the supposed THH, it could be one of the other low concentration alkaloids like Harmane. Perhaps it breaks down upon boiling too.


Right I did that with the manskes in the last post a bit but still had some trouble. Are they supposed to be going in V shapes like that? Do I just need even smaller concentrations? I thought that was even a super lower concentration but maybe still quite high by TLC standards.


I do not have one on hand! I will grab one when I get a chance. I'm curious enough to keep researching into these compounds. Their effects are very interesting to me.

Thanks for your guidance through this process!

Just tried re-wetting the paper to test what was going on with the yellow. I noticed in regular light the 'THH' spot appears more yellow. Then you can see before and after I dip in the solvent. It appears to glow a different color when wet. When wet, looks just like endlessness' results and is a fluorescent yellow. Dry it looks more like the other users results. I think that compound at the very bottom is THH.

Overall a little disappointed as I thought the THH conversion might work. But it's good to know what's going on. My results I think suggest something a little more complicated is going on than a simple reduction from harmaline to THH via just heat or acidic conditions in caapi brews. Either it is occurring but due to something more complex I think, or maybe this doesn't occur at all and there is an alternate explanation as to why the THH content varies from raw material to brew. Does anyone have any more resources that shows why or why not this may be happening in caapi only brews? That is one of the main things I want to confirm here. I had read that some thought the conversion may happen due to the type of pot it is brewed in (aluminum)? But other than that, if it does occur, I think it could be some interplay of more complex chemicals. If it was simple boiling/acid, 8 hrs with a lot of vinegar I think would have made at least some measurable change.

Interested in investigating how/if caapi even does this conversion, and seeing if it could somehow be replicated with rue by perhaps identifying why and finding some plant/compound to add to the rue brew which caused the same reaction.

Another thought I had was to check how grinding vs not grinding the seeds affects the concentrations of different chemicals in various extracts (30 min tea, overnight soak, boil). I think this could yield interesting results because the wikipedia page references https://web.archive.org/...dia/weedinfo/peganum.htm which says the seed coatings contain high levels of harmine. I can't find the original source of this but I think it's in the book "Noxious Weeds of Australia" by Parsons. Doesn't say if the coatings contain high levels of anything else or not but perhaps the inner seeds contain more harmaline while the outer is primarily harmine. I'd like to try TLC on teas and short boils of just the soaked seeds without grinding to check if it might change the alkaloid levels in the extract. Even if they contain all the harmalas, maybe this could reveal it isn't really necessary to grind them and only results in more gunk to filter. Possibly the vasicione chemicals could only be on the inside of the seed too.

Subjectively I notice that sucking on the seeds they don't have a particularly offensive flavor, neither does soaking them in tea (which turns a yellow color and has a semi pleasant flavor). But immediately if I bite into one it's quite a bitter and offensive flavor which numbs my mouth, just the same as I get with my final manske extract. I suspect the numbing yucky flavor is harmaline, and have heard that is the worst tasting of all. I have taken caapi extract in tea and also held large amounts plain in my mouth and never got any numbing sensation that intense. Even licking a trace amount of the manske powder causes quite a significant numbing effect, so I suspect there is a much higher ratio of harmine in the seed coatings and tea made from them. This isn't very scientific but the tea does seem to have a decently strong 'coffee' like smell which I also get from the brew, maybe this could mean the stimulant compounds are present in the seed coatings too? Though I also feel like caapi tastes like coffee and cough syrup and it has no caffeine like effect so maybe that is just some harmala alkaloid relatives. I will try the soaked tea to see if it has the on edge stimulant effect I felt from the brew. The tea certainly appears to have high levels of harmine and low harmaline. When dripped on paper it glows quite well under a blacklight looking similar to harmine. Will need to do another TLC in a few days to confirm that the ratio is much different than grinded seed brews. Also curious as to THH content in the seed coatings (still would be low I presume, but maybe could slightly increase the ratio of THH if there is less harmaline present and the same amount of THH). Will be testing how much of the seed coating tea is needed to get off compared to if you had brewed the seeds too.

Edit: Just microwaved the tea down to see how it tastes in powder form compared to manske. It became a white/tan powder with almost no bad taste or numbing like the manske product and it's almost pleasant even in this concentrated form. Added a little clementine juice to the tea to balance the small amount of bitterness and it's quite tasty with a mild sandy, salty, earthy flavor. It doesn't appear to have any of that stimulant/toxic feel either upon taking more, ~5gs worth of soaked seed tea. Seems to be much less potent but considering how cheap it is, not sure if it matters much. Could be a good easy way to prepare a harmine heavy brew.

Is it possible that the presence of the decyclised, 'retro-Pictet-Spengler' product (as seen in Mindlusion's post in the other thread) may explain the difference in the UV fluorescence results for THH of differing origin?

Looking at endlessness' posts in that thread I'm quite curious if his plates were dry or wet in those pictures. In mine at least the THH glowed a totally different color when wet. Even if that explains some of it, it does look like there are some weird differences in the different types of THH he has there.

Wanted to continue this log here as I have some more thoughts to try to narrow down the possibilities a bit more. One possibility I thought was that the admixture DMT plants in the brews somehow interact with the caapi in boiling producing more THH. Found this paper on the ayahuasca forums which I believe suggests that this probably isn't the case: https://catbull.com/alam...in%20aya%20decoction.pdf On page 2 there is table (attached) which shows the alkaloid content of various brew samples. 2 of the brews have no DMT in them yet one is among the highest THH:harmine levels in the selection and the other is average. If the admixture DMT plants were the source of this THH generation with caapi you would think that wouldn't be the case. Now it doesn't say what exactly was in the DMT-free harmala brews so it could have been more than caapi, but I still feel safe saying it's unlikely it's anything outside of the caapi itself causing this reaction.

Another theory is the type of pot it is brewed in (aluminum, iron) causing this reaction. I find this quite unlikely as well considering virtually all aya brews tested seem to have high THH levels. Even in this study, samples were taken from 5 different groups with comparable results in alkaloid contents. Among the vast amount of groups that use ayahuasca and have had their samples tested I'm sure brewing containers of many different materials are commonplace. I think the theory that the vessel it is brewed in changes the alkaloid content is quite unlikely also.

I think I've already disproved the theory that simply long boiling harmalas will cause them to break down into a THH rich mixture. Another question which would be good to know, is whether pH matters at all. Wish the paper mentioned the pH of each of those brews. It's possible I didn't acidify my mixture enough to cause a reaction. Perhaps I will try boiling with slightly diluted vinegar to see if that causes any changes. Though I think this is a quite unlikely theory as well because traditionally I believe it's brewed with no acids added (need to confirm this further but have read it various places). And again, I'm sure many groups choose not to add acids yet THH is still ubiquitous in most tested samples.

I think the simplest explanation is that it's either a heat/acid encouraged (but not completely caused by) reaction between compounds existing within the caapi plant.

I wonder what could be causing it. Perhaps some antioxidant interaction? I saw someone mention that as a possibility. I'd like to know the levels of antioxidants in caapi vs rue. I would think caapi might be much higher simply due to the amount of plant material that goes into it over rue. If that's the case maybe brewing with a high amount of antioxidants could cause a rue brew to generate THH as well. I saw one poster mention a subjectively very different effect from rue boiled with citric acid or similar.

It's also quite curious why the alkaloids end up always stabilizing with harmine and THH as the highest, with harmaline as the lowest. Perhaps the answer lies in the stability of the compounds, with conversion from harmine -> harmaline being quite hard as harmine is the most stable, but harmaline being less stable more easily and quickly converts to THH by a similar mechanism once in solution? This would line up with what Shulgin thought:

I'm actually all out of new TLC plates at the moment so I can't do any more proper experiments, but I was too curious to not continue. So I did a quick and dirty plate by reusing my past ones. I tried the citric acid brew and it's a bit unclear because it's a reused plate and it came out uneven but I think it does appear that it caused some conversion. I used my 8 hr filtered brew and re boiled it then did TLC in pic attached. Left was with 100g of citric acid in 500mL boiled covered for about an hour and fifteen minutes, adding more water as needed when some evaporated. The yellow shine seems to have gone away and looks more blue. I can't be 100% sure about these results as it's a reused plate but it does look like there's something going on there.

I am currently boiling for another hour with an additional 100g citric acid to see if more conversion happens.

If this is really converting it, I wonder if it's the acid doing it or the antioxidant. It's definitely not the boiling time limiting it, as I had already boiled for 8hrs with a decent amount of vinegar with no change. And I got this change after 1 hr. Will have to test if same happens with a ton more vinegar. Still skeptical though as I am not sure of how acidic caapi is naturally. Having tried the extract goo which was just caapi water boiled down and it didn't taste too sour or potent as 100g of citric acid would, when one dabble on my tongue makes me pucker up. Vinegar is also quite pungent. Have to think if caapi brew was naturally super acidic it would be much more offensive tasting, it's almost pleasant, unlike my eye wateringly acidic 8 hr vinegar boil here.

I also wonder how fast harmine is converting to harmaline in relation to harmaline converting to THH. If they occur at the same speed, the harmaline levels might appear to stay the exact same as a steady supply is being made from the harmine at the same speed it's being turned into THH. This could be a problem if the goal is a low harmaline brew.

I also wonder how much adding more citric acid will matter here, I added a whole freaking jar of the stuff into such a small amount of the brew, tasted some and it's basically sour candy at this point. I think maybe it's a boiling time limited reaction when sufficient antioxidants are present.

Edit: After multiple attempts I could not get the TLC to work after adding the additional citric acid and boiling. I think it was maybe too acidic or concentrated with other gunk. Even after basifying with some sodium carbonate to a less acidic ph of 4-5 it refused to move and stayed at the bottom of the TLC column. Seems to glow a totally different color though. Will have to see if a manske fixes this tomorrow...

I do not have the answer regarding the supposed conversion from boiling. Just talking off the top of my head but from what I remember in the two papers claiming this conversion may happen, they have not detailed how they came to the conclusion, so it's impossible to really review the method and see if maybe they arent mistaken in the first place.

Regarding your plates, when the spots start appearing elongated like that, generally it is because the ammonia has evaporated from the eluent so there is mostly only methanol left. You need to use fresh eluent again. So if you keep your developing chamber open the ammonia evaps fast, or if you reuse it many times, gotta throw that out and put fresh on in (hopefully you kept the main eluent bottle closed avoid ammonia evapping).

As for the yellow in the plate and that spot below harmaline, im sure that is THH. Not sure about the differences you are talking about regarding wet or dry plate, but generally you should always let your plate dry out before visualizing it with the UV.

There are many other possibilities to separate substances further using 2D TLC, basically turning the plate sideways after running it once, and using another eluent, to further separate some substances that are harder to separate . Not saying this should be done with these plates, just mentioning something to keep in mind for your future experiments, things you can try out with different substances.

Another thing, indeed from your plates it doesnt seem there is much if any conversion happening, the relative spot size seems kinda similar in all your samples. That being said, you would need to keep the same concentrations and use the exact same amount of the solution to load the plate in order to be a perfect comparison and very easy to visualize, otherwise you never know if the extra spot or color you see is because there is indeed something different or if its related to concentration, its in both but you just see more in the more concentrated sample, for example.

PS: If you want to make a small investment and have relatively cheaper plates, buy merck millipore 20x20cm f254 aluminium-backed TLC plates and cut them yourself with sharp scissors or an x-acto knife, you can make like 200 4x5cm plates from a box of 25 20x20cm plates.

The eluent itself that BP uses is just methanol:25% ammonia , 97.5ml:2.5ml to make 100ml eluent. You can make different eluents with any mixture of solvents you can think of, though many wont work so well to separate certain substances.. ive found the methanol ammonia one to be a good generic eluent for most substances.

Another tip is regarding the even rising of the eluent front. Are you using this filter paper on the back of the developing chamber? You want the whole thing to be saturated with vapors of the eluent, which is what the paper along the wall of the chamber helps accomplishing. Also you have to try and set the whole plate without shaking too much so it rises evenly, its easier to compare two lanes when you have them both at the same height.

Awesome to know the solvent they used. I'll make my own from now on. And will order the plates too. Yeah I actually just realized the purpose of the filter paper last night after taping it above the solvent slightly rather than dipping it in and soaking. I thought maybe it was to catch vapors or something at first. Good to know thank you.

What do you make of the last picture I posted? After boiling w/ citric acid it glows totally different. All out of usable plates now but seems to be something interesting going on. Also, why do you think it refused to separate? I tried pre boil and post citric boil next to each other and the pre boil raised just fine while the post boil stayed unmoving at the bottom after multiple tries... And just did another dirty TLC on the manske, it separated fine, seems all the citric acid and very low pH was messing with it somehow. No discernible results from it. Will do proper TLCs with new plates soon.

Hopefully not spamming too many posts but I want to write my notes here. Still waiting to do another TLC but here is what I have now (attached pic). I thought the 1hr boil looked a little different, and see below the 4 hr boil looks much different. I really do think some chemical change occurred with the vast color difference. Can't confirm cause it refused to separate before I ran out of plates maybe due to very low pH.

If it did convert I wonder why it worked with pure citric acid but not vinegar. It's possible it was the much lower pH, but I still acidified it a good bit to the point where it was a quite offensive smell on the 8hr boil, dipped pH strip in was maybe 5-6. Maybe could have been the antioxidants, but I also added a few tablespoons of amla powder which is supposedly one of the highest antioxidant foods. Maybe I didn't add enough, or maybe it is the acid causing it and not the antioxidant. Also could it be only certain antioxidants work? Dunno.

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Also attached a spreadsheet I made from J.C. Callaway's B caapi alkaloid profiles paper which gives a table of the contents of many different brews. I sorted it descending towards the highest THH percentage in the brews. One even had as high as 71% THH levels!

Seems like most of the low THH:Harmine brews also often had very high levels of harmaline. Perhaps this shows an incomplete reaction? I don't think most caapi has harmaline levels this high. And if these were all naturally this high in harmaline, would be a coincidence they were all so concentrated at the top, and not boiled long enough to convert much THH. If anything I would think high harmaline brews would cause more THH b/c presumably there isn't an extra step from harmine -> harmaline

There looks to be a sweet spot in the middle (outlined) where most of the harmaline contents are very low. It also seems to be where the THH:Harmine levels stabilize to around 1:1. Maybe this is the perfect boiling time range? There are a couple outliers, but nothing like at the top which is seemingly before much of any THH conversion happened. These middle outliers I could believe were due to high harmaline content moreso than the ones at the top.

Harmaline levels seem to balance out to around this 2% mark after a while even after THH levels soar to 70% at the highest.

If high harmaline caused high THH I might expect to see some high harmaline brews among the highest THH brews as well. It's possible these super THH brews WERE initially high harmaline but the harmaline % stabilized down. That would be another good possibility.

It's possible the pattern shown is a coincidence and the end harmaline levels depend mostly on the starting levels. Though this could show some sort of stabilization process where the ratios of the compounds drift towards an equillibrium point.

But from looking at the data it really seems to me like it suggests longer boiling linearly increases THH/lowers harmine. Harmaline seems to stabilize to around 2%ish.

Would be nice if the stabilization theory was true, as rue's high harmaline content could make it difficult to create a low harmaline brew with the seemingly desirable 1:1 THH:Harmine ratio. If the theory is true, perhaps a medium/long boil is in order to ensure preservation of harmine levels. Too long may result in a THH heavy brew.

So I got some more TLC plates and was able to do some more tests, and I think I can confidently say the experiment was a FAILURE... Citric acid did not seem to cause much if any change in the alkaloid content. I manske'd the product I got after last night but got a very low yield and it looked weird and grey. I think I just burnt up a lot of the product because I had little liquid in the pan and boiled for too long. At some points it got too low. I think that may have been why it started glowing differently. The spot under harmaline in previous post I think could have been a fluke, that's not the color of THH I've seen in other user's posts anyway.

Anyway I boiled 100g ground seeds for 7 hours or so and did a couple TLCs along the way hoping to see some alkaloid change but there was really none at all. I let it boil for a half hour to extract some out. Then I added 16oz of lemon juice, which should have been equal to around 24g citric acid (1.5g/oz). Then let it boil for about an hour as you can see in 1st pic, and the plates were quite hard to see as I think the ones on the right were too concentrated, but there was still a ton of harmaline and seemingly not much THH. I thought it's possible there was some small change, so I added 50g of pure citric acid and boiled for another few hours hoping to see more. pH was around 5 or so from dipping a strip in when I boiled with vinegar before it was even lower I think. Then did another TLC you can see in pic 2 and there was clearly not much change at all. If anything there looks to be less THH.

It's good to know that boiling rue or adding acid/antioxidants does NOT seem to change alkaloid profiles at all. At least I can feel like I've eliminated that. I'm about ready to throw in the towel on this one but there is one final thing I might try tomorrow, and that is boiling with some cocoa powder to see if that changes anything. My thought process here is that I think it is some phytochemical(s) within the caapi enabling this conversion process which rue doesn't have. The main chemicals in caapi we know of are the alkaloids and catechins/tannins. Cocoa is another food high in similar catechins to caapi, so I think I will try just boiling with some cocoa powder as a last ditch effort to see if it changes anything. It's my last idea and if this doesn't work I'm stumped.

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Some more thoughts on why I think cacao/cocoa might work:

• I've proven (at least to my own standards) that it's definitely some specific chemical within the caapi that is causing the conversion to happen. It's definitely not just due to boiling/high temps or low pH or due to just any antioxidant.
• I would presume this chemical is abundant in caapi. The conversion happens readily and in high amounts, twice, from harmine -> harmaline, then from harmaline -> THH. Also from the spreadsheet above it appears to be able to happen endlessly, all the way until the harmine is down to 26%, almost no harmaline, and 70% THH! (assuming we are looking at a gradient of boiling lengths there, that's what I think anyway) Maybe the chemical is even more abundant than harmine to allow so much conversion to happen.
• Because I think this chemical is abundant in caapi, probably as much as the harmalas, I also think it would be a known compound. Unless it's a chemical that is highly abundant in caapi as much if not moreso than harmine, which also hasn't been discovered but I think it's unlikely. It's also possible maybe only a small amount of the compound is needed to for the reaction to proceed in large quantities, and I don't know chemistry, but that seems unlikely to me also.
• What fits the bill? I think maybe the tannin/catechin compounds make sense to me. https://www.ncbi.nlm.nih...pmc/articles/PMC2878139/ This study of caapi showed both epicatechin and procyanidine B2 were present in high amounts, higher than harmine in most of the samples.
• The only other chemicals which are quite high are banistenoside A and banistenoside B which are beta-carbolines I suppose could be breaking down to form THH. But I still don't think that makes sense looking at the spreadsheet above. It seems the ratio of THH to the both other compounds goes up, but the ratio between harmine and harmaline changes independently and the harmaline stabilizes down to a very low amount. It seems not only is THH going up, but harmine and harmaline both go down and at different rates. Maybe it's also possible there's some sort of donation system where these other b carboline molecules enable their relatives, harmine/harmaline to convert but hopefully that isn't the case.

• Cacao has catechin, epicatechin, procyanidin B2, proanthocyanidins, and tannins just like caapi does in high amounts. Hopefully boiling the harmalas with these would cause the reaction to proceed. Cacao is the highest but other foods high in those are apples, plums, fava beans...

Cocoa powder contains about 0.07% procyanidin B2 by weight (http://phenol-explorer.eu/contents/polyphenol/151) https://www.ncbi.nlm.nih.gov/pubmed/16719534 . Per previous study, looks like dried caapi stems can contain from 1% up to 8-10% procyanidin B2 by weight! Might have to use a lot of chocolate here. 5g of cacao is a serving size and caapi can contain up to 100x more procyanidin by weight. This combined with the much larger normal serving size of 100g caapi, sometimes even higher, this is at least 20x higher the serving size of chocolate/cacao. That study linked says "The correlation coefficient between Antioxidant Content and Procyanidins in chocolates was 0.92, suggesting that PCs are the dominant antioxidants in cocoa and chocolates." so could be up to 2000x more antioxidant compounds in a caapi dose than a chocolate serving, and people thought dark chocolate was a health food! One dose of caapi can contain more antioxidants than putting a 5g serving of cocoa in your smoothie every day for 5 years straight (barring intestinal absorption of course).

Looks like cacao powder contains 4x the antioxidants of cocoa though https://bodyunburdened.c...between-cocoa-and-cacao/ so luckily may not need as much if this conversion works.

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In the middle of boiling with 200g of cacao and not noticing much of a difference in the plates again... I'm thinking again about the PC content in caapi and it's just extremely high I think. Looks like for the dried stems the content hovers around 5% of total weight, which is just crazy high. There's multiple sources I'm not sure which for cacao but it seems to be at most 280mg/g PC content, or 0.28% but could be as low as 0.14%. So 20x-35x higher in caapi. And even with that much higher PC content the reaction doesn't appear to be instant, it seems to happen over many hours. I'm searching for other known plants which are at all comparable to that level of PC antioxidant content and I can't find many. Caapi is extremely high in it compared to everything else it seems.

Aronia berries have the highest proanthocyanidins in any fruit assessed to date with 664mg/100g, and that is in fresh weight so that may be worth checking out. https://en.wikipedia.org...Proanthocyanidin#Sources ... https://pubs.acs.org/doi/pdf/10.1021/jf0486850 Could be up to 4x higher dried if not destroyed in drying process so maybe up to 2.4g/100g, 2.4%, which is comparable to caapi. 10-20x higher than cacao at least. They may be worth looking at. Might get some just to eat as they are popular as a superfood. I see an extract on ebay, 1lb for $25. I'd hazard to guess an extract of those may very well be in the same range or even higher than caapi.

Edit: Also just found [Maritime] "Pine bark extract" is dirt cheap, can be found for 100g/$20 and it is 95% proanthocyanidins. 100g should then be equal to about 2kg of caapi in terms of the compound. So theoretically I'd only need to use 5g of the stuff per 100g seeds. Still not 100% if this is the cause of the conversion though, could be not even close or it could be the epicatechin causing it.

I'm gonna finish this boil but I don't expect it to do much. Will look into a couple of these plants with higher concentrations for future use.

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Was looking at this user's thread https://www.dmt-nexus.me...aspx?g=posts&t=41623 who had similar thoughts as me. This is the paper he quotes- https://catbull.com/alam...in%20aya%20decoction.pdf and it says "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 harmal alkaloids, which maybe lost through decomposition" I think it's clear they are not lost through decomposition from my tests, so must be "reduced during the acid process of decoction." Something else to note is the brew's pH there is ~4.75 and they say "naturally acidic conditions." Maybe caapi is that acidic naturally, something to remember, I will acidify thoroughly if I try next time. That poster suggests either a hydrogen atom donation from the acid or from the antioxidant. Still learning about this but I read one of the main ways antioxidants work is through Hydrogen Atom Transfer (HAT), so that would make sense to me. Also unless only certain acids work it seems like the theory that the acid alone is doing it is off the table, I tried boiling super low pH with citric acid and vinegar and neither worked. I think the antioxidant theory makes a lot of sense. Citric acid is an antioxidant too though and I used a ton of that with seemingly no result, so perhaps it must be that specific kind of antioxidant, or it has to be a super powerful one in high quantities like procyanidin B2. I think the antioxidant theory makes a lot of sense. That linked user's last post is trying to boil rue with vit c and acids to see if it would change, but no followup, I wonder if it worked. I tried boiling with some vitamin c (not as much as him) and a ton of citric acid. Mine didn't work either. He only added 3g vitamin C and some bioflavinoids(?). I know the ORAC of 3g vitamin C was only 6000 from the source i found http://healthymelbourne....09-at-1.05.17-pm-300x246@2x.png . Much less than my cacao which is 100k/100g and I used 200g. Just finished my cacao boil and again no discernible difference. I doubt his worked either. And cacao has pretty much the exact same antioxidants as caapi does. It was acidified but maybe I didn't acidify enough, the only thing I can think to try else would be to acidiy more to 4.75ish and use an equivalent amount of the same type of antioxidants.

First of all, thanks for putting the hours in with this, it's a question many here have pondered. Just a few thoughts Ive had; what if the river water used to brew caapi in the amazon contains something which could help the conversion? Also, what if the analyses on raw vine, presumably using a methanolic extraction, as is fairly standard, didnt pull all the alkaloids from the vine samples efficiently, whereas the analyses of brews had them freely available in the aqueous solution?

Liked your trip report of rue extract. Ive found that the experience improves after repeated use, less nausea for example, and mixing with lemon balm or lemon essential oil also improves the effects, as some other nexus members have also mentioned.

You'd probably enjoy the vds thread about converting harmaline to thh.

Glad you found it interesting also! I've invested a bunch of hours in this by this point so I'm a bit hooked.


I considered something similar to this in one of the above posts. My thoughts are, that pretty much every single time caapi is tested in a brew it has THH in it. I would think many different water sources would be common to use and everyone would use different ones. Also I think many of these analyses are probably on more modern day churches that use modern plumbing yet still find high THH. I have similar thoughts about the theory someone said here that the pot it's brewed in might affect it. Again I'm sure there are many different types of brewing containers with different materials among samples tested, which ubiquitously contain THH. I would think THH in brews wouldn't be universal if it was contingent on something so specific. We would see many caapi brew samples with little or no THH.


I can't say for sure this isn't the case but I think it's very unlikely. It seems unlikely that only THH would get left behind, and that everyone would make the exact same mistake over the many analyses of caapi which have never found anything like the 70% THH content we can see in some brews. We can look at endlessness' experiments https://www.dmt-nexus.me...aspx?g=posts&t=29967 and see methanol definitely pulls some of the THH, and that the A/B extract pulled comparable amounts.


Yes I still like the rue alkaloids, but I still feel caapi might be better. It's not terrible, I'm still eating them and they're great. But would be awesome to have a little bit better source of alkaloids as clean feeling as caapi for super cheap. I have seen the harmaline to THH tek but don't want to go that way. I like to keep things as natural as possible. Just eliminates the possibility for removing some potential benefit. For instance in my last post I just found the extremely high presence of antioxidants in caapi that seem to be wayyy higher than chocolate, you lose things like that when you go the synthetic way a lot. Also, I just feel it's too much work and would rather just use caapi if I had to go through all that trouble of using some synthetic chemicals in beakers with lab equipment etc. Ironic I say it's too much work because I put in so many hours to this. But I think it could be a good investment if I find a way for me and others to have a cheaper more abundant source incase it becomes difficult/expensive to get caapi.

What about trying long duration boiling/brewing in like an aluminum or zinc containing pot? I think i've read about that on here how that could be a possibility in the conversion of Harmaline to THH. I still haven't more fully read up on the Harmaline to THH conversion.

Addressed that above but I think that is unlikely. I think THH content is too ubiquitous among all tested brews for every single one of them to be using aluminum. I bet there's many different materials people use. Plus I'd be quite worried about heavy metal contamination if that was why all caapi had THH in it! Would probably just use rue forever at that point. I think we should often see aya brews with little to no THH if that is the case (some sect/group is bound to use a non aluminum pot) but so far I haven't seen that in any study analyzing the alkaloid contents of the brews.

Quite a wall of text but my conclusion near the end is that I think (I'm no chemist just my guess) it's the antioxidants/tannins in the brew doing something. One main way antioxidants do their job in our bodies/nature is by donating hydrogen molecules. That would make sense with one of the studies proposed reduction under naturally acidic conditions where a H gets donated at each step. https://catbull.com/alam...in%20aya%20decoction.pdf (4th page). Specifically procyanidin B2 and epicatechin, 2 of the most abundant chemicals in caapi (even moreso than the harmalas). I tried boiling with cacao which contains these also but it didn't have any perceptible change. Though I did not acidify it to a bit below 5 like that paper states. Plus I added 200g cacao which should only have had at most 300mg of procyanidin B2 for my 100g of rue. 100g of caapi would contain 15x-20x that amount. I'd guess the conversion to THH is slow per the excel graph above, even with the much higher antioxidant levels. My guess is either there was some change but it was so small I couldn't notice, much more of the antioxidant is needed, or I didn't acidify enough, or both. I will be getting aronia berry extract which should have comparable levels of those antioxidants to caapi and I think I'll try that in a week or so.

Got around to doing another test, this time with aronia powder (similar tannins/antioxidants to caapi) highly acidified boiled for 8hrs. Again something strange is happening with my TLC due to excessive citric acid so the results weren't very clear. But I am almost certain there is not much if any change at all. Damn! Well I give up I think..

I initially thought the acidity component might be more important as the only study we have showing both ph and THH levels is https://catbull.com/alam...in%20aya%20decoction.pdf and it shows quite a low pH, I think it should be assumed a pH level at least this low is necessary (at least for this experiment) since this is the only concrete data I have. I wonder, did the caapi alone acidify the brew that much? I have read some posts saying amazon river water can be quite a low pH which could be causing it.

...So I made sure to acidify it to below 4 this time and boil for 5 more hours. In total 8 but first 3 pH was not as low as that. Still no dice. Will do a mankse but from a crappy TLC that was kind of hard to make out, it was clear there was still a ton of harmaline and no yellow spot to be seen for THH.

If it's not directly the acid, or the long boiling, or the antixoidants presumably... What else could it be? Now I'm thinking it could be some enzyme activity after coming across Mindlusion's post in this thread https://www.dmt-nexus.me...osts&t=35984&p=2 . In that endlessness does a cold water extract of caapi plants. The levels of THH are clearly quite high. Far higher I believe than in his caapi analysis thread https://www.dmt-nexus.me...aspx?g=posts&t=29967 . In which most had a 2% or less THH level, the highest being at 8% but the rest were 3% or less of total alkaloids. I believe my rue extract is quite close to this and had identical levels with cwe, boil, and vinegar boil. The low percentages of THH in rue look like an extremely faint glow. I believe if he TLC'd those methanol extracts too there would be almost none visible. If it was enzyme activity causing it that could explain the difference in cold water extraction and a methanol soak which would probably kill of everything in there I would imagine (no chemist just speculating).

I wondered if there might be a difference in fresh/dry samples alkaloid levels. I graphed the difference in excel (attached pic) from this study https://www.ncbi.nlm.nih...pmc/articles/PMC2878139/ to see. I was recently reading a phalaris thread where they said dry/not dry extractions yielded totally different alkaloids, due to enzymes somehow. There does appear to be a difference in alkaloid levels, but looks like mostly only harmaline here. But it shows there is at least some changes when drying probably due to enzymes? Also, interestingly, many of the dry stems even had very high THH levels matching the 70% we see in some brews. Could the 1:1 THH level in all caapi plants be a myth? But endlessness' had similar results in his caapi analysis thread. Well, another thing is in this study-



They did a cold water extraction... Also, the study which is often referenced showing 1:5 THH:Harmine in brews... https://www.docdroid.net/TyWUpcs/callaway2005-pdf Did a methanol extraction..

I'd like to see someone compare CWE and methanol extraction of the same plant. Could this be the enzymes doing some work? Or even just simply solubility differences in THH from the other two? The fact that we see 70% THH in the graph below in some plants makes me think it could be some fumble with the methanol not dissolving THH with such high levels getting lost... But remember this was a CWE- just like endlessness' THH thread which also showed what appeared to be very high THH levels equal or greater to harmaline at least in spot size- way bigger than mine which are almost not visible.

I think this is due to some enzyme that gets activated/deactivated by water and maybe heat. So yeah I think the simple way to prove this is to do a methanol soak, cold water extraction, and a long boil and compare them all. I think methanol soak would have little THH, the CWE and the boil would both have high THH, and the boil might also have lower harmaline levels I think.

Thanks for all these experiments, that is excellent knowledge for the community!

It might have to do with enzymes in caapi, as you suppose I don't know. But also, isn't it possible no conversion happens at all due to boiling, and that aya brews analysed in most aya research showing high THH is simply because it was fresh caapi used to make them, versus the old stored dried caapi used in my own analysis thread and other analysis mentioned by Callaway?

I'd still like to know more details from McIlhenny and Callaway's findings to understand how they arrived at their conclusion, what kind of controls they did in their research.

Hypothetically THH could be converting back to harmine over time, so fresh caapi might be essential for high THH brews