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THH - Harmala Holy Grail

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professor8

Rising Star
A while back I read a very good explanation of the different effects of Harmalas that has stuck with me. I believe it was 69ron that said: ‘Harmine is the Coffee of the harmalas & Harmaline is the Weed and when it comes to THH (tetrahydroharmine) you have The Light.'

Whilst very similar in molecular structure, THH has a completely different personality to Harmine & Harmaline. Calling it The Light of the harmalas is very appropriate. IMHO, it is the Holy Grail of The Harmalas. I have found Harmine very, very helpful in Meditation & Yoga. It energises your Light Body and allows you to see your Chakras & Auric fields; very helpful in a biofeedback sorta way ;)
Personally, Harmaline is too heavy & stony for me but I do respect its power and personality, kinda like a big shaggy & lovable dog.

While we are all aware of the MAOI effects of the Harmalas I would like to suggest additional effects I have noted that our current version of scientific enquiry is ill prepared to explain. For the scientists out there please bear with me, I have found a dramatic increase in Energetic Vibration from the direct use of Harmalas in any form by any means of ingestion. This is as true for drinking Caapi tea as it is for bong hitting rue seeds.

Chakras.jpg

This Vibration can be felt as light headedness or slight dizziness accompanied by feelings of well being and connectedness. It indicates a move up the etheric spiral towards your higher self. Sometimes accompanied by a slight nausea, that goes away as your complementary bodies move into alignment. It is the same energetic feeling you get from doing Kundalini exercises or the tingly afterglow of orgasm. By cultivating this Vibration and slowly allowing it to increase over time you will find you are more psychic, intuitive, compassionate & can bend time at will. Yes, you read it right, Bend Time At Will.

THH has the ability to raise your vibration in a most powerful, yet subtle way. It brings a crystalline prismy texture to spice and adds a super clear watery dimension to Aya, like looking down through 10meters of shimmering Caribbean Sea on clear blue day. It brings a dimension of pure light to the entheogenic experience and encourages entities & intelligences of only the Highest Order. If one is not accustomed to perceiving these experiences with a spiritual perspective most of the nuances & subtleties THH brings on are overlooked and remain unseen and one would better enjoy Harmaline as a house painter chooses a roller over a brush, its about preference & choice.

THH seems to be more concentrated in Caapi leaves rather than the vine, this explains the lighter feeling I get from Caapi Enhanced leaf vs. Aya Vine Tea. There is ample THH in the Vine but more Light in the Leaf ;) I am unsure of the content in Rue, but I have read that Harmaline CAN be converted into THH in a reduction process. I’ve yet to try the Hcl/Zinc method but follows is a very simple oxidation & reduction process using Ascorbic Acid. The initial yields are low but the results are fantastic as I was left with THH & Harmine, harmalas I know and love :)

______________________________________________________
Harmaline to THH (Trail 1)

First I dissolved 20 500mg Vitamin C (Clicks house brand) in hot water, I let the binding agents settle & decanted through a coffee filter into a pot. I then added 1.16g of Harmaline and brought the mixture to a gentle boil. The liquid turned orange/yellow and I covered the pot with a pyrex dish with ice to let the reaction reflux and the H202 to circulate through the solution. I left it to gently boil adding a bit of ascorbic acid water twice to make up for evaporation.

Gradually the solution lightened up a little but never went clear. Little precipitates began to form and I rightly assumed they were particles of the Vitamin C binding agent that had begun to clump together.

After 3 hours I removed the solution from the heat and filtered to remove the inert precips.

I carefully & slowly sprinkled in Bicarb until it stopped reacting. I was very careful to not add too much and bring the solution to a PH of about 7-7.2 as I read that the PKa of THH is 6.9

And like magic a very fine precipitation began. I let it react & settle for an hour & filtered. I then raised the PH to about 9 and watched another round of precipitation.
After Drying here is what I had.

THHprecip.jpg
HarmineReduction.jpg

THH as a gray fb __________________________________ Harmine fb

I have bioassayed both and am sure that I have both Harmine & THH as a result, the THH is as good, if not better than FV's THH HCl

I do not know the underlying chemistry behind such a transformation but am more than happy to chalk it up to Alchemy. I will further reduce the Harmine and a control sample of Harmine HCl and see what happens but in the long run I am quite pleased to convert my Harmaline in this manner even if the conversion is only 60%. I know I can get this figure up after more trials :)

Peace Professor8
 
Thanks you Professor8 for this nice post ,i thought that the zinc reduction was the only way to convert harmalas to THH but i was wondering;do you have a method to convert harmine fb to THH without doing the zinc reduction ?

I have no access to harmaline since its a controlled substance in Canada
 
Wait what? So how are you so sure that you have THH there, just bioassay results and the fact that it precipitated before with lower pH? Did you consider placebo and previous contamination of harmalas?

and what was that you said about adding h2o2, as in, hydrogen peroxide?! Or was that supposed to be just h2o, water?

How pure was your harmaline to begin with? Are you sure there was no harmine contaminant in it?

and also do note that FV's THH is not THH.. This information will soon be out.
 
Dagger said:
I think both are harmine. Your original harmine is dirty brown. Your final result is just more pure.
I agree. Here’s a photo of a small caapi extraction I did recently. Notice that the precipitate is almost white.
 

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endlessness said:
and what was that you said about adding h2o2, as in, hydrogen peroxide?! Or was that supposed to be just h2o, water?

Never added, its a by product in the reaction

Nobuoni said:
Add your Harmine/Harmaline to a strong solution of ascorbic acid and H2O' and heat gently' until the yellow colour has changed to a clear solution'
Of what happens is the ascorbic acid attracts the oxygen and the production of H2O2 donates a hydrogen'
Hydrogen peroxide H2O2 acts as a reducing agent in acid solutions' and is produced by boiling ascorbic acid in H2O'
This natural production of H2O2 is enough in this reacion to add the H ion to the Harmine mole' after the oxygen has been attracted by the ascorbic acid'
The process slows down in acid solutions' but works faster in alkaline'
The stability of ascorbic acid decreases with increases in temperature and pH.
Of which means heat and increased ph makes for the ascorbic acid to attract even more oxygen'
In this reaction the ascorbic acid is oxidised' hence destoyed'
So more ascorbic acid is added to the gently boiling solution as required'

...Anyone wish to attempt to crunch the chemistry with me ???

Heres the Thread: THH extraction tek - Harmalas - Welcome to the DMT-Nexus

The gray powder is definately not Harmine or Harmaline and at 50mg subling gives very blissful effects alone and great MAOI effects with spice.

Dagger said:
I think both are harmine. Your original harmine is dirty brown. Your final result is just more pure.
The 2 photos are the 2 different precips I recovered not the initial Harmaline (which may have contained up to 10% harmine)
I know this procedure requires Harmine/Harmaline but I though I'd start with Harmaline as it a less desirable harmala for my tastes 😉 In the long run I am very pleased with the effects and if 'Real' THH is better than this than I wonder why there arent even more conversion teks. Anyway, I believe Soulfood tried this out but Nobuoni hasnt posted again on this topic. Has anyone else tried it?
 
professor8 said:
The gray powder is definately not Harmine or Harmaline and at 50mg subling gives very blissful effects alone and great MAOI effects with spice.

How do you know this fur sure? Only by the coloring of the substance? How can you be sure that you not only just divided the harmine and harmaline?

I recently did two different rue extractions, one is very crude and used vinegar, this resulted in a reddish end product that needs to be cleaned up further. The other one resulted in a off white and very fluffy powder.

I hope to have the fluffy powder tested soon as to see what it exactly contains. What I wanted to say with this is that you can have a different colored end product that will likely contain the same products.


Kind regards,

The Traveler
 
Wow...

Look the vast majority of harmine/harmaline that people purify using typical techniques on this site do not lead to pure products (ie harmine/harmaline). They are loaded with what SWIM believes are phenolic compounds (i have a post about this somewhere but that was a long time ago) which can be removed by recrystallization and are a deep red color. They are definitely not alkaloids whatever this red stuff is. SWIM extensively analyzed this material and it is not amendable to GC even upon derivitization with trimethylsilyation (very common reagents used to make compounds more volatile and more heat stable).

I believe this material has been called harmala red and its been claimed that this material is a break down product of harmine or harmaline. That is false. Its always there when you extract this material from peganum harmala (using NaCl precipitation or NaCl with base etc etc) you just don't know about it unless you do further purification.

The more these phenolics or whatever they are, are removed the less tan and less yellow the harmine/harmaline mixture becomes.

Therefore the vast majority of dosage information on these compounds is somewhat incorrect.

So I think all that's happening is you are cleaning up your product and getting a more potent dose. Also the ratio of harmine/harmaline varies a lot in peganum harmala sometimes you get 1:1 ratio sometimes you get mostly harmine.


Reducing harmine or harmaline to THH requires STRONG reducing reagents. Like sodium borohydride. Absorbic acid I highly highly doubt would cause such a reaction to take place.
 
Burnt, as I argued with you before, while I concede maybe in some cases some people may simply have some red contamination in the first place, I have seen it myself that something red can form from very clean harmalas. As I said in that link, while I dont have access to analytical equipment, a few times I purified my harmalas obsessively with endless amounts of freebase precipitations to get something like this:


And once I made an experiment of redissolving these harmalas in warm IPA (which didnt dissolve them too good), and re-evaporating. After repeating this a few times, each time it was getting more and more red. Doesnt this point out that there is some sort of reaction, possibly oxidation? If not, where can the red be coming from if there is absolutely no other process being done other than redissolve and re-evaporate? I remember ron claimed this happened with redissolving harmaline hcl in alcohol.

Do we have any information on what harmine/harmaline n-oxide looks like?
 
endlessness said:
Burnt, as I argued with you before, while I concede maybe in some cases some people may simply have some red contamination in the first place, I have seen it myself that something red can form from very clean harmalas. As I said in that link, while I dont have access to analytical equipment, a few times I purified my harmalas obsessively with endless amounts of freebase precipitations to get something like this:


And once I made an experiment of redissolving these harmalas in warm IPA (which didnt dissolve them too good), and re-evaporating. After repeating this a few times, each time it was getting more and more red. Doesnt this point out that there is some sort of reaction, possibly oxidation? If not, where can the red be coming from if there is absolutely no other process being done other than redissolve and re-evaporate? I remember ron claimed this happened with redissolving harmaline hcl in alcohol.

Do we have any information on what harmine/harmaline n-oxide looks like?

To add a bit more information to that: Recently I am experimenting with rue extraction by IPA. I put the rue in a blender, blend in into a fine powder and then add IPA to it.

What surprised me was that when I added vinegar to that mix it instantly turned red. The redness would stay the rest of the process including the manske. When no vinegar was used the red would stay away and I would end up with a nice off-white powder, just as the image in your post.


Kind regards,

The Traveler
 
Good points. I should also add that I nothing I say on this issue is conclusive at all! Color reagent tests are weak indicators. SWIM also did not do this on very pure material. The crude material after manske was recrystallized from ethanol.

If it was somehow converted to harmalol it would have showed up in GC for sure especially after derivitization. Although harmalol does form red needles when crystallized from water. Its solution is reported to be yellow.

One reason I am skeptical about harmine or harmaline turning into something else when mixed with ethanol is that in the MERCK index it sais that they can be crystallized from ethanol or methanol. Why would the MERCK index say this if it caused some kind of weird reaction? I don't expect an answer to that but its got me puzzled.

N-oxide is possible product. Only way to measure is TLC or HPLC preferably with MS. Mystery remains for now...

I'll be quite about this puzzle until there is more proof.
 
nice tek professor8
haha those that have tried this or something simmilar and have tested the end product know its not pure harmine - perhaps it has some harmine - but fx wize its quite diff.
somethings changing - and and making more desirable - far more so than just purification - as iv eaten solid xtals of both now - very diff.
 
Burnt thanks for the mass spec printouts! Taking the time to do that is most appreciated :)
very interested in the FV results; the other day Baron told me he was switching to fb and sent me samples, I should be getting them tomorrow...

Elegant simplicity is always rewarded. I believe there's no such thing as an objectively pure product or reaction, but the quest for subjective perfection is easily attainable when the alchemist becomes the gold he thinks he is searching for; and it can happen anytime, anyplace, why not in a kitchen ;)
 
why is it that lately all new ideas or teks are rather criticized or said to be defunct/placebo - back in the day the nexus was a place where new ideas were positively received.
i kinda became inactive for simmilar reasons.
 
Phlux- said:
why is it that lately all new ideas or teks are rather criticized or said to be defunct/placebo - back in the day the nexus was a place where new ideas were positively received.
i kinda became inactive for simmilar reasons.

phlux, you should know me better than to think im personally offending you or going against new ideas.

I think one of the great things about this forum is that we dont take ideas at face value but try to think critically, consider the different variables. For example, if you've been following the flowing visions THH controversy, you should be well aware that MANY people were completely sure without a doubt that they had THH and that it was better than other harmalas, and truth is, it was never THH.

Dont you think its completely reasonable that I question when someone starts talking about how the effects are different, that I at least bring up the possibility of it being placebo? I never accused you of lying or never said its for sure placebo, I am just considering the possibility and I think the notion that self-suggestion can have so big effects is something that more people in this forum should think about IMO.

I naturally have a skeptical way of analysing things, which doesnt mean im not open to new ideas, but rather than accepting first and asking questions later, I rather ask the questions first and let truth and science speak for themselves. No need to worry about some tek you made or bioassay not being accepted, if it works, it will eventually be seen and tested and proven so please, keep experimenting and posting ;)
 
no no end - sorry man wasnt aimed at you at all i know it came off sounding a bit that way and i was conscious of it at the time of wrighting it
and i know the member that made the op in real life

he, like myself has many many many years of entheo experience, both of us also seem to be analysts at heart so we both approach things with great skepticism.

Constructive Critisizm is the way but when it outweighs the positive feedback, and thus motivation (for some - myself incl) it makes some think twice before posting new ideas.
 
Burnt, as I argued with you before, while I concede maybe in some cases some people may simply have some red contamination in the first place, I have seen it myself that something red can form from very clean harmalas. As I said in that link, while I dont have access to analytical equipment, a few times I purified my harmalas obsessively with endless amounts of freebase precipitations to get something like this:


And once I made an experiment of redissolving these harmalas in warm IPA (which didnt dissolve them too good), and re-evaporating. After repeating this a few times, each time it was getting more and more red. Doesnt this point out that there is some sort of reaction, possibly oxidation? If not, where can the red be coming from if there is absolutely no other process being done other than redissolve and re-evaporate? I remember ron claimed this happened with redissolving harmaline hcl in alcohol.

That stuff does look clean. But its still possible red component is 'hiding' within that powder. Another potential test would be to try to destroy all the harmaline with alcohol but who would want to waste it ;)
 
burnt said:
Burnt, as I argued with you before, while I concede maybe in some cases some people may simply have some red contamination in the first place, I have seen it myself that something red can form from very clean harmalas. As I said in that link, while I dont have access to analytical equipment, a few times I purified my harmalas obsessively with endless amounts of freebase precipitations to get something like this:


And once I made an experiment of redissolving these harmalas in warm IPA (which didnt dissolve them too good), and re-evaporating. After repeating this a few times, each time it was getting more and more red. Doesnt this point out that there is some sort of reaction, possibly oxidation? If not, where can the red be coming from if there is absolutely no other process being done other than redissolve and re-evaporate? I remember ron claimed this happened with redissolving harmaline hcl in alcohol.

That stuff does look clean. But its still possible red component is 'hiding' within that powder. Another potential test would be to try to destroy all the harmaline with alcohol but who would want to waste it ;)

I have some nice off white powder from a rue extraction. The off white powder came from an extraction that didn't use vinegar or any other acid. When I did the same type of extraction with vinegar, when the vinegar was added the liquid turned almost instantly red.

I will now dissolve a little bit of this off white powder in alcohol. If it doesn't turn red I will add some vinegar too. I keep you all updates.


Kind regards,

The Traveler
 
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