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Conversion of Harmine->Harmaline->THH by simple boiling (and storage?)

Migrated topic.
Greetings gang!
Couldn't help but dive back in and shed some light on my travails. Again, I ask simply of you to repeat the experiment before pontificating on the reasons why it wont work. As an Alchemist before a tribunal of chemists. I respect your opinions and hold them as just that. Peace be on you :)

I call this substance Ǣtherithine. A mixture of Harmine & THH.

Dictionary said:
ǣther (ē′t̸hər) noun

1. a substance hypothesized by the ancients as filling all space beyond the sphere of the moon, and making up the stars and planets
2. the upper regions of space; clear sky
3. Rare the air
4. Chem. any of a series of organic compounds having an oxygen atom linking two carbon atoms from two hydrocarbon radicals, generally ROR; esp., ethyl ether, a volatile, colorless, highly flammable liquid, HCOCH, prepared by the reaction of sulfuric acid and ethyl alcohol and used as an anesthetic and a solvent for resins and fats.
5. Physics a hypothetical diffuse, invisible medium formerly thought to pervade space and transmit light, heat, etc.
Click to expand...
* The first 3 definitions do it for me.

FURTHER NOTES & DISCOVERIES on Aetherithine

Ok heres a few more things I’ve found that should help you along the way.

Start with Harmaline rather than Telepathine.

This Ǣtherithine process Will convert your Harmaline to a balanced mixture of THH & Harmine by oxidation using Ascorbic Acid. This ratio can be anywhere from 20:80 to 80:20 and anywhere in between depending on all the variables a kitchen alchemist faces during an op. Ǣtherithine is a subjective substance. Most of all be of Clear Intent and Positive Heart. Your attitude & intention DOES have an effect on your OUTCOME.

There is no such thing as an Objective Procedure. You are creating something sacred which few people will ever have the opportunity to experience and you will be forever changed in the process. Such is the way of the Alchemist.

Read the process described previously over Carefully (THH - Harmala Holy Grail - Harmalas - Welcome to the DMT-Nexus). See yourself doing each step in your head before you start.
Below are a few tips to make it happen:

Make an Ascobic Acid solution by dissolving 20 500mg Vit C tablets in 500ml of water. Filter through a coffee filter. Note: Obtain as pure a sample of Ascorbic Acid as you can; there was some adulterants in other generics I tried that resulted in failure of conversion & loss 80% loss of Harmaline.

Set up your reflux device by using a pyrex glass pie dish filled with ice cubes. You will have to add new ice cubes or better yet, make a couple of 1 or 2 litre blocks the night before.

The 2 hour reaction time is essential. Add about 40ml of the Ascorbic acid solution every 20minues. You’ll be able to smell the H2O2 as it is used up in the reaction process the reaction.

Slow boil works best. After a while you will see little precipitates in the solution, this is the bonding material in the Vit C tablets and you must filter the solution through a coffee filter WHILE it is still hot. Take the pyrex lid off during the last 20minutes and let the solution evap down to 200ml. It is easier to work with at this concentration.

Now you have an acidic solution of THH & Harmine. To separate them take advantage of their relative pKa’s by slowly adding Bicarb a little bit at a time. If the solution is still hot it will react quickly & may bubble over so take your time and do this very slowly. Add bicarb to slowly raise the pH to Between pH 7.5 - 8 your Ǣtherithine will begin to Precipitate. You can max it out with the Bicarb to just over pH 8 and then Filter. You can further raise the pH with Sodium Carbonate and filter again to see if there is any Harmaline left.

You should net Ǣtherithine in amounts of about 50% of the original amount of the Harmaline you used.

Good Luck and enjoy. 50mg subling works great before a changa journey and 150mg to 200mg will orally activate DMT with magical effects unlike the 3 aforementioned harmalas. The effects are much clearer than Harmaline or Harmine and very blissful. Ǣtherithine is about 1/3 as strong as Harmaline & 75% as strong as Harmine. It is a very spiritual & high vibration MAOI.
_______________________________________________
I am sure those of you with better equipment can easily reproduce and refine the process. Remember this is more of an Alchemical procedure than anything so your Intention & Mindset will dictate your results. This may be a bit difficult, but not impossible, for the more empirical of you out there, but I invite you to have a hand at this simple alchemical experiment.

(Edited for clarity in procedure)
 
How pure is your harmaline in the beginning? What process do you use to ensure your harmaline is pure?

Even if this is *only* ultra pure harmaline as some may say, it is by far the smoothest harmaline I have ever tried! And so the process is worthy of investigation!

200mg of this taken sublingually, was like a fluffy powder under the tongue which barely tasted of anything! Five minutes later I chased it down with water. It worked well to catalyse a brew of 8 grams of Chaliponga. (I personally recommend drinking Chaliponga this way to really experience its plant spirit and what it has to offer!)

Next time, I would do 250mg or even 300mg just to see how that was different. But in these situations where I want to really experience the plant essence, with as little of an MAOI imprint as possible, I think Aetherithine really does the trick! :)
 
Harmaline doesn't convert to THH by oxidation, it is a reduction reaction (so double carbon bond is replaced by 2 hydrogens).

Ascorbic acid does not have a strong reduction potential. It might reduce harmaline to THH, or it might not. TLC using ethanol:ammonia at 100:2.5 as eluent could easily tell them appart and say if it worked, you could try looking into it, professor8.

I think it's cool that you experiment! After all, experiments are the basis of this community, so thanks for that!

But a big problem, and something that I would ask you to please be mindful next time, is that you pass assumptions as facts. Until at least TLC or mass spectrometry has been done, you have no idea if the reduction conversion worked. So to say with so much confidence that "you have THH and harmine" is out of place until you can prove so.

To spread speculation as facts lowers the reliability of information in the Nexus. A simple change to "it seems by subjective experiments that the product contains THH and harmine", or "we speculate that the product is THH and harmine" , or whatever else, would make worlds of difference.
 
Well, as far as I understand it, the jury is out and it would be good to get this material tested to find out for sure what this material is.

Big props to Professor8 for sharing his tek here, and coming up with the smoothest MAOI I have ever tried! :)
 
hmmmh....we wonder if/or how the ̶c̶̶a̶̶s̶̶t̶̶ ̶̶i̶̶r̶̶o̶̶n̶ dreaded aluminum pot contributes to this ̶̶f̶̶i̶̶n̶̶d̶̶i̶̶n̶̶g̶̶s̶̶ hypothesis? Many wasterners instruct others against using it for brewing ayahuasca, while it is most commonly & conveniantly used in the Amazon.....
397px-Oxisol.gif

..for unknown reasons this made us also think about oxisol type
of soils..:? edit: perhaps from this angle: why did the ancient
Avestan speakers give so much importance to what (kind of) "river
water" was used for haδanaepata preparation? But we don't know......
 
Acetic acid and FE iron is a common reduction scheme.
That being said, it's GLACIAL acetic acid that is used, so...
Ascorbate hasn't much reduction potential, and no oxidative properties to my knowledge (its actually an antioxidant, clinically), but it had some, and as the basic nitrogen is involved in the double bond systems, let's not rule out ascorbate reduction.
Oxalate would do it, though (anyone read that article on Wikipedia with the reference to Oxalis roots containing reducible compounds like these? Oxalis contains oxalate...), and formate is a preferred reductant.
To my recollection, acid catalyzed means the acid is not present in a large proportion, or other wise present in quantities insufficient to be effective as reagent are required for catalysis...so, a dilute acid solution if any kind may be used if it's merely a proton source, but most organic acids do not dissociate sufficiently to work as catalysts in a dilute solution.
Notwithstanding, the starting material needs to be assayed for identity and purity to do decent science...
 
This is fascinating.

jamie said:
so in theory, this should apply to rue as well I would assume?
Click to expand...

I've taken ACRB with rue both parachuted and boiled 3x for 1 hour each, then reduced, and there were big differences in the resulting experiences. Parachuting the rue, the acacia is firmly in control, while with the rue boiled for a prolonged period resulted in a completely different experience, with less DMT geometry and more cartoonish visions with a female ferry type entity. I should note also that when I parachute the rue, I take that 20-40 min before the light plant, while each time I brewed the rue, I combined the two and consumed together.
 
Any more data or clues about this technique? (because this post is not really conclusive)
Any rue extract that has been boiled down a lot should show THH, if this hypothesis is true (but let's see the quantitative aspect...). By now, we should be able to prove or disprove that?!
 
Nice bump. Missed this thread as I was offline for a while.

endlessness said:
Due to the chemical bonds, is it less favourable for harmine to turn into harmaline, than to harmaline turn into THH ? Can one get an "optimum" ayahuasca alkaloid content by messing with cooking time/storage?
Click to expand...

Without having done the calculations, it's still highly likely that a molecule of harmine plus a molecule of THH have a lower net energy of formation than the equivalent two molecules of harmaline through the aromatic resonance stabilisation energy of the pyridine ring in harmine.

Regarding ascorbic acid, if it reduces harmaline to THH, it doesn't simply disappear completely. The ascorbic acid is correspondingly oxidised to dehydroascorbic acid. This substance may well be capable of receiving hydrogen atoms from another harmaline molecule, wherein the acid is reduced back to plain ascorbic acid and the harmaline is in this instance oxidised to harmine.

What this effectively means is that, should both of these reactions in fact occur, ascorbic acid would be acting catalytically to effect the disproportionation of harmaline into harmine and THH. Which is nice :)

Which brings me onto this:

I've had a bottle of syrian rue tea in my refrigerator for two years! Thankfully it has been preserved with strong alcohol, which is why I haven't really touched it for these past two years. I've simply never got round to distilling off the alcohol and I didn't want to ingest a combination of harmala alkaloids with alcohol, nor risk messing up any kind of base or Manske precipitation attempts. The tea was even made using ascorbic acid, IIRC!

This would be a good reason to press onwards with the experiment. We know that syrian rue typically contains a lot of harmaline and not much THH. Should a sample of the resulting alkaloids turn out one way or the other, well, we'd have another data point to be working from.

The lab beckons!
 
Well, I ended up drinking the rue 'jenkem' (it was fine, the alcohol had preserved it very effectively for over five years, and those years in the fridge had also caused all the sediment to precipitate out.) It was smooth enough but then I've done a few stints of daily rue making me practically immune to the nauseating effects that some speak of.

In the meantime I've got as far as precipitating a good ole heap of crude rue freebase after multiple low liquid volume PC cooks on 1kg rue seed. Each 1.7L cook was acidified with 10g ascorbic acid. Now, it would be better to compare like with like, but the effects of 300mg of the crude freebase precipitate was very smooth while rue tea from 3.5g seeds cooked in an open pot had much more, if not quite dizziness, at least disequilibrium from sensory buffering which seems to be very much a specific effect of harmaline. (I personally rather enjoy the harmaline sensory buffering, particularly the auditory effect.)

The other confounding factor in this comparison is that the current batch of alkaloids is from the later batches. The first three PC boils were precipitated separately, while the remaining 9 boils were precipitated in further batches of three as these 1 gallon amounts were reasonably convenient to handle.

I'm somewhere on the cusp of preparing my own TLC plates (now, where did I put that gypsum?) and, fingers crossed, I'll get some kind of results for the alkaloid profile from these ascorbic acid PC cooks in rather less than 3-5 years :lol:
 
downwardsfromzero said:
...In the meantime I've got as far as precipitating a good ole heap of crude rue freebase after multiple low liquid volume PC cooks on 1kg rue seed. Each 1.7L cook was acidified with 10g ascorbic acid...
Click to expand...
This link:
...The results show that the highest destruction of ascorbic acid or vitamin C occurs at temperatures between 85 and 95°C, especially after 10 minutes of cooking time.
Click to expand...

Will decomposed vitC still perform it's duties in the reduction process?
Thanks.
 
It's not clear from the IJAR paper whether the decomposition is purely thermal, or whether atmospheric and/or dissolved oxygen - or, indeed, the material of the cooking vessel - are in part responsible for the destruction of the ascorbic acid.

As far as the rue PC cooks go, there's a considerable time window during the heating and, especially, the cooling phases where the temperature is outside of the decomposition range found in the paper to which you linked. Add to that the limited amounted of oxygen present in the sealed vessel and should be clear that there's plenty of time for the ascorbic acid to act as a reductant.

What the IJAR paper was never intended to consider is whether the decomposition products of ascorbic acid can also act as reducing agents, what those decomposition products actually are, and what happens to any other components present in the ascorbic acid/porridge mixture during the thermal decomposition process. Part of the "decomposition" may involve reduction of reducible species...

To re-iterate, during the heating process with the rue in the PC the vitamin C will be able to act as a reducing agent and this will be "destroying" the vitamin C. The object of the IJAR paper was to investigate the nutritive value of porridge, not to identify the reactions of the added ascorbic acid.



I've gradually increased the dose of the ammonia-precipitated crude PC/ascorbic rue alkaloids up to 400mg and, while there is still no sign of any harmaline-like (auditory/sensory/equilibristic) activity, harmine-like MAOI activity is apparent - but, I'm sorry to say, in the course of doing so I've not yet got around to performing any further attempts at separation, identification or chromatography. [EDIT - I should emphasize, there is still a strong green glow from a solution of the material which does suggest the presence of at least some harmaline, so either I may have become tolerant to harmaline's 'sensory buffering' effects, or the concentration of harmaline in the mixture may be low enough that those effects do not manifest at that dose.]

So, in the absence of personal experience with confirmed samples of THH it's still too early to say for sure whether this PC/ascorbic acid reduction takes place - especially in the absence of a control case - but there are some clear hints that it may at least be worth replicating by those who have access to plentiful rue and pure ascorbic acid powder (and, of course, a stainless steel pressure cooker).

If any of you out there do decide to replicate, please be sure to include a control case which uses a non-reducing acid.
 
downwardsfromzero said:
...The object of the IJAR paper was to investigate the nutritive value of porridge, not to identify the reactions of the added ascorbic acid...
Click to expand...
:thumb_up:
 
Downwardsfromzero, your pc cooker acts just like the reflux pot setup made by Professor8 when he reduced harmaline to THH in 2 hours using very pure ascorbic acid (you can buy 100% pure ascorbic acid on-line, only use this). Ingenious! Great work. Test the glow under blacklight to see if she turned from the harmaline green glow to light blue of THH. Dab a cue tip in vinegar, take up some of the harmline/THH, smear on a paper plate, hold under UV light...if you have blue glow, then you made THH.
 
ava69 said:
Downwardsfromzero, your pc cooker acts just like the reflux pot setup made by Professor8 when he reduced harmaline to THH in 2 hours using very pure ascorbic acid (you can buy 100% pure ascorbic acid on-line, only use this). Ingenious! Great work. Test the glow under blacklight to see if she turned from the harmaline green glow to light blue of THH. Dab a cue tip in vinegar, take up some of the harmline/THH, smear on a paper plate, hold under UV light...if you have blue glow, then you made THH.
Click to expand...
I used pure ascorbic acid powder, which is available off-the-shelf in my part of the world. The conversion is not complete, because there's still a yellow-green harmaline glow to solutions of the material. I could attempt a further reduction of the crude alkaloidal material by cooking it with a further amount of ascorbic acid but at this stage a TLC analysis would be the most informative step.

I'm also planning a replication using higher amounts of vitC (and at a lower temperature, based on Jees' comment), and another batch using none. It's just a question of priorities at the moment.
 
Re-reading proffesor8's post, his claim - or the one he reports from Nobuoni, at least - is that dissolved oxygen acts as a transfer agent of hydrogen form the ascorbic acid via the formation of hydrogen peroxide. And yes - H²O² can absolutely act as a reducing agent under certain conditions, such as when it reacts with permanganate, for example.

This would appear to imply that simply adding H²O² to the (acidified?) harmaline solution should achieve the same end (whatever the result may actually turn out to be...) It also implies that the pressure cooker anvironment may be less than optimal for the ascorbic acid reaction if dissolved oxygen is required as the hydrogen transfer agent.

And indeed, that's what Nobuoni suggested here. For me the main question might be - do we think any of this is worth revisiting?

The first thing to do is probably checking on the reduction potential of the reaction

H2O2 → 2H+ + 2e- + O2 Eo = -0.682 V

The thing is, hydrogen peroxide tends to perform more effectively as a reducing agent under alkaline conditions, and this reaction (the putative reduction of harmaline) is being carried out under acidic conditions.

Right now, I'm not off the top of my head able to convert this electrode potential into a molar reaction energy to compare with the energy value for the reduction of the imine double bond in harmaline but I'll attempt to remember to check it out once I've had a night's sleep.
 
I've just acquired one of those hydrogen water generator bottles that are touted for their health benefits. It infuses water with hydrogen gas and you can see bubbles while that happens.

I'm wondering if it could, in theory, be used for a harmaline reduction, assuming you run the bubbles for long enough?
 
Jagube said:
I've just acquired one of those hydrogen water generator bottles that are touted for their health benefits. It infuses water with hydrogen gas and you can see bubbles while that happens.

I'm wondering if it could, in theory, be used for a harmaline reduction, assuming you run the bubbles for long enough?
Click to expand...
You would need to use an appropriate catalyst - and be aware of the safety risks in catalytic hydrogenation reactions.

Tangent - What possibly could be the 'health benefits' of bubbling hydrogen through drinking water? That is some weapons-grade woo right there.



Still haven't looked up the reaction energy yet... sigh!
 
downwardsfromzero said:
Tangent - What possibly could be the 'health benefits' of bubbling hydrogen through drinking water? That is some weapons-grade woo right there.
Click to expand...

Just a few papers that come up:
www.eurekaselect.com

Hydrogen Gas Therapy: From Preclinical Studies to Clinical Trials

Background: Mounting evidence indicates that hydrogen gas (H2) is a versatile therapeutic agent, even at very low, non-combustible concentrations. The Chinese National Health and Medical Commission recently recommended the use of inhaled H2 in addition to O2 therapy in the treatment of...
www.eurekaselect.com
www.ncbi.nlm.nih.gov

Neuroprotective Effects of Molecular Hydrogen: A Critical Review

Molecular hydrogen (H[2] ) is a physiologically inert gas. However, during the last 10 years, increasing evidence has revealed its biological functions under pathological conditions. More specifically, H[2] has protective effects against a variety ...
www.ncbi.nlm.nih.gov www.ncbi.nlm.nih.gov
www.ncbi.nlm.nih.gov

Hydrogen-rich water for improvements of mood, anxiety, and autonomic nerve function in daily life

Health and a vibrant life are sought by everyone. To improve quality of life (QOL), maintain a healthy state, and prevent various diseases, evaluations of the effects of potentially QOL-increasing factors are important. Chronic oxidative stress and inflammation ...
www.ncbi.nlm.nih.gov www.ncbi.nlm.nih.gov
www.nature.com

Hydrogen-rich water reduces inflammatory responses and prevents apoptosis of peripheral blood cells in healthy adults: a randomized, double-blind, controlled trial - Scientific Reports

The evidence for the beneficial effects of drinking hydrogen-water (HW) is rare. We aimed to investigate the effects of HW consumption on oxidative stress and immune functions in healthy adults using systemic approaches of biochemical, cellular, and molecular nutrition. In a randomized...
www.nature.com www.nature.com
www.ncbi.nlm.nih.gov

Effects of the long-term consumption of hydrogen-rich water on the antioxidant activity and the gut flora in female juvenile soccer players from Suzhou, China

Expending a considerable amount of physical energy inevitably leads to fatigue during both training and competition in football. An increasing number of experimental findings have confirmed the relationship between the generation and clearance of free ...
www.ncbi.nlm.nih.gov www.ncbi.nlm.nih.gov
 
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