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Harmaline acid conversion

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dithyramb

dithyramb

The Love of the Earth
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Every year I prepare rue medicine soon after harvesting in the late autumn when it has this extremely strong harmaline dominant content + effect. Eating the seeds is really overwhelmingly powerful which is good but it does border on toxicity easily and I assume this is because of excessive harmaline. The medicine I prepare never had this harshness and I had never given thought to this before. This year, I prepared the medicine without vinegar for the first time to see how it turns out. I was expecting it to be weaker than usual, but to my surprise, it is unusually powerful and harsh, similar to raw seeds. I have been reading that acid + long boiling duration might be converting harmaline to both harmine and thh, but I am not clear whether people have been able to verify this in experiments... I wonder if I reboiled the medicine adding vinegar, it would transform... I will report if I do it.
 
There is some info on the topic here here

Acidic Zinc reduction works well for Harmaline -> THH as shown in the forum. I'm not sure about boiling for a long time (+ added vinegar). Maybe concentration and type of metal pot matters. Any tests you run would be interesting (even if no conversion happens).
 
Boiling for a long time in an aluminum pot could easily have an effect and vinegar would accelerate this.
I have not seen that scientifically tested but, when describing ayahuasca preparation in the jungle, Terence McKenna was adamant that it must be an aluminum pot that's used to make really good aya. It is also chemcially feasible since aluminum is an even stronger reducing agent than zinc and its well known that cooking acidic things, like tomatoes, in aluminum pots will slowly dissolve the pot.
 
Dithy, have you tried baking the seeds prior to preparation?

Sabnock turned me onto it, and it seems to completely remove the effects of the toxic chemicals present in the raw seeds if one baked them in an oven at 350F for 15-18 minutes.

It's thought that those nasties are cooked off at that temp, while leaving the harmalas intact.
 
Elrik said:
Boiling for a long time in an aluminum pot could easily have an effect and vinegar would accelerate this.
I have not seen that scientifically tested but, when describing ayahuasca preparation in the jungle, Terence McKenna was adamant that it must be an aluminum pot that's used to make really good aya. It is also chemcially feasible since aluminum is an even stronger reducing agent than zinc and its well known that cooking acidic things, like tomatoes, in aluminum pots will slowly dissolve the pot.
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Aluminium salts would also precipitate tannins.
 
İ have tried reboiling the harsh medicine with added vinegar (in a steel pot). This has not altered the harsh character.

İ have always used steel pots. I am leaning on the possibility that vinegar has never altered the brew and that this unusual harshness is about a slightly earlier harvest time last year (perhaps not allowing for some rain to dilute the harshness).

İt would be interesting to see if baking/roasting cleaned out the energetic harshness. İt seems people usually do it to attenuate nausea, but I never have a nausea problem.
 
Another possibility might be reboiling with ascorbic acid (vitamin C) rather than vinegar. I have conjectured previously that there is a possibility this might at least play a role in harmaline conversion.

I've been considering trying some of the conversion processes as I've been finding my rue extract to be more than a little harsh of late. Interestingly, the crude decoction made with toasted seeds has been considerably more forgiving - but then of course we have a completely different batch of seeds. Toasting did make the same batch of seeds much more tolerable, however.
 
Probably the simplest thing to do first would be to roast/toast the seeds like downwardsfromzero suggested. I have gotten good results from that method. It is true however that I only use what I believe to be a same batch of seeds.

Downwardsfromzero - are you suggesting that different acids might have better results for transforming harmaline to thh ? There are many different "edible" acids one could try.

Do you think boiling the P. harmala water extract in a think manner in an acidic solution like one would be making caramel/belgian candy or invert sugar from sucrose for example makes any sense to achieve harmaline to thh transformation ?
 
Triglav said:
Downwardsfromzero - are you suggesting that different acids might have better results for transforming harmaline to thh ? There are many different "edible" acids one could try.
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No, I'm suggesting that specifically ascorbic acid might be either a strong enough reducing agent to convert harmaline to THH (maybe in the presence of catalytic flavonoids or other phytomolecules with redox activity if we're thinking about what happens in caapi brews), and/or its oxidation product dehydroascorbic acid might catalyse the transfer of hydrogen away from harmaline to produce harmine, again possibly dependent on the presence of other redox active phytomolecules in caapi brews. I posted some molecular structures for this somewhere or the other but it is still an untested conjecture.

The aluminium pot hypothesis holds up better when subjected to Occam's razor, tbh. We need to try boiling some rue extract with ascorbic acid in any case. It could also be the case that other biological reductants like NADH and NADPH could contribute to the reaction but they lack otc availability.
 
I wonder what material was used for pots by the amazon tribes before contact with industrial civilization.

Syrian rue is said to contain vitamin c, btw, but I don't know about the seeds.
 
Good question - I'm pretty sure clay cauldrons will have been used in some circumstances. Metallurgy in pre-Columbian south America is yet another thing to look into. I've no idea whether iron or bronze was available.

I'd cook my aya in a gold cauldron given the chance 😁
 
dithyramb said:
Thank you for your enthusiasm, DFZ.
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I thank harmala alkaloids for my enthusiasm these days. Last night something wonderful happened which deserves its own thread. In an attempt to keep at least vaguely on topic, it was with plain and simple Manske rue alkaloids so harmaline isn't necessarily all that bad. Whether it was just the stars and planets or something I ate that afternoon, the next puzzle is working out how I came to wake up in the night feeling as though I'd had a load of MDMA when all it was was a modest dose of rue alkaloids, some chamomile tea and a pepino (Solanum muricatum Aiton) fruit, as well as one slice of organic cheese. Very curious (and sorry about the tangent!)
 
Actually, I am not sure that Harmaline is what causes the harsh energy. It could as well be non alkaloid components. Harmaline is good for sure, the dream enhancing effects are attributed to it according to people's reports, and also the extra euphoria which lacks in caapi is due to harmaline, according to my understanding. Chamomile has a highly sexual energy for me (as do many many plants:)) and the combination with rue ought to be something like what you describe. The cumulative effect of taking rue often also can bring one to some sort of extreme ecstasy.
 
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