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Harmine vs Harmaline vs Mixed Harmalas

DetritusTheEgo said:
What dose have you both settled into out of curiosity with harmalas and or individually?
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I've always taken them unseparated and I just take whatever feels right at the moment. For pharmahuasca I would take 200+ mg freebase. Recently I've been taking around 100 mg daily in the morning for mood enhancement, today i'll take it before sleep to see.
 
Sakkadelic said:
I've always taken them unseparated and I just take whatever feels right at the moment. For pharmahuasca I would take 200+ mg freebase. Recently I've been taking around 100 mg daily in the morning for mood enhancement, today i'll take it before sleep to see.
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At a 100mg dose, have you noticed any alteration in your perception? And do you need to avoid certain foods to curtail adverse effects like headache? In other words, is there much of a body-load?
 
I took 120 mg harmala freebase yesterday before sleep but did not experience any special dreams. Although I did feel the harmala effects as I was falling asleep. The way I experience these initial effects is with waves that flush both my brain and mind (physically and mentally), it almost feels like fainting but lasts no more than a second.

I've been thinking about the efficiency of harmala ROAs since I started taking them daily, especially when taken for their own effects. I don't think eating them is the most effective way (for oral dmt activation it definitely is). and sublingual does not seem to work so efficiently either, especially for larger doses, it could be that the salt form is better for sublingual but its taste is unpleasant.


So let's consider the freebase dose I took yesterday. First I put it under my tongue and after few minutes it didn't seem like it was being well absorbed/mixed by the saliva, it kind of stayed suspended as it's not really soluble in water. Yes saliva can be slightly acidic and a small amount of the freebase would convert to salt but I believe the pH would raise quickly and the freebase would stop dissolving until new saliva is secreted, so I am not sure how well the freebase would come in contact with the mouth lining cells and be absorbed. So I then mixed it around and kept it in my mouth for few more minutes before downing it with water. I think there is some sublingual absorption because of the initial effects I get within minutes.

Once the harmalas are swallowed, 2 main things happen, some of the harmalas will block MAO enzymes preventing the breakdown of amines including many of the important neurotransmitters, and some would bind to receptors in the gut (potentially triggering nausea and other side effects). And since it's still in the guts, the free flowing neurotransmitters and harmalas binding to receptors will not have major psychoactive effects. So I wonder how much harmalas will be left to be absorbed and transfered via blood to the brain (encountering more MAO along the way), to inhibit MAO and bind to receptors there and induce proper psychoactive effects.


So perhaps we should dose harmala orally starting from a base amount and then topping that for psychoactive effects. But I think the amount needed to overcome the oral route and reach the brain can be highly variable from person to person, from day to day and even time of day, it would be hard to have a controlled and consistent dose I imagine. Of course one solution is to just take moar but this can increase nausea and if my thinking is correct then also wasteful. Other ROAs like snorting and boofing are effective and I've tried both, but they are inconvenient, don't want to be plugging harmalas every morning or night, and I don't like snorting stuff (it's also crucial to have no base traces for this ROA). Smoalking is nice, one can make harmala enhanced leaf or sprinkle it on herb if no means of vaporisation are available.

I would probably still take it orally for the time being because it is very convenient and I will try to find a proper dose for myself. Though it's hard to judge the effects as they are subtle.
 
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TheGreenPhantom said:
At a 100mg dose, have you noticed any alteration in your perception? And do you need to avoid certain foods to curtail adverse effects like headache? In other words, is there much of a body-load?
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I eat normally and don't experience headaches or body load. I think if you're taking less than what is needed for full MAOI effects (150 mg??) dietary interactions and nausea would not be present for most people. One thing I started experiencing since taking harmalas is electrical/tingling sensation in my arms when exercising and getting close to my strength limit. It does not feel concerning so far and I plan to post about it once I am more sure about the connection and observe it more.

At 100 mg I don't experience perceptual alterations, the way I feel harmalas affect me is that they smooth down emotional reactions and allow me to go through the things that trouble me with a clearer head and calmer heart. I have experienced positive effects since I started taking them but it's hard to attribute that to harmalas alone, it becomes like a positive feedback loop and feeling good makes me handle things better which makes me feel good and so on, until I smoke weed :b
 
Sakkadelic said:
some would bind to receptors in the gut (potentially triggering nausea and other side effects)
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Nausea needn't be related to the gut, even if it ends up in vomiting. Nausea can and does come from CNS effects elsewhere, like with 5-HT3 receptors. This is for SSRIs, but harmalas also bind to 5-HT3: Nausea and Vomiting Associated With Selective Serotonin Reuptake Inhibitors - CNS Drugs CNS nausea and gastric discomfort are different, even if the second can trigger the first.

It's clear that eating harmalas is not too efficient in the amounts needed, but what other problems do you find with that ROA? Do you tend to get nausea? I find at first I used to get nausea from them, but it was related to the feelings of "spinning" and the particular kind of visual distortion it sometimes produces. Nowadays I usually don't get nausea from only harmalas, if I do it's because of some emotional reaction in combination with DMT, or because I had plant material with more substances. I think it's because those effects don't feel disorienting anymore.
 
blig-blug said:
Nausea needn't be related to the gut, even if it ends up in vomiting. Nausea can and does come from CNS effects elsewhere, like with 5-HT3 receptors. This is for SSRIs, but harmalas also bind to 5-HT3: Nausea and Vomiting Associated With Selective Serotonin Reuptake Inhibitors - CNS Drugs CNS nausea and gastric discomfort are different, even if the second can trigger the first.
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Yes definitely, smoking a large dose of harmalas is very dizzying and vomit inducing. The nausea from eating harmalas that I experience is of the same kind I believe. Different to the stomach discomfort you describe with taking mimosa for example. At doses below 200 mg the nausea isn't bad for me, but i've taken above 400 mg harmalas HCl and it was extreme nausea, spinning and tracer effects with vomiting/dry heave 15 times within an hour.

blig-blug said:
It's clear that eating harmalas is not too efficient in the amounts needed, but what other problems do you find with that ROA? Do you tend to get nausea?
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At regular doses the nausea is not problematic for me. I am thinking about this bcz when taking doses 50-150 mg orally it's not so clear how much psychoactive effects one gets. And for some like @DetritusTheEgo even at 200 mg harmine effects were minimal. I do want to take harmalas regularly but I do not want to take a full ayahuasca dose and maybe other ROAs are more suitable for that.
 
Sakkadelic said:
I do want to take harmalas regularly but I do not want to take a full ayahuasca dose and maybe other ROAs are more suitable for that.
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Ah, yes, I understand now.

Below 150mg I can still feel some effects. At 100mg there's still something going on, at 50mg I'm not sure. But as you say, on the long term stronger effects aren't desirable.

Maybe it could be worth it to experiment with sublingual dosing several times a day. That way one could probably build up a higher total blood level than what can be absorbed by a single sublingual dose.
 
blig-blug said:
Maybe it could be worth it to experiment with sublingual dosing several times a day. That way one could probably build up a higher total blood level than what can be absorbed by a single sublingual dose.
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That's a good point. I will try a very small dose like 10 mg and see if it actually fully disappears. Maybe other salts than the HCl would be more palatable too
 
Sakkadelic said:
That's a good point. I will try a very small dose like 10 mg and see if it actually fully disappears. Maybe other salts than the HCl would be more palatable too
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Particle size seems like it would be worth taking into consideration too - how might this align with the material you've been using?
 
This patent is potentially of interest:
It was an objective technical problem of the present invention to provide a formulation of harmine characterized by its improved solubility. The objective technical problem is solved by embodiments disclosed herein and as characterized in the claims. The present inventors have surprisingly found that compositions comprising harmine (or a pharmaceutically acceptable salt thereof) and (i) an uronic acid or (ii) a carboxylic acid and a monosaccharide are characterized by significantly improved solubility than the state of the art formulations of harmine, including harmine free base or harmine hydrochloride (see e.g. Table 12 and Table 14). Said compositions show better bioavailability and less subject-to-subject variability in comparison to state of the art composition.
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WO2024023274A2 - Highly soluble formulations of harmine - Google Patents

The present invention relates to a composition comprising harmine and (i) an uronic acid or (ii) a carboxylic acid and a monosaccharide, to a salt of harmine and uronic acid, to a kit of parts comprising (a) the composition or the salt of the invention and a pharmaceutically acceptable carrier...
patents.google.com
 
I skimmed through a few spots and tables in that patent. That's quite interesting indeed. Thanks for the link.

Seems like D-glucuronolactone would be easy and cheap to source which appears there are some resources outlining the degradation of D-glucuronolactone into D-glucuronic acid and vice versa. Though I've not had enough time to try and source the full paper from the vast dark / clear web if it can be located.
 
Reading about it, I don't know if it's very amenable to kitchen chemistry. It looks like it would be quite difficult to get a good yield and avoid subproducts.

But there's the other option:
a carboxylic acid and a monosaccharide
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Preferably the carboxylic acid is selected from formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, glycolic acid, lactic acid, citric acid, 2-hydroxypropionic acid, 3-hydroxypropionic acid, 3-hydroxybutyric acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, tartaric acid, malic acid, maleic acid, fumaric acid, and glutatonic acid.
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Preferably, the monosaccharide is a hexose or a pentose. [...] Even more preferably, the monosaccharide is glucose or fructose.
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Accordingly and preferably, in the composition of the present invention, the carboxylic acid is malic acid or acetic acid, and/or the monosaccharide is glucose or fructose.
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So malic acid and glucose, sounds pretty easy! It's worth a try.
 
Accordingly and preferably, in the composition of the present invention, the carboxylic acid is malic acid or acetic acid, and/or the monosaccharide is glucose or fructose.
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So dissolve freebase harmalas with distilled white vinegar and sweeten with table sugar. Or am I missing something?
 
According to the patent: the molar ratio of harmine to acid needs to be between 0.5:1 and 2:1, preferably 1:1. The molar ratio of acid to monosaccharide has to be in the same range with the same preference. So it should be roughly a 1:1:1 ratio in moles. So for 1g harmalas, roughly 300mg acetic acid or 600mg malic acid, and 900mg glucose.

This estimation is with harmala freebase in mind and it would have to be with harmala salts, but I don't really know how to know the molar mass of the salt. @Transform, is it as simple as assuming one molecule of acid per molecule of harmine or harmaline?
As there is a wide margin for the ratios, it shouldn't matter too much.

It calls for a monosaccharide and table sugar (sucrose) is a disaccharide. So it's better to use pure glucose or fructose.
 
I was wrong, it's with the freebase:
A composition comprising harmine, fructose and malic acid in a molar ratio of 1 :0.5:0.5 was dissolved to 21 % in water by combining 212 mg harmine FB, 90 mg fructose, 67 mg malic acid and 1.0 g water. A transparent solution has been obtained.
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They then later claim the salt as well, but it being a patent it's hard to know if it works or they claim it just to claim as much as possible.
 
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The main contribution of the patent seems to be that harmine glucoronate is extremely soluble when compared to other salts. I wonder if many of the other claims may just be to make the patent as broad as possible. But as the formulation with an acid and a monosaccharide is so simple, I think it's worth a try.

It would be good if more knowledgeable people than I take a look at it. My lack of knowledge of chemistry plus the extremely verbose and repetitive language make it very hard to understand for me.
 
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