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Solubility of harmala/harmaline and DMT alkaloids

Foreigner

Bluelighter
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Mar 18, 2009
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I was gifted some b. caapi and p. viridis recently and I would like to turn them into alcohol tinctures for micro-dosing, but I first want to confirm that I'm not about to waste a bunch of valuable plant material on a formulation that won't work. I think that alcohol extraction of harmala and harmaline is doable but I'm not sure about the DMT aspect of p. viridis, and DMT chemistry is way above my knowledge pay grade.

My understanding is that these plants weakly extract into high proof ethanol (95% or higher). My goal here is to ingest very small amounts of the end product so that the plant medicine is in my body and consciousness as I go about my day, but I'm not having a full on trip. I have many personal reasons for doing it this way that I won't get into, plus my body is too frail to withstand a full on trip right now. I have no scientific way to analyze the concentration of the end product so I would just start with ridiculously small doses (one drop or less) and work up from there.

Finding reliable info about tincturing these plants online is very difficult so I thought I'd ask some of the experts here. I just want to know if the ethanol route is sensible or not. Also, should I add anything else? Normally when you decoct these plants in water on the stove you add a bit of vinegar to decrease PH -- but that's using water, not alcohol. I have seen some info about PH being a factor in efficacy of extraction but I don't know how that would translate to an alcohol tincture, or what I would add to enact this.

If this gets too complicated then I considered just decocting the plants and preserving the end product with alcohol -- but again, no idea if this would work.

Any advice from the chemists here would be appreciated :)
 
That's going to be pretty tough to gauge, you'd be better off micro-dosing with a DMT analog which isn't victim to metabolism by MAO. I assume you intend to take a full dose of b. caapi and then microdose the DMT? Assuming you can get the extraction down right, you'll at least have to take a threshold dose of the DMT extract to give you an idea of the potency. I've acquired DMT through an A/B extraction on Mimosa hostilis root, no idea about alcohol tincture, I don't imagine it would work well or else I wouldn't have gone through all the trouble before. I didn't have access to b. caapi and used syrian rue, but from what I've read b. caapi is the superior choice.
 
That's going to be pretty tough to gauge, you'd be better off micro-dosing with a DMT analog which isn't victim to metabolism by MAO. I assume you intend to take a full dose of b. caapi and then microdose the DMT? Assuming you can get the extraction down right, you'll at least have to take a threshold dose of the DMT extract to give you an idea of the potency. I've acquired DMT through an A/B extraction on Mimosa hostilis root, no idea about alcohol tincture, I don't imagine it would work well or else I wouldn't have gone through all the trouble before. I didn't have access to b. caapi and used syrian rue, but from what I've read b. caapi is the superior choice.

The issue isn't what the drug will do to me, but solubility. I just need to know if an alcohol extraction will work.
 
Salts like DMT and harmaline are very soluble in acidified water. If you want to extract them, do a basic acid-base extraction. Plenty of guides out there and the procedure is pretty elementary.
 
You can go with a general alkaloid extraction method on these plants using 95% ethanol of course, just perform the extraction on dried powdered material. It's best to do an exhaustive extraction with excess of the solvent and then concentrate the extract. You should be aware though that this way you will extract a lot of other stuff from the plant material along with the alkaloids. Extraction using water is done with an acidic solution as alkaloids possess amine functional group which are weakly basic, under acidic conditions they are protonated, gain charge and thus are more soluble in aqueous solutions, otherwise being organic compounds often with fairly complex hydrocarbon backbone they are generally only sparingly soluble in water.
 
You can go with a general alkaloid extraction method on these plants using 95% ethanol of course, just perform the extraction on dried powdered material. It's best to do an exhaustive extraction with excess of the solvent and then concentrate the extract. You should be aware though that this way you will extract a lot of other stuff from the plant material along with the alkaloids. Extraction using water is done with an acidic solution as alkaloids possess amine functional group which are weakly basic, under acidic conditions they are protonated, gain charge and thus are more soluble in aqueous solutions, otherwise being organic compounds often with fairly complex hydrocarbon backbone they are generally only sparingly soluble in water.

Ethanol extraction is undesired in my opinion because ethanol will dissolve more non-basic organic compounds than water would. Acidic water is good because basic amines like DMT and harmala alkaloid are very soluble in it while non-ionized organic compounds aren't. I see no advantage in using ethanol over water.
 
BD, what if I did a water extraction and then used ethanol equivalent to 21% of total volume to preserve it? Would that mess up the chemistry of the end product?

I basically want a bottle that I can micro-dose with that I can use long-term.
 
No, it wouldn't. Ethanol is a popular preservative. I usually make a 1% benzyl alcohol solution of the drug solution if I don't plan on using it quickly. Tryptamines can be prone to oxidation if they have a free phenolic group (-OH, do things like psilocin (4-HO-DMT), 4-HO-MET). Often the phenolic group is protected by an acetyl group, for example 4-AcO-MET, my favourite tryptamine, but also 4-AcO-DMT, aka protected psilocin. Acetyl groups don't change the pharmacodynamics of the drug as they're quickly cleaved by esterases in the blood (including the brain), essentially making them a prodrug that has better pharmacokinetics, which means faster onset - analoguous to heroin vs morphine. 4-AcO-MET's onset is practically instantaneous when plugged in my experience.

If you have any more questions, don't hesitate to ask. I myself use 4-AcO-MET for microdosing purposes as it's very clear-headed and provides a great motivation and creativity boost.
 
Benzyl alcohol, of course! I should just preserve with that instead because much less is needed. I wonder how it would affect my digestive tract though vs. ethanol. My GI is pretty wrecked right now... and I mean wrecked.

I'll lookup water extraction of caapi and viridis (I think they are cooked together), and then preserve the end concentrate with alcohol.

Safety question... I know that caapi is an MAOI. Do I have to do the MAOI diet if I'm only micro-dosing? We're talking 1 or 2 drops of the concentrate.

Cool that you also microdose :)
 
I'm not sure about the MAOI thing. You would still have to take a proper dose of the harmala alkaloids for them to work at extending DMT's duration. As for the benzyl alcohol, since you would only be taking very small doses of DMT, if you prepare the solution with a high concentration, you won't be taking a lot of it at all. For example, I typically only have to take 0.5 ml of my solution, and at 1% benzyl alcohol that would mean just 0.005 ml of benzyl alcohol per dose. I honestly don't think that would affect your GI tract, but maybe someone else could also weigh in. Also, I don't think harmala alkaloids need preservatives apart from those that have free phenolic groups, but IIRC those don't make up a large portion of the plant content anyway.

Also, if at all possible, I would recommend looking into 4-substituted tryptamines, 4-AcO-MET in particular. It doesn't need preservation and it's duration is anywhere between 4-6 hours without a MAOI.
 
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Sorry for throwing my 2 cents in again, I know you have specifically stated you didn't want feedback of this nature. But if you aren't taking a high enough dose of haramala's, then you might as well not be taking any DMT, it won't make it past your gut. You should consider extracting them seperately, so you can adjust the dose of each.
 
Sorry for throwing my 2 cents in again, I know you have specifically stated you didn't want feedback of this nature. But if you aren't taking a high enough dose of haramala's, then you might as well not be taking any DMT, it won't make it past your gut. You should consider extracting them seperately, so you can adjust the dose of each.

Traditionally, caapi and viridis are layered together in a pot, water is poured over, and they boiled over an extended time. Then the liquid is strained off and more fresh water is added. The process is repeated, and then they add the second strained decoction to the first. The combined decoction is then simmered until it reduces to a concentrated sludge, and that's what the people ingest for the ayahausca trip.

I'd like to take that end product and preserve it with benzyl alcohol in a tincture bottle for regular micro-dosing.

Are you saying that micro-dosing that brew won't be effective because the dose of MAOI will be too small to inhibit DMT breakdown?

I am taking a plant spirit medicine approach here, if you know what that means. I want their essence in my body, I don't necessarily need to trip. Even if the viridis breaks down in my body right away, its plant essence should stick around. Though I am considering now that due to the low MAOI aspect, the viridis would break down much faster and I would effectively only be working with the caapi in my body. But seeing as how viridis isn't *just* DMT, that can't be totally true.
 
Viridis has like hundreds of alkaloids in it. B Caapi probably has 3 dozen.

:)
 
The question is, which ones of them does a person want to extract? IIRC P. viridis main alkaloid is DMT.
 
Are you saying that micro-dosing that brew won't be effective because the dose of MAOI will be too small to inhibit DMT breakdown?

Precisely. You can still limit the dose of viridis to avoid tripping. And I am not intimately familiar with the alkaloid content of p. viridis, but I imagine a large swath of the alkaloids are also extensively metabolized by MAO, such as NMT, or they are found in such minute levels that without an MAOI they won't be exerting much effect. Even avoiding the strict pharmacology of it all, you may find more utility by changing the ratio/amount of each. You should still be able to carry out the extractions separately and still combine them to reflect the ratio that would be arrived at traditionally.
 
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Ideally I don't think you even want any NMT. IIRC it has no psychoactive activity. The only active alkaloid in P. viridis is DMT. However, you'd need a more sophisticated separation method than acid-base extraction. Something like normal phase column chromatography, but I don't think it's neither worth the effort nor available as an option to Foreigner.
 
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Oh crap, I thought Foreigner was talking about Vinca, not Viridis. I guess I can't read.

500px-VincaMinor_closeup.jpg


Vinca is a very pretty flower and pharmacologically amazing, with all sorts of alkaloids that act as anti-cancer, DNA-active intercalators, anti-viral, MAOIs, etc. Very cool.
 
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