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THH extraction tek
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Rising Star
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more info on leptactinia densiflora
:%0.5 thh leaves -
seems to be a really interesting plant to investigate
plus I have been told that there is a procedure that can convert other harmala alkaoids to THH... something or other that has to do with pure zinc...
any comments?
more info on leptactinia densiflora
:%0.5 thh leaves -
seems to be a really interesting plant to investigate
plus I have been told that there is a procedure that can convert other harmala alkaoids to THH... something or other that has to do with pure zinc...
any comments?
From Various Alkaloid Profiles in Decoctions of Banisteriopsis Caapi by J.C. Callaway, Ph.D.
In Situ Production of THH
The average ratio of THH to harmine in the vegetals was consistently near 1:1, from all sources (Table 2), while this ratio was closer to 1:5 in a large survey of source plant material (i.e., B. caapi; see Callaway, Brito & Neves 2005 in this issue). It is presently unclear whether harmine and harmaline are being chemically reduced to THH during the acidic process of decoction, or if THH is simply more stable
than the other two harmala alkaloids, which maybe lost through decomposition, or a combination of both processes. Figure 1 illustrates a likely chemical pathway for the conversion of both harmine and harmaline to THH through reduction under acidic conditions.
Figure 1 illustrates a likely chemical pathway for the conversion of both harmine and harmaline to THH through reduction under acidic conditions.
Figure 1:
^^Swim wonders if a similar thing is happening in peganum harmala that THH has detected in? Any thoughts? SWIM tested a peganum harmala extract (using salt method) by GC-MS and saw no THH. The reports SWIM has looked at that have ID'd THH in p harmala tested a water infusion. Perhaps the heat and acid + plant matrix causes THH to form also in perganum harlama by somethign similar to whats going on b caapi?
SWIM's FOAF guess, no.
In his latest p.harmala extration he decided to overdo it with the acidification of the brew; he initially used citric acid for the acid extraction of alkaloids. He then dumped a good amount of 36%HCl, racking the pH down to almost 0. He then did the Manske precipitation.
His alkaloids showed no sign of THH. His evidence is coming from selective precipitation of alkaloids, harmine precipitation at pH range 7.5-8.5, harmaline at pH range of of 9.5-11, but nothing really in between (i.e. pH 8.5-9.5) or above 11.5, say pH 12-14.
He suspects THH to have a pKa either between the pKas of harmine and harmaline or much higher than harmaline. Should THH have a pKa very similar to harmine or harmaline (means co-precipitation under the conditions of the experiment) his observations are a piece of nonsense crap.
So, not the best evidence of no THH presence after very acidic treatment of the brew, but what the hell, it was the best he could do at the time.
In his latest p.harmala extration he decided to overdo it with the acidification of the brew; he initially used citric acid for the acid extraction of alkaloids. He then dumped a good amount of 36%HCl, racking the pH down to almost 0. He then did the Manske precipitation.
His alkaloids showed no sign of THH. His evidence is coming from selective precipitation of alkaloids, harmine precipitation at pH range 7.5-8.5, harmaline at pH range of of 9.5-11, but nothing really in between (i.e. pH 8.5-9.5) or above 11.5, say pH 12-14.
He suspects THH to have a pKa either between the pKas of harmine and harmaline or much higher than harmaline. Should THH have a pKa very similar to harmine or harmaline (means co-precipitation under the conditions of the experiment) his observations are a piece of nonsense crap.
So, not the best evidence of no THH presence after very acidic treatment of the brew, but what the hell, it was the best he could do at the time.
^^SWIM wants to try something similar and inject it into SWIMs imaginary GC-MS maybe would shed some clues. SWIM wonders why then have some reports in the literature detected THH? The data seemed fine in those reports.
69ron
Rising Star
From what I heard it varies by strain and other similar factors, just like with caapi. I’m sure these natural variations are responsible for the different reports of active alkaloids in P. harmala. Some reports say harmaline is the main alkaloid, others say harmine, others say they are present in equal amounts. Some say it contains THH, some say it doesn’t.
Not all caapi contains THH. I’ve seen reports that show no THH at all. And reports show THH is the MAIN ALKALOID.
I’ve read many reports stating that boiling in acidic water may cause THH to form. But they all say “MAY”, none of them are willing to back up this claim with facts.
Not all caapi contains THH. I’ve seen reports that show no THH at all. And reports show THH is the MAIN ALKALOID.
I’ve read many reports stating that boiling in acidic water may cause THH to form. But they all say “MAY”, none of them are willing to back up this claim with facts.
Definitions of oxidation and reduction (redox)
-Oxidising agents give oxygen to another substance or remove hydrogen from it.
-Reducing agents remove oxygen from another substance or give hydrogen to it.
The terminology describes the nature of the reagent in terms of oxygen, which happens to be inverted in terms of hydrogen. A reduction reaction just means that one is using a reducing agent in a redox reaction. Chemistry's language isn't very easily accessible.
-Oxidising agents give oxygen to another substance or remove hydrogen from it.
-Reducing agents remove oxygen from another substance or give hydrogen to it.
The terminology describes the nature of the reagent in terms of oxygen, which happens to be inverted in terms of hydrogen. A reduction reaction just means that one is using a reducing agent in a redox reaction. Chemistry's language isn't very easily accessible.
^^The term oxidation and reduction are in a way misleading. oxidation implies oxygen but oxygen can have nothing to do with a reduction reaction, although in a way it does. SWIM likes to think of it this way. carbon dioxide is the most oxidized form of carbon and methane is the most reduced.
regardless in the case of harmaline to THH, THH gains an H atom.
anyway yes I guess I wonder what is controlling the formation of THH in caapi and peganum harmala. Since it seems to vary so much its 1 either an artifact of extraction or preparation or some non enzymatic degradation product or 2 its enzymatically produced and thus plants can be breed to make more.
regardless in the case of harmaline to THH, THH gains an H atom.
anyway yes I guess I wonder what is controlling the formation of THH in caapi and peganum harmala. Since it seems to vary so much its 1 either an artifact of extraction or preparation or some non enzymatic degradation product or 2 its enzymatically produced and thus plants can be breed to make more.
Aye. Oxidation of an element is "loss of electrons" which effectively means that it's valency is increased. FeCl2 going to Fe2Cl3 means that the valency of Fe (or "charge" in loose terminology) has gone up by one. In FeCl2, iron has a charge of +2, in Fe2Cl3 iron has a charge of +3. It has basically lost an electron (=it got more positive charge), it has been oxidised.
Reduction of an element is "gain of electrons" which means it's valency is "reduced". So the term reduction is absolutely correct here. Fe2Cl3 going to FeCl2 means the valency of iron is reduced from +3 to +2 and that happens because it has gained an electron (= it is less positive)
In organic chemistry and more specifically bio-organic chemistry it is a rule-of-the-thumb that oxidation means addition of oxygen or removal of hydrogen. Reduction is the exact opposite, that is removal of oxygen or addition of hydrogen.
For instance, fumaric acid has a double bond; the two carbon atoms participating in this double bond have a valency of -1. They bind to a single hydrogen nucleus (=proton) which, if lost will give them a charge of -1. Carbon-carbon bonds are too covalent bonds to produce any valency differences so they are not accounted for in valency calculations. Now, fumaric acid can be reduced to succinic acid. In the succinic acid the previously double-bonded carbons of the fumaric acid now have an extra hydrogen each. And their valency goes down to -2. They are "reduced".
Something very similar happens with the beta-carbolines and the number of hydrogens the carbon atoms hold.
Reduction of an element is "gain of electrons" which means it's valency is "reduced". So the term reduction is absolutely correct here. Fe2Cl3 going to FeCl2 means the valency of iron is reduced from +3 to +2 and that happens because it has gained an electron (= it is less positive)
In organic chemistry and more specifically bio-organic chemistry it is a rule-of-the-thumb that oxidation means addition of oxygen or removal of hydrogen. Reduction is the exact opposite, that is removal of oxygen or addition of hydrogen.
For instance, fumaric acid has a double bond; the two carbon atoms participating in this double bond have a valency of -1. They bind to a single hydrogen nucleus (=proton) which, if lost will give them a charge of -1. Carbon-carbon bonds are too covalent bonds to produce any valency differences so they are not accounted for in valency calculations. Now, fumaric acid can be reduced to succinic acid. In the succinic acid the previously double-bonded carbons of the fumaric acid now have an extra hydrogen each. And their valency goes down to -2. They are "reduced".
Something very similar happens with the beta-carbolines and the number of hydrogens the carbon atoms hold.
69ron said:
69ron said:
What would happen if you used hcl+water to extract caapi? Would it mostly pull the THH?
Would this method be able to separate THH from harmine and harmaline?
69ron
Rising Star
I've read that harmine HCl and harmaline HCl are poorly soluble in hydrochloric acid. I assume the same would be true for THH.
What about using caapi leaves? Is the alkaloid profile different in the leaves? I've read that the leaves are more potent (up to 1% alkaloids) than the vine (up to 0.5%), but then if that’s true, why is it no one uses leaves for ayahuasca?
What about using caapi leaves? Is the alkaloid profile different in the leaves? I've read that the leaves are more potent (up to 1% alkaloids) than the vine (up to 0.5%), but then if that’s true, why is it no one uses leaves for ayahuasca?
But didn't you say that THH hcl was much more water soluble than THH citrate? I know that people have used hcl solutions to extract caapi. Seems to have made quite good brews.
The leaves may be more unreliable in how much of the actives it contain. Will try look into it and see what I can find. I remember people have mentioned that it can smooth out the ride if you add a few leaves to an ayahuasca brew. It is also used in the changa mix. It also is more emetic than the caapi stem.
69ron
Rising Star
Dagger said:
Hydrochloric acid is not the same as water.
Tetrahydroharmine HCl seems more water soluble than THH citrate. But that is in pure water, not hydrochloric acid. Harmine HCl and harmaline HCl are very water soluble, but poorly soluble in hydrochloric acid. I assume the same is true with THH.
For this reason, you should not use hydrochloric acid for extracting these alkaloids. I can show you several books which state that the hydrochlorides of these harmala alkaloids are poorly soluble in hydrochloric acid, and furthermore, they are not stable in it especially if the solution is hot. If you boil them in hydrochloric acid, they change into other alkaloids. I don’t recall which ones, but they definitely change. It’s too strong of an acid. A weaker acid should be used.
Dagger said:
More emetic doesn't sound so good. No wonder people don't use the leaves.