ok

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?

^^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.

^^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.

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.

I'm no chemist. Maybe this is a stupid question.

How is THH considered a product of "reduction" when it is heaver, and contains more atoms than harmine and harmaline?

perhaps its using the pieces of harmine and harmaline to recombine into something new...sounds unlikely but its an idea

From the Redox article on Wikipedia:

Well that makes no sense. Reduction means to reduce. How did it come to mean both reduction and addition in chemistry? Is there something I'm missing there?

http://www.chemguide.co.uk/inorganic/redox/definitions.html

-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.

That is such misuse of the English language. That’s like saying NO can also mean YES! What idiot came up with that?

^^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.

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.

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?

because its the VINE of souls...not the LEAF of souls

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.



More emetic doesn't sound so good. No wonder people don't use the leaves.

While SWIM's FOAF has found few vendors selling caapi leaves, he thinks that since this product has really low turnover their stock might be old ('cause nobody is buying it) and not the best one for extracting.

Does anyone know a good source of fairly fresh caapi leaves? Or SWIM's FOAF is getting too anal with yield issues and should go with whatever is sold around?

so would THH, harmine or Harmaline be soluble in acetone?

if not, and Chlorophyll is
the one might wash the leaves first
dry
and follow with an acidified wet alcohol extraction?
or just aqueous

theres some nice data here on alk profiles in B caapi parts

http://www.erowid.org/li...2_b_caapi_analysis.shtml

lets not be forgetting the roots too

Very interesting. Thanks for that link!

According to that data the leaves contain 0.28-1.90% alkaloids. Based on that data I calculated that the alkaloids in the leaves are 78-98% harmine, 0.1%-5% THH, with only traces of harmaline, and who knows what the rest is (the site doesn't say). They are apparently a great source for nearly pure harmine!

But still, rue is much cheaper.

determining pka can be a pain in the ass unless you have a very accurate pH meter. Even then it requires very careful titrations. I have some basic lab guides on how to do but unless someone is serious about deteremining it I wont post.