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THH extraction tek

Migrated topic.
timeloop

timeloop

Rising Star
Ok guys, SWIM has been feeling the energy created from recent THH discussions on this board and SWIM has been getting the inkling that some more THH research is very important.

so SWIM has decided to give back something to this wonderful community and begin a project totally dedicated to creating a tek to easily extract THH from plant sources.

SWIM is no amazing kemist herself... but SWIM does have friends that are... and SWIM is hoping to get some strong support from some of the more talented members of the nexus...

where to begin?

firstly we need to identify a reliable source of THH from an easily obtainable plant. SWIM is based in oz (where you cant import THH) so this tek will focus a little on native plants from SWIMs area, however SWIM will also include other plant sources from around the world.

firstly lets have a look at some of the plants that we may be able to work with.

firstly we obviously have:

Banisteria caapi

working with caapi however we will have to isolate the THH from other harmala alkaloids. column chromatography seems to be the current method hinted at on the forum... however the aim of this tek is to create an easy tek... SWIM is thinking that chromatography is beyond most peoples ability and hardware.

so the next step would be to identify some other sources. lets make a list:

from tikhal:

Calliandra pentandra
Calliandra augustifolia (unsure of thh %)

plus I have stumbled upon a very sparse amount of information about other plants containing THH: the only one so far is:

RUBIACEAE
Leptactinia densiflora Hook. Fil. (tetrahydroharmine (= leptaflorin)


there are a number of other plants that contain thh with other alkaloid, however SWIM thinks that we would be best served by focussing on extraction from plants that contain only thh

so at this stage there is very little information SWIM has found that indicates that thh is abundant in nature... however we do have a starting point.

I will do some more research and post again soon...
 
further research has indicated the tetrahydroharman is more easily encountered in the plant world.

Elaeagnus orientates L. = tetrahydroharmane

Elaeagnus spinosa L. = tetrahydroharmane

LEGUMINOSAE

Acacia baileyanna F. v. Muell = tetrahydroharmane

Acacia complanata A. Cunn. = tetrahydroharmane

Petalostylis labicheoides R. Brown = tetrahydroharmane

Petalostylis labicheoides var. cassioides = tetrahydroharmane, N,N-DMT

and there are some others...


the sources I have found do indicate that there has been some traditional usage of tetrahydroharmane containing plants used as ayahuasca admixtures...

could it be a more readily available source of a thh like molecule?
 
There was already a topic about this. I forget the link, but basically there's not much information in this area. Many of the plants reported to contain THH contain very little or are next to impossible to find. Caapi contains the most, according to all the sources I've seen. But who knows. Maybe there's another good plant out there. It would be nice if someone could find a plant that contained only THH.
 
This is coming from a different thread but SWIM's FOAF believes this is a more appropriate place for it.

Infundibulum said:
SWIM's FOAF had dreams of separating tetrahydroharmine, harmine and harmaline. In theory it is fairly simple if one looks at their pKas and XlogPs.

PKa:
Harmine : 7.70
Harmaline: 9.80
THH : ????

XlogP
Harmine : 2.5
Harmaline: 0.8
THH : 2.376? 1.90? (most likely 1.90)

What that means is that freebases of harmine, harmaline and THH are fairly insoluble in aqueous solutions. Less so for harmaline (XlogP 0.8 ) but it's fine, a fair amount of it precipitates.

The pKas are the most important stuff. What they mean is that at a pH of just above 8 one would only see harmine precipitating. On a pH of say 11 harmaline will precipitate. SWIM's FOAF has done this experiment, even though it needs to be repeated correctly. And it does not even require a pH meter.

Dissolve the harmala alkaloid salts in water, then add sodium bicarbonate (brings pH to around 8.3-8.5 but no much higher) Harmine precipitates and is collected. Then boost the pH by adding sodium carbonate to ~12) and harmaline precipitates.

But if one is extracting from caapi, in which pH THH crashes out? the pKa of THH is unknown, if someone knows is or can roughly calculate it (some people own some THH) it would be a tremendously useful info.

SWIM's FOAF was thinking to do experiment with differential centrifugation when he has time, i.e. extract caapi, and increase pH by increments of 0.5 and see what crashes out at each step. Centrifugation is just to collect the precipitates much much faster.
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Now, which caapi variety is reported to contain the most (or mostly) THH to work with? Ideally one wants a source that either contains only THH. But THH with harmine may be easy to work with as well. But if caapi contains THH, harmine and harmaline things get much more complicated and difficult for the home experimenters. If the latter is the case some column chromatographic separation may be more suited to attack the issue.
 
Here ya go!


One needs not only concentrated HCl and methanol (fine to find) but sodium borohydrite which is difficult to get hold on if not working in a lab.

SWIM has tried just tried mixing harmaline with very concentrated HCl (10M), no conversion was really detected. Maybe he needs to try again, but he believes that a really strong reducing agent is required here.
 
One needs not only concentrated HCl and methanol (fine to find) but sodium borohydrite which is difficult to get hold on if not working in a lab
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SWIMs imaginary friend has some laying around. Any idea on the stability of this stuff being stored in a dark cool place for god knows how long (The worse that can happen is it just won't react, might give it a go one of these days)? But yes this is something that should only be done by people with training in this sort of thing, as SWIM thinks much heat will be released and the reagent needs to be added very slowly.

Hooooowever this might be more feasable.

Harmaline has also been reduced to THH with Zinc & Hydrochloric acid. See Siddiqui et al. 1983 for the procedure. (This should also work for harmine)Siddiqui et al. 1983 found that addition of NH4Cl prior to basification with Ammonia increased the yield for this reaction from 50% to around 80% (by preventing the precipitation of Zinc hydroxide)
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SWIM can't find these papers though. Anyone have access?
 
...or find a good source of THH, re to timeloop's proposed plant sources.

SWIM's FOAF is considering the caapi leaves as a good source of THH alone. Caapi leaves are added in some aya brews, jaguars apparently love to eat them and Duke's Phytochemical and Ethnobotanical Database reports that as far as the phytochemistry of B.caapi is concerned, it is the leaves that contain THH.

Anyone has any thoughts on caapi leaves? they are cheap to buy, so it is worth a try.
 
Anyone has any thoughts on caapi leaves? they are cheap to buy, so it is worth a try.
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Nice find. Also its more lets say...sustainable! If someone knows a source let SWIM know as SWIMs main source for plants doesn't sell the leaves. SWIM can do some tests to see if its present without doing a long drawn out extraction, however that might have to wait till next year as SWIM must be on the go for a while soon.
 
Converting Harmaline and/or Harmine to Tetrahydroharmine

Harmaline or harmine can be converted into tetrahydroharmine by reduction of either in an alcoholic solution by the action of sodium.
Alternately; (example): 5 grams of harmaline, dissolved in 100 ml of water and 20 ml of hydrochloric acid is first heated to boiling and then 300 grams of 3% amalgam is added in three portions. This is done with further additions of hydrochloric acid so that the solution remains strongly acidic. The reaction may be observed by the changing of the yellow color of the harmaline hydrochloride into the colorless tetrahydroharmine hydrochloride. When the solution is cooled, tetrahydroharmine separates in colorless crusts. This should be dissolved in hot water, precipitated with ammonia and the free base recrystallized from methanol to give bunches of needles. The mother liquor will also yield more crystals and a total yield of around 90% is possible in theory. From Perkin & Roberts 1919, on page 961.

Shulgin & Shulgin 1997, pages 584-585, reduced harmaline using Platinic oxide and Sodium borohydride in an acidic aqueous solution using an argon atmosphere.
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I have at least two sources for caapi leaves

1) Bouncing bear in US has them, http://www.bouncingbearbotanicals.com/ayahuasca-vine-p-286.html They are the "foliage" product of course. They also show the jaguar enjoying the leaves, I suppose not because they are rich in meat.

2) Spiritgarden ethnobotanicals in UK also sell them, http://www.spiritgarden.co.uk/cart/index.pl/catid_1/proid_83/_/_/Banisteriopsiscaapi/

There may have a fair source of THH. The vendor of pure THH claims to extract it from caapi (or syrian rue sometimes). Extracting from caapi is not that cost-effective if one is extracting the trunk, even if one is doing it in real bulk.

But leaves could be the key; it is from caapi as they claim and it can be found in massive abundance. Who buys the leaves anyway? I bet if this is their source they can find kilos of them for a very cheap price and extract it. That would make sense cost-effective wise. And caapi growing at one's property can produce a fair amount of leaves.
 
ok great... this thread is coming along very nicely.

I am actually helping out at a entheogen symposium tomorrow... there will be a lot of very knowledgeable and switched on plant heads at this gathering. Im sure I will be able to find someone who has some more experience and information for us.

So the main questions I will try to get answered.

THH content of caapi leaves.
Which is the best caapi species to begin working with.
Easy conversion of other alkaloids to THH.
Other plant species that may contain usefull amounts of thh.
 
One vendor also says:
"[...]Our extraction procedure is environmentally friendly and food grade. All solids used in the processing of tetrahydroharmine are edible. With our new improved extraction procedure, the only solvent used is pure drinking water.[...]"

I don't know much about chemistry but doesn't this seem to hint at a FASA-inspired method that takes advantage of different pKas, as mentioned before? Only solvent used being water and all..
 
They are probably using column chromatography. There are ways to run a column with just water. You don’t need harmful solvents. If the stationary phase is non-polar, you can use water as the eluent.

The XlogP data shows that separation on a column should be easily possible.

The XLogP of harmine is 2.5
The XLogP of THH is 1.9

If eluting with water on a non-polar stationary phase, THH would come out first long before harmine does. It looks pretty easy to me.
 
Ah well, thanks.
That way their pricing does make slightly more sense, i guess.
Still, their text almost read like the introductory paragraph to the FASA post:
* no more nasty solvents!
* or NaOH!
* improved yield!
* almost 100% pure!
* ... !
* profit!

Which made me ponder that considering what amazing progress is being made around here your FOAFs should think about releasing their teks and achievements under an open source license, lest some sneaky bastard patents a novel process they read about here, makes shitloads of $ selling a product until it gets scheduled and meanwhile sends take-down notice to The Traveler for pirating the patent.
I am actually waiting for someone to start selling jungle-spice that's been cleaned of all illegal residue as some shady 'herbal' blend like "spice" and its clones, packaging it in trippy colours and charging a ridiculous premium.

This place is precious. Unfortunately the more precious it gets the more protection it is going to need. They hate our freedoms.
Sorry for derail.
 
Some peganum harmala does contain THH. Maybe if one was to spend some effort on it, they could create a high THH strain of peganum harmala? That would be much cheaper than caapi.
 
Jorkest said:
perhaps traveler needs to put some sort of All Encompassing Open Source license on the entire site!
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You can't patent something if there's evidence for previous use of it. You can only patent a new invention. Posts here are dated and would be evidence of previous use of the tech. So the tech would not be patentable.
 
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