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THH extraction tek

Migrated topic.
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?
 
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.
 
that would be very very interesting.. one could extract from rue, separate harmine and harmaline by being careful with the pH in the basification (ok finally I remember to ask: does this word exist, or? basifying, basification, basidification?) step. Then change the harmaline to thh with zinc and hcl
 
Interesting article T.

From the article regarding Tetrahydroharmine:
It is a much stronger base than its precursors
Click to expand...
The precursors is harmine and harmaline.

Does this mean that its pKa is higher than either of them? Would mean that it might be possible to separate THH from the other two by basifying to about 11-11.5
 
According to page 187, you get THH from both harmine and harmaline reduction. All three alkaloids are metabolites of Syrian Rue, so it might be possible to convert the former two easily to THH. I wouldn't know how though:?
 
69ron said:
TiHKAL explains how to reduce harmaline to THH in pretty good detail.

See here
Click to expand...

The problem is that chemicals listed there are impossible to get for the layman kitchen chemist.
It's possible to reduce harmine and harmaline by using sodium and ethanol, but I couldn't find a desciprion.

Other reduction teks here.
 
Found the method that uses hydrochloric acid and zinc dust.

From Studies in the harmine series of alkaloids
Harmidine/harmaline was isolated from the seeds of Peganum harmala following the procedure described by S.Siddiqui. To a solution of 10 g harmidine in 10% aqueous hydrochloric acid zinc dust was gradually added with occasional shaking and the reaction mixture was heated on the water bath till the yellow color disappeared. Unreacted zinc was filtered off and the colorless filtrate ammoniated with prior addition of ammonium chloride to prevent the precipitation of zinc hydroxide. The white crystalline mass which separated out immediately was shaken out with ethyl acetate. On working up the ethyl acetate layer tetrahydroharmine was obtained as colorless crystallizate in about 80% yield. On recrystallization from methanol-benzene it formed slender needles which melted at 199C. Mass, NMR, IR and UV spectra were found identical with those of an authentic sample of tetrahydroharmine.
Click to expand...
 
It would be interesting to hear about further experiments on these conversions. I may even educate my feeble mind and do some further reading of my own.

Either way I'll be watching this thread with great interest.


P.S.

Isn't this fairly straight forward? The bit I'm confused by is my lack of understanding "Amalgam". All I can find on this reveals it as some sort of mercury solution. What purpose would this serve in the below mentioned reaction?

"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.
 
Hamine/Harmaline conversion to THH with food grade and H2O'


Harmine takes up four atoms of hydrogen when treated with sodium and alcohol' and is converted into tetrahydroharmine'

Hence the oxygen atom is knocked off and replaced by hydrogen' converting Harmine/Harmaline to THH'



Ascorbic acid (vitamin C)

Ascorbic acid (vitamin C) is a water-soluble, antioxidant present in citrus fruits, potatoes, tomatoes and green leafy vegetables.

One important property is its ability to act as a reducing agent (electron donor).
Ascorbic acid is a reducing agent with a hydrogen potential of +O.08V, making it capable of reducing such compounds as a molecular oxygen'

So simply put'
Add you Harmine/Harmaline to a strong solution of ascorbic acid and H2O' and boil gently' until the yellow colour has changed to a clear solution'
Of what happens is the ascorbic acid attracts the oxygen and the production of H2O2 donates a hydrogen'
Hydrogen peroxide H2O2 acts as a reducing agent in acid solutions' and is produced by boiling ascorbic acid in H2O'
This natural production of H2O2 is enough in this reacion to add the H ion to the Harmine mole' after the oxygen has been attracted by the ascorbic acid'
The process slows down in acid solutions' but works faster in alkaline'
The stability of ascorbic acid decreases with increases in temperature and pH.



Just a little heat and patience'


Then base with ammonia to pressipitate the THH'




Harmine/Harmaline mole to THH with foodgrade and water'

:)))



The process would take a little time an is no doubt done under reflux' so the H2O and H2O2 liberated can condence and run back into the flask'


Bliss

Nobuoni +

This is only way I can work out so far without using a reactive metal'

Anyone wish to attempt to crunch the chemistry with me ???:roll:
 
Nobuoni said:
Add you Harmine/Harmaline to a strong solution of ascorbic acid and H2O' and boil gently' until the yellow colour has changed to a clear solution'
Click to expand...
Nice! You tried this method? And it worked? Any idea what the conversion efficiency is?
 
Nobuoni said:
Hamine/Harmaline conversion to THH with food grade and H2O'



So simply put'
Add you Harmine/Harmaline to a strong solution of ascorbic acid and H2O' and boil gently' until the yellow colour has changed to a clear solution'
Of what happens is the ascorbic acid cleaves the oxygen and donates a hydrogen'
Hydrogen peroxide H2O2 acts as a reducing agent in acid solutions' and is produced by boiling ascorbic acid in H2O'
This natural production of H2O2 is enough in this reacion to add the H ion to the Harmine mole' after the oxygen has been cleaved by the ascorbic acid'


Just a little heat and patience'


Then base with ammonia to pressipitate the THH'
Click to expand...

Do we have any ratios or saturation details for these chemicals? I'd quite happily try this one out. Vitamin C is way easy to get.
 
2-4 grams ascorbic acid to 100ml of H2O' you can go higher' but saturation point is too high'
Bliss

Nobuoni +

Consentration of ascorbic acid must be high' but no so high as to smother the H2O solution'
I am guessing the ascorbic degrades as it reacts with the mole'
If the solution is still yellow after reflux' then more ascorbic acid is required'
Reflux is no necessary' just boil in a flask with the lid off' add water as the volune evaps'
A stainles steel saucepan would do with the lid on' to prevent a lot of evaporaion'
I have no clue to conversion rates'
This process shall be slow' becasue of the low reduction process of ascorbic acid'

Bliss

Nobuoni +
 
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