http://www.raell.demon.co.uk/chem/logp/logppka.htm

Good summary.

On page 25 (121 in book), it says that THH can be made from harmaline using Zink and HCl.

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

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

TiHKAL explains how to reduce harmaline to THH in pretty good detail.

See here

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.

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 ???

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 +

salting out removes vasicine and vasicinone from it, so its only harmine/harmaline basically, and some other plant impurities

but remember to get pure harmalas, you have to repeat the steps at least a couple of times. First time for SWIM comes out dark brown powder.. second time a nice light brown/pinkish powder.. SWIM didnt do more than this yet because he is happy with what he got for now, but for sure sometime he will do more consecutive repeats to get really pure stuff

Saturated salt solution in the fridge for a few days gives good yields from Rue'
Then salt it out again'
Dry the resultant goo' crush it up fine' and wash in warm methanol/ethanol'
The salt you used to push out the harmine hydrochlorides falls to the bottomof the flask'
the Harmine hcl dissolves in the warm alcohol'
Draw off the alcohol'
Evaporate on a plate'

Bliss'
Nobuoni +

Wow Nobuoni, thanks for the informative posts!

Let me be the first to Welcome you to the forum of nexus, your apparent knowledge of chemistry is a fresh sign of good things to come

Thank you for the warm welcome bro'

I updated my original post after a little bit more study' and hope that it answers some folks questions a bit clearer'




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 your Harmine/Harmaline to a strong solution of ascorbic acid and H2O' and heat 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.
Of which means heat and increased ph makes for the ascorbic acid to attract even more oxygen'
In this reaction the ascorbic acid is oxidised' hence destoyed'
So more ascorbic acid is added to the gently boiling solution as required'

Exposure to oxygen, metals, light, and heat destroys ascorbic acid, so it must be stored in a dark, cold, and non-metallic container.


# E300 ascorbic acid,
# E301 sodium ascorbate,
# E303 potassium ascorbate,


Tannic acid, gallic acid, pyrogallic acid and formic acid are all excellent reduction agents'



Just a little heat increased ph' but still keeping below the pKa of Harmine/Harmaline so the alkaloids remain water soluble' the same as ascorbic acid'
Ascorbic acid is less soluble in hot water' and less again in alcohol'


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'

(This satement shall have to be tryed out' ascorbic acid is quite reactive' attracting oxygen' so could possibly do the conversion quite quickly' dependant on the amount of ascorbic acid used'
Because ascorbic acid reacts with metals it is unadvisable to use a saucepan to do this experiement'
Ihave no clue if stainlesssteel wuld oxidise ascorbic acid' doubtful !

Ascorbic acid attracts oxygen very easily'


Bliss

Nobuoni +

This is only way I can work out so far without using a reactive metal to attract the oxygen from the Harmine/Harmaline mole'
I mixed up a reasonably strong solution of ascorbic acid an dropped a dirty oxidised silver spoon in it'
It stripped the oxides off in a matter of seconds an left me a with a very shiny spoon'
Ascorbic acid is used in photography as reducing agent/developer'

Anyone wish to attempt to crunch the chemistry with me ???
I believe I have answered this question'


Bliss'

*claps*

Simple kitchen reflux'

Take a stainless steel saucepan and a pyerx dish lid' or large pyrex dish'
Place the lid upside down upon the boiling sauce pan'
and drop some ice on the lid'
The steam then comes off the cooked solution and condences' back into the boiling solution'
The ice is no nessesary but it helps grealty'

Bliss

Nobuoni +

Ok, pending a good yield from a rue extraction I'll probably want to try this out.

Is Ascorbic acid the only way to go with this? If so is there something I should avoid when purchasing it. I know many supplements come with certain additives that arent desirable.

Would this do?

http://www.expresschemis...ic-acid-250g-powder.html

Big shout to Nobuoni for the science!

That's a great source for food grade ascorbic acid. It's over 99% pure. I would use that or something similar like Now brand.

A most fascinating group of molecules' that have had very little research done on them'
A 500 mg dose of Harmine hcl effects similiar end results to high dose Ibogaine'
Except the Harmine dose has non of the after effects of Iboga' ie' being psychicaly wired out'
Has been reported to bring about abstinence from cocaine and opiates and alcohol after a single 500mg dose'
Equivilant dose for Ibogaine would be 1400mg +' but you use Ibogaine to kick substances you are going to be
flying on Ibogamines for well over a month'
Harmine seems to be way gentler but effect the same resset of NMDA receptors and dopermine pathways'
Also to add this molecule is open for "manipulations" of which no doubt other active molecules can be derived'
I shall be working close with this plant alie'
Bliss

Nobuoni +

As to other ways of converting Harmine hcl to THH' I listed some very good reducing agents including ascorbic acid'
Unless you wish to use a reactive metal' the likes of sodium or potassium and HCL acid'
Food grade reduction agents would seem to be the way to go'
Results of experimentations shall tell ))

Pharmacutical grade ascorbic acid'
http://www.iherb.com/pro...rce=gb&utm_medium=f3

To add'
Syrian Rue'
No grind the seeds' boil em gently in acidic water (white wine vinegar) do this 3-4 times' at an hour a go'
Then take the seeds and ring them out inside a tee-shirt'
Combine all your solutions' reduce to 300ml'
Let settle in the fridge'
Filter by decanting through a decent coffee filter' if you let it settle properly' it filters quite quickly' unlike as of when you grind the seeds'
Add saturated salt solution to pressipitate the Harmine hcl'
Stick the container in the fridge for 2 days'
Gently decant off the salt solution' add a little fresh water to the sludge in the bottom of the container and pour into a china bowl'
Dry this product completely in a warm oven'
Bust up this resultant cake and grind it gently in a coffee grinder'
Add this powder to a flask and add a generious portion of methanol'
Warm this solution in warm water bath'
The Harmine hcl dissolves in the methanol leaving the salt behind'
Let settle and decant off this methanol into a china bowl'
Sit this bowl in a bath of hot water and evaporate the methanol' do this in the garden'
The result is a pile of very fine brown yellow crystals'

Bliss

Nobuoni +