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Harmaline/harmine to THH - safe kitchen conversion tek required. Again.

Migrated topic.
Well... "SOMETHING" is precipping at just over pH 7.

Edit: Damn. I think it might be harmine although that doesn't make sense because harmine would have defo precipped in the manske. I'm bored of this now. Some other time maybe.
 
This is important work, and i congratulate everyone involved!

some ideas for ghetto analysis of the product:

Melting point, this is the first logical step you should take with a product like this, get a small marble slab, drill a hole in it for a digi thermometer, and put it on a hot plate and heat it up slow til the stuff melts, note the temp range melting occurs... does all the material melt quickly in a small interval? or does it melt slowly as the plate raises a few degrees?


density:
I was just thinking, it may be possible to figure out the proportions of THH, harmine, harmaline, or at least to get a better idea, if we knew the densities when casted(max density, when you melt it and solidify it you will have this density). If we could find these densities for the components, we could get a better idea of whats in a mixture. If there are two components it is easy to solve.

This is all very exciteing! keep on truckin nexus!
 
Interesting thread, especially in the context of the recent THH controversy!

Ammonia forms a complex ion with zinc that's well soluble. That's why it prevents precipitation of zinc hydroxide (hydrated) when basifying. Excess strong alkali (lye) will also dissolve this precipitate because zinc is amphoteric and zincate is made.
But I'm not sure why this is relevant if the freebase is extracted with a non-polar solvent. Does this precipitate somehow trap the goodies?

Another point: maybe it's not the zinc itself that performs the reduction, but hydrogen in 'statu nascendi'. This is hydrogen at the moment it's formed, before it's bubbled out as H2 molecules. This hydrogen is highly reactive and a strong reducer.

For example, the old Bechamp reduction to produce aniline (aminobenzene) from nitrobenzene, iron and HCl, relied on this.

If hydrogen is the active reducer, other metals that generate hydrogen in HCl could replace the zinc. Aluminium, magnesium and iron spring to mind. Besides that, Al and Mg are much stronger reducers than zinc. I have some of these lying around in powder form but no zinc, so this is at the top of the to-do list! I'll keep you all informed if it works out!
 
Hmm, so far it seems that the mechanism of action for this reduction is not elucidated...I was under the impresion that zinc chloride was formed and hydrogen was liberated that took part in the reduction.

Is anything known about the stoichiometry of the reaction? I would really like to replicate the findings of the original paper, but without knowing what quantities to use its difficult. "Adding a dash of this and a sprinkle of that" simply will not do: it cant be replicated,hence be usefull for others.
 
My dear friends, let me express my opinion on the subject. Harmaline can be converted to THH using Zinc metal. Harmine can't. For any of you that have some chemical education, you can see that Harmine's double bonds that need to be reduced, are part of a fully aromatic ring. Which gives extra stability to the system thus, making it extremely difficult to be reduced. This is the reason why let's say benzene ring is soo much more difficult to be reduced compared to cyclohexadiene. Now on harmaline, this aromaticity does not exist.

Now the reason that you see the bubbling, is not due to harmine reduction. You see zinc, can reduce a double bond, but it can also reduce the hydrogen ions coming from HCl and convert them to H2. That's the bubbles!! Zinc chloride is the byproduct, which will become visible as a white solid when it exceeds its solubility limit.

Another thing to be noted. I think that harmine and THH are blue under UV. You cannot distinguish them. And I think that harmaline is yellowish-greenish. Don't take my word on that though. I personally believe that the way to go is to separate harmine and harmaline with the known method, and apply the process to the harmaline alone. Then, you get pure THH with a small percentage of unreduced harmine in it.

And now let's speculate. My opinion (and remeber, I do not want to raise any voices around here) is that Flowing Visions do the same thing. There is no organic process here. None. Even in the worst case scenario that they precipitate-separate somehow the THH from Banisteriopsis Caapi, they have to make the HCl salt, right?? Do you really think they do it "Manske" style?? No way...can any of you taste the salty salt contamination that accompanies Manske method??? Also, pure THH hydrochloride HAS a greenish tint which makes a pretty nice camouflage for claiming an all-natural method. I mean, come on, they know their target group!! A "natural extraction method" is a perfect marketing sentence!! And I also believe that Flowing Visions have an account in here!! So please, don't attack meee!! I am only speculating!!

All in all, I think it is EXTREMELY easy to have some THH with the zinc method. And fast also. Giving very high yields. And with rue as the harmaline source?? Seems that we will see a shift in consciousness in the next year ;))

And if you see a vendor appearing in Europe selling THH, it's me!!! So you better hurry and kick me out of business!!
 
Well let me correct something here!! Maybe they can do it organically at the very end...I just read a post from 69ron stating that you can crystallize the harmala alkaloids with Manske method without getting any salt contamination....
Nevertheless, we must experiment enough to make it available cheaper...
Maybe with much pure harmalas at hand and a PH meter, we could determine a PH range for the most optimal separation from a mixture!!
 
Well, thank to a guy asking about the details of 69ron's post, I had to trace it back and re-read it!! He actually says that you can get it less than 5% of salt contamination...I am sorry for the misinformation written...Has it ever happened to you reading hundreds of posts sometimes and feeling dizzy?? I guess something like that happened to me and didn't notice the 5% !!!
 
SalooM said:
My dear friends, let me express my opinion on the subject. Harmaline can be converted to THH using Zinc metal. Harmine can't. For any of you that have some chemical education, you can see that Harmine's double bonds that need to be reduced, are part of a fully aromatic ring. Which gives extra stability to the system thus, making it extremely difficult to be reduced. This is the reason why let's say benzene ring is soo much more difficult to be reduced compared to cyclohexadiene. Now on harmaline, this aromaticity does not exist.

Now the reason that you see the bubbling, is not due to harmine reduction. You see zinc, can reduce a double bond, but it can also reduce the hydrogen ions coming from HCl and convert them to H2. That's the bubbles!! Zinc chloride is the byproduct, which will become visible as a white solid when it exceeds its solubility limit.
Click to expand...


I'm no chemist, but it would seem to me that if all it takes is hydrogen ions percolating through the solution in the presence of elemental zinc, why not use electrolysis (DC current hooked up to zinc anode/cathode) in the solution to provide BOTH?

Would that provide the necessary surface area and double bond reduction? I don't see why it wouldn't, so someone would need to explain to me why this notion is hair-brained!

Best to all,

N.B.
 
Nature Boy said:
I'm no chemist, but it would seem to me that if all it takes is hydrogen ions percolating through the solution in the presence of elemental zinc, why not use electrolysis (DC current hooked up to zinc anode/cathode) in the solution to provide BOTH?

Would that provide the necessary surface area and double bond reduction? I don't see why it wouldn't, so someone would need to explain to me why this notion is hair-brained!

Best to all,

N.B.
Click to expand...

Sounds like a good idea, electrolysis is the ultimate redox tek!

Some thoughts anout the electrolyt. Certainly, chloride ions should be avoided because then chlorine would evolve at the anode, and you'd make bleach - which would cause unpleasant side reactions. Sulfate would be better, oxygen then forms and escapes.
That means the electrolyt would be harmaline sulfate, made by dissolving salt-free harmaline in dilute sulfuric acid...
Electrodes: stainless steel?? Or zinc like you say. Platinum would be nice...
Any experts here? (I'm just an amateur)

A few questions:
- are there any oxidation products formed at the anode that can react with the (imaginary) THH? Or is the THH oxidized at the anode, harming yield? If so, the electrodes must be in separated compartments.
- can THH be reduced further? Ha, we don't even know if THH would form at all ;)
- is this type of discussion allowed here? After all this is no extraction but a chemical reaction. Maybe THH can be an exception ;)
 
A quick note : magnesium seems to have a greater reduction potential compared to zinc, and its close to that of sodium :

Sodium:-2.271 v
Magnesium:-2.37v
Sodium Borohydride: -1.24 v
Aluminium: -1.66v
Zinc: -0.76 v

While sodium borohydride and sodium are difficult to access all the others are withing reach. Alumium for example is accesible through aluminium foil, and mangesium can be found in firestarting kits (the ones with the flint and the "metal bar" that you shave). I think they would be worth given a look at.

Maybe aluminium or even better magnesium could substitue zinc...

As always, be careful, clean your product, think twice before you act.
 
AFOAF has volunteered to test out the potential efficacy of this conversion...but how would you recommend he proceed?? Assume he has an ample supple of a mixture of harmaline and harmine from a P. Harmala extraction and is willing to further purify and (insofar as possible) isolate the harmaline prior to attempting the harmaline to THH conversion. What next? There may be some excess salt from the Manske process, so dissolve in water and apply a DC current, allowing only the negatively charged cathode to be in direct chemical contact with the solution?

N.B.
 
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