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turn your harmine and harmaline into tetrahydroharmine

Migrated topic.
shoe

shoe

Rising Star
OG Pioneer
Using zinc and hydrochloric acid. Here is the paper:

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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look at page 10 of the PDF (not the manuscript).
On page 54 of the pdf, you can find the experimental section
detailing his approach towards the item in question.
anonym.to - Anonym surfen - link to other sites anonymously

:)
 
NH4CL (ammonium chloride) can be bought online, it isn't watched.
Its sold as an additive for fireworks, I believe.
 
I've been wanting to try this very thing for months now, but haven't had the time or space.

I can't believe other folk haven't tried this yet as I've been told it's a pretty sound method.
 
soulfood said:
I've been wanting to try this very thing for months now, but haven't had the time or space.

I can't believe other folk haven't tried this yet as I've been told it's a pretty sound method.
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There's a good reason for people not trying that; these conversions are not always complete and most people do not have a good analytical method for monitoring reactions. In practise these reactions are not as simple as ABC. Whoever tries the reaction(s) will always one will end with a mixture of 3 and the success will be far more variable than the original paper suggests.

If we knew more on chemical characteristics of THH and how to separate it from harmine/harmaline mixtures then we'd get a good idea of how successfully the said conversions can be performed in the kitchen. For the moment, for SWIM this conversion sounds like a shot in the dark.
 
does precipping out at the correct ph not work as with harmine and harmaline ? repeating that proceedure with ph aimed at 100% could potentially be a way to separate them.
 
Phlux- said:
does precipping out at the correct ph not work as with harmine and harmaline ? repeating that proceedure with ph aimed at 100% could potentially be a way to separate them.
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it would, but how about THH? We do not know the pKa of THH (we really do not!), we know however that freebase THH is very likely to precipitate out of basic solutions (xlogp is 1.9)

Mind you however that the paper reports a 80% (ideally) conversion of harmaline to THH. How about if one has harmine? The reduction pathway is harmine --> harmaline --> THH. We really do not know much efficiently harmine is reduced to harmaline via this method. Not to mention reaction equilibria that will make these reactions a helluva more complicated that they (in theory) seem.

If only things were that simple...
 
Good points...

I was under the impression that harmine and harmaline change water to yellow when desolved, but THH was clear.

What about if you clean the original harmalas up pretty damn good before hand and kept the reaction refluxing until the yellow solution changes to a clear one?

Even without a complete conversion would you think that enough of a colour change could be detected to inform of a partial reaction?
 
soulfood said:
Good points...

I was under the impression that harmine and harmaline change water to yellow when desolved, but THH was clear.

What about if you clean the original harmalas up pretty damn good before hand and kept the reaction refluxing until the yellow solution changes to a clear one?

Even without a complete conversion would you think that enough of a colour change could be detected to inform of a partial reaction?
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SWIM really does not know whether THH solution was clear. Besides, colour change is a very poor indicator of in this case for the conversions. Human eyes are not that sensitive to certain things and a little colour change may not even be perceived. Ideally a spectrophotometer should be used for colour monitoring or TLC to check for the end-products. Both are however unavailable to most...

The experiment is nevertheless worth trying from however wishes but there are poor indications that it will work nicely. Maybe it will or maybe it won't.
 
Infundibulum said:
Phlux- said:
does precipping out at the correct ph not work as with harmine and harmaline ? repeating that proceedure with ph aimed at 100% could potentially be a way to separate them.
Click to expand...
it would, but how about THH? We do not know the pKa of THH (we really do not!), we know however that freebase THH is very likely to precipitate out of basic solutions (xlogp is 1.9)

Mind you however that the paper reports a 80% (ideally) conversion of harmaline to THH. How about if one has harmine? The reduction pathway is harmine --> harmaline --> THH. We really do not know much efficiently harmine is reduced to harmaline via this method. Not to mention reaction equilibria that will make these reactions a helluva more complicated that they (in theory) seem.

If only things were that simple...
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Harmine should be reduced to harmaline too, depends on the excess of the hcl and zinc, and the temperature.

You will end up with a mix of the three different alkaloids.
Forget about separation, whats the point? I think you'll get more THH for your harmala buck this way :)
 
shoe said:
Harmine should be reduced to harmaline too, depends on the excess of the hcl and zinc, and the temperature.
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Why exactly it should?!?!?!This I do not understand

In theory yes, it makes sense that it may be reduced, but in practise what? Please find me a method for the conversion of harmine to harmaline and then we discuss solidly.
 
shoe said:
why would you doubt that?
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Because in theory, theory and practise are the same but in practise they are not.

And because the battleplan almost never survives the first contact with the enemy.

Chemical reactions, even the seemingly "easy" ones can be too difficult in practise. You understand that adding 2 atoms of hydrogen in harmaline (for instance, to reduce it to THH) is different from adding 2 or 4 atoms of hydrogen to reduce harmine to say harmaline or THH. they are similar, yes but different. In Tihkal harmaline is not getting synthesised by reducing harmine and then separating it out. SWIM has not seen a paper detailing the reduction of harmine to harmaline (or THH). But he may be wrong and such method may exist.

You do not seem to have much experience in chemical reactions and experiments in practise. Think about these examples; Adding FASA (a liquid) to xylene salts out mescaline as mescaline fumarate. Adding glacial acetic acid (another liquid) in xylene to do the same does not work! Adding dry fumaric acid to do the same does not work either. Adding FASA in limonene containing freebase mescaline also does not work! In theory, the freebase mescaline should react with the acids to form salts, but it doesn't seem to happen always. It is because theory and practise are two different things, as explained above.
 
Im well aware that its synthed in thikkal and not reduced - that doesn't mean anything here, why'd you even mention that?

Oh, thats strange: I would have thought that glacial acetic acid would have reacted to form mescaline acetate! Im gonna take a guess
that it is because of pKa of the acid, or the solubility of the product formed, or something like that. I.E the acid itself thats the problem.
is that right?

I haven't got any zinc so, I guess I can't test this for now.
 
shoe said:
Im well aware that its synthed in thikkal and not reduced - that doesn't mean anything here, why'd you even mention that?
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It is mentioned because synthesis of harmaline in tihkal could involve reduction of harmine (just like synthesis of THH involves reduction of harmaline) and separation of harmaline of the mixture. Since this route was not followed in tihkal and no protocol I know (or you have found) that describes an easy reduction of harmine to harmaline, I have to assume that it is nore difficult that imagined.

But please find me a reference of the reduction you propose otherwise do not assume "it just happens".
 
Thanks Phlux-!

But now another question comes to mind; Being able to make a usually expensive substance like TTH from a cheap source like Rue would be a huge advantage, wouldn't it!?

So why is it that this tek seems to have attracted so little interest among nexus users thus far? :?
 
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