Harmaline to THH reduction with zinc and vinegar works! (GC-MS results)

[nen888]

..an interesting experiment would be to combine verified THH with harmine/harmaline (vs just harmine) to see what possible synergy could be happening in ayahuasca..
also, doing the prolonged boiling experiment on just harmine or harmaline to see if this is what led to THH detected in ayahuasca brews (as mentioned by Snozzleberry in his MAPS talk)

 

[arcologist]

..an interesting experiment would be to combine verified THH with harmine/harmaline (vs just harmine) to see what possible synergy could be happening in ayahuasca..
also, doing the prolonged boiling experiment on just harmine or harmaline to see if this is what led to THH detected in ayahuasca brews (as mentioned by Snozzleberry in his MAPS talk)

I'm planning on sometime trying to replicate the relative concentrations of harmalas reported in some of the scientific literature as a pharmahuasca dose. Callaway et. al. report a dose containing approximately 200mg of harmine, 25mg of harmaline, and 125mg of THH. This seems like a good starting point for such an experiment.

There was an earlier question about the blood plasma half life of THH. That same paper shows a graph of the concentration in an individual, showing a peak THH concentration of 80ng/ml at T+100 with a long slow taper in concentration that extends past the edge of the graph (T+500). Estimating from this, I'd say that a concentration of 40ng/ml is reached at around T+650, giving a half life of around 550 minutes or 9 hours! This explains the prolonged aftereffects that some users have reported.

 

[nen888]

^..look forward to the results, arcologist..

 

[anonenium]

i had a combination of harmine and harmaline, basically a jar i split in halt for the experiment.

maybe the harmine is more readily converted, im not really sure.

as for the "scientificness" of what i did i really didnt pay as close of attention as i should have, i just had a long discussion with endlessness and came to the conclusion that excess zinc or excess vinegar was not dangerous, so thats how i proceeded. in fact the only point that i did actually measure anything was when it came time for the salt precipitation.

my advise to you is to get a jar of both harmine and harmaline, put it into a jar, vill it full of vinegar slowly until everything is in suspension, then add around 4-5 grams of pure zinc powder (i had about 10 grams of extract in harmalas in the vinegar) and proceed to agitate it regularly over the period of 2-3 hours, then remove the excess zinc, use lye to base it, let it settle, remove the liquid, vinegar again, remove anything that doesnt go back into suspension, add one gram of salt for 10ml of water, maybe an extra gram for good measure, late the thh settle out and collect and dry it then try it.

as for effects boy do i know how harmine and harmaline effect me, to say i become agitated is an understatement (i basically start pacing holes into the ground) and this is considerably low doses like 50mg. when i took 200mg of thh the effects were very different.

as for matching the profile of brews, i took the alkiloid ratio profile information from Mckenna, River & Lindgren and Don from the ayahuasca apa and prepared a pill with a percentage of 32:3:32:32 harmine:harmaline:thh:dm at 100mg:~10mg:100mg:100mg and am currently working up the nerve to test it.

i have big hopes here, but i wont know until i do it.

im sorry i couldnt be more helpful but let me know if you have any more questions.

 

[Jees]

Interesting.

... then remove the excess zinc...

Is that re-usable over and over, or is it affected somehow so to trow away?

Thanks!

 

[arcologist]

... then remove the excess zinc...

Is that re-usable over and over, or is it affected somehow so to trow away?

I think it should still be ok to re-use again. I've just been throwing mine away since I have a whole pound but I plan on keeping it in the future. Not much zinc actually dissolves so I can imagine that it would last a while.

 

[dooby]

Here's an "out of the box" thought...

A metal is to be used as an reductive agent for the conversion into THH am I right?

So a lot of thought has already gone into finding a way to remove any metal impurities from the desired final product...

Why not look at physics rather than chemistry for a solution?...

Couldn't a magnetic metal be used as a reductive agent, precipitate product + metal impurities, remove impurities with a magnet? (like how you would remove nails out of the ashes of a fire)

If this is not a smart idea, is it at least funny?

PLUR

 

[glorf]

Couldn't a magnetic metal be used as a reductive agent, precipitate product + metal impurities, remove impurities with a magnet?

if iron filings were used, you could just decant before adding base, the excess isn't going anywhere. you'd eventually know if there was iron in your product, by the rust.

i wonder about whichever inorganic's ability to interfere by sorption or who knows what, when the base is added, so no comments for me on all this beyond that.

decent zinc powder can be obtained from cheapo fresh alkaline batteries opened under water in the sink, and the old fashioned zinc-carbon battery casings are easily melted in a covered crucible or soup can with a blowtorch, then poured not-recklessly into a container with small holes on the bottom, over a stock pot with some water in it.

 

[Auxin]

The metal is not an issue. After the reaction you can decant off the liquid and rinse the residual metal with a bit of water, then filter all the liquids. The messy bit that required an extra reagent to be added (ammonium chloride) was to address the metal salts that formed and would precipitate upon basification. A magnet wont remove iron acetate or iron chloride from solution.

Just dont make the mistake of using anhydrous ammonium chloride, as it would explode.

 

[dooby]

The metal is not an issue. After the reaction you can decant off the liquid and rinse the residual metal with a bit of water, then filter all the liquids. The messy bit that required an extra reagent to be added (ammonium chloride) was to address the metal salts that formed and would precipitate upon basification. A magnet wont remove iron acetate or iron chloride from solution.

Just dont make the mistake of using anhydrous ammonium chloride, as it would explode.

Thanks for the clarification

 

[Apoc]

Cool Cool! So this is the same technique to reduce oxidized dmt to N-N. I have used that reduction technique successfully, however, I used hcl + aluminum foil. It worked. It resulted in aluminum chloride precipitating in the acidic solution, which I filtered before basing.

Theoretically, do (Endlessness), or anyone with knowledge, think this reduction should theoretically work just as well using hcl + aluminum? And again, should I filter out the aluminum chloride before basing? THANKS!

 

[steppa]

This may be a stupid question, but why does the first graph in the first post not show zinc carbonate, as it is supposed to be in there?

 

[endlessness]

Because it is insoluble in the alcohol used to dissolve to inject the sample into the GC-MS.

 

[steppa]

Because it is insoluble in the alcohol used to dissolve to inject the sample into the GC-MS.

Ah, I see. Thank you. I just know to little about how GC-MS works.

 

[intosamadhi]

Reviving this thread, as I have a question regarding preparation for oral use.

Does anyone see any potential issues in combining a (crude) manske'd harmala freebase (harmine + harmaline + rue impurities) with zinc and vinegar to obtain a solution that could be used orally without converting back to freebase ? (filtering off any excess of zinc).

Zinc acetate is safe for human consumption from what i can tell online. So if one's aim is to use thh orally, is it feasible to do the conversion and jump straight to oral consumption ?

 

[JAi]

Reviving this thread, as I have a question regarding preparation for oral use.

Does anyone see any potential issues in combining a (crude) manske'd harmala freebase (harmine + harmaline + rue impurities) with zinc and vinegar to obtain a solution that could be used orally without converting back to freebase ? (filtering off any excess of zinc).

Zinc acetate is safe for human consumption from what i can tell online. So if one's aim is to use thh orally, is it feasible to do the conversion and jump straight to oral consumption ?

What if we eat oysters (a non vegan source of zinc), how many would we need to eat? :lol:
It would be noticeable if the rue blend had no harmaline effect, since you will feel no drop off between 3-6 hours (only after 6 hours with harmaline), and harmine seems to be a less uncomfortable experience, less force and side-effecty.

I would think it would work better outside of the body first, whatever form of zinc. Also, givin how easy it is to actually separate the two harmalas, I would be curious to see what separates out after.

 

[intosamadhi]

I attempted a conversion of crude harmala freebase (harmine+harmaline) to THH + Harmine.
10g freebase + 6g Zinc + vinegar.
Lots of stirring, lots of bubbles.
Filtered off excess zinc.
Based with sodium carb.
Collected precip and dried.
Used acetone to pull off goods, leaving zinc carbonate behind.
Evap.
Ended with 8g of freebase.

I just performed TLC on the extract. First x is the supposed conversion. Second is the original extract. Third is a new rue extract for comparison.

This was my first attempt at TLC, so i don't think i used equal amounts of extract for each test.

These spots look so similar that it would appear that there is no significant difference between any of them and the conversion was a failure(?). The first spot is a slightly different shade to the others and slightly lower. In looking at the online pics for TLC of synth thh it looks fairly close, but I am uncertain. Any thoughts ?

 

[Mindlusion]

Looks like the conversion worked, THH and harmaline spots are very close together, the darker blue spot on the bottom is a few millimeters lower than the light blue spot of harmaline in your extract.
It looks like you over-spotted your TLC, they don't need very much, if you spot less the differences in colour and distance may be more apparent, try diluting it and running it again it may give a cleaner test

What solvent mixture did you use in TLC?

 

[Aum_Shanti]

Very interesting.

@intosamadhi:
Could you elaborate more on the details of your conversion?
E.g. how long did you stir? How much vinegar?
Anhydrous acetone, right?
Anything heated?
etc.

 

[endlessness]

As Mindlusion said, it seems to have worked well. And indeed do with lesser concentration of the sample, will prob help separating the spots better.

You can see THH has a quite different UV shine than harmaline, and you dont see any trace of the harmaline lighter shine on the first lane, which is your converted product. That's as you want.

The top spot, harmine, as expected remains the same.

What surprised me is using acetone to dissolve the harmalas. How much acetone did you use ? How many pulls?

Harmine and harmaline in general are poorly soluble in acetone, maybe thh is more soluble. Would be interesting to know