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THH red oil bug strikes

Migrated topic.


Rising Star
So I was following a minor modification of the VDS harmaline reduction tek.
All I did differently was to use a magnetic stir plate and keep the reaction warm so it went faster, and my vinegar is 5%. I opted for the harmine/harmaline combo reduction with subsequent separation by means of bicarbonate/carbonate.
All went well. I got a big light tan ball of harmine and zinc carbonate, and a somewhat darker tan ball of THH freebase. I dissolved each in its own moderate excess of vinegar and proceeded to manske them by heating them, dissolving in salt, cooling a bit, and refrigerating.
When the salt dissolved in the harmine solution it formed that red oil that was observed in the THH project thread when someone tried to directly manske the filtered reduction solution.
I filtered it and more formed. All beakers are in the fridge for the night now.

Has any more been discovered about this oil? Particularly what to do next?...
My current plan is to wait for tomorrow and if I can get crystals out I'll do another manske on them. I'm toying with the idea of including a whopping dose of ammonium sulfate to distract any zinc that may be grabbing on to my alkaloids.

Unvarnished lab notes:
500 grams of P. harmala extracted and 5 successive salt crystallizations performed
0.12 grams of harm(al)ine HCl set aside as reference
400 ml distilled vinegar [5% acidity] heated to scalding, 25.5 grams of harm(al)ine HCl dissolved into it in a flat bottom boiling flask
Solution placed on unheated magnetic stir plate and 12 grams of ultra-pure zinc powder added
Mixture turned milky greenish grey and maintained a gentle vortex
T+2 hrs much of the zinc has dissolved, mixture has now cooled to 37°C, an additional 3 grams of zinc added
T+3.5 hrs mixture has cooled to room temp and reaction has slowed, reaction flask re-heated to 75°C in a hot water bath and returned to the stir plate, fizzing has resumed
T+6 hrs much of the zinc has dissolved, mixture has cooled to 35°C, mixture was repeatedly decanted and filtered to remove the remaining zinc powder. Solution was placed in a 1 L beaker on the stir plate and 35.45 grams of NaHCO3 was slowly stirred in. After 20 grams the
mixture became too thick to stir smoothly, 100 ml distilled water added. pH measured at ~8. Left to stir for 60 minutes.
Mixture filtered to yield the crude harmine freebase fraction. With stirring the filtered liquid was basified with 10 grams Na2CO3 (anh.)
and filtered to yield the crude THH freebase fraction.
The two fractions were separately dissolved in vinegar and subject to a standard salt crystallization procedure.
The harmine fraction, upon addition of salt, promptly became cloudy. 50 ml of vinegar were added. A red oil formed which adhered to the
beakers. It was filtered and new red oil was formed in the new beakers. The mixture was cooled and moved to the fridge.
The THH fraction behaved normally at first. Upon cooling a yellow precipitate formed and traces of oil were seen. It was moved to the

Thanks :)
To go into more detail on my hypothesis of what the red 'oil' is, I suspect the harmine is making a double salt with the zinc and that this zinc chloride harmine hydrochloride double salt is so soluble in water that the common ion effect fails to make it crystallize. Instead the harmine gets arranged like the soap molecules in a soap bubble to make a barrier behind which highly concentrated globules of zinc chloride harmine hydrochloride double salt can hide in aqueous solution.
This would explain its origin and why it leaves no oily residue when washed off things.
Its actually kind of soapy and makes bubbles when sprayed off labware.

I drew a picture to illustrate :lol:


  • Red+Oil.jpg
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we lack the chemistry skills to confirm your hypothesis, but you received a thumb up :thumb_up: for venturing into this. We would only attempt this with harmaline, not the combo. So far we haven't attempted it at all....:p

Do you have a microscope already? Have you not used the ammonia as VDS did?
Let's hope that either One(1), An1cca or Jees sees your post...
I have got a microscope somewhere, but I have not tried testing the different fractions yet.
I opted for the ammonia-free harmine/THH separation in section 2.7b. I think this is what caused my issues. Rather than nice free crystals the mansked alks look like a mushroom mycelium cake thats beginning to pin, but at least it didnt all turn to oil. I ignored them for a day so I could test the saved oil that had adhered to my beakers.
Re-salt crystallizing the oil in 20% ammonium sulfate* wasnt magical but it did get it to a crystalline state. After filtering and pressing dry I dissolved that half gram of crystals in 10% ammonium sulfate, based with an excess of 10% ammonia, filtered and pressed, dissolved in 2% vinegar, and mansked. I finally got nice clean homogeneous crystals on that little sample. So I plan to proceed in the same way to clean up the main harmine and THH fractions now.
I do not intend to again manske zinc filled solutions in the future.

* Ammonium sulfate works just like the more traditional ammonium chloride, it just takes a little more and I have 5 kilos of the stuff. In a rough alkaloid-free test 5% ammonium sulfate seemed to be the lowest effective concentration for even relatively low concentrations of zinc salts. Here I jumped to 20% just because the scale was so small and by that point I was annoyed 😉
People were having trouble before using carbonates to base.
If using them then quite rigorous sticking to VDS protocols has made An1cca registering success.

If you were to perform a separation step anyway, why not at the start before the reduction steps? I see no use in reducing the combo, only making things harder to succeed. Separation at first has shown An1cca to be the best way to go. We've not much redundant executions of VDS-style done here at nexus, and any attempt is in prone to learning/growing pains.

If you have Zn salts retention, and perhaps some carbonate side effects in your little pot, then executing a manske on that doesn't surprise me of resulting oddities.
Using ammonia to base seems to deal with both (post reduction) Zn salts retention and avoiding the carbonate side effects.
Note An1cca was not able to manske successfully a post reduction liquid, containing all the reduction elements still in it (except the hard Zn of course). Using ammonia, drawing (filtering off) off all zn salts that stay quite liquid when done so, washing your products, then manske was able to succeed.

Nice to see you are experimenting. Thank you :thumb_up:
Thanks :)
I certainly now agree with you on keeping carbonates away from zinc! I knew it was risky but it looked like fun [and it was, after a fashion]
The next half kilo will be done with ammonia, as you suggest. I just tried the carbonate method because I was surprised that VDS claimed success with it.
I reduced the mixed alkaloids because VDS claims full separation of harmine and THH in one step, whereas harmine/harmaline separation seems to require about 4 repetitions to get the harmine clean of significant quantities of harmaline. I havent decided which route to go next time. Perhaps pre-reduction separation for experience points if I have the extra time.

I resumed work on the large portions. The mushroom-cake looking harmine HCl block was filtered and pressed dry, dissolved in 10% ammonium sulfate, based with ammonia, filtered, pressed dry, dissolved in hot 2.5% acetic acid and mansked with hot sat. NaCl to give a beaker full of very nice looking crystals. I foresee no problems with cleaning the THH fraction.
Elrik said:
...I reduced the mixed alkaloids because VDS claims full separation of harmine and THH in one step, whereas harmine/harmaline separation seems to require about 4 repetitions to get the harmine clean of significant quantities of harmaline...
This needs some context:
The VDS paper does a lot of experiments. The separation between Harmine-DHH he tried that two ways:
1) pH specific, with need of a pH meter;
2) non pH specific, yet solely depending on the properties/differences between SodCarb and SodBiCarb, with no need for a pH meter per se. He did use a pH monitoring just to see what was happening but the aim here was to see if it works just depending on SodCarb - SodBiCarb only.

Your quote refers to 2) and needs 4 to 5 steps to complete separation between Harmine-DHH mix, and only one step for a Harmine-THH mix (protocol4). So what you say is true.


A) you can still go for the pH specific separation and have a Harmine-DHH mix separated in one go only, so you are not bound to 4-5 steps to make that happen. In the case of VDS-style this is NOT the typical old school pKa @ pH 8.75 approach because VDS makes use of pH depressions (making the conditions right for that).

B) protocol 4, meaning separation after reduction as you suggest, is going to have precipitated Zn-salts in the end product. The only good way to rid of those is an ammonia bath/wash of your end products. The protocol 4 speaks of a soft carbonate wash (sodcarb 0.5%) as sufficient but that wont rid you of the precipitated Zn salts, it's not a good clean up. It's not that unhealthy, VDS is quiet about it, but we know ;)
An1cca said:
... Up until now, the only thing that was not reproducible is the clean-up of the harmine-fraction with sodium carbonate as stated in his protocol 4. In my opinion, he used ammonia and extrapolated its washing capacities to sodium carbonate. As demonstrated above, the work of Jees and myself has proved him wrong.

C) take on 1) is still preferred, and with ammonia. You could use sodcarb or sodbicarb for that but the foaming/forming of CO2 is annoying and falsifying your pH readout. This quote is telling:
An1cca said:
Also, carbonates are prone to form a brown sticky goo if deviating from VDS standards, ammonia is much more forgiving.

My suggestion:
* separate Harmine-DHH with pH depression tek;
* wash both fractions, keep the harmine and cherish;
* reduce DHH fraction with Zn;
* filter hard Zn out;
* base to retrieve a THH rich fraction with a stiff ammonia amount;
(personally, after ammonia I top up with some little lye to get high enough)
* filter and wash, cherish the THH.

Done :thumb_up:
I'm going to try to recondition the probe on a very old laboratory pH meter I got for free, as that pH depression tek looks quite cool. Failing that I'll go the step-wise [bi]carbonate route and just be patient.
Beyond that my next go will be just as you describe. :)

I think I worked out the cause of my red oil. It wasnt zinc, it was heat. I was working with many of the solutions hot.
The first THH manske should not have had any zinc and it got red oil, I got red oil on purified harmine, and ultimately I got red oil when freebasing THH.HCl with ammonia!
In that last case I then chilled it to solidify the oil, isolated the solid freebase, dissolved in a minimum of room temp 0.25M HCl on a stir plate, and mixed an equal volume of room temp sat. NaCl. Instant THH.HCl snow globe, no trace of oil.
Perhaps when they are pushed out of hot solution harmalas can grab a few extra waters and 'melt' at a much lower temp than the dry compound would.
Elrik said:
... I opted for the harmine/harmaline combo reduction with subsequent separation by means of bicarbonate/carbonate...
I'm still puzzled with that red oil you had. But just to be sure: was there a manske precipitation included when making that "combo" starter material? It prolly is, but just asking.
Yeah, I began by boiling half a kilo of P. harmala in 0.01M acetic acid, concentrated some, and then did 5 successive manskes.
I've done that before and in all cases when salting mixed harm(al)ine I would dissolve salt straight into the hot solution and watch the crystals slowly grow as it cooled. Even at the same concentrations, the isolated alkaloids crystallize out so fast I cant do that effectively. If my red oil was caused by working with hot solutions I think that explains why I didnt get it on the mixed harm(al)ine, it goes so much slower that it has a chance to crystallize properly.
In that last stage, where my THH was almost entirely converted to red oil in freebasing, cooling it solidified it into a tan block and dissolving in a minimum of room temp 0.25M HCl and manskeing it with saturated saline produced a fair final yield of extremely clean looking and homogeneous light yellow crystal.

I did an initial bioassay of just 100 mg THH.HCl.2H2O yesterday and my pee had a slight blue fluorescence under 365nm light instead of the neon green of mixed harmalas, new party trick :lol:
Elrik said:
...In that last stage, where my THH was almost entirely converted to red oil in freebasing, cooling it solidified it into a tan block ...
Hmm , I never freebase my harmalas when hot. Might be just that? <-- as you pointed out.

Lol on the pee color ;)
Btw how did the 100mg THH felt for you?
To me THH feels like some sort of pressing feeling, nothing holy TBH (as a feeling).
When I took 100 mg THH.HCl.2H2O [equivalent to 75mg freebase] at the 30 minute mark I felt completely normal. At one hour I noticed I was in an uncharacteristically good mood, that good mood lasted 3 to 5 hours. I got no change in blood pressure, no CEVs in a dark room [I checked every hour], and no hangover.

48 Hours later I dosed 200 mg THH.HCl.2H2O [150mg THH]. At one hour I noted a "subtle and hard to define 'lightness'" and an elevation of mood, by an hour later this had progressed to a mild body high, a hint of a psychedelic headspace and a slight 'psychedelic ataxia' that I get from any hallucinogen [its like standing on a boat in calm water]. I just hit T+5 hrs and CEVs have not occurred and blood pressure has been normal. Although it didnt occur to me to check pupil dilation until just now [normal] there was no photophobia at either dose.

My tentative conclusion on THH alone is that if I were dosed with the low dose without my knowledge I wouldnt have noticed, but it might be good to take before a date. The higher dose might be useful at an art gallery or concert if I couldnt be on anything more overtly psychedelic.

Next will be to test it with other compounds. I want to do harmine+DMT so I have a fresh baseline and then 3 or 4 days later replicate that exactly but toss in some THH. It might be several weeks before circumstances allow that scenario. If I could go back and give my teen self advice it would be 'forget alcohol and do more psychedelics while you have freedom'. 😉
Thanks for that headsup Elrik.
Harmine+D for me is very clear headed, and a very abrupt fall off too.
I've never redosed harmine alone like you asked in that other thread, usually don't redose at all for that matter.
I've no blood pressure reader, might be interesting, its supposed to drop on harmalas.
Good travels wished :thumb_up:
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