not to mention that you won't need to measure anything, just use excess benzoic acid, and do 1-2 washes of naphtha to remove excess benzoic acid. With my divine crossing v5 it didn't work very well, but I think it could work well with a dabbing nail or e-mesh. It does resolidify pretty quickly, so that is a bit of a problem. Also, at around 200-210° C the vapor becomes very harsh, probably because the benzoic acid and DMT become separated or something.

I found that it will crash if you already have uploaded the same file with a different name - but that's probably not what was wrong.

Then secondly it will crash if you try to upload a file with a name that contains strange letters, like =&/"§% and also even SPACE, so must use _ at all times. Maybe that's the reason?






I think there is even a bigger catch:

I was struggling for long time with the purification of a reaction to separate polymers (although not the same like from a bark extraction, indicated by TLC) until Famine gave me a golden tip. Although overal solubility is lower in organic solvents, their solubility does not drop as huge when transformed into the salt. That means while monomeric DMT will precipitate very easily, those polymers still stay in solution.

Reason might be: Pretty shortened down Intramolecular Forces and effects are faster / stronger than Intermolecular Forces, due to the close proximity and high chance of formation. Because of that the charge of a DMT-Polymer might be stabilized much stronger by the molecule itself due to a high amount of whatever-domains that can warp around a possible charge and reduce the overall ionic character. A second reason is also that maybe DMT Polymer salts might not carry 1x Charge per 1x Unit as it might be energetically disfavored and so macroscopically those molecules also inhibit a much weaker ionic character. In any way: you can separate SOME KIND OF DMT-Polymers from Monomers by just salting the latter out. Whatever products I got from this were always the most beautiful white crystals ever - rarely matched with just re-x'ing on and on, which sometimes still stays at the same yellowish state.

Therefore you might even throw Benzoic-Acid saturated Naphtha / Toluene directly on top of your extracted NPS and be good. Just as a sidenote regarding separation from Polymers, it might not work if all-naphtha is used, as maybe the solubility of that Polymers then again is also too low in Naphtha, so an extraction with Toluene already from the based soup might be better.

But that again would again make stuff easier: Toluene pulls much stronger. Problem is only that resulting alkaloids are a goo-mess. But with a Benzoic-Acid-saturated Toluene you would still pretty likely only get crystals. Also IF there is anything psychoactive in jungle spice then you would also carry it over, IF those compounds would be also low-molecular alkaloids.

People would just need to take care that that benzoic salt cannot be washed with organic solvents other than freezer-toluene or naphtha, still too high solubility.

So a quick way could be indeed:

- pH 3 acidic cook
- turn pH 11 with NaOH
- Pull with Toluene (less pulls than Hexane required and 20 °C)
- Throw inside Benzoic Acid in Toluene
- Place in Freezer, while 250 mg / 100 ml will remain inside
- Wash with Naphtha as it evaporates faster



That would be indeed super interesting and I see that Mindlusion said potency will be rather low, but I mean when speaking of ORALLY active stuff then DMT is even less active than Mescaline, but it works like a charm when smoked, right?

Why does the toluene need to go on the freezer? I would imagine the salt crashes at room temp, no? Or is 100mg/250ml the DMT benzoate solubility at room temperature.

Also, as you may know, limonene works very well. It pulls DMT strongly and forms DMT benzoate easily. The process is very simple and yields where great:

- Make bark paste with 1:1.5:0.25 parts bark:water:NaOH
- Pull with limonene, rest, decant
- Salt with benzoic
- Decant, wash (naphtha?), dry

About mescaline, 80% or so is recovered in urine. I think this means a lot needs to be in our blood? There is anecdotal evidence that rectally mescaline is twice as strong and also 1x to 3x as strong. I could be wrong, but we may need 100+ mg of vaped mescaline benzoate (if it is vapable). A way to know for sure is trying of course 😊

Yes so it crashes also at room temperature, but you could precipitate still more when going for freezer temperatures. So at freezer temp then 100 ml of Toluene will still have 250 mg of Salt, not measured at RT but probably quite a good bunch more :/ So from what I saw I was thinking for the Benzoate salt it should be just always freeze precip'd to not loose too much goodies.

But indeed Limonene would then be just as great and maybe even better. I threw away mine years ago, so currently never doing any tests with it But if it works like a charm then people should use that one instead, less toxic and better smell of course. Would be then just also a safety factor to put inside of the freezer, but people could just form crystals at room temp and then see if even more is coming at - 20 °C.



So then this sounds much better and also more healthy

And about Mescaline yes probably will need quite a lot, but I have no clue about this method so then would be up to the cacti experts here to assume effectivity and then try it in reality

Thanks BW, makes sense. Love your work!

Someday I will test mescaline benzoate and vape it. Will post results.

About making it: Mescaline Benzoate did not precipitate from limonene unfortunately, but it did precipitate nicely from toluene. Needless that formed where amazingly beautiful! Unfortunately, I already ate all the mescaline benzoate (was great 😊. Will need a good way to wash it to eliminate all Toluene for sure (naphtha?).

Also I tried to make MDMA Benzoate but in a first trial it also did not precipitate from Aceton. Evaporation just left a goo. Let's hope A) that this is because of not using Toluene (or similar) and B) this will not also be the case for Meskalin.

And I also washed my Benzoate salts with naphtha, all fine.

If you even have a vacuum filtration, then this is a pretty easy way:

Combine both solutions in Toluene (or Limonene etc.) and place in Freezer (just to be safe).

Vacuum filtrate the solvent and then just pour more Naphtha on top, then still continue drawing vacuum to dry. Toluene would take ages drying in air stream, but with Naphtha I had a product pretty much free of smell just after 10 min.

Benzoate crystals seemed much more fluffy, remind me of Supplements which you can buy like 5-HTP powder.

So sadly DMT will form a goo with Citric Acid, but these Meskalin-Citrate Crystals are just over the top with their look. Pretty interesting that many different combinations can lead to a great product, although I guess those Mesc Citrate looks better than anything DMT could look like

Same happens for Bufotenin: Very voluminous precipitation in Aceton and therefore still loaded with multiple X the amount of Aceton. Slowly shrinking while releasing that Aceton over the next 20 min. I think in general very fast precipitation due to highly charged anions is a bad thing. It will basically capture a lot of solvent inside of the agglomerating salt and this will A) greatly increase weight and make it impossible to give precise measurements and B) cause this gooey consistency even apart from any potential water.

Just as a sidenote when I used 50 °C and 50 mbar to dry the DMT-Citrate it also turned white like crystals and was solid in a way that you could have handled it just regularly. Even exposure to ambient air did not drag any more water, so it seemed to remain stable like this?
Still not easy to dry it this way in average kitchen, so I tossed to make more experiments here as it was not readily crystaline :/

assuming that you started with MDMA.HCl, can you tell me how did you basify? and what was the final pH? I tried the A/B route as a purification attempt, basified with NaOH, pulled with toluene, acidified with aqueous HCl, ended up with a goo which just wouldn't solidify...

Prior I grinded it to fine dust and stirred in Aceton for like 1 h to remove Safrol.

Then dissolved in Water, added NaOH until pH 11 and extracted once with Ethyl Acetate, then at a later attempt used DCM.

Next time will also use Toluene in Benzoic Acid. Maybe that small amounts of water inside HCl prevent crystal formation?

You could try throw inside stochiometric amounts of any Acid Chloride (Acetic Chloride, Oxalyl Chloride, even Silanes which act as Lewis-Acids the same way like Silane-Chlorides) and then just again stochiometric amounts of water, which should be microliters.

Tryptamine hydrochloride can be obtained via salting out: dissolve ~2 g tryptamine in 30 mL 10% aqueous acetic acid and slowly saturate the solution with ~7 g NaCl while stirring. The soft precipitate (tryptamine.HCl) can be recrystallized from boiling methanol (decant it while hot off any excess hard NaCl particles).

I have not tried it with DMT though.

DMT.HCl appears to be quite elusive. Shulgin writes:

"To obtain the HCl salt of DMT, the residue was dissolved in anhydrous Et2O and saturated with anhydrous hydrogen chloride. The resulting crystals were recrystallized from benzene/methanol to give N,N-dimethyltryptamine hydrochloride with a mp of 165-167 °C
...
As to salts, this last recipe above, taken from the literature, is the only claim of a valid hydrochloride salt of DMT. In the original synthesis, by Manske, the following description appears. "The hydrochloride could be obtained only as a pale yellow resin which, when dried in a vacuum desiccator over potassium hydroxide, became porous and brittle." I have found no attempts at its synthesis in the literature, and I have personally had no success at all."

That is good informationen - made a link above

I have read elsewhere that DMT-oxalate also precipitates as a crystal.

Yes oxalate and succinate are both good

Thanks for the info.

I checked it today and indeed it precipitates, but it will not form nice crystals, just some very fine powder on the bottom. Also Aceton still looked quite opaque rather than clear.

Not sure if that might be due to fast addition of oxalic acid, maybe creating mono-DMT oxalate and maybe the slower addition (in favor of 2x DMT / 1x Oxalate) would give better crystals?

Still as it's also working for salt precipitation, it looks just like also following the same rules:

High chance of precipitation from organic solvent:
- acid is multi-valent + low van-der-waals interactions

Crystalline instead of goo:
- low solubility in water (with 90 g / L still only 2x as much as succinic)

Added now, but seems overall not so convenient like the others. Also, remember to not eat too much oxalic acid for your kidneys

Great results and discussion Brennandes!

I am willing to try the following available acids at the next extraction cycle: nicotinic, tannic (low molecular weight, it's a strong protein fixative, likely dangerous), boric, mallic, folic.

I don't even know whether they are soluble in acetone though.

Can you give me any precipitations predictions based in your current research for these?

Nicotinic: Guess would not precipitate because has a high count of pi electrons which could still stabilize that salt pretty well in a solvent like Aceton :/

Tannic acid: so I would say pretty huge molecular weight, if we speak about the same. That might be also a problem, because upon giant molecular weight some ions will lose more and more their ionic character "macroscopically". Similar to ionic liquids, which are "too big" to form solid crystals.

Boric: could be worth a try, but strangely HCl and HNO3 also did not cause precipitation. But in those cases maybe was due to water content.

Mallic: Maybe it works as it looks nearly like tartaric acid. Still lactic acid does not give crystals and mallic acid also has some resemblance. Had to google this, funny enough in my language it's just called Apple Acid

Folic: Really sure that wont work - this one again is really big so 1 charge at its absolute end will probably not force any precipitation

Still maybe some of them are not hygroscopic so you may evaporate the solvent under reduced pressure, which turned goo into semi-solid crystals in the case of DMT citrate.

Thanks for giving a piece of your enlightened mind Brennandes. Please keep up with the exploration!

I`ll try small scale to see if anything clouds or drops out. If they don`t, I`ll evap the non-polar like you mentioned.

Originally I was having way too much headache about the conclusion of my Salt Evaporation Experiments! But that riddle is now solved!!

I tried to find out why the heck salts of tryptamines still evaporate quite easily. So some tests were performed sequentially. All of the tests showed that after heating and melting the salt, the vapor formed at > 170 °C will contain both the Tryptamine AND the acid. Now after doing more tests it showed that this vapor is not caustic (neither to pH indicator nor to the lungs) nor does it have the classic tryptamine burn in your mouth.

All of that just pointed towards the vapor still containing Tryptamine+H(+) and acid anion(-). But how the hell can charged molecules evaporate? That would be restricted by the potential energy going into infinity because of the electric charges.

Now the solution is just simple and elegant and easy to understand from the vaporization of Freebases explained here. That is the true reason why FREEBASE of nearly all Tryptamines will evaporate just below 200 °C.

But now when I take this to the salt variants of those Tryptamines I can see the same pattern. And this is also the final puzzle piece why Variant C is correct:

Evaporation of both salt components in their charged state.





But now after all of these experiments with tryptamines and tryptamine salts I think there is quite some pattern to be found from all the empiric data and this is added as some chemical philosophy at the end of the summary.

Adding upon on this I have the feeling that there is an ubiquitous temperature at which Tryptamines start exhibiting this evaporation behaviour through aerosolizing (if that is an english word??). This process is nearly unaffected by the actual chemical formula, only by addition of functional groups with extreme increase of boiling point (like R-OH) the aerosolizing temperature is shifted a little further, but still pretty close to the original temperature. And this temperature is roughly 170 °C.

Now even more as an odditiy, yet observed across all the samples measured within that time this process can be even triggered with the respective salts of those tryptamines! The compound only has to react with a compatible acid (Benzoic acid or alkane acids, although first one preferred) which can also evaporate instead of combust.

If this is given, then ANY Tryptamine will evaporate at latest 200 °C being freebase or benzoic acid salt, unless it has some unusual groups like R-OH, but then still showing evaporation below 250 °C, which is still "nearly the same" when compared to the real boiling point.



It is just a conclusion based on empiric data, but soon I will post some evaporation data about Mescaline. And here the exact same pattern is shown. Mescaline contains 3x Ether groups and has a much more polar -NH2 (compared to -NMe2). Still it show EXACTLY the same evaporation again, when paired with a suitable Acid.

More precisely Mescaline Benzoate basically shows the exact same evaporation like DMT Benzoate, even though it's boiling point must be way higher.

Even more demonstrating this "ubiquitous aerosolizing temperature" I will show some data of Mescaline Fumarate. It has a much higher melting point of around 190 °C (nicely showing that Di-Valent salts need a higher energy to surpass crystal lattice energy for starting melting process than 1:1-type salts, which are all at 130-160 °C measured so far) and INSTANTLY starting to vaporize again as soon as it liquifies.

This shows in my eyes that there is simply a magic temperature at which this aerosolizing effect is happening, pretty much equalizing the temperature to smoke most alkaloid drugs regardless of Freebase or Benzoic Acid salt.

To verify it with "unusual alkaloids" for smoking, I simply smoked 40 mg Meskalin Benzoate which worked great with no combustion, super smooth vapor and my device completely clean afterwards at ~ 200 °C. Effect was simply not too strong, but this amount was less than 10 % of a dose considered moderate when eaten orally. So was definetly interesting and a good demonstration.

Now as thinking loudly this even opens up possibilities of smoking basically any psychedelic after
conversion to the Benzoate Salt at up to 200 °C. Still this would need strong accordance to any safer-use rules possible ...

To further make clear that I really think there is something like a magical threshold at which this droplet formation instantly starts regardless of the actual chemical structure I added also now Mescaline Benzoate to the summary of evaporation diagram I once made.

This is what you get:



So in my eyes this really shows some pattern - check the red box.

DMT
DMT-Benzoate
5-MeO-DMT
Mescaline-Benzoate

all evaporate basically at the same temperature and evaporation speed. That is quite unsual, as they should have completely different boiling points. 5-MeO-DMT-Benzoate basically will be also having the same behaviour, I am sure without even doing the measurement. Quite likely the same for stuff like Ethyl-/Isopropyl-substituted etc ... still I never measured any of these so that's more speculation.

The only stuff that does not vaporize with the same pattern are compounds where there is an obvious reason for it:

Bufotenin = It carries a R-OH group, which has an extreme effect on boiling point.

Harmalas / THH = Conformationally constrained Alkaloids, not classic Tryptamine-type = very different thermal behaviour

Salvinorin A = not even Alkaloid ... Pretty strange high-molecular Terpene instead

Psilocin probably would be same as Bufotenin, but 4-AcO-Psilocin probably not.

So I would guess that any Alkaloid which would follow a structural scheme like these "regular Alkaloids" in the red box they would also just vaporize at 160 - 170 °C and if they are just an oil or decompose, they could be *stabilized* by creating the "-Benzoate salt. Probably any of those might show this "aerosolizing effect" starting from just above 160 °C that makes small droplet particles evolve into air, thus causing the substance *to be smokable*. And this is pretty remarkable, given the background that all of these red marked compounds will boil at completely different temperatures!

True boiling point according to online sources:

DMT = 160 °C @ 0,0008 bar
Mescaline = 180 °C @ 0,016 bar

Which is quite close in temperature, but a difference of 1:20 in terms of pressure