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Summary of DMT-Salt experiments Options
 
Brennendes Wasser
#1 Posted : 2/7/2023 11:22:37 PM

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This is a summary of experiments that were performed with various Tryptamine salts with focus on crystallinity and evaporation. Goals are to understand the chemical nature of these and find possible applications too.

3 Experiments were done:

Part 1: Table of which Salts will have which morphology

Part 2: Table of water content / hygroscopy depending on Salt

Part 3: Experiments to determine the chemical nature of DMT Salt Vapor
 

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Brennendes Wasser
#2 Posted : 2/7/2023 11:23:20 PM

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Part 1: DMT-Salt-Precipitation

Which form will the salt have? Tests were performed by adding the corresponding amount of acid in 500 µl Aceton into 10 mg DMT dissolved in 500 µl Aceton. Tests were only performed for DMT and in Aceton as the go-to solvent. But apart from this test there are many combinations of salts in other solvents and also for other Alkaloids which could produce crystals - see the compilation of alkaloid salting combos from Loveall.

(x) = Tested
(?) = believed, based upon similar substances

DMT-Salts that precipitate crystalline

(x) DMT-Benzoate
(x) DMT-Fumarate *
(?) DMT-Succinate
(x) DMT-Oxalate (dust instead of real crystals)

DMT-Salts that will be a wax

(x) DMT-Stearate (need EtOH to dissolve acid)
(?) DMT-Palmitate
(?) DMT-Myristate
(?) DMT-Laurate

Those are all fatty acids. As you need Ethanol to dissolve the acid, it will not precipitate unless removing the Ethanol.

DMT-Salts that precipitate as a goo

(x) DMT-Sulfate (from 98 % H2SO4)
(x) DMT-Phosphate (from 85 % H3PO4)
(x) DMT-Citrate
(x) DMT-Tartrat

DMT-Salts that are a goo, but dont even precipitate in Aceton

(x) DMT-Chloride (from 37 % HCl, just getting milky)
(x) DMT-Nitrate (from 70 % HNO3)
(x) DMT-Trifluoracetate
(x) DMT-Acetate, DMT-Lactate, other small Alkane Acids
(x) DMT-Ascorbate " (need EtOH to dissolve acid)
(x) DMT-Malonate
(x) DMT-Maleate *

Interestingly, DMT-Chloride and -Nitrate did not precipitate. Just getting cloudy for -Chloride, but nothing more happens. Technical-grade Chloride (HCl, 37 %) and Nitrate (HNO3, 70 %) are only available with too high water content = no precipitation. Maybe possible to add those to Aceton, then use MgSO4 to remove most water. Otherwise must use in-situ methods like Lewis-Acids (Acetyl-Chloride, Toluene sulfonic acid chloride, ...) or enrich Toluene with HCl gas (too dangerous ...).

According to Hailstorm Tryptamin-Chloride can be retrieved by salting out. Maybe it's also possible for DMT.

Conclusion:

The Anion strongly determines the possibility of the DMT Salt to precipitate or not and also if crystals or goo is formed upon any of these possibilities. These rules of thumb are just based on the experiment results, so as usual (and in Chemistry) as we say in my Language "Exceptions will validate the Rule" Big grin

Crystalline -> Acid is soluble to 0 - 50 g / 1 L water

Goo -> Solubility in water is high

Wax -> Acid has low intermolecular forces with low functionalization degree, like fatty acids (similar to Ionic Liquids)

Multivalent Acids -> Higher chance of precipitation, but also higher chance of goo afterwards

Inorganic mineral Acids -> These will always precipitate as Aceton can't solvate these anions due to their high charge density, just like multi-valent carbonic acids written above - IF they dont come loaded with too much water

* You might wonder why DMT Fumarate produces well known crystals since ages and DMT Maleate is a goo that does not even precipitate from Aceton? Just check the solubility in water - it is a difference like day and night due to the cis-trans orientation of these 2.
" turns orange upon air exposure
 
Brennendes Wasser
#3 Posted : 2/7/2023 11:24:04 PM

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Part 2: How much water is inside of these salts?

As an exemplary salt DMT Acetate derived from DMT + Acetic Acid in water was desiccated in a drying chamber with CaCl2. Weight was recorded directly and then the salt was exposed to ambient air (20 °C, 40 % humidity) for 2 h. Weight did not change and therefore at least for the DMT-Acetate goo it was believed that actually the salt is not hygroscopic per definition, as it seems to not absorb more and more water over time. Instead it looks like (this) salt just forms a certain Hydrate (binds a certain amount of water molecules) and simply remains like that. Any goo could then simply be just a load of water molecules complexed to the salt, which cannot be removed except heating / in vacuum. Therefore *hygroscopic* salts may simply catch up to their natural amount of water molecules at amount X and then remain in this state, making it impossible to remove more water at ambient conditions, but also not absorbing more water like a true hygroscopic substance (NaOH, CaCl2, ...).
Also the Salt-Hydrates which you can read further down are not necessarily the actual hydrated states of those compounds which you would also read on Wikipedia. Reason is that for example salts where Aceton needed t obe evaporated would also catch up water throughout this process and that one might remain inside of the precipitated salt. In another trial I used a more chemical approach and dried everything in a vacuum oven at 50 mbar and 50 °C, but that just resulted in many salts not having any water inside at all. Even DMT Citrate was completely white and looked quite crystalline. But as this will not reflect the actual salt which people will create at home in their kitchen, I went with uploading what I got from precipitating, decanting (if possible) and drying in a stream of air at 40 % air moisture. Therefore the Hydrates might not be the ones which you could form in their most-dried state, but be exactly what you get if you prepare them at home in your kitchen and therefore more important I guess.

1H-NMR spectroscopy was conducted to determine this minimum water content in those salts. It was already assumed that Acids with very high solubility in water would also bind more water molecules and therefore not form crystals, but instead form a goo with water complexed inside the salt. Furthermore an even higher water solubility could also indicate that the salt would also interact pretty strongly with Aceton and therefore not precipitate. NMR spectroscopy can show how much water is trapped inside of these salts. As a brief summary it will give a spectrum of signals from (in this case) protons, which are located on an X-Axis depending on their chemical environment, more precisely the directly bound atoms to a maximum distance of ~ 3 chemical bonds. Because of this most structural units have their unique appereance along the X-Axis and therefore can be used to identify the substance. Vice-versa it is possible to look at the expected X-axis position AKA chemical shift AKA ppm-number to check for a certain structural unit - in this case H2O = water, which is 4,79 ppm. Now the integral of this signal compared to the integral of a DMT signal of known proton amount can tell the ratio of water to DMT. This furthermore will tell how much water is trapped inside each of these salts. To not spam this thread all the 1H-NMR spectra can be seen when clicking on the respective salt. That method is probably not the scientifically most established one for determining water content in salts xD but it will give a pretty good idea. To make life easier, DMT and Acid are shown with structures in 1:1 molar ratio. Also to safe time I did not write down the connections of signals to DMT, just to the Anion. To see the corresponding DMT Signals, just refer to my old thread here - just take care that numbering might be different. Not all salts were measured - just the ones that are chemically distinct for a certain group of anions, so comparable salts will probably be pretty close to this value:

DMT-Benzoate = water integral 0,02 = DMT-Benzoate x 0 H2O

DMT-Stearate = water integral ~ 0 = DMT-Stearate x 0 H2O '

DMT-Sulfate = water integral 2,81 = DMT-Sulfate x 1-2 (?) H2O

DMT-Acetate = water integral 8,21 = DMT-Acetate x 4 H2O
DMT-Ascorbate = water integral 1,46 = DMT-Ascorbate x 1 (?) H2O

DMT-Maleate = water integral 2,16 = DMT-Malteate x 1 H2O ~
DMT-Citrate = water integral 2,51 = DMT-Citrate x 1-2 (?) H2O ~
DMT-Tartrat = water integral 2,98 = DMT-Tartrat x 1-2 (?) H2O ~

' DMT-Stearate has some cool properties, but they make it difficoult to measure NMR: Upon creating a salt it will create a gel in H2O and DMSO at room temperature which does not flow at all anymore and it will be completely liquid again at > 40 °C. Gel formation in H2O is even worse, so DMSO was used here, but still the sample gets "solid" throughout the measurement. Therefore it looks pretty crap due to the semi-solid nature of that sample. In DMSO the water signal is shifted from 4,79 ppm to ~ 3,3 ppm. Therefore also no integral value given, but it is basically 0 like Benzoate. Still this gel is really funny. Completely solid at Room Temperature, but will become completely liquid at 40 °C - at least for DMSO. Somehow like a toy from the wizard store for kids?

~ note how you can directly see in the NMR how the salts preferably form their DMT:Acid ratio depending on their multi-valency. DMT Tartrat shows 1x Tartaric Acid + 2x DMT and DMT Maleat shows 1x Maleic Acid + 2x DMT. Interestingly you will also only see for DMT-Citrate = 1x Citric Acid + 2x DMT. Isn't that strange, it has 3x Carboxylic Acids? But actually the pKa for each individual deprotonation is decreasing more and more. That is because even though the 'built-in' acidity determined by the structural units is roughly the same, but a higher charge density per molecule (AKA on a small volume element) is disfavored. Therefore the residual protons refuse to deprotonate more and more, probably 3x deprotonation would only be possible when creating a salt from H2O-solutions.

Conclusion:

A rule of thumb which seems to be concluded from those experiments might be

Higher solubility of Acid in Water = more complexed Hydrate in the salt

more complexed Hydrate in the salt = less chance of Crystallinity or even Precipitation in Aceton at all

The DMT salts with the least complexed water were always those who show a really low solubility in (neutral) water too.
 
Brennendes Wasser
#4 Posted : 2/7/2023 11:24:47 PM

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Part 3: Vaporization of DMT Salts

Normally it would be expected that ions would not vaporize, just as insanely high temperature. Still there was much evidence that many Tryptamine salts can indeed vaporize. First tests showed that Tryptamine salts created from Carbonic Acids of low acidity / pKs would vaporize nearly as fast as the Freebase Tryptamine, with just 10-20 °C higher temperature needed. So what more seems like a scientific oddity, but rather useless. But it was found that these vapors are actually not harsh at all, indicating that there might not be any caustic and acidic component inside the vapor.

It seems like 180 - 200 °C is just fine to evaporate DMT salts, similar observations were made for Bufotenin salts. Interestingly also DMT salts derived from multivalent acids with more than 1 COO- vaporize. I thought their melting point must be much higher and to vaporize, a certain mobility of ions might be important prior to vaproization. But it seems they just vaporize the same way and also have a melting point around ~ 130-160 °C.

Here is a list of Tryptamine salts that are confirmed to evaporate at 180 °C:

DMT-Acetate
DMT-Benzoate
DMT-Fumarate
DMT-Lactate
DMT-Stearate
DMT-Trifluoracetate

Still the vapor efficiency was not tested and still some of them might partially degrade while doing so. The only and by far best salt to create an evaporating salt is benzoic acid, which will not degrade and simply shift the vaporization of the Alkaloid higher by 10-20 °C. DMT-Salts that do not vaporize are the ones derived from Mineral Acids, as these just turn black and decompose. Here is a picture of DMT-Sulfate upon heating to 250 °C:



What is the reason why Salts from some Organic Acids vaporize, while the "classic ones" dont?

It seems those organic acids of DMT are able to vaporize, while mineral acids (*HCl/H2SO4/HNO3/H3PO4) dont. But even then this is only valid for organic acids that dont actually combust themselves. But while salt vaporization not happening is quite expected in general, what is the reason why organic acid salts still can vaporize? What is the chemical nature of the vapor that is always formed from these salts starting from ~ 160 °C? Here I am simply going through some simple experiments that I was doing and meanwhile explain what kind of conclusion I got along the line. You may simply skip to the next post with the summary if you like.


Variant A:
DMT Freebase vaporizes first, the Acid vaporizes solitary later on
And easy way to prove if the Alkaloid evaporates first and the Acid evaporates later or not at all is a Thermogravimetric Analysis (TGA). Here a sample is constantly heated and the respective weight is measured at all times. What you get at the end is a graph that shows the sequential vaporization of the substance with the corresponding temperatures at which vaporization happens. Now a potential reason why Tryptamine Salts can be evaporated could be that the Alkaloid simply back-dissociates into the Freebase and therefore starts evaporating. Then the Acid may or may not evaporate later on too. In this case the TGA would show a curve starting at 100 % (the initial weight) and then first shows some evaporation, which corresponds to the Alkaloid. Then a plateau would be reached and afterwards a new drop of the curve would be observable, that marks the Acid evaporating or maybe it will just stay at that plateau and never drop to 0 % (whole evaporation), because the acid just stays behind.



As you can see there is no plateau, expect completely at the end when vaporization will not happen anymore. This curve is really "harmonic" and looks exactly like a pure substance, so nothing which is an actual mixture of 2 compounds. This means that both the alkaloid and the acid evaporate completely together at the same time. Furthermore you can see in the TGA the Benzoate salt of DMT only requires minimal additional temperature for vaporization, probably just + 5 °C. Same is observed for Bufotenin. Vaporization stops at 9 %, nearly as low like DMT. DMT Benzoate is 39 % Benzoic Acid, which vaporizes at 250 °C due to Wikipedia. Therefore if DMT vaporizes first, it could only do to a minimum of 39 %, then Benzoic Acid would vaporize solitary. This would then show us a plateau - the curve would not have a harmonic slope of a hyperbel. That would mean the vapor at any temperatures is loaded with the same amount of Freebase DMT AND Benzoic acid. Seems like they just evaporate in association, there must be some force which *carries over* the acid even if its vaporization point would be higher actually ...
Now the next step would be to try confirming if this equally-loaded vapor truly carries the Freebase and the Acid in their respective (original) base and acidic form.


Variant B:
Both DMT and the Acid vaporize at the same time together as re-dissociated Freebase and Acid
Even though that TGA is quite showing an harmonic curve of vaporization, this is contrary to the observation of a SMOOTH vapor, that does not feel caustic and therefore should have no acid inside. To further prove that the vaporizing DMT is "dragging the Acid" also into the gas phase even below its boiling temperature an experiment with a high-molecular-weight acid was made = DMT Stearate. Stearic Acid is a fatty acid and therefore insanely long Alkane wax with a Carboxylic Acid at the end. Vaporization due to Wikipedia is 360 °C. TGA was performed with pure Stearic Acid - to determine where vaporization of it would start - and DMT Stearate. TGAs are shown here:



As you can see the curve also does not have any plateaus. Therefore DMT seems to not evaporate solely first and then stearic acid later - both vaporize at the same speed and as it seems associated together. Vapor seems to have the same composition at all times. As a reference also DMT, DMT Benzoate and pure Stearic Acid is shown. You can see pure stearic acid evaporates later than pure DMT, as it is probably also the case for Benzoic Acid. Therefore from what we can see both the acid and DMT again vaporize together and the Acid pushes the overall Vaporization to higher temperatures. But we can see now that when using the even higher-boiling Stearic Acid this shift is even stronger and therefore additional 20-30 °C are required for equal evaporation compared to DMT Benzoate. That again is a strong sign that DMT will vaporize with the acid in 1:1 association, because if DMT would vaporize completely independently, the whole evaporation process would start much earlier like we see with the Benzoate and have a pleateau where the Acid vaporization starts with a delay.

Therefore it looks like it does not matter too much about the acid - it will be also carried over into the gas phase. Now as the vapor is very smooth and not caustic at all, this would be a contradiction to a back-dissociation into Freebase and free Acid. So it seems that the vapor would be still carrying the salt, even though evaporating charged molecules would be physically very unlikely. To further investigate the vapor 2 easy experiments were made:

- Place DMT salt inside of a Banger at 180 °C
- Close the Banger with the Carb Cap and wait for intense vapor to form inside the Vaporization Chamber
- Make a pH Paper wet and place inside of the vapor

The pH Paper did NOT indicate any presence of acidic compounds and just stayed at pH = 7. Therefore vapor seems to be indeed free of any potential acid. Now obviously that is indeed a contradiction to Variant B. It is shown that nearly everything of the Salt vaporizes and it does so without any of the 2 components vaporizing earlier or later.

To indeed try if any trace of unreacted Acid would be instantly recognized in the vapor, I made a small test: In the name of Science 10 mg Benzoic Acid was vaporized. Strong fumes were also present at 180 °C. While first vapor was formed, that little bit was already "tested" so probably just "smoked" like 1-2 mg of Benzoic Acid. Super strong lung irritation. 10/10 noxious. So as a consequence every experiment until now seems to prove Variant C. This shows that the vapor from DMT salts must be free of any free acid and therefore still carry the salt.


Variant C:

Both DMT and the Acid vaporize in ionic form
Now first of all this sounds pretty impossible. Vaporization of ions takes insane energy amounts and therefore temperature - way higher than these molecules would even survive probably. Reason is that the attraction between different charges based on the Coulomb's Law is extremely strong, it simply is mostly neutralized within even atomic distances. But therefore potential energy quickly rises to extreme levels when separating 2 charges very far from each other. By evaporating a molecule the mean free path of molecules quickly increases to about 68 nm at ambient conditions, making the distance of potentially charged molecules way higher than in any solid form of salt, which would be at the Anström-Scale (0,1 nm). Because of this truly boiling away a salt would be impossible ...

... and still the vapor of DMT Salts truly contains no Freebase Alkaloid and no free Acid as you will see now! But how can that be? How can it evaporate as their salted form? To really understand what is happening, read first what another member is describing here for the Freebase Evaporation. Here he describes that actually you do not evaporate the molecules like in a boiling process (AKA water heated to 100 °C). Instead you will form tiny droplets that will migrate into the gas phase, like mist in air. This actually still requires some heat (and increases upon strong airflow) but it still very different from actual boiling AKA true vaporization. And now it seems that this process can even happen with Tryptamine-Salts, as long as they can be liquified!

Because of this the whole process does not violate the Coulombs Attraction. Because within these tiny droplets the molecules are still in very close proximity and therefore dont "fly around far away from each other" with their charges still exhibiting forces to each other. And this is the reason why it would be physically still possible to evaporate ionized alkaloids, you simply dont really boil them!

Variant C is the chemical nature of DMT salts while evaporating them and therefore if a suitable acid (like Benzoic Acid) is used, you are perfectly fine to evaporate them just like your freebase!
 
Brennendes Wasser
#5 Posted : 2/7/2023 11:25:32 PM

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Summary:

Salt formation:

It seems that the amount of Acids suitable to produce crystalline DMT salts is rather low. The salts have to be as hydrophobe as posible, which is obviously not too easy as carboxy groups will already increase it by a lot. Therefore salt formation from acids containing additional OH-groups and comparable seems pretty unlikely - even more so for (highly acidic) inorganic mineral acids. Fumaric Acid, Benzoic Acid and Succinic Acid seem the only possibilities which have been tested so far. Stearic acid will not precipitate as crystals, still the wax is so hard that it can be easily handled. Still not the pretties thing Razz

Evaporation of Tryptamines and Tryptamine Salts:

The actual boiling point (temperature at which molecules will freely dissociate into air in their unimolecular form like water at 100+ °C) of a substance is defined by it's chemical constitution, molecular weight and functional groups. This can be very different for the wide range of tryptamines and is already a pretty big difference between DMT and 5-MeO-DMT alone.
Still Tryptamines can be evaporated at way lower temperatures, while not truly boiling off like water in a cooking pot, but instead forming microscopic airborne droplets, still in their liquid form. Now while we all can simply be happy about this aerosol-formation making it possible to enjoy Tryptamines at rather moderate temperatures, there is an interesting pattern to be observed.

Even though the actual boiling point of Tryptamines can vary greatly, the temperature of forming an aerosol seems to be nearly the same for all Tryptamines analyzed.

That is pretty remarkable as it seems this process is way less influenced by the actual chemical formula of the tryptamine, as now DMT and 5-MeO-DMT will form this aerosol at nearly the same temperature. Therefore I am sure that also all similar Tryptamines like DALT or MiPT will show a similar evaporation and this magic number seems to be 170-200 °C. Because of that this process is only influenced by the thermal energy required to form these small droplets that detach from the molten surface and to a lesser degree also a function of airflow which then influences the evaporation speed.

Now moving further to the Tryptamine-Salts where this thread is about:

Interestingly it is found that this process is also happening to the salt variants of the tryptamines, IF the corresponding acid is able to vaporize. Based on other experiments, acids with high boiling point and multi-valency are very bad for evaporation, while benzoic acid and alkane acid (acetic acid, ...) are ideal for this. The remarkable thing is that temperature for evaporation is still in the same range of 170+ °C, even though the molecules itself are now charged. That shows that probably the energy of forming those droplets is just the same, therefore we can observe exactly the same process regardless if we use Tryptamines or Tryptamine Salts. This is very remarkable to me, as I would have never thought this process would happen even for the charged alkaloid variants!! And ultimately this is the reason why it is totally safe and pleasant to smoke DMT salts: They dont contain any free acid and also no caustic freebase!

Read a little more on this on the next page here.




And what does that all mean? Anything important for everyday life?

Some applications may still come in my mind:

- DMT Benzoate would have basically the same vaporization properties, but be much more UV-resistant against N-Oxide formation

- DMT Benzoate could be used for new applications were different solubilities are needed - allthough Loveall already found DMT Benzoate solubility in PG too low. Still maybe suitable for nebulizing machines.

- Bufotenin Benzoate can be used to overcome the Combustion reaction at > 170 °C which makes vapor too harsh to smoke

- Mescaline (although not a Tryptamine) Benzoate is can be vaporized perfectly fine too. This enables a pretty new ROA for this Alkaloid, even though potency will not be strong.


Maybe some more applications might be found in future, but for now that thread is mostly just for the sake of summarizing these experiments.
 
downwardsfromzero
#6 Posted : 2/7/2023 11:30:59 PM

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You are excelling yourself again, I love this stuff* and thank you deeply for all the dedication. Love


*particularly the charred blob pic Laughing




“There is a way of manipulating matter and energy so as to produce what modern scientists call 'a field of force'. The field acts on the observer and puts him in a privileged position vis-à-vis the universe. From this position he has access to the realities which are ordinarily hidden from us by time and space, matter and energy. This is what we call the Great Work."
― Jacques Bergier, quoting Fulcanelli
 
Brennendes Wasser
#7 Posted : 2/7/2023 11:38:32 PM

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THX Thumbs up Thumbs up I'm just speeding up on all my leftover experiments in my imaginary journal before I will not have access to all that stuff anymore.

Experiments on possible Bufotenin- / DMT-Polymer insights also coming soon.
 
_Trip_
#8 Posted : 2/8/2023 12:09:53 AM

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Thanks for all your hard work Brennendes Wasser.Big grin
Disclaimer: All my posts are of total fiction.

 
Loveall
#9 Posted : 2/9/2023 12:56:59 PM

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This is great work! Thank you 🙏

A few comments:

1) My speculation on vaporization (I'm a physicist not a chemist, so not an expert here): I think it depends on forces between molecules. Could the internal dipole moment of the vaporizable DMT salts be low and close to the freebase value? Maybe there is some sreeening/geometry that lowers the dipole moment from the ionic bond? I think there are chemical simulation programs that can calculate dipole moments? If low and close to the free base value, model B makes sense as the salt units would not attrack each other much and behave like a freebase.

Intuitively I feel that large aromatic molecules with pi electrons could screen the ionic dipole moment, more so if there are electropositive atoms opposite the salt cation and electronegative atoms opposite the anion. Simple salts such as NaCl would not have such screening for the ionic bond dielectric moment.

2) If mescaline benzoate behaves like DMT benzoate I guess we could try to vaporize it in a quartz heat chamber or e-mesh? What about Mescaline citrate? Perhaps 50mg of mescaline benzoate would begin to be active with this ROA? That would be an amazing discovery.

3) Any comments on the stoichiometry? The wiki says di-DMT fumarate forms during FASA, but could it be mono-DMT fumarate? Could we form one or the other or both? With excess acid the mono-DMT salts may be more likely to form. The FASA process asks to add the acid slowly which could be conducive to di-DMT fumarate salts forming. The salt form would change the dipole moment and vaporization temperature (except for monovalent salts such as benzoate of course). For mescaline, we believe beautiful xtaline mono-mescaline citrate forms in excess acid, and that gooey tri-mescaline citrate forms of there is no citric acid excess (at higher pH).

💚🌵💚 Mescaline CIELO TEK 💚🌵💚
💚🌳💚DMT salt e-juice HIELO TEK💚🌳💚
💚🍃💚 Salvinorin Chilled Acetone with IPA and Naphtha re-X TEK💚🍃💚
 
Loveall
#10 Posted : 2/9/2023 1:22:40 PM

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Loveall wrote:
Intuitively I feel that large aromatic molecules with pi electrons could screen the ionic dipole moment, more so if there are electropositive atoms opposite the salt cation and electronegative atoms opposite the anion. Simple salts such as NaCl would not have such screening for the ionic bond dielectric moment.


Wildly speculating, for DMT benzoate the structure is,

(Aromatic ring)-NH3+ -O-(Aromatic ring)

So perhaps the symmetric aromatic ring delocalized electrons on the sides (green) can screen the ionic bond (red) lowering the dipole moment and vaporization temperature?

A similar effect could occur for mescaline benzoate.

I could be very wrong, just throwing out ideas. And again I'm a physicist, not a chemist.
💚🌵💚 Mescaline CIELO TEK 💚🌵💚
💚🌳💚DMT salt e-juice HIELO TEK💚🌳💚
💚🍃💚 Salvinorin Chilled Acetone with IPA and Naphtha re-X TEK💚🍃💚
 
famine
#11 Posted : 2/9/2023 4:39:25 PM

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Loveall wrote:
Loveall wrote:
Intuitively I feel that large aromatic molecules with pi electrons could screen the ionic dipole moment, more so if there are electropositive atoms opposite the salt cation and electronegative atoms opposite the anion. Simple salts such as NaCl would not have such screening for the ionic bond dielectric moment.


Wildly speculating, for DMT benzoate the structure is,

(Aromatic ring)-NH3+ -O-(Aromatic ring)

So perhaps the symmetric aromatic ring delocalized electrons on the sides (green) can screen the ionic bond (red) lowering the dipole moment and vaporization temperature?

A similar effect could occur for mescaline benzoate.

I could be very wrong, just throwing out ideas. And again I'm a physicist, not a chemist.

Not screening, as it can dissociate in water readily. Try think of how it bonds to other DMT benzoate molecules. What does a bulky benzoate do to packing, etc? Also one must remember vaporization temperature of DMT is nowhere near it's boiling point. DMT bp is nearly 400C!
 
downwardsfromzero
#12 Posted : 2/9/2023 4:40:10 PM

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Loveall wrote:
[...]
Wildly speculating, for DMT benzoate the structure is,

(Aromatic ring)-NH3+ -O-(Aromatic ring)

[...]

That's the phenate or phenolate, not the benzoate (and sorry that organic chem nomenclature is such a mess!)

Benzoate would be:
(Aromatic ring)-(CH2)2N(CH3)2H+ -O2C-(Aromatic ring)
Molecular structure attached.
downwardsfromzero attached the following image(s):
DMT benzoate.jpg (5kb) downloaded 398 time(s).
DMT benzoate3d.jpg (7kb) downloaded 381 time(s).
DMT benzoate space3d.jpg (9kb) downloaded 382 time(s).




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Loveall
#13 Posted : 2/9/2023 5:03:42 PM

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downwardsfromzero wrote:
Loveall wrote:
[...]
Wildly speculating, for DMT benzoate the structure is,

(Aromatic ring)-NH3+ -O-(Aromatic ring)

[...]

That's the phenate or phenolate, not the benzoate (and sorry that organic chem nomenclature is such a mess!)

Benzoate would be:
(Aromatic ring)-(CH2)2N(CH3)2H+ -O2C-(Aromatic ring)
Molecular structure attached.


Yes, thanks for adding that.
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Loveall
#14 Posted : 2/9/2023 5:06:06 PM

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famine wrote:
Loveall wrote:
Loveall wrote:
Intuitively I feel that large aromatic molecules with pi electrons could screen the ionic dipole moment, more so if there are electropositive atoms opposite the salt cation and electronegative atoms opposite the anion. Simple salts such as NaCl would not have such screening for the ionic bond dielectric moment.


Wildly speculating, for DMT benzoate the structure is,

(Aromatic ring)-NH3+ -O-(Aromatic ring)

So perhaps the symmetric aromatic ring delocalized electrons on the sides (green) can screen the ionic bond (red) lowering the dipole moment and vaporization temperature?

A similar effect could occur for mescaline benzoate.

I could be very wrong, just throwing out ideas. And again I'm a physicist, not a chemist.

Not screening, as it can dissociate in water readily. Try think of how it bonds to other DMT benzoate molecules. What does a bulky benzoate do to packing, etc? Also one must remember vaporization temperature of DMT is nowhere near it's boiling point. DMT bp is nearly 400C!


Ok. I guess I'm wondering if the structure DFZ mentioned looks vaporizable despite the ionic bond:

(Aromatic ring)-(CH2)2N(CH3)2H+ -O2C-(Aromatic ring)
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downwardsfromzero
#15 Posted : 2/9/2023 6:06:55 PM

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Added a couple more diagrams and hopefully I can add a little animation too - if the Avogadro modelling program behaves itself.

Bear in mind, in the crystal it will be a repeat arrangement of stacks of these, and possible orientations between different stacks are numerous. Only x-ray crystallography would really tell us how the DMT-onium and benzoate ions would be arranged in this matrix and there may also be polymorphs.

What famine mentions about the difference between the vaporization temperature and the boiling point of DMT is that DMT will have a vapour pressure even below its boiling point. If airflow continually removes vaporized DMT from the headspace, more DMT will vaporize to replace it. The boiling point is the temperature at which the vapour pressure reaches atmospheric pressure.

Another thing is that the vapour pressure of benzoic acid and DMT can add together, a bit like the principle of steam distillation. Benzoic acid is moderately volatile itself so perhaps the combination of the two is what facilitates the vaporization of the benzoate, along with favourable intermolecular forces between the two separate aromatic systems.

Technically it should be possible to refine DMT freebase by sublimation at a temperature below its melting point under a very hard vacuum using something like a liquid nitrogen cooled finger for the resublimation. I suspect this would happen very slowly, however. It may be worth trying a sublimation of DMT benzoate since it remains solid at a rather higher temperature.




“There is a way of manipulating matter and energy so as to produce what modern scientists call 'a field of force'. The field acts on the observer and puts him in a privileged position vis-à-vis the universe. From this position he has access to the realities which are ordinarily hidden from us by time and space, matter and energy. This is what we call the Great Work."
― Jacques Bergier, quoting Fulcanelli
 
famine
#16 Posted : 2/9/2023 6:58:44 PM

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downwardsfromzero wrote:
Added a couple more diagrams and hopefully I can add a little animation too - if the Avogadro modelling program behaves itself.

Bear in mind, in the crystal it will be a repeat arrangement of stacks of these, and possible orientations between different stacks are numerous. Only x-ray crystallography would really tell us how the DMT-onium and benzoate ions would be arranged in this matrix and there may also be polymorphs.

What famine mentions about the difference between the vaporization temperature and the boiling point of DMT is that DMT will have a vapour pressure even below its boiling point. If airflow continually removes vaporized DMT from the headspace, more DMT will vaporize to replace it. The boiling point is the temperature at which the vapour pressure reaches atmospheric pressure.

Another thing is that the vapour pressure of benzoic acid and DMT can add together, a bit like the principle of steam distillation. Benzoic acid is moderately volatile itself so perhaps the combination of the two is what facilitates the vaporization of the benzoate, along with favourable intermolecular forces between the two separate aromatic systems.

Technically it should be possible to refine DMT freebase by sublimation at a temperature below its melting point under a very hard vacuum using something like a liquid nitrogen cooled finger for the resublimation. I suspect this would happen very slowly, however. It may be worth trying a sublimation of DMT benzoate since it remains solid at a rather higher temperature.

Even at 0.01mmhg, DMT will have a bp of 105C.. we need some alien technology vacuum to sublime it.

How it arranges as crystal doesn't give us much info. We are looking at liquid phase for vapourisation temperature.
 
downwardsfromzero
#17 Posted : 2/9/2023 7:25:28 PM

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Exactly, really hard vacuum - not really practicable. Crystal arrangement was more a commentary on how showing a single molecule of DMT benzoate isn't necessarily a realistic thing to do.

Anyhow, here is a video of DMT-onium and benzoate doing a little dance.





“There is a way of manipulating matter and energy so as to produce what modern scientists call 'a field of force'. The field acts on the observer and puts him in a privileged position vis-à-vis the universe. From this position he has access to the realities which are ordinarily hidden from us by time and space, matter and energy. This is what we call the Great Work."
― Jacques Bergier, quoting Fulcanelli
 
_Trip_
#18 Posted : 2/10/2023 11:58:11 AM

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downwardsfromzero wrote:

Pretty please, BW - how do you upload to the wiki? I just can't log in for some reason, so if you happened to be able to put the gif on there for me sometime, that would be awesome!



Is this what you were after DFZ?

https://wiki.dmt-nexus.m..._Properties#DMT_Benzoate
Disclaimer: All my posts are of total fiction.

 
downwardsfromzero
#19 Posted : 2/10/2023 10:27:35 PM

Boundary condition

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_Trip_ wrote:
downwardsfromzero wrote:

Pretty please, BW - how do you upload to the wiki? I just can't log in for some reason, so if you happened to be able to put the gif on there for me sometime, that would be awesome!



Is this what you were after DFZ?

https://wiki.dmt-nexus.m..._Properties#DMT_Benzoate

Thanks, you're an absolute darling!

PM with details of how you got it to work if you think that will make sense.




“There is a way of manipulating matter and energy so as to produce what modern scientists call 'a field of force'. The field acts on the observer and puts him in a privileged position vis-à-vis the universe. From this position he has access to the realities which are ordinarily hidden from us by time and space, matter and energy. This is what we call the Great Work."
― Jacques Bergier, quoting Fulcanelli
 
Loveall
#20 Posted : 2/12/2023 9:08:10 PM

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I tested DMT benzoate on e-mesh.

I simply salted naphtha that had been freeze precipitated previously with benzoic acid. Turns out it still had ~0.6mg of DMT free base per ml of naphtha based on salting results.

Vaporized very easily, no residue at all. I snifed it and the white smoke smelled like DMT.

Amazing. Great find BW!

Will test for effects at a later date 🙃

So... there may be no need to partially evap napthat, freeze preciptate, worry about re-X and all that stuff. Simply crash very pure DMT benzoate directly from naphtha (CINLO) and use that instead of freebase (except e-juice since it doesn't dissolve there). Assuming effects are as expected we are looking at a great shelf life + gentler physiological pH + simpler extraction process. What's not to love (only issue is solubility in e-juice)?

This begs the question, what will mescaline benzoate do???
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