DMT-Acetate
Solubility:
Very soluble in water.
Insoluble in all organic solvents - except when used in excess (IPA, Ethanol, Acetontril and comparable). DMT Benzoate is soluble in DMSO and DMF - so DMT Acetate probably too.
Phase Transitions:
Many people have wondered and debated about whether DMT-Acetate can be smoked direclty. Common sense would tell it is a salt and would take insane heat to vaporize. Also it would be caustic to the throat and lung as it is still 1/4 Acetic Acid. So here there is some actual data about this:
Measured with IR Thermometer on a hot plate (give it +- 5 %)
Melting Point
/
First fumes starting
130 °C
Strong fumes from
165 °C+
No fumes arising anymore
190 °C
I think 175 °C is optimal for vaporization.
IR-Spectrum (measured in attenuated total reflection method (ATR))
Water-Uptake
It was reported only -Fumarate/-Maleate/-Benzoate salts are the common variants that are not hygroscopic (maybe Ascorbate too?). I'm not sure whether DMT-Acetate really is also hygroscopic, it may just already be an oil in general - it seems to me - even though thats anti-intuitive, being a salt itself.
Still this could be verified very easily by NMR. Water appears in 1H-NMR at 4,67 ppm.
This means you can determine the water content very precisely by calculating:
Integral 4,67 ppm (s) = I(w)
Integral 2,27 ppm (s) (CH3-) = I(D)
1. Calculate Molecule ratio of Water Molecules to D-Acetate-Molecules:
= (0,5*I(w)) / (0,16*I(D))
2. Calculate Mass Fraction of Water Molecules to D-Acetate-Molecules:
100 * (18/248 ) * Molecule ratio = water content [%]
Example: if 1H-NMR shows an Integral of 2,75 at 4,67 ppm (s), then the
water content in DMT-Acetate is 10 %. But well thats just a random example and not measured. I would have access for measurement, but I dont feel quite well to do that right now ...
In theory water could also at least qualitatively identified in that IR-spectrum. There should be a big peak at ~ 1600 cm^-1, but that could also be from acetic acid. So not really sure, but I also dont really have a Clue about IR.
UPDATE: Now did that test and also find it
here. Same test for many more salts found
here.
Comments:
So it seems that DMT-Acetate
can indeed be smoked, just based on having the same vaporization range as Freebase Tryptamines. Quite interesting that there is practically no difference to DMT. It both starts to emit strong vapors above 150 °C and stop vaporizing below 200 °C. Therefore it does not seem to be retarded strongly by the fact that its a salt. Maybe it may be explainable by counting Acetate as a
soft ion and not a
hard ion like chloride or sulfate.
Bioassay:
A small portion of DMT-Acetate was vaporized according to the optimal vaporization temperature. The vapor was not caustic and no acetic acid smell was present,
neither it was unpleasant to the lungs. A regular DMT-like effect was felt. If it had the same potency, hard to say as this oil is hard to weigh. It would be possible to weigh a loaded apparatus and weigh it after the dose was taken. As normally even the tiniest amounts of Acetic Acid are very irritating to the lungs, it seems there is no back dissociation form Acetate to Acetic Acid and the Acetate is not irritating to the lungs. This also means that the DMT will be delivered to the Lungs as a salt and even this protonated form shows some promising metabolism. This is remarkable as other compounds are often blocked for
desired physiological pathways when not freebased. Still, being a slushy oil, this is not a convenient form to handle your spice.
PS: It seems
hard ions like the sulfate are indeed not vaporizing and just baking to a black cake, no fume release even after 250 °C. So it may be that the Acetate is just being able to be smoked because of being regarded as a
soft ion. So next I checked the Benzoate salt version to also verify on this one.
DMT-Benzoate
Solubility:
Very soluble in water, DMSO, DMF.
Caution: In contrast to DMT Fumarate it also has a high solubility in organic solvents. In general already mediocre at room temperature, but excess Ethanol / IPA will quickly dissolve it. It can be even dissolved in boiling Aceton / Ethyl Acetate. Therefore take care when playing around with this salt - you might actually loose some otherwise. Therefore you would need a much higher concentration of DMT / Benzoic Acid than when creating the Fumarate-salt instead. Much better than the previously mentioned solvents is Toluene, which also requires freezing to get most DMT Benzoate out as a precipitate.
According to Loveall also Limonene has a really low solubility at room temperature so Limonene is probably the best solvent to create DMT Benzoate, as no freezing is required and the solvent is not toxic like Toluene. Still for a purification by recrystallization Toluene might still be better, but solubility of DMT Benzoate in boiling Limonene was not checked and maybe is also high enough.
boiling Toluene (110 °C)
4 g in 100 ml
40 g in 1 L
Toluene in the Freezer (-20 °C)
250 mg in 100 ml
2,5 g in 1 L
boiling Hexan (69 °C)
1,4 g in 100 ml
14 g in 1 L.
Hexan in the Freezer (-20 °C)
< 200 mg / 100 ml
< 2 g / L
Also Hailstorm found that Amyl Acetate works great:
Hailstorm said:
Another way to purify DMT benzoate is to recrystalize it from amyl acetate (which is also a non-toxic non-polar freebase extraction solvent with a logP very close to that of DMT) taking care not to heat it much above 100 °C
To precipitate DMT-Benzoate, use freezer-cold Toluene or Limonene. Better not use Naphtha for DMT only, as it risks Benzoic Acid precipitating instantly before forming the salt. When using Ethyl Acetate the solution should be concentrated to 1 g / ml first, as otherwise solubility is already too high.
Phase Transitions:
Same thing as above with the Acetate. Common sense would tell that salts cannot be smoked / vaped. Even more for a more classic salt like the solid, plain white Benzoate. Same thing even when vaporized, it should also give off Benzoic Acid vapors, possibly caustic to the lungs. So here there is some actual data about this:
Melting point measured with DSC (Heating rate = 3 K / min). Picture is not included to safe space.
Check
DSC
Melting point peak onset = 163 °C
Melting point peak max = 166 °C
Based on TGA-DSC-comparison there is not much of a liquid range. The salt directly evaporates after melting. Probably because of the now increased mobility of ions the process is enabled, that let's those molecules vaporize.
Thermogravimetric Analysis (TGA) (Heating rate = 3 K / min)
Check
TGA of only DMT-Benzoate
So as expected the melting point for the Benzoate salt is really high, being 166 °C and therefore at least 100 °C above any typical freebase DMT polymorph. That comes quite expected, so I would have also assumed this stuff is never smokable. But then as seen in the TGA, it indeed evaporates really easy. Not only the whole process is simply shifted by ~ 30 °C compared to the freebase, it also evaporates nearly completely. That indicates indeed salts like Acetate and Benzoate are completely smokable, as their evaporation temperature is easily hit with any regular vaping device. Even more if you just use a flame to light it, then you would anyways horribly overshoot as you also do with Change in the Bonga (better not do it, waste of material and ultimately simultaneously burning stuff = cancer). But that means DMT Benzoate would be perfectly smokable if you just exchange your Freebase with this one. Because of this further down I had to test if the vapor also is not harsh - like the Acetate - which I assumed to contain some Acetic Acid Vapour but it didn't.
IR-Spectrum + UV-Vis was measured, but not interesting so not uploaded
Comments:
To me now a question is: Why are these DMT salts evaporating so easily. At least Acetate and Benzoate show nearly no difference to the Freebase. Of course the +30 °C is not small, but it does not matter for practical efforts and I would have assumed like +200 °C.
So far the canon was Salts can't be smoked and indeed the Sulfate is just burned to death. But any practical efforts that have been done on this would have probably been with the Fumarate. I dont have any to test. So it would be an interesting thing to test the fumarate - in case it would indeed not vaporize and be the reason for initial salt-non-evaporation-beliefs then probably this might be linked to the whole ionic complex consisting of DMT*1/2Fumarate instead of being a simple salt like DMT+ Benzoate-.
Bioassay:
5 mg of DMT Benzoate were evaporated at ~ 180 °C. Indeed the vapor was not harsh. It gave absolutely no irritation that would come from inhaling acidic components. Only the typical irritation that I get from the freebase ... but then again I'm a noob at smoking. Therefore I would say:
You can just smoke DMT Benzoate as you would do with the Freebase. That could now even be employed by people who are super paranoid about the shelf life. Just create the Benzoate and go on in any matter with this compound as you would with DMT - just creating Change would be a pain obviously.
More DMT-Salts and also a general perspective on all of these is found
here.