CHATPRIVACYDONATELOGINREGISTER
DMT-Nexus
FAQWIKIHEALTH & SAFETYARTATTITUDEACTIVE TOPICS
12NEXT
Chemical Guide to classic Psychedelics (DMT, 5-MeO-", Bufotenin, Harmalas, Salvinorin A, ...) Options
 
Brennendes Wasser
#1 Posted : 1/12/2021 7:20:03 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
This is a Compilation of chemical properties of the Nexus' members most common molecules to come across. Not all are Psychedelics, but some are just other imporant molecules or derivates.

Use Solubility data for adjusting solvent for recrystalization to not overshoot and get less product back.
Use Vaporization data to set up your vaporizer correctly to get the biggest hit while not burning your material.
Some molecules have bonus data / discussion for various reasons.

Besides there is already a page on the wiki, but this data is 90 % new and so I would also like to post it here, as it may be more accessible for people who rarely check the wiki.

In the Internet you will find quite some values for these compounds which are obviously totally wrong, like on Wikipedia the vaporization of DMT (160 °C at 0,0008 bar wtf) and Bufotenin (320 °C at 0,00013 bar wtf). Temperatures given here now are reflecting the actual vaporization point and also give a range of optimal vaporization temperatures.

Now also included an UV/Vis spectrum, measured in Acetonitril.

Now also included an FTIR spectrum, measured in ATR-mode.

Now also TGA / DSC added as a more scientific take on phase transition analysis than hotplate experiments.


Current content:


 

Psychedelic news, articles, interviews and art from the DMT-Nexus and other sources.
 
Brennendes Wasser
#2 Posted : 1/12/2021 7:20:47 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
DMT




Solubility:

boiling Naphtha (80 °C, C6-C7, 60-80 °C)
"infinite"
(the DMT will melt and just create a homogeneous liquid-liquid solution. In the end it may even be a solution of Naphtha in DMT)
Example: In just 5 ml of boiling Naphtha you could easily add 4 g of DMT, while only doubling the initial volume. No precipitation would ever show off.

Naphtha (20 °C, C6-C7, 60-80 °C)
29,3 g in 1 L
2,93 g in 100 ml

Naphtha in the freezer (-20 °C, C6-C7, 60-80 °C)
1,09 g in 1 L
109 mg in 100 ml

boiling n-Hexane (69 °C)
"infinite"
(same as above for Naphtha)

n-Hexane (20 °C)
7,7 g in 1 L
770 mg in 100 ml

n-Hexane in the freezer (-20 °C)
825 mg in 1 L
83 mg in 100 ml

Here 2 additional Hydrocarbons:

n-Pentane in the freezer (-20 °C)
501 mg in 1 L
50 mg in 100 ml

n-Heptane in the freezer (-20 °C)
916 mg in 1 L
92 mg in 100 ml

n-Heptane can be heated to 98 °C and therefore above DMTs melting point. That's why it can also potentially hold infinite DMT at boiling temp. For n-Pentan it's not possible (already boiling at 36 °C so the maximum will be quite low. For recrystallization just go with whatever Hexane/Heptane/Naphtha is the cheapest to get. But always make sure to get a Naphtha that is a mix from Hexan/Heptan isomers.


Besides very soluble in Room Temperature Acetone, IPA, Ethanol, Methanol, DCM, Et2O, MEK, Toluene, Xylene, DMF.



Phase Transitions:

There are at least 3 reported crystal structure modifications of DMT, coming in different crystal grids and thus different melting points. I just know the one that precipitates already at room temperature more yellow and the one that precipitates at lower temperatures fully white. Hence I believe the later one might be more crystaline as it takes longer and slower precipitation, so the melting point might also be higher.


Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
58 °C

Melting Point - DSC (see further down)
63 °C

First fumes starting
100 °C

Strong fumes from
160 °C+

No fumes arising anymore
190 °C

I think 175 °C is optimal for vaporization.


IR-Spectrum (measured in attenuated total reflection method (ATR))




UV-Vis spectrum (0,05 mg/ml in Acetonitril)



No absorption in visible range (400+ nm), so it is white ... But what you can see here nicely is that it just got that typical tryptophane peak at 280 nm - this peak is normally used for protein UV-detection.



Thermogravimetric Analysis (TGA) (Heating rate = 3 K / min)



Here is the thermogravimetric analysis of DMT. Heating rate is 3 K / min. What you can see here is the mass loss of a sample while heating. Thats very nicely demonstrating any evaporation effects. So what you see here: First Vaporization starts at 145 °C (even though I can see trace vapors coming from DMT at 100 °C) and ends at 232 °C. I guess the formerly proposed vaporization range of 165 - 180 °C still seems to be the best choice.



Differential Scanning Calorimetry (DSC) (Heating rate = 3 K / min)



Here is the differential scanning calorimetry analysis of DMT. Heating rate is 3 K / min. What you can see here is the uptake or release of Enthalpy of the sample while heating. Thats very nicely demonstrating any phase transition effects like crystalization / melting. A rising graph indicates an endothermic process, which consumes energy and a decreasing graph vice-versa. So what you see here: There is a melting point onset of DMT at 63 °C. No further melting points detected, so we dont have any polymorphism in this sample. There is another endothermic effect between 200 °C and 245 °C. No idea what that is, but maybe some sort of thermal degradation? Still I think that should only happen > 250 °C ... anyways as the TGA suggest vaporizing your DMT at < 200 °C, this once again shows that for efficient / healthy / non-material-wasting evaporatoin the stuff should not be heated > 200 °C.



Comments:


Not much to say. Dont heat your Spice above 200 °C, this will just cause combustion at some point. Therefore approaches with open flame and Changa will always create unhealthy smoke, that bad charred flavor will just be hidden by the strong DMT-smell. Better use a controlled way of delivering 160 - 200 °C and inhale fresh healthy swiss-alps-DMT.

Also that solubility in the freezer value may now help you to plan your re-x. No more "Maybe you just have to evaporate more Naphtha to get any product? Confused "
Just estimate that ~ 1 mg of Spice will be still held back per 1 ml of Naphtha after freeze-precipitating. This means dont re-x your 100 mg Spice in 100 mg Naphtha Big grin Also if you haven't got any precipitation from 100 ml of Naphtha in the freezer, then you still wont get more than 100 mg from that even if you further reduce ... maybe the problem happened earlier then. Embarrased

That UV/Vis-spectrum is not that interesting, but it shows exactly the Tryptophane-Absorption at 280 nm, which is also used for Protein UV-Detection. Nothing special else though.

If more polymorphs may be accessed with different melting points, these could be measured by XRD and then maybe higher-melting-point-spice will also show greater degrees of crystalinity. It would be senseful if very amorph Spice would be the reason for people observing DMT melting as low as 50 °C and high-crystalinity Spice would be causing 80 °C melting reports. Nevertheless that 58 °C sample looked also quite crystalline ...


Bioassay:

Active



Close-Up: (that left thing looks quite like a micro eagle)


 
Brennendes Wasser
#3 Posted : 1/12/2021 7:21:32 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
DMT-N-Oxide




Synthesis:

Dispense 1 g of DMT in 2,4 ml of 30 % H2O2 (does not dissolve as this is basically water). Add amounts of Ethanol while stirring until all DMT is dissolved. Should be ~ 7 ml Ethanol in total. Stirr this mixture for 48 h at Room Temperature until full conversion. Evaporate all solvent, leaving behind DMT-N-Oxide. (source)

TLC after 48 h still showed a spot in height of starting material. Nevertheless the final product was extracted with boiling Hexane and this Hexane showed no clouds when Trifluoroacetic acid was dropped inside, indicating no residual Freebase so conversion was quantitative.
Also the majority of solvent was evaporated by N2-stream. The last bit was evaporated on a hot plate (Picture 1). This should be done with caution, as it was discovered the N-Oxide is very heat sensitive and decomposes already above 110 °C (Picture 2, turning completely black just within less than 3 seconds). If treaten with care it will form a waxy orange solid (Picture 3).


Solubility:

boiling n-Hexane (69 °C)
insoluble

Aceton (RT)
insoluble

DMF (RT)
insoluble

DMSO (RT)
soluble

Water (RT)
soluble

Wow quite bad solubility overall ... would have guessed it would be soluble in Aceton, but at least at RT there is no dissolving process to be watched. Still its soluble in even neutral water, given the properties of being a salt.



Phase Transitions:

Interestingly pure DMT-N-Oxide is an orange solid and not an oil contrary to popular believe. The oily consistence only arises due to always encounter it in regular ways in a mixture with DMT. Already small mixtures of substances make them not only prevent to crystalize, but also often forming an oil - this sample for example is an oil, yet 80 % DMT purity - even though they may both be an actual solid when being pure.


Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
40-50 °C
hard to determine due to waxy structure

DMT-N-Oxide turning black
110 °C

First fumes starting
130 °C

No fumes arising anymore, black tar residue
150 °C

I think there is no optimal temperature for vaporization. It just decomposes super fast, even on inert surfaces like glass. It does not even give strong fumes, it mostly turns into black tar. That is why even if you HAD some N-Oxide in your mixtures, it would never reach your lungs probably.



IR-Spectrum (measured in attenuated total reflection method (ATR))



DMT-N-Oxide separation:

As the N-Oxide seems to be only soluble in DMSO, this can be achieved to do a purification from other possible tryptamine compounds. Yet it seems this can turn oily stuff into more solid products, but yet I would not call this an actuall recrystallization.

1. Dissolve the N-Oxide in a minimal amount of DMSO
2. Add 20x Volumes of Ethyl Acetate (possibly EtOH/IPA/Aceton could work, too)
3. The solution turns cloudy, place in the fridge for 3 h
4. Decant the clear liquid to retrieve your N-Oxide (Picture below). All non-oxidized Amines will stay in solution, no matter what Tryptamines they may be.





Comments:


So interestingly DMT-N-Oxide is a solid, but thats also what you can observe with DMT: Just having small traces of impurities it will already start to become oily. Still, the substance is quite waxy. Also interesting, but annoying seems the super fast thermal decomposition, starting from 110 °C and running super fast, finishing in seconds. If just started once you will lose your N-Oxide 100 %. This makes it super unlikely that anyone ever has smoked some real N-Oxide, also it seemingly being non-soluble in Acetone as it seems, preventing it to be transfered further into Changa. People still dissolving all their oily DMT in Acetone probably had no N-Oxide pollution, but just oily DMT due to other impurities.
Actually I even think having any reasonable of the N-Oxide in your extracted stuff is just super unlikely. Why should it have become oxidized? You would need a real oxidation agent or UV-rays and pure heat does not oxidize DMT - even when in direct contact with O2. Also UV-Rays will not make a full conversion. Therefore even if there were traces of N-Oxide in a plant-derived sample, they will always come with a big bunch of non-oxidited DMT. Only a real chemical conversion would lead to 100 % N-Oxide. So based on smoking oily residues labelled as N-Oxide and being called active, this may have just been a false positive thing. I more have the feeling that people in general call oily DMT being polluted by N-Oxide, but also even small amounts of pollutants will turn your goodies to an oil, this sample is a classic oily mess and still 80 % of DMT Purity.



Bioassay:

In regard to bioactivity of DMT-N-Oxide I think its nearly impossible to smoke this compound, as it will turn black within less than 3 seconds once heated above 100 °C. By that time it will not even have evaded any fumes to inhale. Further heating does just produce traces rising up from that super uggly and unhealthy looking black tar (see Picture 2). But as the N-Oxide is the natural product of MAO-enzymes, it should not be needed to block these when incorporating the N-Oxide. This means if it HAD any psychedelic effect one could simply eat any amount of N-Oxide and would suspect an effect not too far off from the same amount of DMT, eaten with 150+ mg Harmalas. Now people could argument, eating would be an inefficient ROA, as the high-polarity compound is not likely to tresspass membranes and will have low bioavailability. Actually it is even less polar than DMT when eaten orally: macroscopically the positive charge is decreased due to the additional Oxygen at the protonated N-Oxide. And now DMT is indeed bioavailable when eaten, as people know so the N-Oxide should be too, if it had any activity at all.
The proof can be seen here in this reversed-phase Chromatogram. The solvent protonates any bases, causing them to have uniform charging across the column. This happens to DMT and the N-Oxide, while now being DMT+H(+) more polar than DMT-N-OH(+). In a consequence, the N-Oxide elutes 1 min later in reversed-phase and the solvent can be transferred to our gastric conditions, where also both compounds will form their protonated salts. This way I am very certain, that if N-Oxide HAD an effect it will be visible upon oral ingestion.

80 mg of DMT-N-Oxide was eaten. No effect Thumbs down
But: It tastes like DMT (Ginger-like spicy) + an additional Cherry Flavor. Super cool! Weird sweet bonus, exactly like Cherry Menthol gums.

So while the N-Oxide being a metabolist of DMT and definetly has a metabolic pathway in the body, I highly doubt it would still interact with the same receptors that are also responsible for DMT-effects. That unoxidized Amine would normally be important for in-vivo recognition at receptors, rendering it possibly inactive upon oxidation, as the N-Oxide is a very different chemical species - unlikely to show the same binding behaviour. That said and given the facts that it cant really evaporated and shows no effect upon ingestion, I highly doubt that anybody ever was high on N-Oxide Confused .

 
Brennendes Wasser
#4 Posted : 1/12/2021 7:22:18 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
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.



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. Also soluble in DMSO, DMF.

Insoluble in all organic solvents - except when used in excess (IPA, Ethanol, Acetontril and comparable).


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.

Melting point peak onset = 163 °C
Melting point peak max = 166 °C


Evaporation temperature is measured with TGA. TGA is added with direct comparision to regular DMT.


Thermogravimetric Analysis (TGA) (Heating rate = 3 K / min)



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.
 
Brennendes Wasser
#5 Posted : 1/12/2021 7:23:02 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
Bufotenin / 5-OH-DMT




Solubility:

Bufotenin is the most polar common Tryptamine, only surpassed by Psilocybin. Therefore it is completely insoluble in Hexane/Naphtha, but can be soluble in pH > 12 water due to Phenol deprotonation. It is hard to crystalize and will mostly give just an oil. The following solutions can give crystalline products:


boiling Xylene (140 °C)
48 g/l = 4,8 g in 100 ml (43 outdated)

Xylene in Freezer (-20 °C)
- 20 °C = 15,8 g/l = 1,58 g in 100 ml (14,5 outdated)

Selectively dissolves Bufotenin and not the more polar components of A. colubrina seeds. But you will need a defat with Naphtha before. With 2x re-x you should get pretty pure and light-colored Bufotenin (Pictoral). Nevertheless you might evaporate a little more Xylene before placing in the freezer, to retrieve more of your goodies.
Why is Xylene a good solvent, even though its way more unpolar than Bufotenin? 69ron gives explanation (cant find source): Xylene can heat Bufotenin above its melting point, thus forming a liquid-liquid mixture, which is miscible. This can also be used with Limonene, but Limonene is much worse as it needs to be heaten additional 30 °C to 175 °C, which causes partial degradation of Bufotenin.


1:3 Ethyl Acetate:Naphtha (C6-C7)
Boiling = 7,6 g/l = 760 mg in 100 ml
20 °C = 3,6 g/1 l = 360 mg in 100 ml
- 20 °C = 3,5 g/1 l = 350 mg in 100 ml

Not as good as Xylene - you should only use it as an alternative when not being able to get Xylene. Still possible to get crystalline product (Picture). This will still catch up to 2 % of more polar components from the seeds as you can see here in NMR and GC. Also when pulling with this on Anadenanthera colubrina seeds, defat first with Naphtha.


Ethyl Acetate
Boiling = 280 g/1 l = 28 g in 100 ml
20 °C = 72 g/1 l = 7,2 g in 100 ml
- 20 °C = 50 g/1 l = 5 g in 100 ml

Mentioned for recrystalization in literature. Not recommended, seems to cause a darkening (Picture, right). Also very high solubility overall, means you have to use very minimal amounts of solvent = inconvenient to handle. Furthermore if the Bufotenin has a low purity it will just stay oily after re-x.


Besides very soluble in Room Temperature Acetone, IPA, Ethanol, Methanol, DCM, Et2O, MEK, DMF


Phase Transitions:

Measured with IR Thermometer on a hot plate (give it +- 5 %)

Even though 146 °C is given in literature, both amorph and crystaline Bufotenin gave the following melting point.

Melting Point - amorph
104 °C

Melting Point - crystaline
104 °C

Melting Point - DSC (see further down)
132 °C

First fumes starting
160 °C

Bufotenin turning brown (possible phenol -> keton oxidation)
170 °C

Strong fumes from
190 °C+

No fumes arising anymore ...
230 °C

... leaving behind a considerable amount of charred Bufotenin. Seems that it cant be fully evaporated without causing at least partial degradation.

I think 220 °C is optimal for vaporization.

Interestingly the melting point is really low when measured on a hotplate. Literature value is around 145 °C, but both amorph and crystaline is way lower ... still both are basically pure. Maybe the traces of Ethyl Acetate cause this? Nevertheless when doing a DSC the value is 132 °C, which is much closer to the other literature value. In any way as there might only be traces of contaminants, it could hint that these polymorphism might be kind of common across tryptamines.



IR-Spectrum (measured in attenuated total reflection method (ATR))




UV-Vis spectrum (0,25 mg/ml in Acetonitril)



In contrast to DMT we can see an elongated absorption further than the 280 nm Tryptophane-peak. Bufotenin has that additional 5-OH, so the hydroxyl group donates some electrons into the Indol-chromophor and therefore changes the minimum required energy for absorption (= electron excitation). Thats why the substituent causes a shift in absorption properties or more precisely an elongation.



Thermogravimetric Analysis (TGA) (Heating rate = 3 K / min)



Here is the thermogravimetric analysis of Bufotenin. Heating rate is 3 K / min. What you can see here is the mass loss of a sample while heating. Thats very nicely demonstrating any evaporation effects. So what you see here: First Vaporization starts at 182 °C and ends at ~ 275 °C. This is pretty close to what I saw with my Ghetto-Hotplate-Experiments. Sadly it also confirms that instead of fully vaporizing, the Bufotenin will also form pyrolysis products and combust into black tar, which makes any evaporation stop at 50 %. The heating rate is very gentle and only 9 mg of sample were used, so even in that very controlled heating conditions this decomposition cant be avoided. Thats why it will always be a mess when vaporized in any way. Still it seems the best vaporization range is then 200 - 250 °C.



Differential Scanning Calorimetry (DSC) (Heating rate = 3 K / min)



Here is the differential scanning calorimetry analysis of DMT. Heating rate is 3 K / min. What you can see here is the uptake or release of Enthalpy of the sample while heating. Thats very nicely demonstrating any phase transition effects like crystalization / melting. A rising graph indicates an endothermic process, which consumes energy and a decreasing graph vice-versa. So what you see here: There is a melting point onset of Bufotenin at 132 °C. Previously with another batch a melting point of 103 °C was measured for amorph and crystaline Bufotenin. But as there were traces of Ethyl Acetate left, this new value was put into the properties table. Literature tells 148 °C if I recall correctly, but this sample here was definetly also free of solvent.



Comments:


So Bufotenin is hard to crystalize, but easy when using the 2 mentioned solvents. When not heating to 170 °C it seems quite stable and that phenol is not prone to oxidation as people may think. It stays clear white for months even at room temperature. Sadly it does not vaporize cleanly and will degrade by 50 % instead into a black tar. This 5-OH group seems to cause a lot of trouble here not only for crystalization.



Bioassay:

The vapor in low concentrations tastes nicely like toasted nuts. In high concentrations it may feel nauseating. But maybe thats just as the overall effect of Bufotenin is a little bit nauseating. Seems this cant be avoided, as Bufo is quite similar to Serotonin and therefore causing intense vasoconstriction and tingling in the face and fingers. Not too pleasant. Also face turns quite cold. Red coloring at the face could not be observed. Still other people have reported very promising / intense / interesting experiences when vaped.
Oral consumption seems rather ineffective. 100 mg of Bufo-Fumarate just gave a slight effect, comparable to 1 g of Mushrooms possibly, while still being bad to the stomach.



Close-Up: (it looks like cauliflower hehe)


 
Brennendes Wasser
#6 Posted : 1/12/2021 7:23:48 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
5-MeO-DMT




Solubility:

boiling Naphtha (80 °C, C6-C7, 60-80 °C)
4,5 g in 100 ml
45,0 g in 1 l

Naphtha (20 °C, C6-C7, 60-80 °C)
104 mg in 100 ml
1,0 g in 1 l

Naphtha in the freezer (-20 °C, C6-C7, 60-80 °C)
70 mg in 100 ml
700 mg in 1 l


boiling n-Hexane (69 °C)
1,9 g in 100 ml
19,0 g in 1 l

n-Hexane (20 °C)
84 mg in 100 ml
840 mg in 1 l

n-Hexane in the freezer (-20 °C)
46 mg in 100 ml
460 mg in 1 l



Compared to 5-AcO-DMT the solubility in Hexan is still more than 4x as high, which still dissolves slightly in Hexan. But upon freezing the Solubility drops basically to 0, in contrast to other Tryptamines and their respective solvent-of-choice. So when doing a recrystalization there is basically no chance to loose material, even when only cooling to RT. Also in the freezer you dont get any more precipitation, so just stay with RT. Regarding crystalization, you can find some thoughts here.


Besides very soluble in Room Temperature Acetone, IPA, Ethanol, Methanol, DCM, Et2O, MEK, Toluene, Xylene, DMF.


Phase Transitions:

Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point - amorph
47 °C

Melting Point - crystaline
49 °C

Melting Point - DSC (see further down)
62 °C

First fumes starting
118 °C

Strong fumes from
170 °C+

No fumes arising anymore
190 °C

I think 175 °C is optimal for vaporization.

These values are quite unexpectedly low. Regarding melting point, my first idea was that it might be due to some polymorphs and I got a low-melting variant, as literature value is 69 °C. Same was also observed with Bufotenin, where the pure compound showed a much lower melting point on hotplates and in DSC. Nevertheless the DSC of the same Sample is much better in accordance with that value - like Bufotenin. Maybe the Hotplate Test still contained some solvent.
The boiling point is also remarkably low. By adding the 5-OH from DMT to Bufotenin the vaporization temp should have been well above 250 °C, but in this case it was also much lower. But now comparing 5-MeO-DMT to DMT we have nearly the same vaporization profile. This can be even better seen at the TGA measurement later on if you compare both. Also 5-MeO-DMT leaves behind nearly no brown residue, just like DMT and 5-AcO-DMT, indicating that only Bufotenin is a Tryptamin with a *dirty evaporation* which leads to charr. Seems like this OH- of Bufotenin really is the root of all evil, as it can oxidize.



IR-Spectrum (measured in attenuated total reflection method (ATR))




UV-Vis spectrum (Acetonitril, didnt write down concentration)



The UV-Vis looks quite like 5-OH-DMT / Bufotenin. That of course comes expected, both share the same electronic properties regarding their chromophore: Oxygen induces +M effect in the Ring, enriching it with electrons. In both cases we see a red-shift of absoption compared to DMT. Still this is not visible for 5-AcO-DMT, here the moiety is basicallys locked from any interaction with that Indol and therefore causes no red-shift.
Still for both MeO-DMT and Bufotenin the absorption has a cut-off before any visible range, so a pure compound will still resemble clear-white.



Thermogravimetric Analysis (TGA) (Heating rate = 3 K / min)



Here we can see the same observation like during these hot-plate experiments: 5-MeO-DMT just vaporizes like DMT basically, maybe needs only a few K more. Also I was happy to see that it has a really clean vaporization, regarding more than 90 % vaporized at 245 °C. If you compare: 95 % of DMT has vaporized at 230 °C. That is remarkably similar, given that we add this 5-OMe. Furthermore I tried vaporizing a dirty crude mixture. This was still containing most 5-MeO-DMT. But it did only give slight fumes and was moreover burned as a black tar into the hot-plate. So given that your substance has (reactive) impurities the vaporization might be much less clean.



Differential Scanning Calorimetry (DSC) (Heating rate = 3 K / min)



In contrast to a hot-plate 49 °C melting point there is now a melting observed starting at 62 °C. Later on at 240 °C+ there is another endotherm process, maybe that's also the reason why the last 10 % are not vaporized and instead probably decomposed. Same was observed with DMT before.



Comments:


So based on these results 5-MeO-DMT and DMT seem like quite close brothers, whereas Bufotenin is more of an oddity.
Regarding phase transition I would have expected at least 50 °C more for vaporization, but we saw that even Harmalas can vaporize at 200 °C.
Seems like an electronic device to be used for the whole spectrum of the Nexians' favorite molecules doesnt even need more than 250 °C max. Temperature.


Bioassay:

Might try some sublingual stuff in future. Here you can find some dosages for Psychoactivity Threashold derived by Jonathan Ott, quite the same study like above the link at Bufotenin from him.



Close-Up: (Rainbow light refraction when illuminated from top)


 
Brennendes Wasser
#7 Posted : 1/12/2021 7:24:34 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
5-AcO-DMT




There is practically no information about 5-AcO-DMT on the Internet (not to be confused with 4-AcO-DMT). Here is some maybe helpful stuff.

Solubility:

boiling n-Hexane (69 °C)
5,0 g in 1 L
500 mg in 100 ml

n-Hexane in the freezer (-20 °C)
1,3 g in 1 L
130 mg in 100 ml

Besides very soluble in Room Temperature Acetone, IPA, Ethanol, Methanol, DCM, Et2O, MEK, Toluene, Xylene, DMF.



Phase Transitions:
Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
83 - 88 °C

First fumes starting
190 °C

No fumes arising anymore
240 °C



IR-Spectrum (measured in attenuated total reflection method (ATR)





UV-Vis spectrum (concentration < 0,01 wt-% in Acetonitril)





Bioassay:

no effect lol


long story:

20 mg 5-AcO-DMT were vaporized over the course of 10 min.
The vapor taste is very smooth and not yukky like 5-OH-DMT. Also it does not turn black upon heating and vaporizes without any residue - just like pure DMT. In contrast this is not the case for 5-OH-DMT. It quickly turns black above 170 °C and only 50 % will vaporize, while the other 50 % will form a black burned layer on the surface, no matter how soft and gently you are heating it.
Seems like the 5-OH is the source of evil regarding the properties of 5-OH-DMT aka. Bufotenine which makes it hard to crystalize and also generates an unconvenient vaporization profile. Therefore the 5-AcO seems to make the molecule much easier to handle in any way.

Nevertheless no effect was felt. Rolling eyes

Vaporization overcomes first-pass-effect by the liver, maybe this is a reason. 5-AcO-DMT should be a prodrug of 5-OH-DMT. De-Acetylation should be fast in the body, but no idea where it takes place - maybe that step is skipped when inhaling vapors. Nevertheless that would mean the prodrug is totally inactive. Compared to Psilocin, its prodrug 4-AcO-DMT is reported to be instantly active when inhaled, suggesting it has an effect itself. Therefore it would be strange if thats not the case for 5-AcO-DMT. Only solution would be: What you see in the first picture is not 5-AcO-DMT, which is nearly impossible, but cant be proven by MS or NMR right now.
Still, it has a distinct Tryptamine / Alkaloid taste. Maybe I should spend some time comparing the IR to this one.

3257 is hard to see, but might be there
(2186 not in literature spectra)
1752 is there
(1698 not in literature spectra - Acetic Acid?)
1373 is there
1216 is there
1168 is there
948 is there

... seems like true 5-AcO-DMT. 2186 + 1698 might be any residual stuff, but their signals are quite strong and in contrast the purity should be super high.
 
Brennendes Wasser
#8 Posted : 1/12/2021 7:25:19 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
Harmala Alkaloids




Solubility:


Many people have debated about Harmala Solubility and what to use if making Changa. Myself I had the feeling like they are soluble in exactly nothing. Here are the most common solvents, from good to bad.


boiling DCM (40 °C)
24,9 g in 1 L
2,5 g in 100 ml

hot DMSO (100 °C)
23,3 g in 1 L
2,3 g in 100 ml

boiling Methanol (64 °C)
12,7 g in 1 L
1,3 g in 100 ml

boiling IPA (82 °C)
8,2 g in 1 L
818 mg in 100 ml

boiling Ethanol (78 °C)
8,0 g in 1 L
802 mg in 100 ml

boiling Ethyl Acetate (77 °C)
7,9 g in 1 L
787 mg in 100 ml

boiling Aceton (56 °C)
3,6 g in 1 L
360 mg in 100 ml


Seems like from any good solvent DCM would still be the most healthy one. DMSO is totally healthy, but will never evaporate, so this does not help for Changa people. But if you can be sure to 1000 % evaporate stuff, then Methanol would also be an option. If being more on a safe side, Ethanol is then the best. It is also possible to just prepare everything in an even 1-layer and just sprinkle the Harmalas on top.



Phase Transitions:

Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
/ sublimating directly

First fumes starting
180 °C

Sublimation while forming small black clumps
205 °C

No fumes arising anymore, leaving behind black residue
240 °C

I think 225 °C is optimal for vaporization.
Interesting, I thought it would be ways above DMT. That means that vaporizers like the Crafty / Mighty can indeed also partioally vaporize Harmalas, it was always stated they could only be used for infused herb. Maybe in future I may test Harmin and Harmalin on their own, for now only the mixture. But they should not differ too much anyways.



IR-Spectrum (measured in attenuated total reflection method (ATR))




UV-Vis spectrum (0,05 mg/ml in Acetonitril)



In contrast to DMT we can see a slight absorption in the visible range (> 350 nm). Thats why Harmalas are not colorless. They have the same molecular size, but the chromophor has a slightly bigger pi-system. Thats because it's partially reduced and carries more pi-electrons and therefore the energy between lowest occupied orbital and highest non-occupied is smaller. This will shift the absorption towards lower energies aka. higher wavelengths. I bet that if you would measure it for ONLY Harmin and ONLY Harmalin you would see that the 350 nm+ absorption is caused by Harmin - as it has the biggest pi-system and should therefore be mostly causing the coloration.



Thermogravimetric Analysis (TGA) (Heating rate = 10 K / min)



Here is the thermogravimetric analysis of Harmala Alkaloids. Heating rate is 3 K / min. What you can see here is the mass loss of a sample while heating. Thats very nicely demonstrating any evaporation effects. So what you see here: First Vaporization starts at 192 °C and ends at 270 °C. Sadly we can see the same thing as with Bufotenine - very ineffective vaporization and most of the material will just undergo pyrolysis and form a black tar residue. At 250 °C only 25 % of the Harmalas evaporated even though the temperature program is very gentle and only 8 mg of sample have been used. So this once again shows smoking harmalas may not be the most rewarding ROA.



Differential Scanning Calorimetry (DSC) (Heating rate = 3 K / min)



Here is the differential scanning calorimetry analysis of Harmala Alkaloids. Heating rate is 3 K / min. What you can see here is the uptake or release of Enthalpy of the sample while heating. Thats very nicely demonstrating any phase transition effects like crystalization / melting. A rising graph indicates an endothermic process, which consumes energy and a decreasing graph vice-versa. So what you see here: Basically nothing hehe. Just confirming the Ghetto-Hot-Plate-Experiments there is no melting point and Harmalas sublimate directly.



Ratio of Harmalin/Harmin

This can be easily determined by 1H-NMR. The additional sp3-Protons of Harmalin give Signals at 3,8 ppm (t) / 3,97 ppm (t) both not being homotop, 2,73 ppm (t).

1H-NMR can be seen in this picture.

Ratio is:

1,1:1 regarding Harmalin:Harmin at most, if not even more close to 1:1. No Vasicin can be seen.


Comments:


More comments on this and the 1H-NMR can be read in this post at 8.).


Bioassay:

400 mg Harmala Alkaloids were eaten. Just a quick test to verify whether they indeed also contribute to Nausea. Intense vomiting. Nausea for hours. Really strong effect, like a mixture of LSD / stoned. Walking not easy. All in all bad experience.
 
Brennendes Wasser
#9 Posted : 1/12/2021 7:26:15 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
Tetrahydroharmin




Solubility:

Insoluble in Naphtha

Besides medium solubility in Room Temperature Acetone, Ethanol, Methanol, DCM.


Phase Transitions:

Melting Point derived from DSC
179 °C onset
187 °C Peak maximum

Literature: 187 - 190 °C


Vaporization Temperature from TGA
Starting from 190 °C+


IR-Spectrum (measured in attenuated total reflection method (ATR))




UV-Vis spectrum (Acetontril, didnt write down concentration)



Similar to Harmalas we can see a small absorption towards the transition from UV to visible light. Nevertheless the absorption is much lower in UV-A, as some the right ring looses even more pi-Electrons, thus we get a slight blue-shift for the whole photochromic properties. That would be also the best explanation why THH is slightly less brownish colored than its oxidized precursors.



Thermogravimetric Analysis (TGA) (Heating rate = 10 K / min)



What can be seen is a evaporation starting from 109 °C. That's basically the same value as for Harmalas. What is interesting is that we have a much higher degree of vaporization. Harmalas only evaporate to a very low extent as seen above, which is why we all just smoke a small amount of the stuff, which is stuffed on Changa or whatever other vaping/smoking method. This is a very ineffective way of ingestion and I would advise just eating them. But for THH instead of vaporizing 30 %, we could vaporize a theoretical 60 %. Compared you will see the Harmala Evaporation stop at 260 °C, probably forming any kind of charred agglomerates. This seems to be postponed for THH so you can actually smoke quite a lot of it, so I wonder why I didnt read any vaping experiences of THH so far. Compared with Bufotenin it evaporates even better, while the latter is definetly said to be able to be smoked.



Differential Scanning Calorimetry (DSC) (Heating rate = 10 K / min)

[center]


Here we can see a melting transition around 179 - 195 °C. This is not too bad in accordance with the literature value of 187 - 190 °C. Originally I was not expecting any real melting point, as this also was not observed for Harmalas neither on a hotplate nor in DSC. Still, the conversion seemed to at least affect the melting properties, whereas not any vaporization behaviour of THH.



Bioassay:


Will try soon if Vaping is possible.
 
Brennendes Wasser
#10 Posted : 1/12/2021 7:27:06 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
Salvinorin A (Salvia Divinorum)




Solubility:

boiling IPA (82 °C)
(slightly soluble, just try low amounts, like 5 ml for 200 mg Salvinorin-Chlorophyll-Mix)

IPA (RT)
0,74 mg in 1 ml due to Erowid
1 mg in 1 ml due to another Erowid page, but cant find

Aceton (RT)
~ 23 g in 1 L
~ 23 mg in 1 ml
due to Loveall here

Water (RT)
12 mg in 1 L
so basically 0 ...
according to PubChem

After dissolving your Salvinorin in boiling IPA to separate it from Chlorophyll, add 3 Volumes of Naphtha to the IPA and place it in the Fridge. This will not only speed up separation, but also further decrease Solubility of Salvinorin in the IPA-Mixture. This way you should loose nearly no Salvinorin with these re-x steps.

By using this method its possible to precipitate nearly all Salvinorin, so better to it multiple times until there is no more greenish colour and the IPA is not green anymore. But only use a few ml at once for re-x. This way you can get pretty crystals, much better than in the picture above. See the ones by Loveall here.



Phase Transitions:

Salvinorin is a giant molecule (M = 432 g/mol) and thus should either not vaporize at all or just combust. Still regular vaporization is possible as some people may agree.


Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
/ sublimating directly

First fumes starting, Salvinorin A turning brown
190 °C

No fumes arising anymore
270 °C

I think 250 °C is optimal for vaporization. Still it will not vaporize 100 %. Seems like that molecule is just too big: Degradation cant be avoided completely.

Apparently Loveall got promising results evaporating Salvia in Acetone on an E-Mesh and fumes were active on a setting of 180 °C.


IR-Spectrum (measured in attenuated total reflection method (ATR))




UV-Vis spectrum (2,7*E-04 mol/L in Acetonitril)



WOOPS something went wrong here. Negative absorption Confused Big grin Measured again but still looks weird. No idea what is wrong here, but guess I'll repeat this at day X when I get my hands on some fresh one.



Comments:


Quite unusual that this molecule vaporizes so early. But like with Bufotenin and Harmalas it seems that a clean vaporization is not possible - there are seemingly too many options for that molecule to be also destroyed / broken down while being heaten up. Still, I think Temperatures up to 270 °C are still reachable with electronic vaporizers. Would be quite interesting if people may have success with these and pure Salvinorin.

Also that UV/Vis looks terrible, with negative absorption at some point. Maybe Salvia cannot only create light in your head, but also in Acetonitril. Or there was some problem with the Blank :/ Still as most compounds here, transparent until UV-B Region starting.
Nevertheless there is no real absorption visible, which nicely aligns with the fact that there are no big pi-Electron-Structures in Salvinorin. There is just that Furan Ring, but its rather small so its already expected that all the Tryptamines have a stronger Absorption due to their Indol-"chromophor".


Bioassay:

XXX
 
downwardsfromzero
#11 Posted : 1/13/2021 2:56:52 PM

Boundary condition

ModeratorChemical expert

Posts: 7392
Joined: 30-Aug-2008
Last visit: 07-Dec-2022
Location: square root of minus one
Great work as ever, BW!

I'm thinking of tabulating the data as you complete it.

(As an aside, most of the chemical terminology can be anglicized by adding an -e on the end of the German term:
acetonitrile, ionophore, etc. but phenol and the -OH "-ols" stay the same. "Indol" becomes "indole", however, on account of its lack of an -OH group. Etheric -ols like "cineol", "anethol" and "safrol" take the -e, so to speak Big grin, and "-in" becomes "-ine" if it's nitrogenous: e.g. "anilin" → aniline, but salvinorin, for example, stays the same. And for some reason, psilocin, baeocystin and psilocybin are random exceptions to this rule - with bufotenin(e) seemingly randomly switching between both camps Laughing

Anyhow, I think your bandwidth is best taken up doing what you do best but the footnote is here for those who may have been wondering about some of the chemistry terms.)




“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
#12 Posted : 1/21/2021 11:10:07 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
So I now have a 1H-NMR of the Harmalas and the Ratio is at most 1,1:1 in regards of Harmalin if not closer to 1:1. Also there seems to be no Vasicin, possibly due to excessive washing (Vasicin should be more water soluble than the other 2). Spectrum can be seen in that other Analysis Thread - link above.
 
endlessness
#13 Posted : 1/22/2021 10:19:55 AM

DMT-Nexus member

Moderator

Posts: 14064
Joined: 19-Feb-2008
Last visit: 07-Dec-2022
Location: Jungle
Thanks for the experiments and sharing of data!

When this is completed, we can update the wiki to add such data.

Great work friend Smile
 
Brennendes Wasser
#14 Posted : 1/22/2021 7:39:30 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
Now DMT-N-Oxide added.

In short:

When handled pure and in the correct way its not a red oil, but a light-orange waxy solid.

Furthermore when heating that stuff it decomposes even on Quarz Glass already just above 100 °C, making it nearly impossible to ingest by smoking.

But even when eaten there is no effect felt. At least it tastes like Cherries! So I think that despite people calling the N-Oxide active, they probably never smoked the real N-Oxide, instead just real DMT with at maximum traces of it, as much as I think the *Jungle* experience from Jungle Spice just arises from the still majority of DMT.

Therefore I think this stuff is near-safe inactive.



PS:

Now had to correct something, N-Oxide is not only soluble in HCl, but also just plain water.

Also I forgot the maybe the most important thing of the Bioassay: It tastes like Cherries!
So it has that slightly spicy ginger-like burning taste from regular Tryptamines, but it adds this cherry flavor, making it tasting quite like these Chewing Gums Big grin Big grin Big grin .
 
Brennendes Wasser
#15 Posted : 5/12/2021 6:10:15 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
Some new data added:

Differential Scanning Calorimetry (DSC)

and

Thermogravimetric Analysis (TGA)


But only for DMT, as this may be the most important one Confused

This does not show any ground-breaking new stuff, but havent seen it elsewhere. It's basically a way of investigating when the sample melts and vaporizes. Looks quite like what we know, but now thats some different way of taking a closer look.
 
Brennendes Wasser
#16 Posted : 6/1/2021 3:25:57 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
More data added:

Bufotenin and Harmalas now complete.

Summary:

Bufotenin

- slightly adjusted solubility in Xylene
- UV/Vis added, it absorbs a little further than DMT because of 5-OH
- TGA added, only 50 % will vaporize and rest does pyrolysis
- DSC added, melting point ~132 °C
- Closeup picture looks like vegetables Big grin (DMT also added, looking like Flowers as seen before)

Harmalas

- UV/Vis added, slightly absorbs in Vis-region in contrast to Tryptamines
- TGA added, only 25 % will vaporize and rest does pyrolysis
- DSC added, no melting point observed as before
 
Loveall
#17 Posted : 6/4/2021 10:54:03 AM

❤️‍🔥

Chemical expertSenior Member

Posts: 3184
Joined: 11-Mar-2017
Last visit: 08-Dec-2022
Location: 🌎
Brennendes Wasser wrote:
DMT-N-Oxide




Synthesis:

Dispense 1 g of DMT in 2,4 ml of 30 % H2O2 (does not dissolve as this is basically water). Add amounts of Ethanol while stirring until all DMT is dissolved. Should be ~ 7 ml in total. Stirr this mixture for 48 h at Room Temperature until full conversion. Evaporate all solvent, leaving behind DMT-N-Oxide. (source)

TLC after 48 h still showed a spot in height of starting material. Nevertheless the final product was extracted with boiling Hexane and this Hexane showed no clouds when Trifluoroacetic acid was dropped inside, indicating no residual Freebase so conversion was quantitative.
Also the majority of solvent was evaporated by N2-stream. The last bit was evaporated on a hot plate (Picture 1). This should be done with caution, as it was discovered the N-Oxide is very heat sensitive and decomposes already above 110 °C (Picture 2, turning completely black just within less than 3 seconds). If treaten with care it will form a waxy orange solid (Picture 3).


Solubility:

boiling n-Hexane (69 °C)
insoluble

Aceton (RT)
insoluble

DMF (RT)
insoluble

DMSO (RT)
soluble

Water (RT)
soluble

Wow quite bad solubility overall ... would have guessed it would be soluble in Aceton, but at least at RT there is no dissolving process to be watched. Still its soluble in even neutral water, given the properties of being a salt.



Phase Transitions:

Interestingly pure DMT-N-Oxide is an orange solid and not an oil contrary to popular believe. The oily consistence only arises due to always encounter it in regular ways in a mixture with DMT. Already small mixtures of substances make them not only prevent to crystalize, but also often forming an oil - this sample for example is an oil, yet 80 % DMT purity - even though they may both be an actual solid when being pure.


Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
40-50 °C
hard to determine due to waxy structure

DMT-N-Oxide turning black
110 °C

First fumes starting
130 °C

No fumes arising anymore, black tar residue
150 °C

I think there is no optimal temperature for vaporization. It just decomposes super fast, even on inert surfaces like glass. It does not even give strong fumes, it mostly turns into black tar.



IR-Spectrum (measured in attenuated total reflection method (ATR))



DMT-N-Oxide separation:

As the N-Oxide seems to be only soluble in DMSO, this can be achieved to do a purification from other possible tryptamine compounds. Yet it seems this can turn oily stuff into more solid products, but yet I would not call this an actuall recrystallization.

1. Dissolve the N-Oxide in a minimal amount of DMSO
2. Add 20x Volumes of Ethyl Acetate (possibly IPA could work, too)
3. The solution turns cloudy, place in the fridge for 3 h
4. Decant the clear liquid to retrieve your N-Oxide (Picture below). All non-oxidized Amines will stay in solution, no matter what Tryptamines they may be.





Comments:


So interestingly DMT-N-Oxide is a solid, but thats also what you can observe with DMT: Just having small traces of impurities it will already start to become oily. Still, the substance is quite waxy. Also interesting, but annoying seems the super fast thermal decomposition, starting from 110 °C and being done before 150 °C. This makes it super unlikely that anyone ever has smoked some real N-Oxide, also it seemingly being non-soluble in Acetone as it seems, preventing it to be transfered further into Changa. People still dissolving all their oily DMT in Acetone probably had no N-Oxide pollution, but just oily DMT due to other impurities.
Actually I even think having any reasonable about of the N-Oxide in your extracted stuff is just super unlikely. Why should it have become oxidized? You would need a real oxidation agent or UV-rays and pure heat does not oxidize DMT - even when in direct contact with O2. Also UV-Rays will not make a full conversion. Therefore even if there were traces of N-Oxide in a plant-derived sample, they will always come with a big bunch of non-oxidited DMT. Only a real chemical conversion would lead to 100 % N-Oxide. So based on smoking oily residues labelled as N-Oxide and being called active, this may have just been a false positive thing. I more have the feeling that people in general call oily DMT being polluted by N-Oxide, but also even small amounts of pollutants will turn your goodies to an oil, this sample is a classic oily mess and still 80 % of DMT Purity.



Bioassay:

In regard to bioactivity of DMT-N-Oxide I think its nearly impossible to smoke this compound, as it will turn black within less than 3 seconds once heated above 100 °C. By that time it will not even have evaded any fumes to inhale. Further heating does just produce traces rising up from that super uggly and unhealthy looking black tar (see Picture 2). But as the N-Oxide is the natural product of MAO-enzymes, it should not be needed to block these when incorporating the N-Oxide. This means if it HAD any psychedelic effect one could simply eat any amount of N-Oxide and would suspect an effect not too far off from the same amount of DMT, eaten with 150+ mg Harmalas. Now people could argument, eating would be an inefficient ROA, as the high-polarity compound is not likely to tresspass membranes and will have low bioavailability. Actually it is even less polar than DMT, when eaten orally and DMT is indeed bioavailable when eaten, as people know.
The proof can be seen here in this reversed-phase Chromatogram. The solvent protonates any bases, causing them to have uniform charging across the column. This happens to DMT and the N-Oxide, while now being DMT+H(+) more polar than DMT-N-OH(+). In a consequence, the N-Oxide elutes 1 min later in reversed-phase and the solvent can be transferred to our gastric conditions, where also both compounds will form their protonated salts. This way I am very certain, that if N-Oxide HAD an effect it will be visible upon oral ingestion.

80 mg of DMT-N-Oxide was eaten. No effect Thumbs down
But: It tastes like DMT (Ginger-like spicy) + an additional Cherry Flavor. Super cool! Weird sweet bonus, exactly like Cherry Menthol gums.

So while the N-Oxide being a metabolist of DMT and definetly has a metabolic pathway in the body, I highly doubt it would still interact with the same receptors that are also responsible for DMT-effects. That unoxidized Amine would normally be important for in-vivo recognition at receptors, rendering it possibly inactive upon oxidation, as the N-Oxide is a very different chemical species - unlikely to show the same binding behaviour. That said and given the facts that it cant really evaporated and shows no effect upon ingestion, I highly doubt that anybody ever was high on N-Oxide Confused .



I agree that we don't encounter DMT-N-Oxide, at least I have never come across it.

The orange oils are mostly DMT. I think even pure DMT can take an oily form since it is a polymorph. Simply melt and cool to convert it from xtal to oil. Also, during the water basing step, if DMT is concentrated and in a high ionic strength solution, some FB DMT can polymerize in the water and come out as an oil during extraction. I think it is a good idea to keep ionic strength below ~10%, not have the DMT too concentrated, and pull quickly when basing or better yet have naphtha present while adding NaOH). I believe the max ion Tek is a good example of avoiding DMT polymerization.

The DMT oil takes a longer to dissolve in hot naphtha. I fear a lot of good DMT has been thrown away during re-X. Next time anyone is chasing xtals and has a leftover oil from re-X, perform and A/B on it, xtals should appear. Another potential waste of good DMT is people not using warm naphtha because that gives oil instead of crystals. That could be just leaving perfectly active polymerized DMT behind.

There are claims on the nexus of converting DMT-N-Oxide into DMT using metal dust and acid. I think that is not correct. They were simply breaking up the DMT oil polymorph with the acid, (the metal dust was not needed) and getting the DMT xtaline form.

I could be wrong, but that is what all my experiments are telling me.

By the way, thank you for this work Brennendes Wasser.
💚🌵💚 Mescaline CIELO TEK 💚🌵💚
💚🌳💚DMT salt e-juice HIELO TEK💚🌳💚
💚🍃💚 Salvinorin Chilled Acetone with IPA and Naphtha re-X TEK💚🍃💚
 
Ruffles
#18 Posted : 9/19/2021 6:48:59 PM
DMT-Nexus member


Posts: 119
Joined: 20-Jun-2021
Last visit: 30-Jul-2022
Location: Earth One
You are a beautiful alchemist Brennendes!

Regarding acetateDMT, here`s a quote:
Quote:
Maybe it may be explainable by counting Acetate as a soft ion and not a hard ion like chloride or sulfate.


Can you expound some of your wisdom regarding vaping DMT salts? Is there any prediction on which salt specifically would provide lower vaporization temp compared with fumaric DMT?

Yes, salts vaporize poorly, perhaps there is a simple solution to that and your data may provide some guide into it (nicotine benzoic or levulinic salts recently surged into the vaping market as an example).
 
Brennendes Wasser
#19 Posted : 1/27/2022 6:00:28 PM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
Quote:
Can you expound some of your wisdom regarding vaping DMT salts? Is there any prediction on which salt specifically would provide lower vaporization temp compared with fumaric DMT?


Actually I dont even know why the DMT-Acetate does vaporize and not even feel bad to your lungs. But just following logics, I would use any acid with a Molecular Weight as small as possible. So Vitamin C / Benzoic Acid / Tartaric Acid will all be way heavier than Acetic Acid, so I would naturally simply start with the last one before investigating any other ...

If you would do an aerosol based inhalation (like some people tried to investigate here years ago) it might not make a difference, but choosing an acid favored by pharmacy might be the best option regarding physical uptake, then I would go with Benzoe or Tartaric.
 
Brennendes Wasser
#20 Posted : 1/28/2022 9:29:43 AM

DMT-Nexus member

Chemical expert

Posts: 597
Joined: 23-Sep-2017
Last visit: 07-Dec-2022
Now also THH added.

Summary:
Quite the same as Harmalas of course, but doesnt stop vaporizing after 250 °C. Maybe some kind of pathway of thermal combustion / polymerization is blocked here, enabling further evaporation. That may make the question interesting how vaping pure THH might be, if it might then even be a really strong uplifer, compared to the more gentle feeling upon oral ingestion.
 
12NEXT
 
Users browsing this forum
Guest

DMT-Nexus theme created by The Traveler
This page was generated in 0.383 seconds.