Chemical Guide to classic Psychedelics (DMT, 5-MeO-", Mescaline, Harmalas, Salvinorin A, ...)

[downwardsfromzero]

Thanks for the addition and insights, it's great to see you posting here again.

 

[Loveall]

Brennendes Wasser, have you tried warm ethyl acetate for harmala solubility? _Trip_ and I have seen that it is somewhat soluble. Cheers.

 

[Brennendes Wasser]

Now finally the thread is complete, basically 1 year after creation - 5-MeO-DMT added now!

Summary:
It shares basically the same vaporization temperature like DMT, isnt that unusual :? Besides solubility drops basically to 0 even at RT, so recrystallizing is then much easier, considering not losing any material upon solvent disposal.

Thanks for the addition and insights, it's great to see you posting here again.

Thanks man! But I just had to finally complete this and now dont have any further plans so at most I might become a silent reader if at all.

Brennendes Wasser, have you tried warm ethyl acetate for harmala solubility? _Trip_ and I have seen that it is somewhat soluble. Cheers.

Indeed that would have been something cool / interesting. I never thought about EA for all these standard tests. Might see in future ...

Also need to replace that failed Salvinorin UV/Vis at some point, but no idea when to do both :?

 

[downwardsfromzero]

Thanks man! But I just had to finally complete this and now dont have any further plans so at most I might become a silent reader if at all.

Ach, Männow! But you're not allowed to leave until you've tested some nice crystals of psilocin. And haven't posted any data for mescaline yet!

Just looking at the entry for harmine/harmaline, it seems that you refer to:

Here is the thermogravimetric analysis of DMT.

and

Here is the differential scanning calorimetry analysis of DMT.

Surely this is a mistake and you perhaps mean harmine/harmaline mixture?

 

[Brennendes Wasser]

Oho yes thanks and also the pictures of MeO and THH were shuffled weirdly - that comes seemingly when naming all the pictures like

Bild 1
Bild 2
Bild 3
...

Wish I could delete the Pictures that are now Duplicates after uploading better named ... but dont know how

 

[Loveall]

Oho yes thanks and also the pictures of MeO and THH were shuffled weirdly - that comes seemingly when naming all the pictures like

Bild 1
Bild 2
Bild 3
...

Wish I could delete the Pictures that are now Duplicates after uploading better named ... but dont know how

On the message header click "ATTACH". You will see a list of the files updaloaded to that message. At the right side of each line item there will be a clickable "delete" link.

 

[Brennendes Wasser]

No No I meant in the Wiki because I always upload them there - so I can put them into the text instead of hanging all stuff at the end. Also anybody can see them and not only logged in members.

But no idea how to delete fotos on Wiki that are outdated.

 

[endlessness]

I've been mostly away from the nexus for the last year and missed amazing gems such as this thread

Thanks so much for all the work, this is beautiful!

Hopefully I'll be able to contribute soon again with a new lab we're setting up.

Be well friend!

 

[_Trip_]

Awesome work.

 

[Brennendes Wasser]

I said this thread is complete now but there were still the solubility values for simple DMT missing. Naphtha in Freezer was added 1 year ago, but now we have the full spectrum of possible re-x solvents. Of course solubility in strong solvents could be identified, but thats rather boring as it may just be super high and it wont precipitate from these anyways.

Summary:

Obviously Solubility from n-Pentane -> n-Hexane -> n-Heptane is increasing.

Overall when looking at the respective boiling temps that makes sense as Heptane can store the highest amount of thermal energy and solubility increases with rising Temp. Still at Freezer temperature it decreases when also shortening the n-Alkane length, as this may decrease possible interactions further and also increases the amount of molecules to reach a certain state of solvation. That is non-favored as it would reduce the whole solutions Entropy - and people know you cant win against Entropy :twisted:

Besides its rather unexpected that C6-C7 Naphtha dissolves ~ 15 % more DMT (at -20 °C). As it it a mix of Hexane-Heptane-Isomers I would have expected this to be inbetween. n-Hexane content in this Naphtha is said to be > 5 % so maybe the mixture is really high in the Heptane-Isomers anyways. Still then it would be only close to pure n-Heptane.

But possible reasons could be:

> Stronger interaction possibilities of branched alkanes in contrast to n-Alkanes

> Chemical potential is decreased in mixtures, causing binary / ternary / ... mixtures to behave differently than original properties of pure compounds have been. So maybe that also affects DMT solubility in a ternary phase mix of C6/C7/DMT. I always sucked in physical chemistry so not sure if that makes too much sense.

> Traces of BTX-Aromates might be still present as Naphtha is just a fraction from distillation of crude mineral oil. Their solvation power of tryptamines is superior so maybe this increases solubility?

In any ways it seems n-Heptan still does not hold any reasonable amount even at - 20 °C so its just as good for re-x as n-Hexane. Still both are quite expensive OTC compared to Naphtha, that's why they might not serve any direct benefit except evaporating faster as they are not a mixture which slows evaporation.

 

[Brennendes Wasser]

I had some DMT Benzoate and thought it's just another boring salt form, but I still did the Hot Plate Evaporation test to see if I can get at least towards a melting point before 300 °C.

It melted at ~ 150 °C but then something weird happened:

It started to give off fumes and fully evaporated before 200 °C.

So I thought this is just like the Acetate - being a salt but surprisingly exhibiting the same evaporation profile like DMT freebase. Because of this I made some experiments and indeed - you can smoke DMT Benzoate just like DMT Freebase.

That is more of a scientific odditity, because I would assume these salts to not evaporate before 300 °C and even then just decompose (like the Sulfate version). But as you will see: You can basically handle it like Freebase DMT in any of your evaporation devices.



In Short:

Melting Point around 163 °C

Evaporation starting at 165 °C and ends at 240 °C, leaving only 10 % residue behind. Basically the whole evaporation process is shifted by 30 °C.

Now as a practical consequence overly paranoid people might simply convert their stuff to the Benzoate and still use it with their GVG/whatever while its shelf life is now 100 years +.


But on a theoretical level this opens up the question salt forms seem to evaporate just like the Freebase.

At least this is the case for

- Acetate
- Benzoate

and therefore I guess it's the smae for -Ascorbate.

In contrast I have never heard that anybody told the Fumarate would be smokable. I did not try, but I guess someone must have already tried it.

Therefore maybe Salts with DMT*1/2Acid are having a high evaporation point, while DMT*Acid type salts evaporate like DMT?

If yes then

- Fumarate
- Succinate
- Citrate
- Tartrate
- ...

would also be non-smokable, just like the Sulfate and behave the way you would expect originally.



As there is no space for a new compound the post is just added here at the end of the Acetate. There you can also see the direct comparison between DMT and DMT Benzoate evaporation in just 1 diagram.

 

[_Trip_]

Although anecdotal, when I was able to crash out bufo benzoate in acetone I found it was way smoother to vaporize in the GVG than freebase (I only tired a small amount). I always wondered if DMT benzoate would be similar. If the consensus is it should theoretically have a decent safety profile, I'd have no issue testing this.

 

[Brennendes Wasser]

Well for me that would be worth a try, because as a 100 % non smoker it is too difficoult to get anything down when vaporized :thumb_dow And especially from Bufo I never got any big hit at once ...



Also something anecdotical:

It seems like this reaction is highly reversible?? :?

I saw that the compound over soon now to be 2 years of storage in an air-right container got a quite brown colour and changed from nice crystals to some fluffy brown stuff - as you can see in that picture.

When I opened it there was a terrible acetic acid smell.

It was recrystallized in Hexane so initially there was absolutely 0 smell of any Acetic traces left behind.

And now also the color changed - which could be just a random aging effect (but we all tell permanently that would not happen if stored correctly) so maybe that also indicates a back-reaction to Bufotenin.

The O- from Bufo can interact in the aromat and thus have an effect on the absorption properties via electron donation. That AcO- on the other hand is not that prone to electron donation. So ultimately this is quite the reason why Bufo (even pure) has a slight brownish tint like Harmalas, while the AcO is completely white.



Now TLC added and it looks quite like a complete back reaction. That Acetyl-" should run quite faster, still it does not look like any real difference. Furthermore no second spot visible, so if there was a back reaction, seems it is already proceeded completely. Guess then that acetic smell should evade also soon when the vial is kept open for a while, otherwise there would be still some 5-AcO reaction backwards I guess, which it does not look based on TLC.

 

[downwardsfromzero]

While on the subject of benzoates, could you clarify this point:

Soluble to no extent in water. Also soluble in DMSO, DMF.

The phrasing regarding the solubility of DMT benzoate in water becomes unclear in the quoted context. Does this mean the salt is practically insoluble in water, or freely soluble?

Also, do you think a post on the solubility of freebase DMT in various concentrations of aqueous ethanol might be helpful? DMT's solubility in high-proof ethanol is ludicrously high, but dropping the ABV percentage down to 40% starts to produce interesting results in the temperature-solubility curve. I'll copy some results over from my thread on the subject but the investigation was pretty rudimentary. Hence, if you did happen to find some spare time in the lab this would be a fairly easy thing to look into.

PS: it's really great that you've been back here to share this data with us!

 

[Brennendes Wasser]

While on the subject of benzoates, could you clarify this point:

Ah maybe was unclear expression I better removed it for all other posts also:

Should just mean with no restrictions but wrote now with simpler language.

Also, do you think a post on the solubility of freebase DMT in various concentrations of aqueous ethanol might be helpful?

That water-content based solubility sounds interesting - but not sure if I soon would spare some time

PS: it's really great that you've been back here to share this data with us!

Hehe yes I'm happy that I found a new interesting substance worth for a post, but still I thought this thread is basically finished.
I told I dont have access for NMR/HPLC/GC/MS since 3 years and next year will ultimately leave university, so no practical efforts anymore to come.




Last thing I need to do before I can count this finished for me is correcting that eye-hurting diagrams for Salvinorin A. So soon there will be an improved post with also Vaporization profile with TGA - that is actually what really interests me since ages. Then it aligns quite well with having no lab environment to do stuff.

Mescaline is also missing, but it's only handeled as salt and therefore many cool measurements cannot be taken.

Also then a post with all the evaporation profiles in just 1 diagram coming to get all the information for smoking/vaping these compounds as condensed info.

 

[Brennendes Wasser]

Last Update of this Thread:

- Note on TGA that a substance can be evaporated 100 % even at the onset temperature of TGA if ventilation / surface area is high enough. Otherwise it would be a wrong implication that you need for example 240 °C to fully evaporate DMT. TGA more precisely gives the minimum temperature at which you can start evaporating your substance PLUS the information if you have some pyrolysis (Bufotenin / Harmalas) or if you can indeed fully evaporate your substance.

- New ATR IR of Harmalas - the old one looked crap

- Microscope Close-up of Harmalas. I was not expecting too much, just a boring amorph powder. But indeed there is at least soooome order at the micro scale.

- New Microscope Close-up for Bufotenin. The previous old crystals looked super funny like Cauliflower . But they were retrieved from decanting Xylene during re-x into a cold new beaker. Therefore crystal formation was super fast. These new crystals are grown much slower and therefore are a better representation of crystalline Bufotenin. It also grows in flowers quite like DMT Just compare both: Bufotenin has round ends, while DMT has more like brutalist basalt-block ends. And then a total difference is 5-MeO-DMT: No flowers and crazy perfect 90 ° angles - something not exhibited by any other of these molecules here. If humankind will ever understand crystal geometry formation based on structural features of the molecule itself? It seems just too random

- Salvinorin A now finally complete: New TEK with definetly pure Salvinorin A and therefore new completely new data. New ATR IR + new UV Vis which does not have negative absorption (lol). Concentration must be higher than Tryptamines, as only that Furan Ring will give any reasonable absorption. Traces of Chlorophyll are seen, which are probably in the ppm or less. Also a link to a sample with more Chlorophyll just to compare. Previously I saw evaporation on a 220 °C hotplate. But now TGA suggests that Evaporation starts above 250 °C. Therefore probably everything I saw was just Chlorophyll decomposing and giving fumes. Still, as only microgram-amounts are needed for Salvia Experience, evaporation might still be performed below that as traces might evaporate earlier?? Loveall found promising results even as low as 180 °C. :thumb_up: Also before there was no melting point ... probably also because of too much Chlorophyll inside. Now DSC indeed shows a melting point from 220 - 230 °C.

- As all data is here now there is a summary of all the evaporation temperature profiles of all molecules here. I just hung it as close to the original posts as possible but still at the end. It gives a good summary what can be evaporated at the same temp and which molecules are mostly decomposing ...

So that's now finally finished 2 years after creating and no more stuff planned. :thumb_up:

 

[Brennendes Wasser]

So DMT Benzoate is a weird thing: it already started with a lot of anger when it was not precipitating instantly in various situations. Even waiting did not help. Now I realized it is kind of a chimera: Dissolves PRETTY well also in organic solvents. Maybe that is due to the Benzoic Acid having a high solubility in organics in general, in contrast to fumaric acid. The latter one even takes ages to dissolve in Aceton ... :thumb_dow

So the key is if you would precipitate it then just assure a really high concentration of 1 g / ml or even less maybe. Then crystals start to grow after ~ 30 seconds, interestingly WITHOUT causing any clouds before. They will just directly drop from solution, everything stays clear meanwhile. Concentrations of 0,01 g / ml did not create any crystals - not even in the freezer. That made me lose quiiite a lot of stuff

In literature Tryptamines are often purified by creating the HCl-salt by bubbling HCl gas through a Tryptamine-enriched solution in Toluene for example - or use a Lewis-Acid that will dissociate while forming HCl in-situ. These Tryptamines*HCl can only be dissolved in boiling Methanol or Ethanol. So that obviously works for DMT-Benzoate too, but there is more due to it's additional interactions enabled by that Benzyl ring:

Soluble in room temperature (!) Acetone or Ethyl Acetate if enough if used (> 50 ml / 1 g).

Soluble in boiling Acetone or Ethyl Acetate even with low volumes solvent.

Soluble in boiling Toluene and even a liiiittle in boiling Hexane ? ), which is not much, but man would you ever have thought DMT Fumarate could do that?

All in all it's rather a bad thing ... it makes Ethanol-re-x more wasteful and even washing a Benzoate salt with organic solvents wasteful if you use a solvent like Ethyl Acetate or more polar.




In any way, if things above are taken in account then it is still a convenient salt to handle. The solubility data is added now, but I just paste it here too for Toluene: Toluene is a really good solvent for re-x!

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​

Also Hailstorm found that Amyl Acetate works great:

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

Also:

Solubility of Bufotenin in Xylene was corrected to 0,1 g / 100 ml - so basically 0. It was weird when I measured still like 1/3 being dissolved. It only dissolves it because of heating above its melting point. So below that melting point the solubility will drastically drop to nearly 0 again. That old result wondered me already all the time, but now finally tested again and corrected.

 

[Brennendes Wasser]

I made that theoretical calculation of water content in DMT Acetate back in the days:

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 [%]

Now checked this out, but also if DMT Acetate will absorb more and more water or is just creating a hydrate of a certain kind that remains in its form rather than catching up more moisture.

In 1 ml water put 30 mg DMT + 19 µl Acetic acid

place into a air-tight container filled with CaCl2 (drying agent)

wait 24 h

Mixture after 24 h ... still a goo​

Still in its 'water-free' state it was a goo, but probably it might form a hydrate where it is impossible to remove the residual complexed water just with a drying agent at 1 bar and 20 °C. Actually many more salts are forming hydrates, even if they look crystalline and solid. Now it is just a question whether DMT Acetate might just have too many water molecules assoziated at ambient conditions to ever NOT be a goo?

I checked the weight freshly out of the chamber and after 4 h in a fume hood with constant air flow at 40 % ambient air moisture. Aftewards weight was same, so probably it does not take up water other than from the 'maximum dried' state, which seems to be the minimum Hydrate it forms at ambient conditions.

Now the 1H-NMR was measured in D2O to see how many water molecules are associated. Here is the picture, this time no predicted spectra, it would just look like here, and with a new signal for the Acetic Acid at around ~ 2,06 ppm with Integral ~ 3.

So what you can see is 8 Protons of water per 1 molecule of DMT. That means DMT Acetate binds to 4 water molecules, which cant be removed by 'simply drying' processes. More precise molecular formula would be then:

= DMT-Acetate x 4 H2O (Tetra-Hydrate)​

Maybe vacuum and more heat are required, but they will probably always form the same hydrate at similar conditions, meaning it will absorb it again from ambient air at 20 °C and regular air moisture level.

Same is also happening for DMT Lactate, although the Hydrate might be even 5x or more, due to the added OH-Group of lactic acid, making it even more hydrophile.

 

[Brennendes Wasser]

THH had to be corrected - it was not pure at all it seems. When I had this sample it just had the same brown colour like unreacted Harmalas. Still the melting point was in accordance with Literature so I thought it might be traces of Harmin causing that colour.

Now after X times of mistaking and swapping Harmin / Harmalin I'm not even sure that what I had back in the days was even derived from a Harmalin-Reaction or if I just again threw Zink-Acid on Harmin :roll: :thumb_dow

So now corrected with some pure white THH and while most data might not be giving any great new deals, the vaporization is now much cleaner. While Harmalas dont vaporize much and mostly decompose, THH seems to vaporize nearly as nicely as DMT. Also interestingly melting point and vaporization start are nearly at the same time.


Besides I now ate some THH to really know the effect, but it just felt like a buzz from like 3 beers :? (420 mg THH + 80 mg Harmin). Will try soon the vape method as it should be really effective (still, just THH not having a strong potency per mg nevertheless) and see if there might be any difference ...

 

[Hailstorm]

I confirm that the melting point of DMT benzoate is 166.0 °C.
The melting point of 5-MeO-DMT benzoate was 123.6 °C.

5-MeO-DMT freebase had a melting point of 68.4 °C (0.1 °C / min) compared to 69.5 °C in literature.