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

Migrated topic.
Brennendes Wasser said:
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 :oops:

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​

Is the comment of high concentration to precipitate DMT benzoate is to increase the concentration of DMT benzoate itself or benzoic acid? With limonene, bark yields and xtalization were great when adding excess benzoic acid at room temp.
 
That is meant indeed regarding the overall salt concentration so not about the benzoic acid itself. I always just used it slightly in excess like 1:1,05 in case I would have to distill off the whole solvent (which I did in the first tries, when I did not know ethyl acetate is bad to precipitate the benzoate salt).

But if it works great with Limonene then this is pretty cool. Considering the polarity Limonene is probably the most unpolar, yet still effective, solvent out there ... I think the logP value is also extremely high and therefore toluene would be regarded still quite more polar than Limonene.

Because of that it seems limonene is simply so unpolar that you can get a near-quantitative prcipitation from basically any concentration if you say. Then this would be surely a better solvent to create this salt than Toluene, as it is much less unhealthy.

Sadly I dont have any limonene anymore as I poured away my 1L bottle years ago ... :(

Otherwise would always also include Limonene in tests like this. But then will write down that people should use that one and dont even need to care about concentration.

Still then probably Limonene cant be used to re-x DMT-Benzoate.



EDIT: Now finally added.

Hailstorm said:
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.

Thanks for the info! If I'm not mistaken then the polymorphism was said to result from the flexibility of the sidechain as Benzyme told, which results in various different constitutions and thus crystal structures. Maybe for salts the possibilities are less and so less polymorphism is seen. Maybe I could check that MeO-Benzoate too.
 
Small Update:

Evaporation of Salvinorin was only checked until 350 °C, which resulted in like 60 % evaporated. But I was curious about the residual 40 % - will it combust or still have a nice evaporation until the very end like DMT?

Now measured until 450 °C and link provided below Salvinorin TGA / DSC. TGA just added here also.

You can see exactly at 350 °C there is a drop in evaporation speed. Probably some thermal degradation going on. So just add enough ventilation at 300 °C and you will still pretty nicely evaporate all your Salvinorin - especially as you only need trace amounts. Whatever reaction that is can be also seen in DSC with a small heat uptake.

Still 350 °C without combustion is quite thermally stable. Reason could be probably 1) no amine in structure that can react as nucleophile and 2) very low double bond count.



Also now small NMR summary of most compounds measured when they have been pure. Prediction software is not always perfect so that can be used now as prediction.

The NMR device which I used is still pretty bad, but at least it shows the correct signals :roll: :roll:

Note that while the numbering of aromatic signals from DMT - 5-OH/5-MeO looks different, that is not an error but the effect of the oxygen, shifting its neighbours positions along ppm-axis.
 
Thanks! But I have to say: Even though I try to post a lot of stuff like this, I have nothing like advanced training in either biochemistry or organic chemistry, I simply (for now) have access to all of these machines, so I just throw whatever I can inside to generate data. That means from all the topics that nexus is about I am not really an expert in real life and all these experiments are (on a chemical level) very basic, I just know just enough to kind of interpret most of stuff on a convenient level. But as I dont need what I learned in my study in my life now anymore, I gradualy forget all the stuff ...



So now with your help the (this time) finally last chapter added! Title says 'classic Psychedelics' (allthough now containing also compounds which are not even regarded a true Psychedelic ...) but still one of the most classic Psychedelics was missing all the time being Mescaline.

I didn't think I would get my hands on some, but now as I have it there is no Place Holder, so the data is now posted well-fitting by our professional cacti gardener DF0 - link in his post! Mescaline Citrate and Mescaline Benzoate both added.

Summary:

Mescaline Citrate has a worse solubility in organic solvents than Mescaline Benzoate, which comes at no surprise as all those R-OH / R-COOH groups greatly destabilize this salt inside of non-polar liquids even on top of being charged molecules. Therefore it also does not vaporize very well, thermal decomposition seems to be happening instead. Therefore Mescaline Benzoate indeed can be vaporized and was already tested to be very smooth, but further testing will be required to see if that is even worth it or mostly remains an intersting curiosity ...

The only little intersting fact could be the absorption compared betweeb both and also with the other Tryptamines posted here.

Mescaline Citrate absorbs much stronger, as it has also the Benzoic Acid engaged in absorption. Still both show the "least advanced absorption" of all the Alkaloids tested here, having the most narrow absorption peak and least shift towards visible light, because their molecular structure contain the least amount of structural units required for absorbing higher-wavelength light.

Purity of both samples was measured with HPLC/MS to verify if any other trace components are still hiding in a CIELO product. But the sample I got was re-x'd from Ethanol so not sure if this has already removed some other Alkaloids, but it would be unlikely. That also means an NMR of this sample cannot show if there is also some water stuck in the crystals, as re-x might have removed it.

See HPLC/MS of Mescaline Citrate here. Mescaline runs at 6,45 min. It is only 1 peak, because citric acid does not absorb at 214 nm. The sample injection is a bit overloaded, but that means the occurence of other Alkaloids would also be amplified. Still Mescaline is way more than 99,9 % of the analyzed sample, so I'm quite sure what this CIELO TEK produced was very pure Mescaline Citrate.

Mass Spectrum is also added. Method was ESI and Mescaline is visible at 212 u (211+1). Still the most prominent peak is another one at 195 u. This is the fragment of the first occuring reaction in ESI, which is shooting off the Amine. In the case of Mescaline that would be Ammonia, therefore resulting in 212 - 17 = 195 u. We can also see 253 u, which is Mescaline + Acetonitril adduct.

Regarding Mescaline Benzoate I made 2 different samples. One contained a rocky chunk which crystallized first, the other one is part of the very fine needles that slowly crystallized on top. I was at first a little worried that these extremely fine needles look exactly like pure Benzoic Acid, so I thought I got a contamination into my product. Still these crystals dissolved in minimal water, which would be impossible for pure benzoic acid. Furthermore I compared both in FTIR and both are completely the same as you can see below:

FTIR_comparison_mesc_benz_rock_vs_needle.png

So don't worry if you create Mescaline Benzoate and it rather looks like re-x'ed Benzoic Acid. The acid seems to navigate the salt also towards this very beautiful morphology!

See HPLC/MS of Mescaline Benzoate (Needles) here. Here you can see Mescaline Freebase again at 6,35 min. Furthermore now we can see also Benzoic Acid at 10,32 min. It shows a really nice Ratio of 2:1 which corresponds to the mass ratio between both molecules. No other peaks visible, so pretty much a pure compound like Mescaline Citrate. ESI MS shows similar peaks like Mescaline Citrate.

See HPLC/MS of Mescaline Benzoate (Rocks) here. Just like the needles it has the same ratio, just a little of the Mescaline is cut off due to overshooting, so the ratio is a little more towards Benzoic Acid by 2 %. Still another proof that needles and chunks are both the same compound and free of other contaminants.

Now for future it would be interesting to analyze a true crystallize CIELO product and check its water content. Regarding the salts precipitated from Toluene and Limonene I would be quite sure that these dont contain any salt. But for practical use that of course makes no difference.

One last thing would be intersting here. It seems for CIELO it is very important to use a base which does not dissolve well in water. This is achieved by using Calcium hydroxide instead of sodium hydroxide. Still the base does react very well with any cacti powder. But as many trace Mescal Alkaloids not only contain Methoxy groups, but also hydroxy groups as seen in PiHKAL here. Calcium Hydroxide would deprotonate those alcohols to alcoholates, making them insoluble in ethyl acetate. Therefore a weaker base like "-Carbonate could be used to selectively freebase only the amines, but not react with any possible trace alcohol alkaloids. In analogy to using an insoluble base like calcium hydroxide the obvious decision would be calcium carbonate. It would be quite interesting if the result from a TEK using this would be different and showing also other compounds in the HPLC. Still as their potency would be most likely not too much different from Mescaline (as all carry the 3,4,5-substitution pattern), so if they would not be present in unexpectedly big amounts they would be probably not noticable anyways. Still the conformationally constrained variants (Isoquinoline-types) like Pellotine might act as weak MAOI at lower concentrations.

I also have this small NMR Library at the end and also at least Mescaline Benzoate added. Mescaline Citrate coming also soonish I hope and I hope to get a sample directly from the TEK, which will also answer some questions about water content. Is it just an artefact from the mandatory water inside of the EA? Can it be removed upon drying with CaCl2? If not can it be removed upon drying with > 50 °C and < 50 mbar? Mescaline Benzoate shows some water, but this water is part of the (by now pretty much aged) solvent. Still perfectly pure spectrum, so once again showing there is no Alkaloid Mix from CIELO, but just pure Mescaline. This sample has underwent re-x in IPA, but that would probably not change anything. Maybe I will replace this one picture in future and let the Mescaline Benzoate DSC be measured again, as it shows weird peaks which I have no clue of. But besides the data shows both samples are pure and results consistent with expectations.
 
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professional cacti gardener DF0
If you're not an expert organic chemist - you're competent at presenting the data that you generate, to say the very least - then there's no way in lumpy rice pudding I'm anything like a professional anything, let alone a cactus gardener. Shambolic enthusiast is about a fair assessment in all truth. That's what we've got teamwork for, and it's why I share my meagre experience - to help others shine.

:love:
 

Sadly all the links on the new forum still go to the old one. Is there a way how to auto-correct them for the new forum? Those are not many, but I have some other stuff that might be quite hard to manually track and correct ...
[MOD EDIT - this has been sorted :) ]


Also I want to add a new link here at the NMR-Summary, but cannot do it because old posts cant be edited in the new forum. Can a moderator do it?

Post:

Mescaline Citrate [coming]

If you scroll down to the NMR-Library, the placeholder text should be now replaced with the true Link:

Mescaline Citrate


THXXXX! 🥰🥰🙏
 
Sadly all the links on the new forum still go to the old one. Is there a way how to auto-correct them for the new forum? Those are not many, but I have some other stuff that might be quite hard to manually track and correct ...



Also I want to add a new link here at the NMR-Summary, but cannot do it because old posts cant be edited in the new forum. Can a moderator do it?

Post:



If you scroll down to the NMR-Library, the placeholder text should be now replaced with the true Link:

Mescaline Citrate


THXXXX! 🥰🥰🙏
This is exactly something I've been concerned about. I think it's best that the archived version remains self-consistent. I can help with updating the links on the migrated version.

And I'm here for you as ever when you require any assistance and/or technical support 🥨 [brezel in lieu of retort]

Update: 1. small start made, added the mesc citrate NMR link.
2. Edited most recent link in this thread.
To do: learn how to automate, or semi-automate, the link updating process as doing this manually will be cumbersome.
 
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Sadly all the links on the new forum still go to the old one. Is there a way how to auto-correct them for the new forum? Those are not many, but I have some other stuff that might be quite hard to manually track and correct ...
It's on my ToDo list to perform this action, so for now set a hold on doing it yourself. :)

Also I want to add a new link here at the NMR-Summary, but cannot do it because old posts cant be edited in the new forum. Can a moderator do it?
As a senior you should now be able to edit all your posts.


Kind regards,

The Traveler
 
I can help with updating the links on the migrated version. And I'm here for you as ever when you require any assistance and/or technical support 🥨 [brezel in lieu of retort]

Thanks a lot - I see you also made a TRANSFORMation when going to the new Forum. But I am quite sure we will still find you at the square root of -1 🤓



As a senior you should now be able to edit all your posts.

Ok cool! Thanks for the Editing-Batch, it just has the Irony that in RL I am still pretty much a Youngster I would say :rolleyes:😝😝

Will now see if I have any other links to edit ...
 
Nice work!

Hope to see some more info on other mescaline salts in the future. I think mescaline benzoate and citrate are not the most common although more people seem to make citrate.

Bit lazy (busy) just scanning through, so I probably ask stupid questions make stupid comments.

Vaping Mescaline, never heard of it, doubt if it's usefull (the advantage about vaping or snorting in general I think is that it gives a faster and therefore steeper peak, needing a lower dose but also maybe most important makes the duration often shorter which can be an advantage which I doubt would be the case with a long lasting substance as mescaline and is probably even is a waste?)

However, both crystals from benzoate and citrate looking nice. Again didn't read very good, so don't know how hygroscopic, stable and good they are for storage but what really interests me (sorry for spamming but I am a bit fixated on this topic and planning to do some experiments myself). Is how these salts influence the solubilty of the other alkaloids in different solvents from the cactus? Which might be interesting in separating wanted or unwanted alkaloids and or purifying with less or even completely without the need for 1 or more recrystallizations.

But this is my plan based on my feeling or assumptions (so correct me if I am wrong):
- people often say that the full spectrum alkaloids (talking about San Pedro, not Peyote) give a different experience then pure mescaline. (Pure mescaline being more stimulating and full spectrum more sedating and calmer/relaxed)
- but asking what other alkaloids are sedating, synergistic or psycho-active by themselves I never found a clear answer. Still never saw an answer which alkaloid makes it more sedating/relaxed?
- Now the main other alkaloids found are: 3,4-DMPEA, 3-methoxytyramine, and tyramine. Other alkaloids seem to be only mere traces, which I assume can hardly have any real big influence. (ok synergy between many different alkaloids can't be excluded but if any alkaloid have any serious effect by themselve that would make them a lot more potent then mescaline by itself).
- Now as far as I know all these three main alkaloids have not shown any effect at all in humans, certainly not positive.
- 3-methoxytyramine has been found in the urine of cancer patient and people with other brain disorders (Trouts notes on Cactus alkaloids)
- I am curious how much 3-methoxytyramine, and tyramine is left after an A/B extraction, my gut feeling thinks very little if anything at all.
- 3,4-DMPEA on the other hand is difficult to separate. While human experiments showed no effects. Experiments in dogs showed: ataxia, clonic and tonic convulsions, ataxia and muscle rigidity in monkeys. Further more: mydriasis, salvation, piloerection, dyspnea. Also a strong inhibitor of succinic dehydrogenase and showing MAO inhibition. (Trouts notes on Cactus alkaloids)
-
In general MAO inhibition don't go well with both phenylethylamines and tyramine cause increase in blood pressure.
- So all this information together has led me to believe that 3,4-DMPEA probably can be a major factor in negative side effects and other postive effects of other alkaloids are for the biggest part based on dose, set and setting.

The only thing I found is (Trouts notes on Cactus alkaloids):
- The hydrochloride salt of 3,4-DMPEA is soluble in both ether and chloroform while the hydrochloride salt of mescaline is not.
- So it would seem very interresting to me what are solubilities of other salts of 3,4-DMPEA in different solvents, so there would be more and maybe easier ways to separate this (again probably reducing negative side effects and reducing and skipping need for recrystallization.

Since I like the sulphate more the the hydrochloride because it is less hygroscopic and grows bigger crystals (making it more pure and stable I assume?)
I am planning on doing a double A/B extraction:

- So first convert to hydrochloride
- Extracting with Ether to get rid of the 3,4-DMPEA (since chloroform is more difficult to come bye)
- Then a second extraction coverting to sulphate
- Then see if and how many recrystallozations are still needed

Just my thoughts
 
DMT Solubility:
Naphtha (20 °C, C6-C7, 60-80 °C) 29,3 g in 1 L
Naphtha in the freezer (-20 °C, C6-C7, 60-80 °C) 1,09 g in 1 L​
This is such essential information, thank you! I can play with temperature from -30°C to 50°C, do you know what the solubility is for temperatures from -30°C to 50°C in steps of say 10°C? Its not at all linear, is it? Linear would give a 7.0525 g less in a L per 10°C colder, so a negative solubility of -5.9625 at -30°C which cant be correct...

DmtSolubilityLinearWRONG.png

So, what are the best estimated (or even better, experimental) solubility numbers?
 
This is such essential information, thank you! I can play with temperature from -30°C to 50°C, do you know what the solubility is for temperatures from -30°C to 50°C in steps of say 10°C? Its not at all linear, is it? Linear would give a 7.0525 g less in a L per 10°C colder, so a negative solubility of -5.9625 at -30°C which cant be correct...

So, what are the best estimated (or even better, experimental) solubility numbers?
The slope of the curve levels out at lower temperatures, of course (although it would be handy to be able to manifest infinite DMT by cooling naphtha to just above it's freezing point - in our dreams!) There's not a lot to be gained by lowering the temperature much below that of a domestic freezer - take a quick look at this:
I would recommend to go even further:

Buy 1 L of Naphtha and use this for every extraction. Do 3 pulls as you will only need that low amount due to excess Naphtha - well of course that sticks to every person's own technique - and then put this whole 1 L in the freezer.

Now decant the 1 L Naphtha back into your 1 L container that you bought this stuff in. You will have ~ 1 g of DMT "loss" as this will go back into the 1 L container with the 1 L Naphtha. But now you will re-use that 1 L for the next extraction and now the Naphtha is already saturated at - 20 °C. So this time you get 100 % and also any further time - until you stop using that Naphtha. Of course due to separation you will always loose like 5 % of the Naphtha each time. But that wont do much.
That way you will never have to evaporate stuff and need to buy new Naphtha only after many extractions and as you dont dispose the Naphtha after decanting you will have even more DMT already with your 2nd extraction. (y)
I seem to recall a recent post around here somewhere that highlighted @Samvidbuho's information regarding crystallization. There was a useful solubility chart in there somewhere, and you should (maybe 😁 ) be able to find it with that information.
 
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