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.



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

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.

New update added in sequence here.

Thanks once again, BW, for all the fantastic work!

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 Mescacline 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:



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 crystallinze 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 caclium 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.

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.