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:
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.
[brezel in lieu of retort]
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