Hi, I'm looking for a little clarification. Lets say I perform an extraction using the Cielo Tek, and it yields 1.5% mescaline citrate.

Later decide to have a different cultivar tested at a certified lab using HPLC-DAD technology. The lab results come back as 1.5% mescaline hydrochloride (tests were done on dry material)

They both test at 1.5% mescaline, but in different forms. Is Cactus #2 the stronger cultivar?

Cactus #1 > 1.5% M. citrate
Cactus #2 > 1.5% M. hydrochloride

Note- I understand that mescaline HCL is more potent than citrate when it comes to weight. My question is in regards to yield percentage.

Question about your question.

In a sample of dried cactus material, the mescaline was present in the form of a hydrochloride salt?

Cactus #2 has higher mescaline yield.

These lab tests I see on the interwebs usually seem to give the % yield in terms of HCl. Seems to be the standard?

Yes. It boils down to the MW of the anion. The chloride weighs less than the monomescaline citrate per unit of mescaline, so the dose size of the hydrochloride is correspondingly lighter. Hence your latter percentage gives you more doses from an equivalent amount of starting material.

I thought the natural form of mescaline in cactus was mescaline malate, not mescaline HCl? So I'm confused about the lab testing dry material and reporting the results as mescaline HCl.

Regarding the 1.5% yield from CIELO versus 1.5% from the lab, if the CIELO tek was not followed properly (or CIELO is not 100% effective at extracting all the mescaline), then it's possible there is still some mescaline remaining in cactus #1 and it could potentially (although unlikely) be more potent than cactus #2.

I found this on the Nexus wiki page

Amount needed to carry one millimol of mescaline:
Mescaline HCl: 248mg
Mescaline Citrate: 275mg
Mescaline Hydrogen Citrate: 307mg
Mescaline Dihydrogen Citrate: 402mg
Mescaline Acetate: 271mg
Mescaline Malate: 278mg
Mescaline Sulfate Dihydrate: 278mg
Mescaline Bicarbonate (rare): 274mg†

The Cielo Tek states that monomescaline citrate salt is ~57% as strong as Mescaline HCl. How does this correlate to the numbers above?

I assume these are results from Altitude Consulting's lab in Colorado. Their results show percentage mescaline in hydrochloride because their certified reference material is hydrochloride. I asked them as soon as they got their CRM about this and they they were honest that they didn't know if it really mattered what salt form samples were in with their HPLC-DAD but they wanted to be transparent the test was against hydrochloride CRM. Maybe their stance has changed on this, you can ask them certainly, they were very open with me then. I've not sent them any CIELO result crystals specifically. Maybe someone here has some better knowledge with HPLC to clarify.

The ratio of the (milli)molar masses of the respective salts gives their relative 'strengths' so 248/402=~0.617 (61.7%)
By an amusing coincidence, the ratio with freebase mescaline (211g/mol), 211/402, gives 52.5% but if you take the average of these two, (52.5%+61.7%)/2, you get the 57% value; however, let's take a look at exactly what it says on the wiki:
So, following through with the working: 93.1%*61.7%=57.4%.

Always check for all the relevant data, and always show your working!

Looking a bit further through the wiki we find:
So, the hydration level of the salt explains both the 93.1% purity result, and the need for residual water in the EA at the crystallisation stage.

This data point, when combined with the solubility data for water in EA, can also inform us wrt a maximum concentration for mescaline above which the crystallisation process will possibly begin to break down due to insufficient water. Additionally, it seems a minimum of about 2% water is required for (anhydrous) citric acid to dissolve successfully in EA. This is a large molar excess compared to the 57mmol of CA that was used, so citric acid remains the limiting factor rather than the water.

If Endlessness' experiment proves to be representative, the theoretical maximum yield of monomescaline citrate sesquihydrate that can be obtained via CIELO in 250mL EA is ~24.8g. The equivalent amount of mescaline HCl would be 14.3g. However, the 11.1g may well have been an arbitrary amount. We should also note that Endlessness' method deviated from the standard CIELO through the use of CASEA. Moreover, neither the volume of cactus extract EA, its suspected water content, nor the final yield of MMC is stated in that excerpt.

Regardless of that, here are my workings:

11.1g CA anhyd C6H8O7=72+8+112=192g/mol 11.1/192=0.0578125mol
5ml water H2O=18g/mol 5/18=0.27777777777777777778mol
250ml EA MW irrelevant
M C11H17NO3=132+17+14+48=211g/mol 211*0.0578125=12.1984375g
MC1.5H2O=211+192+27=430g/mol 430*0.0578125=24.859375g

MHCl=211+36.5=247.5g/mol 247.5*0.0578125=14.30859375g

I don't know how HPLC works. But it sounds like the lab is using mescaline HCl to detect mescaline malate? Does that actually work? Or is the natural form of mescaline in cactus actually mescaline HCL?

So, assuming the natural form is mescaline malate, and assuming HPLC can use mescaline HCl as the reference material to detect mescaline malate...

Does this mean the mescaline HCl yield needs to be converted to mescaline malate? Do we know if the mescaline malate is 1:1 or 2:1? According to the handy salt->freebase calculator, mescaline 1:1 malate is 71.7% as strong as mescaline HCl (1.173 / 1.635). And mescaline 2:1 malate is 89% as strong as mescaline HCl (1.173 / 1.317).

Unless the mescaline salt is present in the cactus as crystals, while the cactus is alive there will simply be solvated protonated mescaline cations and solvated anions both organic and inorganic. Depending on where the mescaline is localised, it seems likely that in some areas there will be a preponderance of malate, but possibly in other areas there might be more things, e.g. bicarbonate, phosphate and/or chloride as the local counter-ion. Some of the mescaline may also be bound to various substrates within the cells as a result of the living cactus' own biochemical processes.

Bear in mind also that the malate itself is formed as a storage intermediate for carbon dioxide which has been absorbed during the hours of darkness and is therefore in something of a state of flux - during hours of daylight it will get split up into carbon dioxide, and pyruvate (etc.) to facilitate photosynthesis. Mescaline, as a relatively strong organic base, appears to help in this absorption of CO2, viz the ready formation of mescaline carbonate (and I'd love to look into the possible biochemical role of mescaline a whole lot more).
Diagram of the malate bit here:
https://en.wikipedia.org...le:CAM_cycle_English.svg

Once the cactus material gets dried, all of this material becomes bound in the organic matrix. Without having attempted to even find out, I can't really say what Altitude Consulting's (witty name, btw!) exact methodology would be, but it's likely to go something like this: extract dried cactus material with methanol, evaporate, defat, adjust pH, pull alkaloid fraction, possibly adjust pH, move into final solvent, filter, inject into HPLC. The size of the mescaline peaks in the detector at the end of the HPLC are then compared against peaks from using know concentrations of the mescaline standard, which is the M.HCl. Because of the pre-processing of the cactus sample, the salt form in the cactus becomes irrelevant in this particular context.

Thanks for the thorough explanation!

I'm not sure if this is exactly how Altitude does its testing, but this video explains the HPLC process from two other labs that are offering alkaloid testing. https://www.youtube.com/...i-CDuJQsfEeKW&t=1982