Gentlemen,

A common organic reaction employed throughout the world, from making soap to de-protection of vulnerable functional groups after certain specific reactions, is that of the saponification of ethers (e.g. 5-MeO-DMT contains a methyl ether group dangling off the 5 position of the indole ring, which is an Sp^2 hybridized carbon in the aromatic system) via both acid and base-mediated hydrolysis. Prolonged exposure of ethers to strong, highly basic/acidic aqueous (e.g. aqueous >>>6M NaOH and/or CONCENTRATED HCl solutions, etc.) conditions prior to extracting with an aromatic non-polar solvent (e.g. p.m, & o--dimethylbenzene solution AKA Xylene). Oftentimes these extraordinarily basic (FFS 6M+ NaOH is enough to eat-through most forms of flesh, too) solutions of mescaline freebase may sit around in a variety of conditions and for unspecified periods of time before pulling with Xylene. How long it sits around in a 6M NaOH solution is dictated by the experimenter, and any potential unwanted side reactions (e.g. aldols, acid/based catalyzed reactions, etc.) along with their choosing.

As a chemist, I can comprehend that nothing happens at once, and that oftentimes in reactions entailing the hydrolysis of ethers & esters, temperature fluctuations, extremely high concentrations of base/acid in the solution, etc. vary based on the molecule itself & its intrinsic properties, but remember that the thousands of other molecular species may also further catalyze other unwanted side-reactions and potentially lethal byproducts, especially so in high base and high acid solutions for extended periods of exposure.

Mescaline, AKA 3,4,5-trimethoxyphenylethylamine, if left in an extremely basic solution for a good amount of time (Many tend to let the NaOH sit for awhile in order to lyse every single goody out of its cells, oftentimes adding pure NaOH directly into solution such that the exothermic reaction from it dissolving may further catalyze cell lysis and/or degradation of actives.) before extraction into Xylene, as well as during backsalting into the hydrochloride and/or sulphate salt via adding concentrated acid to fresh pulls of xylene from 6M NaOH solution.

Given the violent exothermic nature of dissolving solid NaOH into the reduced brew, coupled with an emphasis on waiting several hours to a day or so before pulling (w/occasional agitation & burping regularly before separation), we may have set ourselves up for a perfect storm of disappointment, doubt and fear, which makes me doubt the legitimacy of nearly every extensive "mescaline" extraction tek out there tends to make use of such highly basic/acidic environments, as I would be highly inclined to predict that at least one of the methoxy groups on Mescaline, or perhaps two, or three. Depending on the rate of rxn at RT, incubation period etc. the more likely it is that the methyl ethers on mescalito may become alochols, leaving one with a (theoretically) degraded mesalito yield being affected by hydrolysis to undesired compounds such as 3,4,5-trihydroxyphenylethylamine, mescaline-N-Oxide, 3-hydroxy-4,5-methoxy-PEA, 3,5-dihydroxy-4-hydroxyphenyl-1-ethylamine, etc. which may alter the characteristics of the trip greatly so.

IME, drying out & encapsulating dried outer trichocereus flesh (Chased down with 4mg ondansetron and very strong ginger tea) for consumption, or doing a traditional "resin tek" wherein its cooked ayahuasca style, then reduced to a thick syrupy slime, oftentimes served alongside cacao-ginger concoctions and 100-200mg of a P. Harmala extract, for balance and guidance (typical dosage is dependent on cacti, with concentration of actives being determined from crude chemoassays from small segments of material from a clone of the I plant I intend to sacrifice (i.e. a crude TLC/spot to see if such an endeavor may be worth the cost of extraction from raw/dried cacti, as I deplore the very idea of eating my plant children, sans in moderation, so as long as for every dose's worth consumed, twice as many trich cuttings shall be propagated in its place) , is my ideal means of utilizing trichos as psychedelics. If "resin" is created properly from a home-grown strain which is a direct clone whose parent has an established alkaloid content (as confirmed via bioassay from whole raw flesh and/or analyzed via analytical chemistry methodologies) w/o use of intense acids or bases, I would safely say that this is the most wholesome means of prepping and ingesting mescaline cacti IMO & IME.

In order to combat nausea from ingesting resin, I typically eat a smoothie/protein shake, along with fresh fruit/nutes along with 4mg of ondansetron and 500-1000ug of clonazepam/lorazepam (take as little as possible at beginning, repeat every 6-8 hours PRN for nausea) taken at least 30 mins prior to ingestion; I also like chewing ginger throughout thge experiences as well.

I have found cacti alkaloid salts made via traditional 'teks' have had a far far far more speedier/slurrier/dirtier/superficial feeling to them, as opposed to traditional cacti resin, which tends to feel much more wholesome, and seems to teach me more, as an entity by the name of "mescalito" is an excellent teacher who only appears before me and guides me down a rabbit-hole of self-discovery if--and only IF--I consume the product of an entire cactus, whether that be an aqueous extract(S) concentrated into a snot-thick sea of resin, or an entire spineless TBM cutting just big enough to fit into a Kielbasa bun.

I have tried "Dirty Sanchez" grade un-washed crystals extracted from pre-powdered peruvianus outer green flesh via A/B w/ 6M NaOH over a few days followed by a couple 400ml xylene pulls & backsalting with HCl, along with the slightly more sparkly Hydrochloride salts of the alkaloids, now only weighing 1/2 of crude mass due to impurities found & separated in anhydrous acetone wash and re-x of alkaloid from the same batch as before, reducing the active dose from 500-700mg of dirty sanchez to 400-600mg of purified product to open The Doors of Perception, this time with a more speedy, more astute tone to it. Although I've worked with all three major Trichs,--each one having its own special psychoactive flavor of interesting--I figured peruvianus would be a good example as I noticed that the majority of the alkaloid was mescaline, and its subjective effects similar to such).

I have had the fortune of experimenting with pure, synthetic Mescaline HBr, and have found that, based on the handful of experiences I have had with ACS grade Mescalito, one is best off with a simple resin tek. Pure Mescaline, albeit colorful and cute and needle-y and kaleidoscopic, has a nasty speedy tinge to it which lacks the soul of naturally-derived mescaline. I find it hard to use words to describe the difference: this is similar to how pharmahuasca compares to freshly brewed ayahuasca tea, for some. It's more speedy, less venturesome, and all-around less intriguing than ingesting unmolested cactus resin instead.

Mescaline seems to be an emetic, which I believe is via 5-HT3r agonism in the digestive tract. Mescaline itself is too fragile (IMO) to withstand concentrated strong acid/base conditions for a prolonged time, even at RT; although more energy intensive, XS base/acid has just as much capacity to saponify ethers as it does esters, which may lead to unknown amounts/rates of ether saponification during conventional extraction methodologies (e.g. the teks on this site; I couldn't find any papers concerning the kinetics of this specific reaction regarding the rate at which saponification of phenolic ethers occurs at RT under varying NaOH & HCl concentrations, and would appreciate some help regarding this phenomenon.

If possible, would it be possible for someone on the forums who has the analytical technology to analyze mescaline-alkaloid family containing trichs via advanced methodologies of chromatography and other practices of analysis (e.g. C13 NMR, tandem GC-MS/MS, UV-Vis, IR, etc.), comparing the alkaloid content from whole outer alk-rich plant in the aqueous solution pre-basification, then make a 6M NaOH solution of the vessel, agitate it every few minutes, BURPING it after each agitation (PV=nRT...) for a few hours, then take samples of solution on a 1-2 times a day basis (solutions stored in darkness) & analyze them for change over course of for 7 days. On the 7th, extract with 3 pulls of dimethylbenzene. pool the extracts together, re-analyze both mother solution and xylene pulls, and then salt out alks from xylene after analyzing the xylene solution. The final step is addition of concentrated ~1-5ml 35% HCl to 50-100ml distilled water. This aqueous solution is then mixed with the pooled (pre-analyzed) xylene extracts in a sterile beaker over a magnetic stirring plate, to which 1 magnetic stirring bar is added and stirs solution at an RPM which can create a vortex and total immersion of solvents through it. This process will continue at approx. 50-70 centigrade for upwards of an hour or so, then quickly add to separatory funnel (Sans metallic stir bar), let layers completely separate whilst maintining warm temps, quickly separating acidic aqueous soln of concentrated HCL and the xylene (to be used for future purposes). Aqueous phase is slowly evaporated, and then re-x'd with some various solvents followed up by an anhydrous acetone wash. Analysis of final product should be done as well.


When using the "resin" of plant teachers, it feels as though the plant teachers are manifesting before myself in their true, unaltered form (harmalas help with guiding yourself throughout the journey.) and guide me calmly, gently, and bewildered throughout the wonders of the lost subconscious, followed by a 6-8 hour introspective exploration of what it means To Be.

Due to the lack of research surrounding the synthesis and consumption of 3,4,5-MeO-PEA derivatives (my biggest interest is in 3,4,5-trihydroxyphenylethylamine, as I was unable to find any mention of its synthesis and/or psychoactivity, along with other mixed 3,4,5-alochol/MeO derivatives in the literature--PIHKAL included), as well as the unknown psychoactivity of their different saponified forms in comparison to the 3,4,5-trimethoxy parent.

I would like to know if we are really extracting mescaline, or if we are really extracting a soup of saponified God-Knows-What phenylethylamines via commonplace teks for extracting mescaline HCl/H2SO4.

http://www.masterorganic...14/11/19/ether-cleavage/

https://chemistry.stacke...ether-to-phenol-reagents

Thanks for posting your thoughts

Is it possible your expectations affected how you felt about the synthetic mescaline? My experience was unlike yours, I felt peyote, pedro, bridgesii and extracted purified mesc trips to be equivalent in beauty, potential for inner transformation, psychedelia, etc (given doses are 'corrected' ).

Regarding 3,4,5-HO-PEA (and other phenethylamine analogues) in mescaline extractions, we have done a bit of research on it which you can find here:
https://www.dmt-nexus.me...aspx?g=posts&t=71353



There are a couple of unknowns and mass spectra is posted, not sure if you can find the mass spectra of 3,4,5-HO-PEA and then we can see if it matches with these unknowns. DMPEA is there in some extractions. In either case, for what we generally find, mescaline is the main compound found in these extractions. In some, it is the only compound.

Before considering minor alkaloids affect the experience (if they are there in the first place), I think a double-blind protocol would be essential and doable by anyone interested.

Maybe if someone can find this publication:
https://www.ncbi.nlm.nih.gov/pubmed/5788765

Might have useful information.

I've had a look into the relevant references found in the Shulgin Index and none of them is available through normal means. Mostly they're too old and obscure. We need someone with access to printed copies!

As far as demethylation of mescaline goes, HCl typically would not achieve the removal of a methyl group from a phenolic ether. HI or BBr3, and also AlCl3/pyridine are normally used for this reaction.

I doubt basic conditions would be removing methyl groups from mescaline.

The trihydroxy compound would oxidise very rapidly in basic conditions so we'd be unlikely to see much of it turn up in normal extractions. Maybe with a limetek, if it was there already. Its (mono-) and di-methylated counterparts are (minor) components of biosynthesis so it would take some careful analysis to show that their presence was quantitatively affected by the extraction conditions.

Would localised heating by NaOH get this hot? I doubt this would have a significant direct effect on the yield. Pictet-Spengler condensation would be a more likely cause of losses. Purification steps would then lead to the removal of the isoquinolines fraction.

As a footnote, I would add that mescaline-N-oxide won't be forming as only tertiary amines form oxides.

(And personally I'm a fan of cactus tea )

you mean Esters



No it doesn't...

Do you really think you're going to dearomatize an indole with a hydroxide ion? Do you have any idea how much energy that requires?




That's wrong.
You seem to be misunderstanding some basic organic chemistry here, the difference between an ester and an ether. Esters are cleaved via hydrolysis, this can be acid or base catalyzed. The resultant -OH group is actually derived from an outside source, from water or hydroxide. That's why its called hydrolysis. Ether cleavage occurs through an entirely different mechanism. In the cleavage of an ether, the oxygen atom is conserved. The alkyl group (methyl in this case) is substituted with a proton.



Not gonna happen.


And if demethylation ever did happen (not through the way your suggesting obviously), its going to happen at the 4-position. You'll never get all the way to 3,4,5 trihydroxy, not in a million universes.

Also, might I remind you that phenols are soluble in highly basic solution? They are easily deprotonated above pH 10 to form anions. Unless pH is controlled, you're not going to be extracting any in your non-polar regardless if they are there or not.



The most powerful and life changing experience I have ever had was with synthetic mescaline. It completely blew out of the water any other cactus experience I had, but this is simply a matter of dosage, not magic. I asked myself the same thing too, how could these white crystals produced from all sorts of strange orange and neon coloured crystals possibly be anything like that out of a cactus? Then i ate them, and there it was, no doubt in my mind, the cactus, ramming me with infinity waves for 16hours. Other than the intensity, and the 'clean' feeling, no difference. Initially was intense nausea, and was very difficult mentally as associated with any high dose of a psychedelic.



Totally wrong. ..
--
Mesc is actually pretty stable for a primary amine, relatively speaking. freebase amines (especially primary) degrade relatively quickly in open air, so it will degrade if left in that form.
The salts however, are rock hard. And will remain pristine white for years stored under open air (especially sulfate).






We're really extracting mescaline, we've run samples through HPLCMS..

PS: I've actually refluxed 5-meo-tryptamine in concentrated KOH at 150C. Yup, no demethylation.

I too have sampled pure synthetic mescaline (in hcl form) on a number of occasions, at good doses (a few sessions with 666mg, one with a gram). The latter experience with the gram has to rate as one of the most rapturously pleasurable experiences of my life. Even at that dosage, the come up was very gentle, mentally at least (there was some nausea and vomiting, and my friend and I were floored for a number of hours). However each of my synthetic mescaline experiences had some definite consistencies in experiential qualities compared to my many experiences with cactus (mainly San Pedro). Obviously there are other alkaloids bar mescaline joining the party when one ingests cactus, and I have to say I ingested Syrian rue with cactus on almost every occasion I ingested it, as one needed to consume less to get to an equivalent place. I also got the impression (although hard to be certain) that the Syrian rue coloured the cactus experience less than it did when ingesting it with mushrooms, or DMT (in comparison to B.caapi).

For myself, there was none of the depth of the cactus on the synthetic mescaline...it was very pleasurable, but I can't say I had any interesting insights or teachings or perspectives under the influence of it. The visuals were also distinct for me...I recall cactus (at least with the presence of the Syrian rue) at high doses producing some very fine, beautiful, mystical visions, with very beautiful colours behind closed eyelids. On the synthetic mescaline, for whatever reason, my CEV's were always just a jumbled confused mess of monochromatic fractals, really quite dull actually! Those experiences were much more about a sensory appreciation of the exterior world, and certainly there was beauty to be found there. These qualities were consistent and dependable for me, seeming to transcend set and setting, and I'm not sure of the reason. Certainly I think the Entourage effect of the other alkaloids in the plant has an effect. (I've also sampled pure ibogaine hcl, iboga "Total Alkaloid" extract and iboga root bark, and found the latter two to go a fair bit deeper, with a much longer afterglow period).