TEK Ethyl acetate approach [CIELO]

[Transform]

I don’t quite understand quaternary alkaloids since it’s the same alkaloid but water soluble base alkaloids? Will be my next research to better understand

Quaternary alkaloids have four carbon bonds joined to a positively charged nitrogen. The nitrogen retains its positive charge even when the counter-ion is replaced with hydroxide as there is no N-proton to be removed.

 

[bodhidharma]

Yes, environments can affect the process.

MgSO4 dries the extract too much. Freezing does too.

Yes, adding water back or being letting some ice melt while separating is successful for some people. This is not supported by the TEK.

Have you tried the wet crumbs? They should work

Without fridge rest? As in,should work with EA at what temp for pulls and xtalization?

If not, should work with EA in which temprature?

 

[modern]

Quaternary alkaloids have four carbon bonds joined to a positively charged nitrogen. The nitrogen retains its positive charge even when the counter-ion is replaced with hydroxide as there is no N-proton to be removed.

Can mescaline be found in that form? DMT and 5-meo were both found in that form which I don’t understand. They also used a different technique to salt

Paper is unrelated to Cielo but related to possible different forms? There they extracted the “water soluble base alkaloids” which I think is the same as quaternary alkaloids no? Made that jump based on term used to precipitate. “reineckates”

Other papers also show higher extraction of alkaloids using citric acid and was wondering if the 3 pka had anything to do with it.

I mean if it works it works. Had interesting results with caapi precipitating with Citric acid… I’ll play around with mescaline citrate some more. Any more informed insight would be welcome.

 

[Transform]

Can mescaline be found in that form? DMT and 5-meo were both found in that form which I don’t understand. They also used a different technique to salt

No, mescaline only has the one, single carbon-nitrogen bond. Mescaline cations form through protonation at nitrogen. Methylation leads to different molecules - N-methylmescaline, trichocerine and the N-methyltrichocerine quaternary cation. Both N-methylmescaline and trichocerine may (also) be protonated - reversibly - to form cations, but only the N,N,N-trimethylmescalinium [N-methyltrichocerinium, N-methyltrichocerine quaternary cation] counts as a quaternary ammonium compound.

• mescaline is a primary amine
• N-methylmescaline is a secondary amine
• trichocerine is a tertiary amine

Only these compounds in the series have the spare lone pair on the nitrogen atom for reversible protonation to occur. Removal of a methyl group from a quaternary ammonium cation requires a more vigorous chemical process which needn't be discussed here.

reineckates

Reinecke's salt - Wikipedia

en.wikipedia.org

This can be used to precipitate alkaloids as a convenient analytical reagent. Perhaps the quaternary ammonium compounds are selected by being far less soluble.

“water soluble base alkaloids” which I think is the same as quaternary alkaloids no?

Hm, "water soluble base" is a bit vague, on reading the paper we see:

[...] Amberlite IRA-400 (OH-) resin was
used for separating phenolic from the non-phenolic bases ( Lundström and AgurelI, 1967),
the corresponding Cl- form was used for preparing the quaternary chlorides and some of the
hydrochlorides. De-Acidite FF (OH') was used for regeneration of bases from the reineckate
salts

The defatted plant material was continuously extracted with alcohol for 16 hr. The alcoholic
extract was evaporated under reduced pressure to yield a thick consistency (62 g). It was poured
into aqueous acetic acid (4%, 100 ml) with stirring. The clarified acidic solution was extracted
with chloroform to isolate the chloroform-soluble acetates (Fraction 1). The aqueous acidic solution
was basified and the liberated bases were extracted with chloroform (Fraction 2). The aqueous
alkaline mother liquor (pH ~9) was treated with a saturated aqueous solution of ammonium
reineckate. The precipitated reineckate complex was collected by filtration (Fraction 3). The
filtrate was brought to pH ~9 another crop of the reineckate salts precipitated (Fraction 4). The aqueous mother liquor, after
separation of Fraction 4, was strongly acidified (pH=<1) with 4N-H2SO4, and the solution was
kept overnight at ordinary temperature.

The reineckate salt of water-soluble weak bases thus
precipitated was collected by filtration (Fraction 5).

"Weak" does rather imply that these weren't the quaternary ammonium compounds, which form strong hydroxide bases due to the lack of a labile proton.

[As you may also be aware, Desmodium triflorum, as per the paper which you attached, has since been renamed Grona triflora]

Grona triflora - Wikipedia

en.wikipedia.org

 

[bodhidharma]

Another question that came to my mind is this.

CIELO product(s) Analysis - Generic - Welcome to the DMT-Nexus

Beautiful writing and experiment, truly.

But if M.citrate needs water to form, wouldnt the ammount of water be differnt using every cactus?
Maybe fumarate will solve this.
This made me think that cielo, although people make genuine mistakes with it, is quite individualistic, in a beautiful way tho, if u learn all the principles, no reason it shouldnt be amazing

 

[Transform]

Another question that came to my mind is this.

CIELO product(s) Analysis - Generic - Welcome to the DMT-Nexus

Beautiful writing and experiment, truly.

But if M.citrate needs water to form, wouldnt the ammount of water be differnt using every cactus?
Maybe fumarate will solve this.
This made me think that cielo, although people make genuine mistakes with it, is quite individualistic, in a beautiful way tho, if u learn all the principles, no reason it shouldnt be amazing

Interesting - this thread doesn't show up on the forum search here on the new forum. Here it is, though:

CIELO product(s) Analysis

1.) CIELO crystal formation vs. water content Here is just a small test to check what is the influence of the water content on the crystal formation. Loveall and coworkers found a nice sweet spot at around 2,3 wt-% of water, which should be the fridge-level equilibrium of water miscibility with...

forum.dmt-nexus.me

Could you explain you reasoning about the water content a little more? Why would different cacti require different amounts of water? Do you mean wrt the differing concentrations of mescaline across various specimens?

 

[bodhidharma]

Interesting - this thread doesn't show up on the forum search here on the new forum. Here it is, though:

CIELO product(s) Analysis

1.) CIELO crystal formation vs. water content Here is just a small test to check what is the influence of the water content on the crystal formation. Loveall and coworkers found a nice sweet spot at around 2,3 wt-% of water, which should be the fridge-level equilibrium of water miscibility with...

forum.dmt-nexus.me

Could you explain you reasoning about the water content a little more? Why would different cacti require different amounts of water? Do you mean wrt the differing concentrations of mescaline across various specimens?

Indeed

 

[Transform]

Indeed

So, the differing concentrations of mescaline across various specimens, affecting the amount of dissolved water required? I think some calculations were done regarding this, somewhere far earlier in this monster of a thread. Maybe around pages 12 to 15, I could be wrong and I'm not looking through it all tonight!