CITLO DMT Benzoate [A CISLO® experiment]

[merkin]

There are a bunch of threads with info about salting DMT solvent pulls directly with acid all over nexus right now. As this post applies to all of them I wasn't sure where to put it so pardon another thread if not appropriate. Brennendes Wasser's thread has a lot of detailed info but chemically above my pay grade so I don't want to pollute that.

Le Grande Architect of the CISLO methodology, Loveall, was trying for an easy route to a PG soluble, cart vapable, DMT salt and he has posted many good ideas and results all over, as well as the core ideas in his main CISLO thread.

This paragraph from Loveall got me sold:

"So... there may be no need to partially evap naptha, freeze preciptate, worry about re-X and all that stuff. Simply crash very pure DMT benzoate directly from naphtha (CINLO) and use that instead of freebase ... What's not to love...?"

What's not to love, indeed?!

The simplicity of a CIELO type tek for spice extraction plus the fact that DMT-benzoate seems to be not only stable, but both smoakable AND 'edible' is a huge bonus. Why bother with FASA or freebase freeze precips if Benzoate is a better option? Plus I have issues with my "naphtha" (nothing with that name here so I use local equivalents like hardware 'benzine' or lab solvents like n-Heptane) freeze precipitation yields, but no such problems with FASA. And given I'm quite familiar and practiced with CIELO I definitely figure this is a route for someone with my lack of skills and chem knowledge to pursue.

So I began by trying Loveall's 'mud pie' tek (from this post) with fine MHRB powder that usually gives ~1-1.2% freebase yield:

Basically it failed completely! Limonene never clouded or precipitated anything at all after salting with Benzoic acid. Left for 2 weeks without change. My limonene is quite old - could that be a problem? Not sure what happened here but majorly disappointing.

I then tried again using a Toluene pull via Cyb's Max Ion tek (except no salt added). Added BAST (Benzoic Acid Saturated Toluene) dropwise to Toluene pull similarly to the FASA tek. Approx one drop per second, around 50ml BAST solution total).

This time the solvent clouded immediately similarly to FASA. The cloud slowly sank and after a few hours there were three large white crystal clusters sitting atop some orange coloured precipitate on the bottom (the more jungle-y stuff?).

Left to crystallise room temp for 24hrs+, I placed the beaker in the freezer for about 12 of those hours per BW's recommendation. Then I decanted. The precipitate stayed fixed to the beaker and the golden coloured clear liquid decanted easily. I am still drying the crystals with small USB fan. The jungle-y stuff is obviously taking the longest to dry.

I really like how this idea is turning out so far! Pictures of pull 1 attached. The darker stuff is getting lighter as it dries.

Since my limonene attempt failed for unknown reason I am a bit wary to use it instead of Toluene as the NPS so as not to waste precious bark. Apparently though it is a lot friendlier than Toluene. But risky for me until I understand my first failure better.


Now, I have some questions for y'all:

1. Will this need cleaning / washing / re-x, and if so how would one go about it?

2. What would the equivalent freebase DMT content in what I assume I have is DMT-Benzoate - i.e. how would I calculate standard dosage with this for oral or smoak?

Thanks!

I CISLO®!

 

[_Trip_]

I can confirm the d-limo benozic acid works very well. I must note I have only ever used it to convert freebase to dmt-benzoate. It is a rather fast reaction and converts even the most orangey/ brown goo/ wax dmt into nice off yellow dmt benzoate crystals. Which smell of oranges.

Shame you didn't have success.

 

[Loveall]

I wonder why your limo didn't work Merkin. Where you able to get DMT out of that bark eventually? Should be in the limo (uncristalized) or in the bark still? If the DMT was in the limo and didn't crash maybe your limo has other stuff in it that keeps benzoate soluble (?).

If anyone can figure out how to dissolve DMT benzoate in e-juice that would be amazing. I read some people add water to e-juice (distilled/purified). Bacterial growth is a concern with water, but benzoate is a preservative so we should be good (?). Could that work? Ethanol is added sometimes also.

Maybe making a saturated DMT benzoate water solution and adding PG/VG to that will keep everything soluble and e-vape well?

Maybe a nicotine e-juice veteran can weigh in?

 

[downwardsfromzero]

Awesome xtals, merkin :thumb_up: :want:

Yes, limonene can get old and slowly oxidises - it's a less inert solvent than, e.g., naphtha or toluene. And if it was orange oil terpenes this will be worse. There will be a bunch of alcohols, aldehydes and ketones in there, any of which might contribute to keeping the benzoate in solution.

Did you wash the failed limonene experiment with water? That should allow you to recover your missing product.

 

[Toshido]

I just love this because I can see myself getting here eventually. It's cool to see the future experiments that I will try, and it's wonderful to see the community work together to fine new avenues to new places!

Great job! Those xtals are alluring!

 

[merkin]

I wonder why your limo didn't work Merkin. Where you able to get DMT out of that bark eventually? Should be in the limo (uncristalized) or in the bark still? If the DMT was in the limo and didn't crash maybe your limo has other stuff in it that keeps benzoate soluble

Yes, as DFZ says I think it was a problem with my Limonene. Unfortunately I never recovered anything. I was going to try some Toluene with the mud pie (I thought the limonene had pulled nothing) but I forgot it and it died out and wouldnt soften with the Toluene and I gave up.

Awesome xtals, merkin :thumb_up: :want:
Yes, limonene can get old and slowly oxidises - it's a less inert solvent than, e.g., naphtha or toluene. And if it was orange oil terpenes this will be worse..
Did you wash the failed limonene experiment with water? That should allow you to recover your missing product.

Thanks DFZ.

Yeah I think it was probably the age of it. It was also not a lab store bought product (but did work with mesc extraction when I got it) - and yes, it had "(Orange Oil)" on the label too. The limonene extract was so absolutely clear of even the slightest precipitation I thought it hadn't picked up anything at all.

I am afraid I didn't do anything with it and when I did wash it and the beakers out with water I disposed of it at the local dump's solvents section. I didn't realise water might retrieve the spice!

So in the end I retrieved about 2.8g of the crystals in 4 pulls. There was always some orange/tan crystals mixed in with the clear crystals even though it did diminish relative to the clearer crystals.


I do like the method though, even if it involves Toluene. Its even simpler than the FASA method and the crystals crack up and come off the glass surface very easily, unlike fumarate.

Any idea about dosage of this?

Is it a similar structure to the fumarate @ ~70% of freebase dmt content or something else.

 

[Loveall]

Compared to free-base DMT benzoate should be 61% as strong as freebase. I'm assuming there is no water in the xtals structure.

I would rinse it with naphtha before smoking it.

Also, we don't know how safe it is to smoke benzoates with flame, so I think there is a risk there of unwanted compounds (e.g. benzene which is a carcinogen?). E-mesh may be ok - I would personally try that but each one should make their own choice and be cautious.

Orally I think it is fine. Benzoates are used as food preservatives and most of us are already ingesting those.

 

[Hailstorm]

Benzene in vaped benzoates is present in trace amounts that are not of a major concern unless you smoke it every day like cigarettes. doi: 10.1371/journal.pone.0173055

 

[merkin]

Compared to free-base DMT benzoate should be 61% as strong as freebase. I'm assuming there is no water in the xtals structure.
I would rinse it with naphtha before smoking it.
Also, we don't know how safe it is to smoke benzoates with flame, so I think there is a risk there of unwanted compounds (e.g. benzene which is a carcinogen?).
Orally I think it is fine. Benzoates are used as food preservatives and most of us are already ingesting those.

Thanks Loveall, I will do the rinse - since we don't have 'naphtha here as a label, any other solvent suggestions for that? Like something more pure like pet ether or heptane etc?

@61% that is a good yield for me from the bark so not a lot of downside to this method.

Benzene in vaped benzoates is present in trace amounts that are not of a major concern unless you smoke it every day like cigarettes. doi: 10.1371/journal.pone.0173055

Thanks Hailstorm - I was aiming for a GVG vape of the product to confirm this is a viable route for storage, pharmaH and vape. Looks like it worth a try after I get it washed it.

 

[Loveall]

I think clean evaporation heptane should be a good rinse.

 

[Loveall]

Benzene in vaped benzoates is present in trace amounts that are not of a major concern unless you smoke it every day like cigarettes. doi: 10.1371/journal.pone.0173055

Thanks Hailstorm.

Unfortunately DMT benzoate does not dissolve in e-juice. That leaves e-mesh and flame as the main ways to smoke it.

I would personally use e-mesh as it feels safe if temperature controlled and based on BW's work.

However, I still worry about flame/torch if ~30mg of DMT benzoate is pyrolyzed at high temperatures, couldn't that result in a few mg of benzene? Benzoic acid decomposes around 500°C with the formation of benzene and CO2 (see attached).

 

[Hailstorm]

Yeah, that's a good point and we won't know for sure until it gets tested.

I wonder what DMT benzoate could dissolve in, for vaping. Could water vapor lift some of it, like what happens in steam distillations?

 

[Loveall]

Yeah, that's a good point and we won't know for sure until it gets tested.

I wonder what DMT benzoate could dissolve in, for vaping. Could water vapor lift some of it, like what happens in steam distillations?

I tried dissolving it in water, it is very hard to dissolve. It stayed powdery after 1 part water (surprisingly). After several water additions it became runny but milky. My conclusion is that it is poorly soluble on water.

Tried some 40% vodka, didn't seem to help (and e-juice are not recommended to beore than 4% ethanol).

If we could find some way of dissolving DMT benzoate in e-juice that would be amazing. It is very easy to salt cleanly from an efficient limonene pull of a super simple STB bark paste.

I need help because I can't figure out how to make a DMT benzoate e-juice formulation.

 

[doubledog]

I tried dissolving it in water, it is very hard to dissolve. It stayed powdery after 1 part water (surprisingly). After several water additions it became runny but milky. My conclusion is that it is poorly soluble on water.

This is interesting and could be probably useful for recrystalization. Maybe it's worth to test if solubility of dmt benzoate (in water) is similar to solubility of benzoic acid - low in room temperature, but much higher in boiling. Benzoic acid crystalizes very well from water.

Did you test solubility of dmt benzoate in some other solvents (ethanol, acetone) ?

 

[downwardsfromzero]

Hey Loveall! Have you tried sticking the benzoate plus PG in the microwave for a few seconds? Based on the experience with recrystallisation of benzoic acid from ethanol and water, I'm thinking heat might be a way to go with this. Maybe it'll promptly crystallise back out again on cooling - well, there's only one way to find out (and if I had any benzoic acid I'd consider trying this myself).


Merkin - looks like my suggestion to wash the DMT benzoate out of the limonene might have turned out equally unsuccessfully had you tried it.

But - what if something in this orange oil is the thing that we need to get the benzoate to dissolve in PG?
Characterization of Aroma Active Compounds in Fruit Juice and Peel Oil of Jinchen Sweet Orange Fruit (Citrus sinensis (L.) Osbeck) by GC-MS and GC-O may give us some ideas, for example. My hunch is that fatty aldehydes such as octanal and decanal may have a role here. I wonder what a drop of butyl acetate might do for it, for that matter.

 

[Hailstorm]

This is interesting and could be probably useful for recrystalization. Maybe it's worth to test if solubility of dmt benzoate (in water) is similar to solubility of benzoic acid - low in room temperature, but much higher in boiling. Benzoic acid crystalizes very well from water.

Yes, DMT benzoate is soluble in hot neutral water and poorly soluble in room-temperature water, much like benzoic acid itself. It has to be a property of the benzoate anion.

I vaguely remember DMT benzoate dissolving readily in dilute acids, so it may be sufficient to add a bit of citric acid to help it dissolve. Although you would be vaping DMT citrate in that case, I guess.

DMT benzoate does indeed recrystallize from hot neutral water, although crystallization is rather annoying to initiate (which may be good news for vaping?) and it takes forever to dry. I usually recrystallize DMT benzoate from hot amyl acetate (which doubles as a great DMT freebase extraction solvent, with some pros and cons compared to limonene) and wash it with heptane for fast drying (the salt is insoluble in room-temperature heptane).

Did you test solubility of dmt benzoate in some other solvents (ethanol, acetone) ?

I did, a while ago. DMT benzoate was somewhat soluble in acetone, and very soluble in anhydrous ethanol at room temperature.

I have never tried DMT (benzoate) nasally or buccally/sublingually. Those administration routes work well for 5-MeO-DMT, resulting in medium-pace experiences.

 

[Loveall]

Will try dissolving in dilute acids, thanks Hailstorm.

DWZ, I didn't try microwave but I did try to dissolve it over a boiling heat bath in PG and still didn't work. Do you think the microwave is still worth it?

 

[Loveall]

Hailstorm, DMT benzoate finally dissolved in a PG after adding lactic acid Was very interesting to watch.

Got to test the ratios, but it was pretty dramatic how adding lactic acid made DMT benzoate dissolve. There are a few tiny specs of white powder at the bottom, perhaps some benzoic acid was pushed out of solution. Easily decantable.

Will the concentration/taste be practical? I don't know, but this would be the lazyest way to make vapable DMT I can think of...

 

[Loveall]

Hailstorm, DMT benzoate finally dissolved in a PG after adding lactic acid Was very interesting to watch.

Got to test the ratios, but it was pretty dramatic how adding lactic acid made DMT benzoate dissolve. There are a few tiny specs of white powder at the bottom, perhaps some benzoic acid was pushed out of solution. Easily decantable.

Will the concentration/taste be practical? I don't know, but this would be the lazyest way to make vapable DMT I can think of...

Unfortunately while it dissolved nicely with heat, overtime the e-juice became a gel, so this did not work.

I still can't make a vapable DMT benzoate e-juice.

 

[downwardsfromzero]

Will try dissolving in dilute acids, thanks Hailstorm.

DWZ, I didn't try microwave but I did try to dissolve it over a boiling heat bath in PG and still didn't work. Do you think the microwave is still worth it?

Microwaves sometimes make stuff happen that plain heat doesn't. The plus side is, even if it doesn't work it was literally just a few seconds for the attempt.