Here is a thread discussing this. DMT benzoate was made from limonene, and (in that thread) Dasein mentioned how it works for naphtha too.

The weight difference is not an issue. It was super easy to convert DMT benzoate to FB and it looked very pure and also looked free of polymorph forms 😊

I think it's worth someone doing a confirmation. This might be a very easy way to get clean crystals without heating xylene to re-x. Which in my view could become dangerous to the average kitchen chemist. Think about the average kitchen chemist desperate to do a bufo extraction that lives in a one bedroom apartment (sometimes it's best to cater to the lowest common denominator as they may likely go ahead and heat xylene in a confined space).

The other advantage is that bufo benzoate may be easily collected and smoked. At this stage it is purely anecdotal but it was less harsh than freebase bufo. I saw your work with DMT benzoate (love your work by the way), bufo benzoate may be worth a write up.

In addition, If it is soluble in PG/VG, (which I will test soon) one could just add it to a vape. This would not be the case for fumaric from my understanding. I imagine furmaric would be harsh and is not a salt form used in vaping, i believe furmaric causes throat nose and respiratory irritation. Lactic acid would be another good potentially safe candidate for vaping.

So indeed Benzoic Acid can be used instead of Fumaric Acid and seems cooler for about any usage, but at this stage I still think in terms of purity or steps during the TEK it would not make stuff faster :/

Because it will precipitate the same Alkaloids and also with the Fumarate there are unwanted more polar Alkaloids in the mix. These ones will be present with Benzoic Acid too and therefore those crystals not pure Bufo Benzoat. When you are doing the bufo-selective Extraction with either that Naphtha-EA-Mix or Xylene it will leave behind quite some tan powder. That stuff previously will be in either the Fumarates or the Benzoates.


A way which I could imagine to still purify and avoid Xylene:

Famine told me about how to easily get rid of some more-polar side products of a DMT reaction. And these ones will not run during a TLC analysis. Therefore if you create the (for example) Benzoate salts of all Molecules, these polar side products can be removed in an Ethanol re-x. DMT will precipitate again, while that other stuff stays dissolved in Ethanol, even though being a salt. Maybe that can be done for these Benzoat Crystals too at this step.

Heat in Ethanol until dissolved
Precipitation might be voluminous so you cant just decant liquid.
Put inside of a funnel + filter (preferably all pre-cooled in freezer)
Wash with -20 °C Aceton to get rid of the Ethanol
In the best case the orange colour of crystals would go to white

Maybe it works?

But Bufo itsels is already super polar, even at -20 °C you might lose quite some to the Ethanol.

I'm now writing to the first page that Benzoic Acid can also be used, because there is absolutely no reason to only use Fumarate

So I gave this substance another go for vaping, after my initial experiment in 2020 felt rather sick.

Reason was I recrystallized some recent Bufo twice to get more beautiful crystals. Therefore (even though being slightly tan due to red shift absorption compared to DMT) it is now free of that 2 % impurity. That encouraged me to just try it once again ... even though the whole composition is basically the same.

Back then:
> Super harsh to the lungs (I'm non smoker otherwise, count that in too)
> roasted nuts smell, enjoyable diffused, but concentrated its nasty
> super strong vasoconstriction, forehead and hands feel numb and cold ... unpleasant!
> nausea

Also ate 100 mg Bufotenin + 200 mg Harmalas. Effect was more underwhelming, probably poor absorption like most drugs. More like 1 g Mushrooms but with a decent nausea.


So now I weighted 10 mg and tried to vape with this thing but put 2x new lego plates below so total distance to flame was 6 mm less. For spice it works like a charm, so with that low distance more I probably hit the 240 °C just fine and will not overshoot to 300+ which would cause harsh vapor ...

Then loaded 5 mg and vaped - barely could hold the vapor for 3 seconds and it was not even the full 5 mg. Tried another rip and so on.

Got some effects, but wasted most of the 5 mg. Threw in the other 5 mg and it ended the same.


In total maybe 3 mg vaporized. Now for that really low amount there is still at least some remarkable effect.

- slightly distorted colors and patterns in low light, but maybe comparable to 3-5 mg DMT
- body high was very present
- serotonergic effects / vasoconstriction also came on rapidly, but it was much less unpleasant like last time. Just a little tingling in fingers with no freeze/shaking effect
- no nausea
- absolute absence of that roasted-nuts smell

So in total that effect was weak, but my (estimated) 3 mg dose is also quite low. Still, compare that to a 3 mg 5-MeO vape. I have not tried it so far and it is not really visual at all, but will give quite a big buzz at 3 mg only.

Still it's a little remarkable that any side effect was more on the gentle scale this time. Anyways this is not helping anything as I can hardly vaporize 2 mg (probably). Therefore that seems like the only barrier for me now, with vasocontriction effects being quite on a tolerable level. No nausea and that roasted nuts vapor is quite a good thing, but at least for #1 it may also be linked to the low dose. Anyhow my last trial was probably also that low, but still with some nausea, so it may (partially) be linked to that 2 % contamination during that time. Therefore from the effect itself it might be not a problematic substance as I thought before, but ingestion is more of a problem. Going down straight your mouth in a pill also seems not rewarding. Did it also because I want to compare with 5-AcO-DMT soon.




Kind of underwhelming, but now at least I have some interesting Hypothesis:

Some of the Bufotenin-Pyrolysis products also vaporize and give a big irritation to the lungs. Most likely they are indeed oligomerization products similar to Psilocin as discussed here, but obviously only a 5,5-position aka ortho coupled pathway would be possible. Maybe reaction barrier without enzymes (see Psilocin) are way too high, that is why Bufotenin is stable at RT forever.

But when heated to > 170 °C the ambient oxygen will promote this reaction fast. Therefore my Bufotenin TGA showed only ~ 50 % vaporization, other 50 % polymerized and will bake to the ground. Even though traces might vaporize as I wrote and cause this harsh irritation, even when vaporizing Bufotenin super clean at just above 200 °C. I could easily verify it by handing out a Thermogravimetric Analysis (TGA) again with Bufotenin, but this time measure in N2 in future.

Now __Trip__ wrote that the Benzoate salt was quite not too bad. It anyways remains a big question what exactly happens if Tryptamine salts vaporize, which provenly happens just at + 10 % of their freebase temperature (considering the anion is compatible). But this might be worth investigating, as creating a form like this might actually prevent polymerization via repelling coulomb forces, IF the Tryptamines stay in Salt form at least until they finally transist from liquid to gas. The big question to me then again would be WHERE IS THE ACID GOING, if there is a back-dissociation before actually vaporizing. 10 mg of Benzoic Acid / Acetic Acid would give a severe lung irritation, but this does not happen. On the other hand, I believe dissociating in a IONIC state would require 100s of Celsius and probably decompose anything before ...





> Place 10 mg of DMT Benzoate on a hotplate at 200 °C
> wet a pH paper and just hold it ~ 1 cm above

Even airborne vapor of conc. HCl will instantly react with a pH paper like this. Therefore any non-dissociated acid will have the same result.

That would at least prove if the vapor is back-dissociated (pH paper coloured, Freebase) or still dissociated (no reaction, salt). Maybe next week I will do it and make a new thread about it. I never believed when people said you can smoke DMT Acetate, but it works and I think this whole thing deserves some kind of discussion.



Anyways a much easier solution for vaporizing Freebase:
Just do it on Titan or any other inert (or reducing) rather than oxidized atmosphere here on earth. If Elon Musk stops ruining his reputation on Twitter, maybe he has time to do this experiment which would make Mankind benefit much more

So _Trip_ I may have some interesting news: Your idea of shortening that TEK altogether by salting out with Benzoic Acid may be indeed viable.

I was unsure, because whatever you salt out, with boiling Xylene you will end up with some black dust at the end. That made me think it would consist of even more polar Alkaloids which are left behind. Actually I can hardly imagine something even more polar, considering it will not have any charges like Psilocybin. Maybe molecular weight could be too high to melt, but as Bufotenin repeatedly melted at below 120 °C (opposed to 140+ in literature) I believe you would need to add a lot of stuff to the molecule to get a melting point above Xylene boiling temperature. Therefore any residual black stuff at the end could also be just Bufotenin which was decomposed at that temperature, it happens quite fast. Only argument against it would be that this decomposition stuff would form a black tar burned into the glass, rather than being dark tan powder which is still free-flowing. I said a good way to find out would be an analysis on the whole Salt-mass, but did not want to do an extraction again.

Now I found a sample standing around since years, with a rather cryptic labelling. Normally trying to give it not too obvious names, but still able to recognize what's inside even if I forget everything. And what it sounds like may be what I get from this salt after freebasing. That would mean it is exactly what you would salt out with FASA or Benzoic Acid and contains Bufotenin together with potential other Alkaloids.

Analysis is shown here. Some signals have an unexpected shift and integrals of indol is a little too low. But well that machine is pretty badly configured / calibrated so when instead just taking a look at the peaks it would fit pretty perfectly with pure Bufotenin, just some aliphatic impurity at 2,10 ppm which I see often, but have no clue what that is.

If that is indeed the sample which I suppose (I'm sure I kept some until the day I could go to the NMR again) then this would make it pretty likely that whatever Alkaloid is precipitated from the Acetone, it would be pretty much pure Bufotenin indeed. Therefore your idea of shortening that whole procedure might be indeed correct

That's very exciting and easy for the average person to do. Love all your hard work BW.

I'm a sloppy kitchen chemist at best but I did get some nice clean crystals (perhaps a better defat could give even cleaner crystals). I really need to send off the bufo benzoate crystals for analysis. They were easy enough to grow in acetone.

Thanks But I am also not a real expert on anything that Nexus is truly about like Tryptamine Science, Organic Chemistry or Biochemistry unlike other people across this website. I just have access to all these technologies right now and so try to get the most out of it using what I know and once can't use them anymore will probably be gone from this website.

Those crystals look really great. As seen on first page my Fumarates were pretty orange. I guess they were still pure enough. But that slight coloration could be removed by a re-x in Ethyl Acetate probably. Toluene would not work as it's too unpolar.

Now regarding small crystals, have they been just small or also overall yield not much? I guess Aceton might be still a too well solvent for precipitation. Ethyl Acetate could be a little worse, but that would make it better for dropping the Benzoate. Anything inbetween regarding polarity would be not feasible like DCM / Benzene. And Benzene probably even not possible to dissolve Alkohols well. Just something more exotic like Butyl Acetate or the nice find of Hailstorm Amyl Acetate.

So here is a new TEK based on your initial idea that would directly go to the Bufotenin Benzoate which can be smoked directly without combustion, not sure if I would ever test it, but no idea why it would not work. Will also be linked from first page as it's maybe even more viable.





Shorter and easier TEK, goes directly directly into a smokable product:

Proceed as normal with Steps 1. - 3.

4. Extract the seed powder with Ethyl Acetate in the same way like with Acetone.

5. Reduce Ethyl Acetate down to 100 ml per 100 g Seeds (not sure if such low amounts are needed, but it will reduce the chance of loosing Bufo due to much staying left behind in solution at step 9).

6. Remove residual water by filling vessel 1/5 with MgSO4 and let it rest overnight - even better when stirred - this step would be important as due to concentrating down the Ethyl Acetate also the water content will increase in % and thus prevent more crystals from precipitation.

7. Decant Ethyl Acetate and wash MgSO4 with 10 ml fresh Ethyl Acetate, combine all EA together.

8. Dissolve 3 g Benzoic Acid per 100 g Seeds in Ethyl Acetate in the minimum amount of Solvent possible.
(better warm Toluene / even better boiling Naphtha - because it lowers the solubility of Bufotenin Benzoate even more)

9. Add Benzoic Acid to your Extraction Ethyl Acetate - this time speed does not matter as you cant form multivalent salts.

10. Place in the Freezer over night

11. Wash crystals with Naphtha

Optional:

12. Evaporate residual Ethyl Acetate and check how much other stuff was inside of EA (by knowing initial amount of Benzoic Acid)

13. Purify Bufotenin Benzoate by recrystallization in boiling Ethyl Acetate (start with 10 ml on 1 g) and if it poorly dissolves you can try Ethanol instead.

Also this process would evade precipitation of a sticky freebase glob in water, which then also needs to be extracted with boiling Xylene (not perfectly kitchen safe).

Yield appeared good but I can not confirm numbers I had only 50g of seeds and ran multiple experiments.

Within the first couple hours, crystallization was minimal. I left the acetone in a cupboard for a week or 2 because I forgot about it. When I looked at it again a lot more crystals had formed and many quite large. The solubility of benzoic acid in acetone is 69.1 g/100 g. So that was one reason I used acetone as excess benzoic acid would not crash out. I couldn't find the numbers for EA. IIRC and I could be wrong but I believe I tried EA with very poor results. I tried many different solvents though so perhaps I am not remembering correctly.

To get the crystals the way I did:
I simply made the base paste with sodium carbonate and the seeds (ground up).
Conducted a defat with hot naphtha, D-limo and then naphtha again (decanting each one) until naphtha was clear.
Pulled with acetone and salted it out with benzoic acid. The crystals stick a little so it is easy to decant.

It would be interesting to see how you go with the EA. It would also be interesting to see how pure the acetone crystals are, could make it as simple as above. No freezer or chemical drying steps needed etc. But perhaps purity would likely be worse with acetone, I don't know?

Unfortunately, I am having a hard time sourcing more seeds.

I finally had a chance to extract some seeds and tried to keep it as simple as possible based on the info from this thread. I also wanted a full spectrum with all the alkaloids so no defat was performed.

30g of seeds were toasted. Weight after toasting was 28g.

I did one freeze/thaw then microwaved the sodium carbonate mix and dried all the water in the microwave.

Pulled with acetone at boiling 3 x 100 ml, filtered.

Dried with MgSO4

Salted with 1g of benzoic acid which I just added directly. No clouds formed so I left it in the fridge and when I checked on it 20 minutes later a layer of very fine brown crystals had covered the bottom of the dish. They are very easy to handle as they are not sticky at all.

Final yield: 2.2 g bufotenine benzoate or 1.32 g freebase (not sure if I did that conversion right) = 4.4% yield.

I am curious about the purity and I wonder if simply adding the benzoic acid slowly (maybe using BASA) could lead to bigger crystals.

EDIT: subsequent addition of BA yielded no more precipitate.

Thanks for reporting woolmer I have not been able to get more material to test.

I was questioning if my original findings with acetone and benzoic acid worked after I mislabelled a jar I sent for testing.

This is great news. I think a defattting would give whiter crystals which is what I originally found. Less acid may have produced bigger crystals.

If you confirm them to be active i can reinstate the tek on the wiki page. Thanks woolmer.

Your sample would be great for lab testing.

It's a very nice short method. Thanks to you _Trip_ and BW for your work.

I'm going to assay it in a few days.

I'll try send a sample in for testing. Would love to see which alkaloids are present.

Me too, keen to hear your results.

I added a small bit more BA (did not weigh it) to the acetone and more stuff crashed out. 0.6 g

I then added 0.84g of BA and even more crashed out. 0.76g

I think that may be the last bit since less is crashing out than the amount of BA I added.

Total: 3.56g benzoate, 2.14g freebase = 7.1% yield!

After each addition of BA the colour is becoming more white.

EDIT: A fourth addition of BA yielded no precipitate.

According to a paper I tracked down benzoic acid has good solubility in acetone so hopefully it isn't excess BA. A quick Acetone wash could get rid of any excess BA that may have gotten through and or may clean up the product further, but 69g to 100ml it probably isn't excess BA likely a good yield. Either way this is looking good.

3 mg vaporized in 2 tokes using e-mesh convection produced threshold effects - sharpened vision and a strange body high that I have not felt before. Seems like a slower come-up and longer acting than DMT.

The vapor was pretty smooth, just a slight tingle in the throat.

A small black residue is left on the mesh.

Charming effects with the sunset and silhouette of trees

This was for the first precipitate that I collected that has a browner color. I will try the whiter sample to compare effects, though I suspect they will be indistinguishable.

Keep us posted woolmer! Sounds promising. I might have to reinstate the tek.

Hey you 2 wow that are cool news!

Indeed the TEK is quite long and is giving a pure product. But it would be cool if steps can be made easier and also if it could go directly into Bufotenine Benzoate.

So the sad thing still to note is that it seems the vasocontriction effect is indeed bound to Bufotenine itself. That is why smoking quite a lot would still give some cold feeling in hands / etc even when Bufotenine Benzoate is used. But it will overcome the combustion, which will make it otherwise unpleasant to smoke, which the Freebase will always give ...



Still seems pretty reasonable! Those seeds were partially reported to have quite high yields (for alkaloids). I only tracked down the yield 2x and when going the full route it is quite possible that stuff gets lost on its way.

Still it could be of course possible that this product still contains some unwanted stuff.





So about this procedure: The only possible additional contamination that I could imagine could be the tan/brown powder that is left behind at step 5 when doing a hot xylene extraction on the freebase goo. While extracting more and more Bufotenin from the goo, it will at some point go from goo to solid powder. So still it could be that this is just more Bufotenine or that this could be degraded Bufo (it will always degrade a little bit at 140 °C when doing this step or re-x the same way). So no idea if that remaining stuff is a contamination, I never checked it. But that would probably be the only thing that you could still migrate into your product.

Because this stuff is also received through salting, it means that it could be also an alkaloid, but then it is pretty weird that it does not even dissolve in boiling xylene.

Now it could be possible to do a TLC on your product and see if you only have 1x spot. Whatever is a solid brown remaing must also give a spot on TLC. So if it might be also in the product of the shorter TEK, it would be trackable with this.

Regarding your picture this is still pretty much the Bufotenine colour, my Bufo Benzoate was also brown and not white. So just from colour everything is still pretty fine.




Now going faster ending with the salting step would make this TEK easier and also without the need of heating Xylene to such high temperatures. Still I would say a Naphtha defat at the beginning should be done, because these seeds are said to also contain some DMT and 5-MeO-DMT. I believe the amount is super low (I never got clouds when salting the Defat-Naphtha), but it might be good to just know that you 100 % dont accidentally get like 3-5 mg 5-MeO when you go for a big 20 mg "Bufo" Dose. Content of that other Alkaloids will anyways be really low, so it might be better to just exclude them completely for convenience.

As long as we dont know what is the remaining brown powder there could be 2 options

1. = more polar Alkaloid, that does not dissolve in Xylene
Would be pretty unlikely, what could be more polar than Bufotenine? Then to definetly get rid of this a boiling Xylene separation would be mandatory, but maybe it does not even make problems when vaping

2. = instead just some trash from the extraction that made its way over / degraded Bufotenine
This would be more likely and this could be then easily removed by doing a re-x of the Bufo Benzoate in IPA or maybe even EA (because in IPA maybe quite a lot is lost).

An easy way to find this out would be doing the regular TEK with the hot Xylene extraction, then whatever remains at the end is dissolved in Acetone + Benzoic Acid added. If no precipitation is coming, then it is just # 2.
I could buy some more seeds, but now I wanted to not buy any ethnobotanic stuff anymore

Now wrote at the first post that it might be also fine to just go the short route and added a link to the wiki page that _Trip_ was writing

I agree with the defatting step could clean the color if not an extra acetone or EA clean at the end could work too.

I've reinstated the tek for now. Would love to hear more feedback on activeness of the crystals when you're up to explore it further Woolmer. Regardless it sounds promising.
I think lab testing would really bring this home and give us a good idea of what's exactly being yielded. I've left the disclaimer on the wiki page, 'still pending lab results'. I'll see if I can get a hold of more material for testing.

CIALO tek anyone?

So I wrote in regards of Woolmer that the tan colour seems just like what I had observed for Bufo Benzoate. But then I again read your wiki article that shows super nice clear crystals of Bufo Benzoate. That would then make up the question why seems in our case Bufo Benzoate be more of a dirty tan opaque powder instead of your crystal clear beauty crystals? Actually expecting a pure product the nice pictures in your TEK look much more of a reasonable candidate for a pure product. And therefore I believe what you actually have received might be the true Bufo Benzoate instead of the dirty stuff that we have obtained.

The actual difference is:

I took some Bufo Freebase and converted it it Bufo Benzoate in the minimal amount of liquids to maintain minimal solubility. Woolmer took EA and then evaporated it further down. That means both our products were crystallized at pretty harsh conditions, while you crystallized your Bufo Benzoate straight from the extraction liquid. Therefore I am sure your conditions were much smoother, potentially resulting in a slower and therefore well-ordered crystallization.

So while I was thinking Bufo Benzoate would most certainly be just the same ugly brown low-crystalinity solid as Bufo Freebase itself it might be just a product of a truly forced crystallization.

So all bla bla aside when I was feared that a precipitated Bufo Salt from Acetone might still hold back some higher-polarity gunk that needs boiling Xylene RE-X it might be evaded by your crystallöilzation inside of Acetone with Benzoic Acid within the original extracted Acetone. The speed will be slower (no super-high concentration), but therefore the chance of incorporating gunk is highly minimized. This was the biggest flaw that I could seek when directly going for the salting, but at the same time I argued it might be highly low-probability that either HIGHER polarity alkaloids are the source of brown gunk (which one??) or other fats are carried over.

So actually going slower on the crystallization might avoid these 2 problems at all (using benzoic instead of fumaric). Therefore it could be quite plausible that your idea of salting straight with benzoic will precipitate the Bufo quite pure, making your super nice clear crystals probably be just pure Bufo Benzoate.

As before it would be super easy to confirm this theory by doing TLC as Bufo is pretty polar and moving quite apart from other alkaloids (but still only roughly at 50 % when doing Methanol TLC). But if there would be any other impurity it should give a 2nd spot, which I highly doubt when looking at these crystals.

It would be cool do to your TEK and collecting the crystals, checking their weight and then observing what happens if you evaporate down the Acetone to 20 % of its volume. If the Bufo Benzoate seems to be pure, thats already a great thing and if not much more will precipitate along the way to 20 % (meaning solubility of Bufo Benzoate in Acetone is low, unlike DMT Benzoate) then your new TEK is definitely the way to go - also regarding it produces the directly smokable-desired product of this Alkaloid.

I wish I had more material to help further, regardless I'm still weary after my little lab sample mix up.

But I think getting woolmers sample lab tested will be the decider as to how viable this acetone route is. I agree with what your saying and like the idea that it could be refined further, (pending results).