A problem while performing Bufotenine extractions is an instability of Bufotenine in high pH media. It seems it gets destroyed in very alkaline conditions, while being rendered inactive. It is always just labeled as some Oxidation process and this may only occur to the phenolic OH. What I could think of would be the following reaction:
Here you can see: The phenolic proton is "acidic" with a pKs of ~ 10 and can be deprotonated by strong bases. This requires a more alkaline environment than the regular freebasing step of the amine - which is pH 9-10 for most alkaloids. Using very strong bases like NaOH is therefore not advised when handling Bufotenine, as it will most likely destroy the compound, hence every TEK recommends to only use soda (Na2CO3).
Now across the internet you can find some quotations of "Calcium-Bufotenate". This would be a salt formed when deprotonating the phenolic OH in conjunction with the counter ion Calcium. In theory one would easily achieve this by a reaction of 2x H-Bufotenine and 1x Ca(OH)2 (= Lime) and then evaporating the 2x H2O to give Bufotenine-Ca-Bufotenine aka. Calcium-Bufotenate:
Ca(OH)2 is exactly inbetween Na2CO3 and NaOH in terms of base strength. Therefore it should be strong enough to convert the phenol, but not as strong to cause immediate decomposition, like NaOH is reported to do. Here is some stuff that you can find about it while browsing the nexus or other sites:
69ron wrote:The problem with using calcium hydroxide is that if left to react for too long,
it alters the bufotenine making it inactive by vaporization, thereby ruining your extract.
If only reacted for a few minutes, it just freebases it, and all is well. However,
the intermediate reaction between freebasing and ruining your bufotenine,
is an extremely nice compound, much better than bufotenine, DMT, etc.
It is the best psychedelic SWIM knows of, but unfortunately to make it requires
that the reaction time be just right. Too little time and the bufotenine is just freebased,
too much time and your bufotenine can no longer be vaporized. I don’t know the optimal time to use.
SWIM tried many tests and could not find a time frame that always worked. What he knows is that
24 hours is too long and converts the bufotenine into a non-vaporizable compound. 15 minutes is
not enough and just freebases it. The time needed is somewhere between 2-6 hours, and seems to
vary every time. The safest reaction time is 2 hours. That seems not to be enough time to get to
the third reaction stage. And if it doesn’t work, and just freebases the bufotenine, and then you
can do another 2 hours and it will usually work.
I HIGHLY RECOMMEND PLAYING AROUND WITH THIS REACTION. When the calcium hydroxide reaction hits stage 2,
the results are nothing short of amazing. But when it hits stage 3 your fucked. So don’t do the reaction
with all of your bufotenine. That’s why SWIM doesn’t use calcium hydroxide for extractions, and uses sodium
carbonate instead. With sodium carbonate there’s no worry about ruining your entire extract, but with
calcium hydroxide there is. I think probably sodium hydroxide would have similar reactions with bufotenine
so it also shouldn’t be used for extraction.
The product of the stage 2 reaction with calcium hydroxide is smokeable, about 1/2 the potency of bufotenine,
has the same duration of effects (2-3 hours), the same onset of effects (2-5 minutes), and same peak (10-15 minutes).
It’s visuals are of a completely different character. It’s more DMT-like, but much nicer than DMT.
It’s extremely euphoric, up there with mescaline in that respect, and completely without side effects.
It has a much milder feel on the body compared with bufotenine. It feels like an entirely different compound.
It’s actually SWIM’s favorite psychedelic (bufotenine is his next), but since it has no name and it’s structure
is unknown, SWIM doesn’t refer to it normally when talking about psychedelics. It is without the “mind fuck” of DMT,
but visually almost identical.
When Yopo is made properly, the effect you get is from this stage 2 compound. It’s very DMT-like,
and you might easily mistake it for DMT, except that the duration is 2-3 hours even when smoked and
it lacks the “mind fuck” of DMT. Also you feel “grounded” with this compound whereas with DMT you can
feel disoriented. It’s like a friendlier version of DMT. I think most people would prefer it over DMT.
SWIM has given some to other friends and they all liked it more than DMT. However, that’s not the case
with bufotenine. Some people like it, some don’t, and some people don’t get much visual effects from it.
SWIM likes them both very much, but prefers the unknown stage 2 compound. It’s more visual and far more
euphoric, and feels more body friendly.
On
Erowid you will find a post reagrding how to produce it:
- Dissolve Bufotenine in a minimal amount of IPA
- Add the same amount of water
- Add some Ca(OH)2
- Let it sit for 2-6 h
- Evaporate everything
- Extract Ca-Bufotenate with Acetone, evaporate
On the other hand you can read the post by
Entropy Mancer, which states that it should be impossible to form it: Ca(OH)2 does not dissolve in water and therefore both compounds will never be in the same phase in contact. This will practically render the reaction speed to 0, making any reaction impossible.
Now I tried to reproduce this myself:
50 mg Bufotenine + 39 mg of Ca(OH)2
In theory to fully transform 50 mg Bufotenine to Ca-Bufotenate, you will need 9 mg of Ca(OH)2 = 0,5 mole : 1 mole Bufo
Now by conducting the procedure mentioned above, one should get a leftover of 30 mg Ca(OH)2, IF Ca-Bufotenate is formed and IF it is soluble in Acetone.
If Ca-Bufotenate is formed, but not soluble in Acetone, then there should be a leftover of 89 mg after the Acetone pull in the end.
IF no Ca-Bufotenate is formed, then 50 mg of Bufotenine should be dissolved, leaving behind 39 mg of Ca(OH)2 after the Acetone pull in the end.
So I let it stirr for 5 h with just a minimal amount of IPA + Water. Afterwards evaporating everything only granted 69 mg in sum, even though the initial material was 50+39=89 mg. The lost 20 mg are exactly the amount of water, that is created upon combining 2x H+ with 2x OH-, evaporated as 2x H2O for every 1x Ca(OH)2.
I threw Acetone on it, stirred it for 10 minutes and evaporated the Acetone.
Weight:Residue, not dissolved by Acetone = 60 mg
Residue, dissolved by Acetone = 8 mg
If no reaction happened, then ~ 50 mg of Bufotenine should be removed by Acetone, which it wasn't obviously.
IF Ca-Bufotenate formed and is indeed soluble in Acetone, then only 30 mg should be left over. No real answer to be given here ...
Now I placed both samples in water (what Acetone pulled over and what it left back) -> nothing dissolved
So either Ca-Bufotenate is not water soluble or no reaction happened (Bufotenine is only slightly soluble in water and Ca(OH)2 nearly not at all).
Evaporation:My freebase Bufotenine that was used melts at ~ 104 °C (literature says 146 °C, still I can confirm I have pure Bufotenine) and starts evaporation at 180 °C. So by throwing both the Acetone-soluble and Acetone-insoluble samples on a hot plate and measuring the Temperature with a IR-Thermometer, I thought I may compare that new stuff's phase transition with pure Bufotenine.
But there is NO phase change. Even at 400 °C the stuff just remains brown powder. Not even a slightest hint to fumes. Then I torched it with a lighter from ~ 3 cm distance. The flame is at max 1200 °C and the samples just started to glow, not releasing any fumes nor melting.
IF Ca-Bufotenate is formed, it seems to have an insanely high melting point / vaporization temperature.
IF no Ca-Bufotenate formed, then of course the Ca(OH)2 has an insanely high melting point, indeed it decomposes instead as per Wikipedia. But still this remainder should consist of mostly Bufotenine and if the Ca(OH)2 inside of that sample is not melting, then the Bufotenine should definetly make any macroscopic change visible.
Left: both samples from that "Ca-Bufotenate conversion", left: Acetone soluble, right: Acetone non-soluble remainder
Middle: Torching the non-soluble remainder with a Butane flame. No visible degradation, just glowing
Right: Mixture of Bufotenine + Ca(OH)2 powder, starting to melt at 105 °C+
So in summary:
Sadly no clue what happened. I cant conform that a new compound was formed that is soluble in Acetone - only 8 mg of theoretically 59 mg was dissolved in Acetone.
But also in case there was no reaction and both Bufotenine and Ca(OH)2 are still present as monomolecular, separate compounds, then there should be a distinct temperature where you can observe the Bufotenine melting and evaporating.
To proove this I just mixed 10 mg Bufotenine and 10 mg Ca(OH)2 and mixed it to a homogeneous mixture. Now I placed it on a hot plate and the Bufotenine starts melting at 105 °C+ and it turns dark after 160 °C+ while releasing fumes.
So there must have been a conversion somehow, but whatever came out, it did not show the reported properties of a hypothetical Calcium-Bufotenate and it is not smokable.