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Why is lime the most common base used in snuff and quids?

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69ron

69ron

Rising Star
Why is lime (calcium hydroxide) the most common base used to increase the activity of Betel quids, Yopo/Vilca snuff, Virola snuff, as well as coca leaf chews. Why isn’t another base used? Lime is quite irritating and has a high pH of 12.4. It actually leaves chemical burns after being used. So why has lime become the base of choice for helping absorb these drugs?

Here’s a quote form one seller "Most people don’t realize that edible lime needs to be mixed with the Virola resin to make snuff active". Why? Why not some other base that isn’t so caustic? It there some unique quality to lime that favors it’s use?

Why not use a base like calcium carbonate? It doesn't burn as much. Why lime?
 
Man has had lime ever since he learned how to harnes fire. If your living in some hunter gathering community without access to science and scientific knowledge, your going to use whats to hand. Since lime is a by product of your average simple camp fire, it seams resonable to be using it. The tradition continues because nobody is being encouraged to think differantly.
 
I've wondered this as well... kind of in conjunction with your other question, about the ammonia smell. The ammonia smell issue is curious indeed... I hadn't realized it occurs with pure alkaloids as well. All the more curious. It seems like ammonia being freed would indicate decomposition into something that isn't likely to be active...

I'd assumed that the reason for lime being the most popular base in coca and betel quids was simply because it's so alkaline; that way only a small amount of the lime paste has to be used. The changes that seem to occur in the yopo material when lime is added seem to indicate such a simple explanation might not be the case.

And for that matter, I don't actually know that baking soda is as effective as lime for these other quids. In my experience with betel, adding baking soda did not seem to significantly alter the psychoactivity of the material. I'll be getting some lime within a few days to test whether these principles seem to apply generically to other alkaloids as well. (Fortunately consuming betel is still legal in the US, even if its sale for human consumption has been banned)

I suspect that if there is in fact a reason for lime's popularity in snuffs, it may be exclusive to particular chemicals. I read a reference on bufotenin recently that said something about the potential for the alkylamine to hook back onto the 5-position in a ring structure, this being called dehydrobufotenin (looks exactly like the product you proposed on Drugs-Forum in the post where SWIY's results can't seem to be duplicated). So there may be something to that. But I'm having trouble finding which reference that info was in; when I run across it again, I'll be sure to post it.

Also, lime may not be quite as important as we make it out to be these days. In the ethnographic literature, the use of ashes seems to be about as common as calcined lime from snail shells. And there are a few reports of it being prepared without the use of any alkaline agent (as this was remarked on specifically, it can't have been an error of omission).

Very good question.
 
not really sure why lime is more popular but swim has noticed that works better than sodium bicarbonate when making yopo snuff. he's tried it multiple time and it seemed not to work as well.
 
endlessness said:
wouldnt the whole calcium bufotenate deal be an explanation for it? (in the case of yopo)

as for the ammonia smell, could calcium bufotenate have some sort of similar smell?
Click to expand...

Calcium bufotenate is just a theory at the moment... The person who first advocated for it (that I'm aware of) used multiple screen names to try to drum up enthusiasm with positive experience reports... the second being Erik Smyth (Erik's myth?) And on top of that, they never gave any indication that they'd actually characterized the material they were calling calcium bufotenate; for all we know, it could easily have been freebase bufotonin. The chemical reasoning makes sense, but the duplicitousness of the one proposing the theory makes me suspicious, especially that he posted it as fact all over wikipedia (i've removed all references I found).

But no, the ammonia smell wouldn't be explained by calcium bufotenate; the amine stays entirely intact.
 
Entropymancer said:
endlessness said:
wouldnt the whole calcium bufotenate deal be an explanation for it? (in the case of yopo)

as for the ammonia smell, could calcium bufotenate have some sort of similar smell?
Click to expand...

Calcium bufotenate is just a theory at the moment... The person who first advocated for it (that I'm aware of) used multiple screen names to try to drum up enthusiasm with positive experience reports... the second being Erik Smyth (Erik's myth?) And on top of that, they never gave any indication that they'd actually characterized the material they were calling calcium bufotenate; for all we know, it could easily have been freebase bufotonin. The chemical reasoning makes sense, but the duplicitousness of the one proposing the theory makes me suspicious, especially that he posted it as fact all over wikipedia (i've removed all references I found).

But no, the ammonia smell wouldn't be explained by calcium bufotenate; the amine stays entirely intact.
Click to expand...

isnt it possible for someone of you science ppl with lab connections to run a supposed calcium bufotenate through some sort of chromatography test and see if it is true?
 
I saw a post by 69Ron on another board where a SWIM tried to form the calcium salt from freebase bufotenin... the results of that particular experiment argue against the calcium bufotenate idea. But apparently there are issues with the reproduceability of results.

My suspicion is that calcium bufotenate is a myth. There is evidence that something happens when lime is used, but if it were as simple as calcium bufotenate, I think we'd know by now.
 
is it possible that the high ph of calcium hydroxide causes lesions that make it easier to absorb into the blood stream?
 
It definitely causes lesions. If you put enough lime in your mouth for a few minutes, it will cause damage to your mouth that you can feel the following day. However, sodium carbonate causes more damage, but it’s pH is lower. Lime is pH 12.4, and sodium carbonate is pH 11.6 according to some sources. Lime is much less water soluble than sodium carbonate, so that’s probably why sodium carbonate burns more.

Maybe it’s the lack of solubility of lime that’s important, as well as the high pH. It won’t all dissolve quickly, instead it stays for a long time.

Lime is actually a very powerful base, it is not a weak base as some have stated. Its limited solubility in water keeps it’s pH at a possible maximum of pH 12.4. Gram for gram, sodium hydroxide and lime are pretty much equal in their strength. In order to bring a solution to pH 12.4 with lime, you need 0.1 g/100 ml, which is the most lime water can hold. According to my pH calculator, the same amount of sodium hydroxide will also give a solution of pH 12.4. But because more sodium hydroxide can be added it can bring the pH even higher than calcium hydroxide can.
 
Entropymancer said:
I suspect that if there is in fact a reason for lime's popularity in snuffs, it may be exclusive to particular chemicals. I read a reference on bufotenin recently that said something about the potential for the alkylamine to hook back onto the 5-position in a ring structure, this being called dehydrobufotenin (looks exactly like the product you proposed on Drugs-Forum in the post where SWIY's results can't seem to be duplicated). So there may be something to that. But I'm having trouble finding which reference that info was in; when I run across it again, I'll be sure to post it.
Click to expand...

Hey Entropymancer, take a look at this page:

pubchem.ncbi.nlm.nih.gov

7,7-Dimethyl-2-aza-7-azoniatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraen-9-olate

7,7-Dimethyl-2-aza-7-azoniatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraen-9-olate | C12H14N2O | CID 5316436 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.
pubchem.ncbi.nlm.nih.gov pubchem.ncbi.nlm.nih.gov

That shows the structure of dehydrobufotenine.

Here is the page for bufotenine:

pubchem.ncbi.nlm.nih.gov

000487934

Substance record SID 153516 for 000487934 submitted by ChemIDplus.
pubchem.ncbi.nlm.nih.gov pubchem.ncbi.nlm.nih.gov

Dehydrobufotenine exists in nature and is commonly found where bufotenine is found.

Maybe dehydrobufotenine is being made when bufotenine is mixed with lime and water for a few hours? Maybe at the high pH of 12.4, the H is pulled off bufotenine’s HO at the 5 position, and then the amine side is attracted to the O, but can’t reach it and instead attaches to the indole ring? Is that even possible?

I can’t find an XlogP for dehydrobufotenine. I’m sure its solubility is very different from bufotenine. It might be very lipid soluble.

I ran across a report that states that dehydrobufotenine lacks the pressor activity of bufotenine. I can't find anything that talks about hallucinogenic activity for it though. But that doesn’t mean its not hallucinogenic.

Here's some interesting quotes from Bluelight members concerning dehydrobufotenine:

one possibility is that adding lime and heating causes the formation of dehydrobufotenine a three ring compound where the amino tail ends up joined back to the phenyl ring, this supposedly is active. I am not certain how dehydrobuftenine arises it is quite common in analysis, I think it might be heat and base.
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There has been plenty of confusion regarding dehydrobufotenine which is an extraction artifact of bufotenine and which is believed to be psychoactive rather than a violent poison
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Here's a quote from the book TiKHAL in #19. 5-HO-DMT:

Dehydrobufotenine: There is a covalent bond formed between the dimethylated nitrogen atom and the indolic 4-position, by the theoretical removal of a molecule of hydrogen. It is no longer a simple tryptamine but as it is a commonly found component of the chemistry of several toads, and a few giant reeds as well, it is included here. It is, by definition, a quaternary amine salt. The original structure assigned it was that of a vinylamine (with the loss of a hydrogen molecule from the alpha/beta chain positions. This was shown to be incorrect.
Click to expand...

So according to TiKHAL, it is theorized that removing hydrogen, as would happen when bufotenine is exposed to pH 12 and above, is what causes dehydrobufotenine to form. If this is right and dehydrobufotenine is indeed more psychedelic than bufotenine then this would sure answer the mystery of Yopo! It looks pretty logical to SWIM.

It seems like a lot of people are thinking this happens.

Can anyone test this? All you should need is to put pure bufotenine in pH 12 solution for maybe a few hours. Maybe the reaction also requires heat (the natives usually heat the Yopo both before and after mixing it). Then when done have the results analyzed to see if indeed dehydrobufotenine is created.
 
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