Freebase/Salt yield question

[Pup Tentacle]

I just finished my first d-limo...FASW extraction and have a nice little pile of mostly dry dirty DMT fumarate. I'm about to use boilinghot IPA to clean it up, but I'm curious about the different in weight of yields between freebase and salts.

If I know the yield of my bark in % (as far as freebase goes), what can I expect the fumarate yield to be? Is there a simple multiplier that will give me a ballpark estimate of what to expect?

Thanks for he help

 

[endlessness]

hmmm hard to say.. Theoretically 76% of dmt fumarate should be dmt, but even with reasonably pure (apparently) dmt fumarate, when converting, I had around 50% freebase... If its dirty, expect more than half loss, maybe significantly more..

Can I suggest something? Try two different methods of cleaning up your dirty fumarates to compare, dont do everything one way. Maybe for example with half of it, try this method: Cleaning up dirty fumarates - FASA/FASI/FASW - Welcome to the DMT-Nexus

and with the other, do your IPA re-x.. or whatever other method you want to compare.. and please share the results there, good or bad.. And take pictures if you can!! Thanks

 

[ChemisTryptaMan]

You need to look up the molecular weight of DMT Fumarate, or calculate it yourself based on the molecular formula. Then you need to look up the molecular weight of DMT freebase, if you divide the mass of the fumarate that you have by its molecular weight, then multiply by the MW of the freebase, that should be what you expect to yield as a freebase. Good luck in getting those Molecular Weights, they are very easy to calculate if you cant find them, just remember that there are two fumarates per molecule of DMT in the fumarate. The molecular weights of fumarate and DMT I'm sure you will find with simple searches.

 

[ChemisTryptaMan]

The molar mass of DMT is 188.269 grams per mole. Fumaric Acid weighs 1167.07 grams per mole. Fumarate is Fumaric Acid minus two protons(hydrogens). SO that would make two fumarates weigh 227.824. Add that to the Molar mass of DMT and you get 416.093 grams per mole as the molar mass of DMT Fumarate. Now If you divide the MW of the freebase by this number you will have the multiplier your looking for. The value comes out to 0.452469. Hope this helps, just multiply the weight of your fumarate by that number and that is what you should get in freebase(assuming its pure) any impurity will lower the value even further.

 

[endlessness]

Quoting our wiki:


"Freebase DMT has a molecular weight of about 188.269. Fumaric acid has a molecular weight of 116.07. DMT fumarate has a molecular weight of about 492.608 (DMT + fumaric acid + DMT) " So DMT comprises of 76% of the weight of DMT fumarate.

But, fumaric acid being a diprotic acid and if pH isnt carefuly taken when salting, things may get more complicated than that and its hard to know the amount of fumaric acid involved and the fumaric acid excess that may be there, or so does benzyme say. Im not knowledgeable enough to discuss it, but regardless, whatever DMT is there, you can retrieve it, so it doesnt matter much in this case

 

[ChemisTryptaMan]

Sorry endlessness, didn't realize you had this one already. When I had opened the page it was before you responded and so I didn't see your response until after. Essentially the same answer though, the conversion factor I gave was right around 50% as well.

 

[ChemisTryptaMan]

I believe it's two fumarates per DMT, not the other way around. Am I wrong about this?

Also, the weights of these molecules are so high that the question of whether they are protonated once, twice, or not at all will have less than a one percent effect on the weight so it really wouldnt be significant.

 

[endlessness]

hmmmm something is wrong there, the calculations come out differently... you say 0.45, wiki calculation says 0.76. How do we solve this, where's the mistake?

 

[ChemisTryptaMan]

hmmmm something is wrong there, the calculations come out differently... you say 0.45, wiki calculation says 0.76. How do we solve this, where's the mistake?

The mistake was just that you had two DMT's per fumarate instead of two fumarates per DMT. a very easy mistake to make. Unless it was me who made the mistake and your had the formula right. Either way there is a correct answer in here somewhere. Sorry if I'm wrong and caused confusion, but my logic in showing how to calculate the conversion was correct if there is ever a need to do a similar calculation.

 

[Pup Tentacle]

hmmm hard to say.. Theoretically 76% of dmt fumarate should be dmt, but even with reasonably pure (apparently) dmt fumarate, when converting, I had around 50% freebase... If its dirty, expect more than half loss, maybe significantly more..

Can I suggest something? Try two different methods of cleaning up your dirty fumarates to compare, dont do everything one way. Maybe for example with half of it, try this method: Cleaning up dirty fumarates - FASA/FASI/FASW - Welcome to the DMT-Nexus

and with the other, do your IPA re-x.. or whatever other method you want to compare.. and please share the results there, good or bad.. And take pictures if you can!! Thanks

I will definitely try both methods, but I think I'm just going to use the IPA on this batch... time is of the essence as I am headed out into the forest for 5 days with a pile of druids and have to have this ready by Thurs morning. My next batch done with d-limo, I'll split in 2 and try both methods on, compare, photos, the whole 9 yards.

Thanks for the input!

Blessings,
Pup

PS: it smells like, if I don't clean it up, that it'll be like snorting a firey orange creamsicle :/

 

[endlessness]

Im pretty sure that was right, though, given fumaric acid's structure, wouldn't it bond to two dmt molecules, and not the other way around? We need some chem expert to jump in.

 

[ChemisTryptaMan]

I actually am a chemist and you were right about the structure, I had it backwards. That changes the conversion to 38.2%*2=76.4%

Sorry for the mistake. Thanks for correcting me.

 

[endlessness]

Alright, now the question is, in certain pHs, isnt it possible that only one dmt molecule binds to the fumaric acid?

How do we go about calculating this or finding out at what pH this happens?


(Pup, thanks for planning the experiments, sorry to derail the thread )

 

[ChemisTryptaMan]

This would be very difficult because the pKa of the first proton to be removed is 3.03 and the pKa of the second is 4.44. With the pKa's being so close, there is no pH where there is a significant amount of singly protonated fumaric acid. At pH around 5 you would start to see singly protonated without seeing any completely protonated. At pH's between the two you would have the fumarate in all three forms.

Edit: I forgot to mention that at pH 5 while you would have singly protonated fumarate, most of the fumarate in solution would now be completely deprotonated. also fixed the paragraph, should have said protonated at the end there.

Edit2: If you start at pH 0 and work your way up. around 1 you would have 1% lose the first proton, 2 10%, and 3 50%. However the second proton would be 1% removed at a pH of 2, 10% at pH 3, and fifty percent at 4.5. So you're right this is a tricky question. There is no way to make singly protonated fumarate the primary form in a solution. You could isolate it as a solid if you could find the right cation to make it insoluble in the solution your working with, but it would have to be selective for the singly protonated form.

 

[ChemisTryptaMan]

Alright, now the question is, in certain pHs, isnt it possible that only one dmt molecule binds to the fumaric acid?

How do we go about calculating this or finding out at what pH this happens?

The answer lies in the pKa's of the removable protons. When pH=pKa, the molecule exists in 50% each form for that site. One pH unit above will mean 90% is deprotonated, 2 pH units 99% deprotonated, 3 pH units 99.9%, and so on. Hope that clarifies things a little.

 

[endlessness]

Thanks for the answers

Now im curious what is the pH of a fumaric acid saturated water solution, which is what is often used for salting limonene.

More complicated would be to measure the pH of FASA or FASI, im not sure if pH pens will work well if acetone/IPA are dry, plus, Im not sure how this whole pH thing would work once you mix FASI/FASA to a complex mixture of solvent, alkaloids and impurities such as limonene from mimosa pulls.

Not that it matters much though, because in the end what matters is that it works, and works very well, but im curious about the theoretical aspects of whats happening when we do it.

 

[benzyme]

Alright, now the question is, in certain pHs, isnt it possible that only one dmt molecule binds to the fumaric acid?

How do we go about calculating this or finding out at what pH this happens?

The answer lies in the pKa's of the functional groups. When pH=pKa, the molecule exists in 50% each form for that site. One pH unit above will mean 90% is deprotonated, 2 pH units 99% deprotonated, 3 pH units 99.9%, and so on. Hope that clarifies things a little.

fixed.
diprotic acids like fumarate only doubly bind DMT at certain concentrations, i.e. pH < 3