Oops...Fumaric Acid into Naphtha + Alkaloids Solution

[Karnov]

So, if one were to add fumaric acid to naphtha one knew to have alkaloids in solution, what would happen?

My friend didn't feel like freeze precipitating the naphtha and having to evap it, so he dumped a couple of grams of fumaric acid into ~ 500 ml naphtha + alkaloids.

What would be the best course of action at this point to retrieve the alkaloids?


Thanks.

 

[endlessness]

Did you add it dry?

Your fumaric acid for sure didnt dissolve, but the question is whether your alkaloids are able to be protonated with your fumaric acid and precipitate when fumaric acid is added dry to naphtha. Did you mix it well or just poured it in? Where the quantities that precipitated the same as what you added, or does it seem like more powder?

Now you would have either excess fumaric acid at the bottom and all DMT in the naphtha, or some DMT also precipitated as fumarate together with the fumaric acid, or all dmt precipitated together with fumaric acid.

What you can do is filter the precipitation/undissolved solids. Store it. Then wait a couple of days to see if any DMT fumarate starts late-precipitating from the jar.

You can wet mix the solids with sodium carb and bit of water, let it dry completely and pull with IPA and do FASI or with acetone and do FASA to precipitate clean fumarates (if the solids contain alkaloids and not just excess fumaric acid... )

With the naphtha, you can evaporate it or freeze precipitate and see if you get anything out of it. Or salt with FASW to retrieve any potential alkaloids in it. And then base the FASW for water precipitation of freebase DMT or evap it for fumarates, if alkaloids are there.

 

[Karnov]

Thanks for all of the info!

Yes, fumaric acid was added dry to the naphtha. However, this mixture was put into a warm water bath and agitated several times. Initially, the "precipitate" looked like balled up wet popcorn--the result of adding dry powdered acid to the naphtha.

However, after very warm water baths and swirling, the fumaric acid took on the yellow color of the naphtha (which had been used several times for past pulls--graduated on to heptane and had just left it in a glass jar). It looks as though some DMT has precipitated out, given this color change. Also, the precipitate/excess fumaric acid began to disperse into individual grains rather than clumps.

Question: could xylene be added to dissolve the fumaric acid excess and then it would be clear what was DMT precipitate?

What is the ratio of fumaric acid to water to make a solution, btw?

Thank you.

 

[Karnov]

On a whim, about 75ml of water (to put the fumaric acid in solution) was added to the Naphtha and Fumaric Acid solution. Now there is a clear separation between a yellow-tinged water solution with clumps of some kind of solid, and a white layer of solids floating in the naphtha layer. Swirled vigorously a few times.
Will wait to see if any changes occur.

 

[benzyme]

Question: could xylene be added to dissolve the fumaric acid excess and then it would be clear what was DMT precipitate?

What is the ratio of fumaric acid to water to make a solution, btw?

xylene isn't going to dissolve fumaric acid because it's a completely nonpolar solvent with no hydrogen-bonding interactions.

you'd also have to look at the pKa's of fumaric acid, because it is polyprotic (it's a dicarboxylic acid).

two sites will be your fav for chemistry, Wolfram|Alpha: Making the world’s knowledge computable and Chemicalize - Instant Cheminformatics Solutions

enter a search for dimethyltryptamine in chemicalize, and search manage calculations for protonation, pKa. look at the chart carefully, to see where 99% of the molecule is in a protonated state.
then do the same for fumaric acid.

in wolframalpha, you can look up a concentration (or pH) of fumaric acid, it will list a method of preparation to get that conc./pH.

 

[Karnov]

Thanks.