san pedro alkaloids part 2

[burnt]

I have compiled the following information that I made up in my spare time for educational purposes. The purpose of this theoretical lesson is to discuss the identification of alkaloids in san pedro. We will discuss what happens after rinsing crude mescaline-HCl isolated by A/B (see part one).

Mescaline-HCl (lets just make up number 900mg) rinsed 2x with 10ml acetone. Rinses made cold at -20 C. decanted off acetone. Rinsed one time with 10mL IPA and did the same thing as with acetone.

Acetone and IPA rinses were kept separate. They were dried. The acetone residue was a deep dark red / brown oily crystally material. The IPA rinse looked like mescaline HCl crystals but more brown. Mescaline HCl after rinsing was an off white color.

All material was analyzed by GC-MS in the same manner as in part one.

Results:

Acetone rinse material (~95 mg): Had the same chemical profile as the crude mescaline except a major difference in ratios between compounds. Instead of mescaline being massively more abundant in the crude HCl mixture the acetone rinses contains an almost 2:3 ratio of 2,4DMPEA to mescaline. Also the other two alkaloids are more abundant relative to mescaline but they are minor compared to others.

IPA rinse material (~25mg): Also had the same chemical profile but mescaline was much more abundant again.

Cleaned mescaline HCl (700mg): Very pure. No impurities detected but probably with more concentrated injections some could be found. But this can risk overloading the instrument and is not necessary for this discussion.

Explanation:

More detailed ratios cannot be given with this kind of detector. An FID detector would give more accurate ratio comparisons and a quantitative comparison could be made. Perhaps this is an area for future educational theoretical experiments. However it is clear from the results that by rinsing with acetone and IPA nearly all impurities are removed. However so is mescaline. This could result from a number of reasons:

1- Imperfect decantation. Meaning some tiny crystals were poured into other glass vessel on accident.

2- Mescaline hcl partially dissolves in both solvents. This could result from water being present in the solvents. All solvents were of analytical reagent grade but sometimes even then solvents can suck up moisture from the surrounding environment. This water could have increased solubility of mescaline hcl in the solvents. Or mescaline hcl is partially soluble in them as would be expected that at least some dissolves

The question now becomes how to minimize mescaline HCl loss at clean up steps? Decant very carefully. Perhaps acetone and IPA rinses should be kept cold -10 or 20 C for many hours to precipitate more mescaline hcl that dissolved. Use minimal solvent for rinses. Perhaps a different solvent might be more appropriate as well. Maybe ethyl acetate its a bit more non polar.

Anyway if one does a very rough calculation (these numbers are not accurate). If 95mg of acetone rinse is two thirds impurity (roughly) that means about 60 mg impurities present and another 20 mg's (lets assume ratio was 1:5 just to make math easier) from the IPA rinse means about 40 mg's of mescaline was dissolved by rinsing solvents. This can probably be minimized by above said methods and will most certainly vary depending on technique. We should also note that there is a net loss of something. 95 + 700 + 25 mg = 820mg. Thats 80 mg of missing mass. So in total roughly 130 mg of mescaline lost from original 900mg. This could result from the original material not being completely dry which messes up original weight, spillage(?), or an undetectable impurity that seems to be removed by rinsing. This undetectable impurity might not dissolve in toluene and thus may be lost in sample preparation for GC-MS. It might also evaporate away with acetone or IPA. Its difficult to say without more tests. More quantitative analysis and perhaps this missing mass would be completely accounted for and its all just from numbers that are off who knows.

In part 3 and the final part of this short educational series will be a discussion about the composition of the exhausted plant material. In other words whats left over after completely emptying the cactus of mescaline.

 

[w0mbat]

Acetone and IPA rinses were kept separate. They were dried. The acetone residue was a deep dark red / brown oily crystally material. The IPA rinse looked like mescaline HCl crystals but more brown.

I take it that these observations were made at room temperature? My friend told me that his dark-brown impure mescaline acetate was sticky at room temperature, but storing it at below-freezing temperatures turns it into a nice powder. Seems that one of the alks melts at room temp...

In your opinion, could dissolving some of the crude mescaline HCl in boiling IPA and then freeze-precipitating have produced equally pure (or more pure) crystals, relative to the methods you used? Do you think this freeze-precip from IPA would entail more or less loss?

Thanks for contributing this theoretical knowledge!!

 

[Crystalito]

Burnt, for one i like the research hypothesized here and in the equivalent part 1.Its not often that original research is presented at forums ,mostly its source reiteration.

Perhaps acetone and IPA rinses should be kept cold -10 or 20 C for many hours to precipitate more mescaline hcl that dissolved. Use minimal solvent for rinses. Perhaps a different solvent might be more appropriate as well. Maybe ethyl acetate its a bit more non polar.

For how long was the acetone/IPA wash hypothetical kept at those temperatures?

I was also thinking...If one is looking at reduced polarity of a solvent, why not take advantage of "chromatograpy" trick where one by mixture of solvents can more or less adjust solvent polarity? Hmmm maybe one could dissolve in acetone small quantities of a non-polar solvent?


Just some ideas on the table, i think the "hard for many" part (analysis,equipment) is already nicely given in this thread.

 

[w0mbat]

I was also thinking...If one is looking at reduced polarity of a solvent, why not take advantage of "chromatograpy" trick where one by mixture of solvents can more or less adjust solvent polarity? Hmmm maybe one could dissolve in acetone small quantities of a non-polar solvent?

This is more or less what SWIM is trying to do with mixtures of IPA and d-limonene. He has had some limited success so far but research is still ongoing, I hear.

 

[burnt]

Seems that one of the alks melts at room temp...

Yes or the mixture causes them to not be able to form crystals.

In your opinion, could dissolving some of the crude mescaline HCl in boiling IPA and then freeze-precipitating have produced equally pure (or more pure) crystals, relative to the methods you used? Do you think this freeze-precip from IPA would entail more or less loss?

It might. Also rinsing with cold acetone might do the trick too.

For how long was the acetone/IPA wash hypothetical kept at those temperatures?

lets say for this experiment not long at all. 10 minutes or so.

I was also thinking...If one is looking at reduced polarity of a solvent, why not take advantage of "chromatograpy" trick where one by mixture of solvents can more or less adjust solvent polarity? Hmmm maybe one could dissolve in acetone small quantities of a non-polar solvent?

this could certainly help. but there are many combination's. it could be done very systematically to minimize experiments needed though.

 

[kemist]

A good experiment, but Ilpt think is not much help for us as your swim using a/b and toluene and NaOH as base while many swimmers and ilpt using lime and limonene. Some alks could be just too fragile and breaking down in naoh enviroment. Ilpt using minimum water, less then the tek suggesting and calcium hydroxide so there isn't plenty of OH iones floating around. Just a monkey wrench though.

 

[69ron]

Thanks a million for posting this thread Burnt!

Kemist makes an important point about others using different extraction procedures. With each different extraction procedure, there’s likely to be a variation in final results.

For example, in an A/B, the phenolic compounds in peyote are soluble in water, unless sodium carbonate is used (or some other non-hydroxide), according to the tests I’ve seen. So the base used will affect the results. Also, the solvents used would affect the results as well. This is the nature of extraction. They are so many possible variations that will affect the final results. But that aside, these results are not going to vary that much. But there could be a few alkaloids missing from the test that were excluded by the extraction procedure used. Or other factors.

What’s an important finding is that the final product appears to be pure mescaline. This matches SWIM’s personal experience with the final product. He cannot tell the difference between it and pure synthetic mescaline. If there are impurities, they are at such small amounts that its not detectable in the trip for SWIM and so they do not matter at all for SWIM.

Now considering the acetone and IPA washes remove the same set of alkaloids, why is it that you cannot clean mescaline as well with just acetone? SWIM has tried and it remains smelly. But after a the IPA washes the smell is gone. I wonder, could you just use IPA alone to get the same purity level?

 

[w0mbat]

What’s an important finding is that the final product appears to be pure mescaline.

Indeed - any chance you could include a melting point analysis in your next theoretical report, burnt?

Now considering the acetone and IPA washes remove the same set of alkaloids, why is it that you cannot clean mescaline as well with just acetone? SWIM has tried and it remains smelly. But after a the IPA washes the smell is gone. I wonder, could you just use IPA alone to get the same purity level?

This is the $64 question for me. Removing acetone from the picture makes such a big difference in terms of safety, risks of contaminants, and accessibility.

 

[burnt]

A good experiment, but Ilpt think is not much help for us as your SWIM using A/B and toluene and NaOH as base while many swimmers and ilpt using lime and limonene. Some alks could be just too fragile and breaking down in NaOH enviroment. Ilpt using minimum water, less then the tek suggesting and calcium hydroxide so there isn't plenty of OH iones floating around. Just a monkey wrench though.

True. But many things will also cause variation such as the source of plant material etc. Numerous repeated experiments under many conditions with lots of different and same batches plant material could of course provide a broad overview. Thats quite a task though.

Now considering the acetone and IPA washes remove the same set of alkaloids, why is it that you cannot clean mescaline as well with just acetone? SWIM has tried and it remains smelly. But after a the IPA washes the smell is gone. I wonder, could you just use IPA alone to get the same purity level?

Yea the smell is weird and not really sure what to make of it. But yes IPA can probably be used to get similar purity but there might be more loss of mescaline unless decanting is perfect. If skipping acetone and going to IPA it might be best to do a full on recrystallization instead of just rinsing. Perhaps a mixture of IPA and acetone would work. Maybe only a small amount of IPA like 10% could be enough to remove whatever the smell is.

Its tough to say for sure how soluble the other alkaloids were in IPA because the ratio was much less in the final rinsing. But this could be purely because acetone was used first. Would be interesting to see the reverse.

This is the $64 question for me. Removing acetone from the picture makes such a big difference in terms of safety, risks of contaminants, and accessibility.

Acetone is very safe. But yes if the sources of acetone are not perfect then its a different story. Especially if its not water free. But one solvent is always cheaper then two so yea its worth knowing.

 

[w0mbat]

Acetone is very safe. But yes if the sources of acetone are not perfect then its a different story. Especially if its not water free. But one solvent is always cheaper then two so yea its worth knowing.

For me it was mostly that few people have access to anything better than technical grade acetone. Use that and then you've got to distill it (or worry about heavy metals, etc in your extract), and distilling it is almost of costly and time-consuming as the rest of the extraction procedure. SWIM just really likes knowing his products are as safe as he could possibly make them.

 

[burnt]

^^Good points. SWIM doesn't know the impurities in technical grade acetone. Best to be safe.

 

[kemist]

How come no MMDPEA was detected. Maybe swim should try different extraction method (semi dry STB) and try to detect alks differently :?: