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Dry ice to precipitate NMT carbamate out of NP solvent for ACRB extract

Migrated topic.
I was more or less using 'Acacia Confusa Extraction by Yours Truly' by Joshisom, which is an A/B tek tailored to a kilo of AC bark.

The non-yield of the first pull baffles me. Perhaps I didn't heat it up enough after the dry ice treatment? At those temperatures, EVERYTHING falls out of solution. But of course I was measuring the temp. of the solution in the bath. It was around 84 degrees when I pulled it out, which is approx. ambient.

The waiting is over!
The results are in: It worked!

Here's the photo's of Pull 2, 3, and 4:


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It scrapes up quite adequately!

Thanks for your innovation with dry ice.

I was starting to think it was going to be another goo batch, but it crystallized hard on the 3rd day.

The only downside? is my yield: 2.2 grams
I have a feeling I lost a good chunk on my first pull. It was getting late, but I had the dry ice...
I must have made a mistake, as the rest of it went to plan.

Thanks again for your help!



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Arcologist- You have devised the easiest method yet for separating NMT from DMT, yet very few people on the Nexus have taken notice.

Perhaps its politically incorrect to want clean DMT crystals?

Although its fine to extract DMT from MHRB, its anathema to do the same with ACRB.

I think it's silly to let a tree do my thinking for me.

As far as NMT is concerned, if you really want to, you can always extract it out of the carbamate, and adjust the admixture to your hearts content.

Afterall, this is the DMT Nexus, not the NMT Nexus!

Finally, your post should be pinned, so people can easily find out how to separate NMT from DMT.

Aww thanks :) I'm just glad to share the info, I'm surprised no one else thought of it first.

Personally I'd rather have clean crystals, if only for the ease of handling and storage, and to have to smoke less material to break through. However the goo is certainly smoalkeable and works just fine.

As an addendum, I did end up converting the NMT carbamate back to fumarate. At some point I want to bioassay the pure NMT to see what it's like on its own.
arcologist said:
At some point I want to bioassay the pure NMT to see what it's like on its own.
I'm going to use this method on my next acrb extraction so that I can bioassay the NMT on its own. Thanks for some clever thinking!
I noticed that as soon as I placed the dry-ice cooled N.P. solution (naphtha) into the warm bath, it boiled.

What is going on there?

Also, I was afraid that with such sudden swings in temperature (ambient to sub-zero with dry-ice, sub zero back to ambient in the heat bath) the glass would fracture/shatter. The glass held up fine!
Great job. Assuming dry ice isn't too hard to obtain this sounds like a great method that isn't out of reach for most. I think I'm going to start sniffing around for some.
DonPeyote said:
I noticed that as soon as I placed the dry-ice cooled N.P. solution (naphtha) into the warm bath, it boiled.

What is going on there?

Strange, I didn't notice anything like this, maybe it has to do with the temperature shock since I think I let my solvent warm up a little bit in open air before putting it in the bath (I was figuring out what to do next). How warm was your bath? Mine was probably around 60 C (hot tap water).

There are some websites (google dry ice locator) that will show you the closest stores that carry it near you. It took me a whole day of driving around town looking for it, only to give up, go online and find a store 2 minutes from my house. Go figure.

The main issue I see with the method is that if you plan to add dry ice to your pulls as you do them, you're going to have to find a good way to store the dry ice for a few days so that it doesn't all sublime before you're finished. I bought a large block (4 lbs?) and it was gone within 24 hours (I kept it in the freezer). Maybe a closed cooler would be better, since my freezer was blowing (warm) cold air onto the dry ice constantly, speeding sublimation.
Yes, dry ice lasts only hours, depending on storage! Mine lasted about 12 hours in the tropics, in a cooler.

My solution was to do all the pulls back to back, using fresh naptha for each pull, then treating each pull consecutively.

My logic is that un-saturated solvents have more room to 'pull' molecules. This probably hurts freeze precipitation somewhat?

Dy Ice is an excellent CO2 generator- It precipitates NMT carbamate like crazy!
In my thinking, would not the "NMT carbamate" (which is a misnomer for reasons I will go into) also be pulling some DMT with it when it precipitates? Here is my reasoning - get ready for some proper chemistry...

The carbamate is formed because NMT is a secondary amine. This means there is a hydrogen (H) atom attached to the amine nitrogen (N). It is this N-H bond which reacts with the carbon dioxide:
R2NH + CO2 -> R2NCO2H
This product is a carbamic acid. ('R' here is shorthand for an organic group, in this instance either the N-methyl group or the remainder of the tryptamine molecule - the 2-(indole-3-yl)ethyl moiety, to be precise. So what we are looking at is N-methyl-N-(2-(indole-3-yl)ethyl)carbamic acid).

The carbamic acid has a proton (H+) which may then transfer to any nearby basic nitrogen - which in this case could be on either the DMT or the NMT:
R2NCO2H + R3N -> (R3NH)+ (R2NCO2)-

This is the same process as that which occurs when, e.g., fumaric acid is added to a non polar solution of methylated tryptamine(s). With the carbamic acid in this case the precipitate is likely to be a mixture of DMT N-methyl-N-(2-(indole-3-yl)ethyl)carbamate and NMT N-methyl-N-(2-(indole-3-yl)ethyl)carbamate. That is, the respective DMT- and NMT- salts of the aforementioned carbamic acid.

Conclusion: there is still plenty of research to do here. The relative proportions of NMT and DMT will affect the amount of DMT which co-precipitates - if indeed the precipitate is the amine-carbamate salt, rather than the free carbamic acid. This may in part explain the low yields reported by some forum members who have used this technique.
Thanks for your input, so I presume what precipitates is actually a carbamic acid, not a carbamate?

downwardsfromzero said:
The carbamic acid has a proton (H+) which may then transfer to any nearby basic nitrogen - which in this case could be on either the DMT or the NMT:
R2NCO2H + R3N -> (R3NH)+ (R2NCO2)-
So the question is whether or not this reaction proceeds to any great degree.

Actually, looking at the reaction as stated in the original patent (attached to first post), it seems like the NMT would instead form a carbamate salt with itself more readily than with the DMT:

patent said:
2R2NH + CO2 -> (R2NCO2)-(R2NH)+
I'm no chemistry expert though, so correct me if I'm wrong.

I will note that there was a significant qualitative difference between the pre-dry-ice alkaloids and both the DMT and NMT that were collected separately afterwards. Both NMT and DMT fumarates were crystalline solids after separation but were a goo before separation. If there is any DMT that does precipitate with the NMT, it is surely a small quantity. I would love to do TLC to confirm this but I don't have the capabilities right now.

From further testing, it seems like it is better to use xylene as a solvent when adding dry ice, rather than naphtha, because too much DMT precipitates due to the drop in temperature, making it hard to make sure all of the NMT is reacted without several cycles of dry ice/warm bath. This doesn't happen with xylene.

My yields have been consistently around 0.7% DMT freebase (using the same source of bark). It's nothing near the 1.5% reported in the literature, but maybe my bark is not so great?
Having done this reaction a few times, I think one must be careful not to "throw the baby out with the bath water".

The dry ice precipitates both the NMT and DMT, due to its low temperature.

Heat and agitation re-dissolves the DMT, which is stuck to the NMT carbamate, but
it's not obvious WHEN all the DMT is back in solution.

I think its probable that you will lose some yield in this process.

The first photo shows the preciptates after dry ice treatment of an ACRB extraction.

The second photo is of the NMT carbamate after decanting the DMT solution.


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Yes, the naphtha can be a problem because the DMT precipitates with the temperature drop. I've had better results doing the reaction in xylene because this doesn't happen.

Keep in mind, you can always recover nearly everything by dissolving the precipitates in acidic water, basing with NaOH to ph 12, and then pulling with your solvent of choice.
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