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Another way of partitioning 1° and 2° amines from 3° amines

Migrated topic.
DonPeyote wrote:
The precipitate, assuming it was NMT locked up as a carbamate, was not soluble in Naphtha, however, it readily dissolved in acetone.
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..NMT is only partially soluble in naptha..i assume it's soluble in acetone..

pure NMT base forms circular needles, begins white, rapidly darkening on exposure, and smells like DMT..
.
 
After checking on the state of my experiment this afternoon, I am very happy to report that CRYSTALS are growing!!!

I am so very happy!

Its not over yet, of course, until all or most of the remaining goo/extract has crystallized.

But its still hallelujah time in this old house!

I'll give it some days, and then photograph the crystals, and my crude CO2 rig.

Happy Happy Joy Joy,

DP
 
Here is a picture of some DMT crystals extracted from Acacia Confusa, using CO2 to eliminate NMT.

Out of the 3 "pulls", one has a noticeable orange tinge to it.

The other two pulls are typically white DMT crystals.

Whats up with the orange? What is oxidizing?

When the crystals finally dry, I will weigh them, of course. However eyeballing it, I would guess there will be no more than a gram.

That is a low yield from 1/2 Kilo of AC. But consider: I used 50% root bark and 50% from a fallen tree branch. The tree branch did not look as though there was any spice in it, but I thought, why not?

Practice makes perfect, and the next run will be with root bark from a very tall, very old, and Wise? tree....

DP
 

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One week Later:

I think that all the crystals that have grown, are all thats going to grow, and its over and done (I'll give them another week to grow or dry anyway, for the hell of it).
There remains some "Gel" in amongst the crystals, which I'll assume is the stubborn NMT.

My technique of gassing the DMT/NMT laden Naphtha with CO2 was less than ideal.

I would like to control the reaction to determine the best temperature, pressure, and saturation? of the CO2 to lock the NMT away in a carbamate (no hard feelings Mr. NMT), so that I can yield pretty crystals.

Has anyone else tried this yet?

I'm having fun!

DP
 
I just realized I'm posting in the wrong place!

My posts should be in "How to Remove NMT from Extractions" by Dr_Sister.

Please accept my apologies.

Is it possible to move my posts to the correct thread?

Si posible, muchas gracias.

DonPeyote
 
As my results with CO2 were unimpressive, me thinks its time to try the Aspirin answer
Getting ahold of ETOH seems dangerous. Will denatured alcohol work?
 
Call me an NMT hater, but for the sake of Crystalline DMT,
I am going to try to separate the 2° NMT from the 3° DMT using Apirin as the acetylating (re?)agent.

I know it will not be as easy as 1-2-3, but I am patient, and not afraid to lose some product learning the reaction.

Forgive me for not "gelling" with the gel.

I'm having too much fun learning about Organic Chemistry.

Wished I paid attention in High School!

Slowly I am trying to work through the "Virtual Textbook of Organic Chemistry".

If I read it ten times, and do the tests, I might get it. Or not.

But it is starting to make sense. Kinda....

DP
 
Denatured alcohol should work fine. Methanol works and is readily available in many parts of the world. Keep in mind methanol vapors are toxic. Denatured alcohol usually has methanol and IIRC methyl-isobutyl-ketone. The reaction is incredibly easy no need to fear. Just use a safe source of heat and have good ventilation.

edit - also keep in mind color is an observation not a form of characterization. DMT exists in two isomorphs. One is orangey the other is white/clear. There is a thread about this posted by Shaolin somewhere.
 
Regarding the aspirin technique, the indole nitrogen looks like it could be receptive to acetylation. If this happens, of course, the technique would not separate these two tryptamines. So is there something about the bonds it participates in (such as their being cyclic) which prevents the acetylation here? This seems potentially more promising of a procedure than dry ice, because of the relative abundance of aspirin an 99% IPA at grocery stores.
 
Acetylation of NMT allows it to be separated from DMT by taking away the basic nature of that nitrogen. DMT could still go into salt (water soluble) form while acetylNMT could not (until it decomposed from the acid and water).
Even if the ring nitrogen of DMT were acetylated by aspirin (which I'm guessing it wouldnt) the other nitrogen would still be basic and thus the compound could form a salt.
If NMT were acetylated on the chain nitrogen but not the ring nitrogen it would still not be made in to a water soluble salt by mild to moderate strength acids, that ring nitrogen is a very low strength base and it takes hydrochloric acid or better to get it to react.
 
Hello,

Another out-of-the-box thought from the less chem-savvy ;)

For the sake of argument I am assuming NMT to be insoluble in water...

If all the molecules one wants to separate are in freebase form and not soluble in water, wouldn't it be possible to adjust the density of the water (by adding salt for instance) so that the denser or heavier molecule would sink while the other would float?

This is of course not to be taken seriously in any way as I am convinced that there is a plethora of reasons why this is not a good idea - hopefully it's dumb enough to make you smile for a second ;)

PLUR

PS: Seriously, why would this not work? Becaouse it's physics and not chemistry? ;)
 
dooby said:
Hello,

Another out-of-the-box thought from the less chem-savvy ;)

For the sake of argument I am assuming NMT to be insoluble in water...

If all the molecules one wants to separate are in freebase form and not soluble in water, wouldn't it be possible to adjust the density of the water (by adding salt for instance) so that the denser or heavier molecule would sink while the other would float?

This is of course not to be taken seriously in any way as I am convinced that there is a plethora of reasons why this is not a good idea - hopefully it's dumb enough to make you smile for a second ;)

PLUR

PS: Seriously, why would this not work? Becaouse it's physics and not chemistry? ;)
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Truly clever idea, but it wouldn't work in practice, at least not easily. First off,we do not know the density of nmt (for dmt it is 1.099g/ml). But even if we knew or someone find, a mix of freebase dmt/nmt would stay lumped together in water via hydrophobic interactions. That means that molecules would not be free to diffuse and partition in water.

You could try using wot water so dmt/nmt are in liquid form or try to base them from an acidic solution so that when in basic ph the density of water allows the partition of dmt and nmt freebases...but both approaches sound too fiddly to get it right in an easy, reproducible manner. Who knows, someone else might think an easy way to go around said problems.
 
Is there an easy way to recover the secondary amines (NMT) with this? Evap the wash and then add a basified solution to what ever is left behind and then pull with NP solvent?
 
lysurgeon said:
Regarding the aspirin technique, the indole nitrogen looks like it could be receptive to acetylation. If this happens, of course, the technique would not separate these two tryptamines. So is there something about the bonds it participates in (such as their being cyclic) which prevents the acetylation here? This seems potentially more promising of a procedure than dry ice, because of the relative abundance of aspirin an 99% IPA at grocery stores.
Click to expand...

Sister isn't sure exactly why the indole nitrogen resists acetylation, only that it does. In fact it withstands acteylation using the much stronger acetylation reagent acetic anhydride as well,

Erowid Online Books : "TIHKAL" - #6 DMT

Entry #6 DMT from TiHKAL by Alexander & Ann Shulgin.
www.erowid.org

Erowid Online Books : "TIHKAL" - #3. DET

Entry #3 DET from TiHKAL by Alexander & Ann Shulgin.
www.erowid.org

so it is pretty safe to say that the weaker acetylation reagent Acetylsalicylic acid would also be inert to the indole nitrogen.

Rifle said:
Is there an easy way to recover the secondary amines (NMT) with this? Evap the wash and then add a basified solution to what ever is left behind and then pull with NP solvent?
Click to expand...

No, not easily anyways. When dmt is acetylated it changes from being an amine to being an amide. While amines are quite reactive, amides are considerably less so. In most cases requiring harsh reagents to reduce. If one were successful in reducing N methyl, N acetyl-tryptamine, they would end up with N methyl, N ethyl-tryptamine, not DMT. All the reagents that would do this are beyond the scope of this forum.

There is one far out possibility using clorox bleach as the reagent;

Hofmann rearrangement - Wikipedia

en.wikipedia.org en.wikipedia.org
This reaction shortens the amide by one carbon while reducing it back to an amine, so it could turn the acetyl group into methyl group, rather than an ethyl group. But the Hoffman degradation is notoriously low yielding and may not even work on a tertiary amide, only on primary amides. Chlorine can be substituted for bromine in this rxn.
 
Dr_Sister said:
[...]
Rifle said:
Is there an easy way to recover the secondary amines (NMT) with this? Evap the wash and then add a basified solution to what ever is left behind and then pull with NP solvent?
Click to expand...

No, not easily anyways. When dmt is acetylated it changes from being an amine to being an amide. While amines are quite reactive, amides are considerably less so. In most cases requiring harsh reagents to reduce. If one were successful in reducing N methyl, N acetyl-tryptamine, they would end up with N methyl, N ethyl-tryptamine, not DMT. All the reagents that would do this are beyond the scope of this forum.

There is one far out possibility using clorox bleach as the reagent;

Hofmann rearrangement - Wikipedia

en.wikipedia.org en.wikipedia.org
This reaction shortens the amide by one carbon while reducing it back to an amine, so it could turn the acetyl group into methyl group, rather than an ethyl group. But the Hoffman degradation is notoriously low yielding and may not even work on a tertiary amide, only on primary amides. Chlorine can be substituted for bromine in this rxn.
Click to expand...
reduction?? I thought Rifle was talking about recovery of the amine (NMT) through hydrolysis. And unfortunately, yes, the Hofmann rearrangement applies only to primary amides as it works via an intermediate isocyanate. Plus the halogen would substitute onto the indole ring somewhere too.
 
Ah, that's too bad. Really only interested in this as a way to get NMT that's pure enough to experience its effects on their own. I've tried the dry ice method and had poor results with respect to recovering nmt. I may change some things and give it another go sometime in the distant future. Does work well to give cleaner DMT though, seems to clean any fats and oils out too.
 
Okay, I can confirm that the aspirin technique works. The input, from confusa, has a toothpaste-like texture. The output has a powdery texture and formed mimosa-like crystals in freeze precipitation. The flavor of the output is extremely similar to mimosa alks, while the flavor of the input is harsher and more complex.

I followed the technique as detailed in the first post, except I used an excess of 91% isopropyl rather than the minimal amount of what I assume is meant to be a dry alcohol that is boiling. Also I used a 4x excess of aspirin. Used xylene to separate the methyl-acetyl-tryptamine from acidified mixture, then after washing with bestine I basified with lye and extracted with bestine. The bestine was freeze precipitated to yield the powdery mimosa-like alkaloid.

The only problem is the yield. I put in 500mg acacia spice, and got out 30mg powder. Tried using lyewater to hopefully cleave the amide by mixing thoroughly with the xylene. Xylene was discolored, kind of yellow and opaque. Obviously it had something in it but it seemed too gross to evaporate it. The lyewater did not take up the amide.

I wonder if over-excess of aspirin causes a problem here? Or maybe the bark I used just has a low amount of DMT in it.
 
I hate to be the one to ask complete amateur questions in these types of threads, but what exactly does it mean to use a 1.2 molar excess of aspirin relative to tryptamine? I would like to give this procedure a shot just for the sake of experience, but apparently I'm a little behind on my chemistry homework compared to everyone else in this thread :lol:
 
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