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

[primordium]

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

Did you leave it out those days?

 

[Dr_Sister]

DMT Fumarate - DMT-Nexus Wiki

wiki.dmt-nexus.me

I'm also wondering if the carbamate is smokeable.

Thanks for sharing this method.

The carbamate is supposed to be thermally unstable, so it is possible vaporization temperatures might revert it to the freebase. Try putting some in a bulb pipe and apply heat, see what happens ...

 

[starway6]

Great news! The freeze-precipitated crystals haven't turned to goo!

I had 2 bowls of material in the freezer - in one, which I only put dry ice in once, there was still some goo formation. The other was all crystals. I guess I should have put the dry ice in both 2 or 3 times in order to make sure all of the NMT was removed.

Unfortunately I don't have access to TLC to confirm that the NMT was removed, but I'll say that these results are as good as anything I've ever gotten from mimosa, so I'm very pleased. Interestingly, it doesn't have the same flowery smell that mimosa DMT would have, it has no smell at all. Edit - it does smell, but not like mimosa DMT or even the acacia goo. It is a kind of faint acrid chemical smell, somewhat like vaped spice. This is definitely some of the purest spice I've ever seen, shiny white crystalline powder and totally devoid of any waxiness.

I'm trying it again on a final xylene pull of my base soup to see if it's possible to do the same thing when there are other plant oil impurities in the solution. Update: it worked great, produced a ton of NMT carbamate (xylene picked up lots of NMT). I was afterwards able to precipitate nice white fumarate crystals from the xylene using FASA, plus a mystery red waxy alkaloid.

You can tell if it feels like pure NN DMT it should get intense like mimosa spice...
Have you tryed it yet?

 

[ooo0ooo]

I'd just like to say a big thank you to arcologist and all the wise heads who have contributed to developing this technique.

Tried it out over the weekend and it has worked brilliantly!

Thank you very much!!

0.

 

[downwardsfromzero]

My word! Is it really that long since I posted in this thread?!

Now I've finally looked at the patent...

Thanks for your input, so I presume what precipitates is actually a carbamic acid, not a carbamate?

It says on line 31-ish of column 2 of the first page that "Because of the differences in the reactivities of primary and secondary amines[...] mixed carbamates do not occur[...]" and "Any tertiary amine remains present in the solvent, unreacted."

So no DMT is lost through salt formation with the NMT-N-carboxylate, apart from possible negligible losses through crystalline occlusion.

The precipitate is the NMT carbamate salt [NMT.H]+ [NMT.CO2]-. One molecule of CO2 pulls two of NMT!

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:

2R2NH + CO2 -> (R2NCO2)-(R2NH)+

I'm no chemistry expert though, so correct me if I'm wrong.

You were absolutely right there. I would have seen this had I read the patent the first time around. Hopefully it's been worth the discussion

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.

This strongly suggests that the separation is highly effective - thus there are scant grounds for concern over DMT losses.

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?

What about the mass of NMT auto-carbamate? If your yield was the same as that of DMT then that would about make for the 1.5% as total alkaloids.

Congrats, Arcologist, on finding a very useful method!

 

[DonPeyote]

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

Did you leave it out those days?

Yes, in a cool, dark place, covered with cheesecloth.

Patience is my friend now.

 

[Synkromystic]

Can this method work with a Polar solvent like Acetone, or must it be a np solvent?

 

[downwardsfromzero]

Can this method work with a Polar solvent like Acetone, or must it be a np solvent?

I've no idea but there's a distinct possibility that the carbamate will be soluble in acetone, especially once it has warmed up a bit.

Dry ice + acetone is a standard low temperature bath formula, for chilling reaction vessels to -78 C.

 

[Synkromystic]

Can this method work with a Polar solvent like Acetone, or must it be a np solvent?

I've no idea but there's a distinct possibility that the carbamate will be soluble in acetone, especially once it has warmed up a bit.

Dry ice + acetone is a standard low temperature bath formula, for chilling reaction vessels to -78 C.

hmm, interesting. If the carbamate is soluble in the acetone, after doing the procedure one could evaporate the acetone leaving the alkaloids, then use naphtha to make soluble only the dmt.

I am looking for another way besides using something like xylene because its nasty stuff, and there is no clean xylene around here...and using just naphtha with dry ice doesn't look to be very effective since naphtha freeze precipitates...

 

[downwardsfromzero]

I'd say you have nothing to lose from trying a small experiment.

 

[Entheogenerator]

IIRC it works well with naphtha, you just have to let the naphtha warm back up and redissolve the DMT freebase after precipitating the NMT carbamate.

 

[Synkromystic]

IIRC it works well with naphtha, you just have to let the naphtha warm back up and redissolve the DMT freebase after precipitating the NMT carbamate.

Yeah, it seems to be working very well with naphtha. Thanks for the advice everybody. Gonna try to grow some xtals with heptane over the next few days with the separated dmt. So far it looks incredibly pure

 

[downwardsfromzero]

Do you have any plans for the NMT carbamate?

 

[Synkromystic]

none that I can think of right now. Although it would be an interesting experiment to convert the nmt carbmate back to nmt freebase and then mix into a mushroom grown since theoretically (or factually?) nmt is a precursor to dmt.

Do you have any ideas for me?

 

[Parshvik Chintan]

it would be an interesting experiment to convert the nmt carbmate back to nmt freebase and then mix into a mushroom grown since theoretically (or factually?) nmt is a precursor to dmt.

interesting indeed. i vaguely remember someone (i think shulgin?) saying something about 5-meo-dmt in the mushroom substrate will make 4-ho-5-meo-dmt. so it seems plausible.
i found this mention of it, which talks of a thread (i couldn't find) that came to the conclusion tryptamine hcl was optimum.

In Paul Stamet's Psilocybin Mushroom's of the World on P.36 of the first edition he wrote

"Gartz (1989) found that raising tryptamine concentrations of cow dung and rice media by 25 millimolars directly affected the potency of Psilocybe Cubensis mycelia, Specifically in psilocin content: from .09% to 3.3% of dried mass.

also from that first link i posted:

The biosynthesis of psilocybin has been investigated by feeding labelled precursors to Psilocybe cubensis. The following specifically labelled compounds were synthesized: psilocin-3H, 4-hydroxytryptamine-14C, N,N-dimethyltryptamine-14C and -14C-3H, N-methyltryptamine-14C=3H and DL-Tryptophan-3H. A number of other indoles were labeled by acid catalyzed exchange in tritiated water. The experimental data suggest a sequence: tryptophan -> tryptamine -> N-methyltryptamine -> N,N-dimethyltryptamine -> psilocin -> psilocybin. The fungus can also by an alternative route convert 4-hydroxytryptamine to psilocybin. Large differences in the rate of absorption of different closely related precursors has been observed.

almost everything i could find was talking about either tryptophan or tryptamine. but if you have a way of testing (maybe dose half of your cakes in the same tank under the same conditions as your control) the alkaloid content.. then it definitely be a worthwhile experiment, regardless of the results

EDIT: looking at this

it seems NMT is quite effective at increasing psilocybin content.

 

[downwardsfromzero]

it would be an interesting experiment to convert the nmt carbmate back to nmt freebase and then mix into a mushroom grown since theoretically (or factually?) nmt is a precursor to dmt.

interesting indeed. i vaguely remember someone (i think shulgin?) saying something about 5-meo-dmt in the mushroom substrate will make 4-ho-5-meo-dmt. so it seems plausible.

it seems NMT is quite effective at increasing psilocybin content.

IMO the 5-MeO-psilocin thing is a total red herring :!:

NMT supplementation of mushrooms sounds like a worthwhile experiment to repeat, however.

Decomposing the carbamate may be problematic; the only method I've found mentioned is refluxing with NaOH or KOH in ethylene glycol. Probably propylene glycol would work for a slightly more food-safe version. I wonder what the mushrooms would make of the carbamate as is?

Another possible experiment would be attempting hydroxylation using Fenton's reagent, which might possibly produce 4-OH-NMT - the dephosphorylated version of baeocystin (norpsilocin, I suppose, although I prefer the logically analogous name 'baeocin' ) - and 5-OH-NMT - norbufotenine or N-methyl serotonin.

Gartz reports baeocystin as having a similar activity to psilocybin so 4-OH-NMT might be interesting.

Of course, NMT carbamate will still yield 50% NMT if based and NP extracted, won't it?

 

[Synkromystic]

Thanks for the info. I just started a new thread so we dont completely derail this one

Ideas for using the Nmt left over from a Dry Ice separation of DMT - Advanced/Enhanced chemistry - Welcome to the DMT-Nexus

 

[starway6]

ive gotten snow white to off white crystals from acrb..using evaporation only .[no freezer]
Im no shure how this happened except it took a lot of pulls from 200 grams of bark..first 6 or 7 pulls were waxy and oily..then the ..[solvent turned clear!].. when i used cybs salt tek...dooing the hot water baths and shaking the jar up to 4 times at each napatha pull..
For some reason i havent duplicated this on my last extractionbut im getting very active light yellow spice but not white like in photos below from evaporation and plant oil pour off..

 

[DonPeyote]

I had a thought, as I'm processing a bit of ACRB now:

Concerning the Dry Ice reaction stage: After formation of the NMT Carbamate (carbamic Acid?), its advisiable to re-heat your solution up to the melting point of DMT, and agitating the solution vigorously, then decanting, freeze precipitating, etc.
This is probably obvious? But you do want to do your best to re-dissolve ALL the DMT that may be locked up in that precipitated NMT goo-ball.

 

[DonPeyote]

Acetone dissolves NMT Carbamate completely