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

[Talkswithtrees]

Has anyone tried this procedure with different solvents? Im specifically interested in doing it with limonene for a few reasons:
1 the dmt would probably not crash out at the same time (like it does with naphtha because of the sharp drop in temperature) because dmt is so soluble in limonene
2 xylene smells horrible
3 limonene is food safe whereas neither xylene or naphtha are
4 xylene smells horrible
5 (if using naphtha) how can you be sure a simple heat bath will pick up the dmt that precipitated while the nmt sublimated? This seems less efficient to me but this is just conjecture feel free to critique this idea I would love to hear it if the sublimated nmt carbonate (carbomate?) is easily penetrated by the warm naphtha this could be a non issue
6 did I mention how xylene smells?

 

[benzyme]

2 xylene smells horrible
...
4 xylene smells horrible

lies.

 

[1ce]

2 xylene smells horrible
...
4 xylene smells horrible

lies.

I dunno, alkyl benzenes take some getting used to xD

 

[benzyme]

:shrugs:

I like them.
I only use limonene for cleaning rifle parts and sfe parts, in an ultrasonic bath.

toluene smells heavenly to me, better than limo, and xylene isn't too bad.
dmt is soluble in limonene, but more soluble in xylene.

 

[downwardsfromzero]

:shrugs:

I like them.
I only use limonene for cleaning rifle parts and sfe parts, in an ultrasonic bath.

toluene smells heavenly to me, better than limo, and xylene isn't too bad.
dmt is soluble in limonene, but more soluble in xylene.

There's no accounting for taste!

Xylene aroma is intense, but neither good nor bad. Not truly horrible like organic sulphides. Even too much limonene odour can drive one a bit mad.

 

[1ce]

I never said it was bad, just takes some adjustment. Much the same way you probably never enjoyed coffee or beer upon first taste. For me, I love, love, LOVE the smell of chloroform. I had some shoot out of an alihn condenser once, and unfortunately I can say it taste like alcoholic candy too.

 

[Jees]

... Not truly horrible like organic sulphides...

I had this very odd occasion to have a few inhales of hydrogen sulphide (H2S) at a factory, quite accidental as it is lethal big time in such high concentrations context. I managed to get myself in safer area before it could knock me out. It is known as one of the most horrible smells on earth, but crossing above a certain threshold (from 50 to 100 ppm or 0.005% to 0.01%) that smell is gone! One could think it smells harder with more but not so.

The really stoned period following was actually pleasant and non comparable with anything, it affected mind and body. Even out in fresh air, it continued as if it was "in" my system for a while. Not recommended, but there was that silver lining on that industrial variation of Jenkem.

Sorry for the off-topic.

 

[1ce]

... Not truly horrible like organic sulphides...

I had this very odd occasion to have a few inhales of hydrogen sulphide (H2S) at a factory, quite accidental as it is lethal big time in such high concentrations context. I managed to get myself in safer area before it could knock me out. It is known as one of the most horrible smells on earth, but crossing above a certain threshold (from 50 to 100 ppm or 0.005% to 0.01%) that smell is gone! One could think it smells harder with more but not so.

The really stoned period following was actually pleasant and non comparable with anything, it affected mind and body. Even out in fresh air, it continued as if it was "in" my system for a while. Not recommended, but there was that silver lining on that industrial variation of Jenkem.

Sorry for the off-topic.

It's interesting you bring up H2S, a previous occupation had alarms that would sound if the gas leaked, at which case we'd put on respirators and follow our evacuation routine. I was always under the impression less than a few wiffs would kill you. I'm glad you're still with us Jees.

Side note: isn't h2s commonly found in sewers? I've often pondered why it's never killed anyone in all those action movie --sewer-escapes.

 

[downwardsfromzero]

Above a threshold H2S paralyses the olfactory nerve (or something like that ) From what I've been taught in a previous job, it sounds as though Jees is lucky to be alive without major brain damage. A few years back some guy was awarded huge damages after being rendered a vegetable in an industrial H2S leak.

Back on the methylated benzenes, I know this guy who runs a paint store for several decades and he doesn't know what day it is. Tragic cognitive impairment from solvent overexposure - but he seems to keep the paint store going ok none the less :?

I never said it was bad, just takes some adjustment. Much the same way you probably never enjoyed coffee or beer upon first taste. For me, I love, love, LOVE the smell of chloroform.

Yeah, that was the other guy. Chloroform ain't too bad either - no matter what I may have said in the past
I rather enjoy a small whiff of nitrogen dioxide on rare occasions, quite refreshing.

 

[tregar]

Interesting thread,

Has anyone thought to use paintball c02 tanks?

C02 tanks are available from select sports stores for use in paintball or on-line, for example, the 20oz C02 tank with pin valve.

This article has more:

"The Use Of CO2 In The Frog Hobby, Building and Using a Co2 Generator"

http://www.dendroboard.com/forum/parts-construction/56812-building-using-co2-generator.html

article:

Paintball tank sizes run from 9 oz, 12 oz, 16 oz and 20 oz.

I wanted to calculate how much CO2 a tank would generate to see what size would be most appropriate.

CO2 => Mole Weight of 44g/mole.

1 mole of gas at STP is equivalent to 22.4 liters => 16g will make approximately 8.1 liters and 1 ounce = 28.3495231 grams.

From this I generated the following table.

This will produce the following amounts of CO2

Cylinder…Liters……Gallons
…9 Oz.………129.9……=…34.3
12 Oz.………173.2……=…45.8
16 Oz.………230.9……=…61.0
20 Oz.………288.6……=…76.4

If you have a paint ball tank, refilling it runs between $2.00 - $4.00 at the your local sporting goods stores. If you aren’t into paintball, check to see if any of your friends might have the equipment that you need, as you might not even have to buy a tank or remote, just borrow theirs for a quick squirt into your tank.

If you want your own equipment, the tanks cost from $9.00 - $40.00 and can be purchased online or from almost any sporting goods store or any paintball shop. I did quite a bit of researching for this article and found that the prices at our local sporting good store’s and paintball establishment’s, were quite a bit higher than many of the online sources, even with shipping factored in.

While the most common paintball tank size is probably the 20oz tank, the smaller sized tanks should be just fine for our hobby.
Beyond the cost of a tank, you will also need to purchase what is called a “Paintball Coiled Remote with quick disconnect.” The Remote is designed to power the gun while the tank is located remotely on a belt or backpack unit. The remote is able to connect to the paintball tank’s oddball thread size, it has an on / off valve, a coiled supply line, some standard sized connection fittings, as well as a quick disconnect. This unit is real cheap when compared to the cost of all of the fittings you would need purchase in order to connect to the tank if you went out to buy all of the fittings on your own.

Here is the best price that I have located on line for the pair.

Coiled Remote and CO2 Tank Combo

I also found that **azon.com had some of the best prices for the individual parts, and if you combined a tank and the “Paintball Remote”, you can sometimes get free shipping.

The best prices that I found for both the 20oz. tank and the remote were found online and prices were running between $28 - $49. The paintball and sporting goods stores around here were almost twice that.

Newbies Guide to CO2 / CO2 Tanks.

A google search of “Paintball CO2 tanks” will give you a lot more info.

If you want to adjust or regulate the pressure stream that is ported out of the tank you will need to add a pressure regulator.

A regulator is required if you are planning on using bottled CO2 for euthanizing your frogs and tadpoles. Without it you can eject too much CO2 too quickly which can freeze an animal or stress them out from too high of a volume flow. (More information is posted below.)

In order attach a regulator you should know that the threading on every paintball tank is an oddball fitting. The international ASTM thread standards designation is known as F1750-05. The ASA designation for the paintball threads is CGA-320. I share this because without the proper adaptor, it is impossible to connect to the tank outside of using epoxy as one home brewer did that I read about. The home brewing industry has developed an adapter that can covert the tank’s thread into a standard regulator fitting size so that one can attach a pressure regulator to the tank.
Click the image to open in full size.

BREWER'S EDGE® PAINTBALL REGULATOR ADAPTER

The Adapter" CO2 regulator to Paintball tank Adapter

Regulators are relatively inexpensive and you should be able to use a cheap ¼ inch air compressor regulator.
Cheap 125 PSI Air Flow Regulator

You may need to get a few other fittings to convert the lines to a ¼ inch regulator thread. I have found that Lowes seems to have a larger array of fittings than does Home Depot.

You have the coiled remote, you may not need the home brewers adaptor to connect a regulator as I believe the fittings on the quick disconnects are standard fittings.

Tips on using a Paintball tank with remote.

When connecting the Remote to the tank, make sure that the valve on the remote is in the off position. Otherwise when you make the connection, you will blow CO2 all over as you are screwing the remote onto the tank.
Keep the tank in an upright position or you will vent liquid CO2 rather than CO2 gas.
If you do not run a regulator, turn the valve on very slowly, and only crack it a small amount. You don’t need full pressure. It is after all a high-pressure tank.
--------------------------
Bike CO2 tanks:
Bicycle shops also carry small CO2 tanks little bigger than a pencil which they use to re-inflate bike tires. These are small and relatively inexpensive. The cartridges come in many different sizes, 12g, 16g, 25g, 38g, 40g, 45g, and 88g. The non-threaded cartridges are usually much cheaper than the threaded.

Different Size CO2 Bike Tanks

Here’s kind of a cool video of how these bike cylinders are made.

You can get a Schrader tire valve with an 1/8” fitting at your local Auto Parts store. You can also get Schrader valve at your local tire shop. If you go in and ask how much the all metal screw in Schrader valves costs, they will usually just take you in back and hand you one no charge. These are very easy to install into a chamber by drilling a 3/8 hole and popping it in place with a washer and nut. These valves even have a rubber bushing on the base to seal it up.

The problem that I see with using these non-refillable cartridges is the expense per gallon of CO2 produced. I calculated the volume of CO2 contained in the various size cylinders.

Cylinder ……Liters…Gallons
12 Grams ………6.1………1.6
16 Grams ………8.1………2.2
25 Grams ……12.7………3.4
38 Grams ……19.3………5.1
45 Grams ……22.9………6.0
88 Grams ……44.8………1.8

Because of the convenience, some might find using the bike CO2 tanks appealing so I added the information.

 

[Mindlusion]

Here is what the N-methyl-tryptammonium carbamate should look like.

According to the paper you can only have like molecules forming the carbamate, which is great. It also opens doors for methylation of amines, an easier method of separation of the over-methylated products.

The amines the paper was working with were much more volatile than tryptamines, they were actually high MW alkylamines, usually liquid at room temp. The fact that tryptamines aren't as volatile means you can have some decomposition after separation without much issue other then it dissolving itself back into the residual solvent (which might be why you have goo).

Perhaps you've stumbled onto something really great here, those are some nice looking crystals.

But that's not enough to say for sure this process actually works, although it is looking promising.

Has anyone run a TLC yet?

 

[eastlancsguy]

If you're struggling to source dry ice, invest in a small CO2 fire extinguisher and a pillowcase.

Wrap the pillowcase round the end of the nozzle, squeeze, and hey presto - nice little globules of dry ice

 

[Stochastic]

a decade later... I can't help but wonder, using sodium carbonate as the alkali instead of Na/Ca hydroxide produces CO2 in situ; would this work?

 

[Icon]

I haven't bitten into the polymer threads yet, but I've gleaned that it's potentially related to supersaturation? Could the flash precipitation of DMT when adding dry ice to naphtha, that was suspected to be locking some of the DMT up in carbamate goo, be causing the DMT to polymerize? And thus forming its own indistinguishable goo?

It seems arcologist was able to get solid NMT fumarate though which might suggest no polymerized DMT, or that the polymer broke down and turned to fumarate along with the nmt.

 

[Stochastic]

I haven't bitten into the polymer threads yet, but I've gleaned that it's potentially related to supersaturation? Could the flash precipitation of DMT when adding dry ice to naphtha, that was suspected to be locking some of the DMT up in carbamate goo, be causing the DMT to polymerize? And thus forming its own indistinguishable goo?

It seems arcologist was able to get solid NMT fumarate though which might suggest no polymerized DMT, or that the polymer broke down and turned to fumarate along with the nmt.

well, I went for it and tried a basification using sodium carbonate... and now have a CO2-in-naptha emulsion to contend with. In case anyone was wondering...

 

[Transform]

well, I went for it and tried a basification using sodium carbonate... and now have a CO2-in-naptha emulsion to contend with. In case anyone was wondering...

Are you saying the emulsion got compounded by the gas bubbles? That's a major disadvantage of using carbonates to neutralise acids, or amine salts of acids in this case perhaps. It's best not to have immiscible liquid phases with bubbling going on, unless you want to make mousse.

In Nexus extraction processes where SC is used as a base, most often the reaction mixture is allowed to dry out before any further solvent gets added.

Were you attempting to limit NMT content in your naphtha? What were you extracting from?

I haven't bitten into the polymer threads yet, but I've gleaned that it's potentially related to supersaturation? Could the flash precipitation of DMT when adding dry ice to naphtha, that was suspected to be locking some of the DMT up in carbamate goo, be causing the DMT to polymerize? And thus forming its own indistinguishable goo?

It seems arcologist was able to get solid NMT fumarate though which might suggest no polymerized DMT, or that the polymer broke down and turned to fumarate along with the nmt.

Back on the topic of this thread, CO₂ separates NMT from DMT freebases in naphtha by first precipitating the NMT as its auto-carbamate (or ipso-carbamate, if you prefer). After warming and filtering off the insoluble NMT.CO₂NMT, the DMT can be collected as usual, and the carbamate can be converted to whatever, initially probably some salt or other. NMT is far from useless…

@Icon - good point about the possible flash-precipitation of DMT. I'd suggest you experiment a bit to check out your assumptions.

 

[Stochastic]

Are you saying the emulsion got compounded by the gas bubbles? That's a major disadvantage of using carbonates to neutralise acids, or amine salts of acids in this case perhaps. It's best not to have immiscible liquid phases with bubbling going on, unless you want to make mousse.

In Nexus extraction processes where SC is used as a base, most often the reaction mixture is allowed to dry out before any further solvent gets added.

Were you attempting to limit NMT content in your naphtha? What were you extracting from?

Yes; the naphtha layer and the interface with the aqueous layer became a foam, presumably stabilized by the tannins in solution. I had added sodium carbonate to a filtered room-temp soak of ACRB in water and vinegar. & yes, I was curious about minimizing NMT in the naphtha, as I had previously ended up with an extremely acrid clear white goo from freeze precipitating an NaOH-basified extract. Although it's clear that NMT alone would not have caused the extreme acridity.

 

[Transform]

Yes; the naphtha layer and the interface with the aqueous layer became a foam, presumably stabilized by the tannins in solution. I had added sodium carbonate to a filtered room-temp soak of ACRB in water and vinegar. & yes, I was curious about minimizing NMT in the naphtha, as I had previously ended up with an extremely acrid clear white goo from freeze precipitating an NaOH-basified extract. Although it's clear that NMT alone would not have caused the extreme acridity.

And had you waited for the fizzing to stop before adding the naphtha? I'd guess that you probably did. What I do recall seeing is that, at an insufficiently high pH, you'll get a surfactant effect from the tannins (as you yourself have observed), but these tannins can be broken down by pushing the pH higher with (more of) a stronger base, typically NaOH.

I expect you probably know that tip for breaking emulsions in acacia extractions already, but using it will most likely cancel out any hoped-for benefit of carbamate formation.

Also, I don't think carbamate formation will be particularly favoured in the aqueous environment anyhow.

Thanks for reporting though - negative results are useful to know as well.

 

[Icon]

I'm testing the dry ice wash on an MHRB extract dissolved in hexane. It certainly worked to separate the solvent from the vessel, as gas expansion overwhelmed the container. Good thing it was a small test. The remaining half of solution was hazy for a minute but there doesn't appear to be anything that precipitated, goo or otherwise. I freeze-precipitated a large amount of crystals within the solution last night, then re-dissolved them today, so I know the solvent is loaded. I was surprised by how much gas a small piece of dry ice created, I think it is fair to say if there was NMT it had its chance. I wasn't necessarily expecting NMT from MHRB, but I've heard a rumor about traces. I've already done a couple A/B's and many washes on this extract though, so any NMT could have been removed long before I got around to dry ice.

 

[Icon]

I'm testing the dry ice wash on an MHRB extract dissolved in hexane. It certainly worked to separate the solvent from the vessel, as gas expansion overwhelmed the container. Good thing it was a small test. The remaining half of solution was hazy for a minute but there doesn't appear to be anything that precipitated, goo or otherwise. I freeze-precipitated a large amount of crystals within the solution last night, then re-dissolved them today, so I know the solvent is loaded. I was surprised by how much gas a small piece of dry ice created, I think it is fair to say if there was NMT it had its chance. I wasn't necessarily expecting NMT from MHRB, but I've heard a rumor about traces. I've already done a couple A/B's and many washes on this extract though, so any NMT could have been removed long before I got around to dry ice.

I may have spoke too soon. I treated the rest of the solution with dry ice because it didn't seem to hurt anything. There wasn't any noticeable precipitation, but then I wondered how it might look if it's just a trace amount. Like, would the nmt carbamate deposit as a very thin film, or maybe even stay caught in the non polar solvent.

I looked closely at the solvent and it was swirling. I think I was seeing convection currents in the solvent, but can only really imagine what's going on at the molecular level. Maybe high amounts of dissolved CO2 make the convection more visible? or trace carbamates in suspension?

I wanted to give any potential carbamates an exit point, I figured water, but didn't want to expose the freebase to carbonic acid, so I used NaOH. I'm not sure if carbamate can dissolve in alkaline water though so I doubt that was the right idea for separating suspended carbamates. But I figured it wouldn't hurt to do one more alkaline wash on the NPS.

After thoroughly mixing, both solvents in solution remained hazy, and as things settled overnight there was a bit of something at the interface between alkaline water and hexane. Maybe a few concretions of oil, and a thin white film. I'm not sure why there would be anything at all, but maybe the DMT had started to precipitate and was just having a hard time with the water below it.

I used a 0.22 micron inline PTFE membrane filter, tygon tubing, peristaltic pump - to pull the hexane off the water. In case the haziness is from suspended water molecules, the PTFE membrane should deny those, I believe. A few strange things happened that I don't understand.

1. On the downstream side of the intake filter there was bubble generation. The entire filter was submersed, so I think the bubbles had to be coming from the solution. I was reading about de-gassing solutions this afternoon and coincidentally saw a couple suggestions to start with 0.22 micron filtering. The membrane filter did seem to be separating the dissolved gas, and once the gas molecules got grouped together on the other side of the filter they eject up the line as a stream of bubbles.

2. As the hexane was being transferred to the other container, through the filter, the remaining solution waiting to be filtered started to become more clear. Not as clear as what was coming out the outtake, but clearer than before I started the filtered transfer. I'm wondering if there was a large amount of dissolved CO2 from the dry ice, and whether the filter was somehow sucking the dissolved gas out of the hexane faster than the hexane itself? And less gas = more clear?

3. The outtake half of the line was fitted with a second filter. Between the pump head and the outtake filter, a lot of precipitate formed in-line. It eventually clogged the outtake filter and I had to swap it. This was unexpected too, but since the pump is manipulating pressure, that must have something to do with it. When the line is fitted with filters it tends to build up a vacuum on the intake and positive pressure on the out line. Maybe pressure was precipitating the spice out as the solvent passed through this higher pressure section of line. Or maybe something about the way the peristaltic pump releases pressure for a split second before the next roller catches vacuum. The line develops a pulse from the beat of the pressure slips.