That's the way SWIM does it, but he prefers DCM to diethyl ether. Diethyl ether is very flammable and can form explosive diethyl ether peroxide. If you're not careful you can easily set your lab on fire.

SWIM's favorite solvents are DCM, d-Limonene, heptane, water, MEK, IPA, and acetone. They are all easy to get and have their own unique purposes. SWIM doesn't like xylene, naphtha, ether, or toulene.

SWIM now uses DCM as the non-polar solvent in every case. He found it is far superior to all over solvents. It pulls a larger array of alkaloids and a larger quantity per ml than all the rest. That stuff about DMT reacting with DCM is way over blown. SWIM tried very hard to get DCM to react with DMT and failed every time.

SWIM now extracts with DCM, and then vacuum distill off the DCM (a big time saver) to recycle it. Then he dissolves the mixed alkaloid extract in warm heptane. The DMT (and 5-MeO-DMT if any) dissolves in the warm heptane. This leaves all the DMT n-oxide and other heptane insoluble fun stuff at the bottom of the container as yellowish brown residue. SWIM then pours the heptane into another container leaving behind the insoluble alkaloids and then freeze precipitates the DMT (and 5-MeO-DMT if any). This way SWIM has pure white DMT, and also a bunch of DMT n-oxide and other fun stuff to play around with.

You can’t beat DCM. WHY?

* it extracts more alkaloids per ml than nearly all the others solvents.
* it extracts the alkaloids faster than most other solvents.
* it extracts a broader range of alkaloids than nearly all the others solvents.
* it is non-flammable, while almost all the others are very flammable.
* it evaporates many times faster than most other solvents.
* it has a lower boiling point than most other solvents. The boiling point is lower than the boiling point of freebase DMT so it’s perfect for extracting DMT.
* its very easy to distill off cleanly, and easy to recycle.

As long as you take the proper health precautions, don’t breathe it in or get any on your skin, and you recycle it, then it’s fine to work it.

It is however potentially carcinogenic, like most other solvents. And it is man made. You should not let it evaporate into the atmosphere. You should distill it and recycle it.

SWIM has been using the same DCM for nearly a year because he recycles all of it.

SWIM uses DCM without a fume hood, like it's no big deal, because it really isnt (compared to carbon tet and chloroform). unlike toluene and xylene it evaporates quickly and cleanly, and isn't spark-sensitive like ether. excess gets redistilled, never poured down the drains.

Methylene chloride is very nice stuff.
As far as the simple chlorohydrocarbons go its the least toxic.

I more careful with that than say MeOH or Acn but its really pretty safe.

SWIM never uses methanol much. SWIM has heard some very bad things about using Methanol: "Dangerous doses will build up if a person is regularly exposed to vapors or handles liquid without skin protection". What really scares SWIM is the possibility of permanent blindness from over exposure.

The unique polarity of methanol makes it a good choice for extracting certain types of compounds. The low boiling point of 64.7 °C means it’s great for use in a Soxhlet for temperature sensitive compounds.

Whenever SWIM used it in the past, he was too paranoid about the possibility of permanent blindness. So he was extra cautious with it. Is this overblown? Or is this something to really be extra cautious about?

Well I have heard some people freak out about MeOH but it always surprise me.
I only think it’s dangerous if you drink it or you bath in it.

I use it all the time cleaning benches, cleaning glassware etc. In the general lab setting it’s looked at great because it evaporates so fast and doesn't leave residues. Also it’s cheap.

But I don't know as a non-polar extraction solvent, I wouldn't suggest it for that.
Its way to polar I would think. Decent for HPLC but Acn is better, nope pretty much just think its good for cleaning stuff

Of course, it's useless as a non-polar solvent because it's water soluble and has a pretty high polarity. It’s often used as the initial extraction solvent for some compounds because of its low boiling point and high polarity.

In Soxhlet extraction, which SWIM prefers, he usually uses either isopropanol or acetone if he wants to extract a polar compound. SWIM knows that methanol will often work when isopropanol or acetone are not polar enough to extract the desired compound. But SWIM has always opted to use water instead because he’s so paranoid about using methanol.

SWIM has often thought about Soxhlet extracting Anadenanthera colubrina using methanol instead of isopropanol. It will extract much faster because methanol distills faster than isopropanol. All of the desired alkaloids are in their salt form and are very soluble in methanol. SWIM could get much more efficient extractions in less time.

Hmmm...maybe SWIM should rethink using methanol.

My expertise is not plant extractions, I am here to learn that, but Methanol sounds absolutely perfect for your application.

Sorry I really didn't know what you were doing.

It’s exactly as you say it is very soluble in water and you can extract polar compounds into it easily.
Protein chemists use it all the time for peptides and amino acids. For my work applications it’s all about volatility. MeOH is great for that.

methanol isn't the greatest for plant extractions because it's so polar, it pulls chlorophyll and other gunk you don't want in the final product.

yes methanol will make things gunky. hehe. its a great solvent but not for this purpose.

but yes agree with safety concerns with ether. and ron also yes your right about that the odds of DCM chloronating dmt are low. i think this happens when one uses DCM as a mobile phase in a silica column. this kind of thing often happens with alkaloids when being purified in silica with chloronated hydrocarbons. it opens up the chances for artifact formation when the molecules are also interacting with silica.

but then again so does letting your mixture sit with DCM for days. the only way to test for real is do an analysis on final product with some analytical equipment. however i bet its really low still. also DCM SWIM has observed low emulsions which is another reason its a nice solvent.

Emulsions are a pain to deal with. Each solvent seems to have different types of emulsions with different plants.

Long ago when SWIM used naphtha mostly, he had times when he was extracting Mimosa hostilis and such nasty emulsions occurred that didn’t settle even after many days. It was SWIM’s fault because he was shaking the separatory funnel wrong and causing the emulsions. SWIM tried everything, heating, filtering, waiting, salting out, adding alcohol, etc. The only thing that worked was evaporating all the solvent and trying again and shaking the separatory funnel less vigorously.

Since then SWIM was learned the proper way to shake a separatory funnel in order to avoid emulsions. He does several swirls and then a few tilts and rolls. If no emulsions happen from that, only then does he shake it vigorously. It’s hard to get it right, but once you do, you no longer have much problems with emulsions.

The type of emulsions you might get are also determined by the initial plant extraction solvent. When SWIM extracts initially with acetone, he gets very few emulsions when he later does a water/non-polar a/b extraction. SWIM gets the worst emulsions when he uses alcohol.

One thing that helps prevent emulsions is doing an initial defat before extracting the alkaloids from the plant. For example, if you were going to extract with heptane as your non-polar solvent in an A/B extraction, you’d do a few washes with heptane prior to extracting the plant alkaloids in water or alcohol. You’d then let the plant dry and then extract from the plant with water or alcohol. It works very well.

SWIM found out about the helpful pre-defat because a while back he had heard that DMT was present in plants as freebase. SWIM tested this by extracting many different DMT containing plants using just DCM and no base. Freebase DMT is very soluble in DCM and would get extracted if it was present in freebase form. SWIM was unable to extract any freebase DMT from any plant using just DCM. After extracting with DCM, and then doing an A/B extraction, no emulsions were encountered even if vigorously shaking the separatory funnel. The A/B extractions yielded normal DMT yields, showing that DMT is present in salt form in all the plants tested. This makes sense because the natural pH of most plants is acidic (pH 5-6.5). At pH 6.68 99% of the DMT is in salt form.

this is key



yep this is a commonly employed method with alakloid isolations, works fine as long as the solvent you defat with wont dissolve much spice like heptane. could cause yield loss however it might be minimal for reasons you state.

one more thing about DCM though. check out this report.

Record 1 of 1
Author(s): Brandt, SD (Brandt, Simon D.); Martins, CPB (Martins, Claudia P. B.); Freeman, S (Freeman, Sally); Dempster, N (Dempster, Nicola); Wainwright, M (Wainwright, Mark); Riby, PG (Riby, Philip G.); Alder, JF (Alder, John F.)
Title: N,N-Dimethyltryptamine and dichloromethane: Rearrangement of quaternary ammonium salt product during GC-EI and CI-MS-MS analysis
Source: JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 47 (1): 207-212 MAY 12 2008
ISSN: 0731-7085


seems the rerrangement can occur regardless of silica purification.

quick aside, i read xylene is one of the additives in cigarettes and occurs in hundreds of micrograms concentration per cig. (one of the many reasons i dont smoke cigs)

is this true?

yep, there's also formaldehyde, benzene, and a few benzene fused-ring compounds (i.e. phenanthrene)

If the DMT was in freebase form then yes it would cause loss in yield. But DMT is in salt form in all the plants SWIM tested and so it is completely insoluble in heptane.

It’s an easy experiment to try. Just soak some powdered Mimosa hostilis root bark in warm heptane (50 C or less) overnight. Then attempt to extract DMT from the heptane by extracting with pH 3-4 water. Then freebase at pH 9.5 (I know everyone likes pH 13, SWIM doesn’t use pH 13, he uses pH 9.5) and extract into clean heptane. Then evaporate and you’ll see if DMT is present in freebase form or not. SWIM’s tests shows nothing gets extracted this way so it is not present as freebase in the root bark.

Besides if it worked, the “Straight to Base” extraction tech for mimosa wouldn’t require sodium hydroxide like it does.

Most plants have a pH of about 5-6 and most soil is acidic (pH of 4-6). Because these are roots, and the soil they grow in is probably acidic, I makes logical sense that the root bark pH is about the same as the surrounding soil. At pH 6.68 99% (or is it 90%? I forget) of the DMT (with a 8.68 pKa) is in salt form. I’ve never heard of a mimosa growing in alkaline soil.

I think we can put to rest the rumor that DMT is present as a freebase alkaloid in all plants. It just doesn’t make sense, unless a plant grows in alkaline soil and has a high internal pH, then the DMT can’t be present in freebase form.


Yeah, but SWIM tried to cause that to happen and can’t seem to detect any changes to the DMT. If it happens it must only be in extreme trace amounts. So SWIM is not concerned about it.

Mostly they are added as fuel to help them burn more evenly.

If you want to smoke cigarettes, only use 100% all natural cigarettes. This can be bought commercially if you look around. They don’t have any nasty chemicals added to them, but smoking itself produces some nasty chemicals from the combustion process.

i'm not much of a cig smoker, but I like the occaisional nat sherman or djarum

good deal about the solubility check. SWIMMERs should always check to be sure.



does SWIY mean the bioassay detection method or the analytical one? edit: ignore discussed in other post.

so conceivably, one could 'defat' powdered MHRB by simply washing it with DCM BEFORE performing a STB tek?

Swim assumes this might interfere with whatever could be potentially left over as red spice though? At least whatever components of it that arent alkaloids....?

It is likely that some of the spice would go into the DCM and hence lower yields. But you do not need to defat with mimosa anyway so SWIM would advise against doing what your saying.

toluene is the nastiest. but it's supposed to pull the best jungle spice. i got a bit on the back of my hand once and within a minute i had developed a really bad rash which hurt like hell. evil stuff. i only use it when i really have to.