Hexane or Heptane?

[Trickster]

Is heptane any better than hexane as a non-polar solvent for extracting spice from mhrb?

 

[UK Explorer]

Seems a massive shame to lose the 'full spectrum of goodies' on a first attempt, so much so that leaning against hexane now.

Please excuse my friend's ignorance as a newbie, by limo take it D-limonene? If so he can source this much easier anyway, would this be okay?: D'limonene supply

...the environmentally and user friendlier make up of this option certainly appeals also.

Xylene appears easy to obtain also, and looks cheap too: Xylene

Would both these items require an evaporation test for any residue as you would to check naphtha?

 

[mandelbrot]

now see, this is when miscibility is a factor.
limonene and xylene are slightly miscible with water, so those solvents will pull a bit of the water soluble compounds (whatever is in the basic aqueous phase). completely nonpolar solvents like hexane and heptane will not. better overall yields are observed with the former solvents, as the latter are not very efficient for extraction. they're more appropriate for crystallization.

Can you go a little deeper, benz?

I've read recently that (with HPLC results) the "jungle" is upper 90 percentile DMT. If that is so, how does hexane/heptane not capture those DMT molecules? Is it forming a bond with something else causing it to be water soluble and not allowing the uptake with lighter solvents?

UK Explorer:
Yes, D-limonene. There are teks on the wiki for it. A lot of people on the nexus swear by it. I'm not sure if that supplier/product is good, as I've never used limo before.

Evaporation tests are always recommended for higher solvents but generally with xylene and limo, evaporation is avoided. It takes too long and is quite a stink. After extraction with those solvents, you would salt the DMT out of solution. Go to the nexus wiki and look at the food safe extractions.

 

[Infundibulum]

Please excuse my friend's ignorance as a newbie, by limo take it D-limonene? If so he can source this much easier anyway, would this be okay?: D'limonene supply

...the environmentally and user friendlier make up of this option certainly appeals also.

Xylene appears easy to obtain also, and looks cheap too: Xylene

Would both these items require an evaporation test for any residue as you would to check naphtha?

Yea, by limo we mean d-limonene. The product you linked to is limonene the stuff you want, even though this one is a bit too orangey. Limonene has no colour and you may be able to find crystal clear limonene if you're really into as-pure-as-possible-solvents by searching a bit further. But the former will work fine too.

Xylene is fine too, maybe even more desirable than limonene. Limonene will stink your house like oranges, xylene on the other hand will give it a far more desirable (by many) aromatic hydrocarbon tint.

 

[benzyme]

I've read recently that (with HPLC results) the "jungle" is upper 90 percentile DMT. If that is so, how does hexane/heptane not capture those DMT molecules? Is it forming a bond with something else causing it to be water soluble and not allowing the uptake with lighter solvents?

the old chem adage: like dissolves like.

while tryptamines have an alkyl group (attached to an amine), the aromatic character of the indole group dictates solvent accessability. for this reason, DMT is more soluble in aromatics, such as xylene and toluene, than aliphatics like hexane and heptane.

 

[Trickster]

... DMT is more soluble in aromatics, such as xylene and toluene, than aliphatics like hexane and heptane.

That would mean that distribution coefficient in a system of an aromatic + aqueous basic solution is higher than in a system of an aliphatic + aqueous basic solution, right?

Does it mean that with aromatics as extraction solvents every pull collects more spice? So, with aliphatics if one does a few more pulls one will get the same yield as with aromatics?

 

[mandelbrot]

thanks for the clarity, benz. brings more questions though, sorry.

So are there variable indole groups of trypamines (specifically NN-DMT)?
If DMT is still soluable because of the alkyl group, does that not hypothetically mean you can still pull close to 100% of the freebased DMT with lighter solvents? Even if it requires more pulls/more solvent..
Or is the alkyl group been bonded to by something else, disallowing solution with the non-polar solvent?

 

[Infundibulum]

... DMT is more soluble in aromatics, such as xylene and toluene, than aliphatics like hexane and heptane.

That would mean that distribution coefficient in a system of an aromatic + aqueous basic solution is higher than in a system of an aliphatic + aqueous basic solution, right?

Yes

So, with aliphatics if one does a few more pulls one will get the same yield as with aromatics?

No, not actually. And that is because the system is far more complex than basic solution + dmt + non-polar solvent. It usually is basic plant aqueous extract (+dmt) + non-polar solvent. Things inside the basic solution can chelate dmt in one way or another (e.g. clathrate structures) thus hindering dmt from being pulled. As a rough explanation, let's say that when a dmt molecule has the choice between a hiding pocket versus aliphatic, it will most likely choose the hiding pocket in the basic solution. But if it has the choice between hiding pocket and aromatic, it will choose aromatic solvent.

There is plenty of experience that indicates that MHRB solution that have been exhausted with aliphatics (8-10 pulls) will still yield a lot when switching to aromatic.

If DMT is still soluable because of the alkyl group, does that not hypothetically mean you can still pull close to 100% of the freebased DMT with lighter solvents? Even if it requires more pulls/more solvent..
Or is the alkyl group been bonded to by something else, disallowing solution with the non-polar solvent?

The reasoning is wrong here; dmt is not pulled by aliphatics because of its alkyl group, it is pulled by aliphatics because as a whole it is somewhat soluble in them. Both the alkyl chain and the indole chain are soluble in aliphatics.

 

[mandelbrot]

Things inside the basic solution can chelate dmt in one way or another (e.g. clathrate structures) thus hindering dmt from being pulled

This is what I was looking for!!
It makes sense now. But a question still remains. How does xylene/tolune break up the chelation? Or is it merely pulling the whole chelate out of solution? This is why it is a goo and not a crystal I assume (if I'm correct)?

The reasoning is wrong here; dmt is not pulled by aliphatics because of its alkyl group, it is pulled by aliphatics because as a whole it is somewhat soluble in them. Both the alkyl chain and the indole chain are soluble in aliphatics.

Thanks for the clearing up.

 

[Crystalito]

On another note : Can we disrupt the celation somehow,thus "liberating" DMT to be picked up by aliphatics more readily? For example i wonder if something celates better with the clathrates so it displaces the molecule of interest.

 

[Infundibulum]

Things inside the basic solution can chelate dmt in one way or another (e.g. clathrate structures) thus hindering dmt from being pulled

This is what I was looking for!!
It makes sense now. But a question still remains. How does xylene/tolune break up the chelation? Or is it merely pulling the whole chelate out of solution? This is why it is a goo and not a crystal I assume (if I'm correct)?

Well, I said above. Aromatics "break" the chelation by giving a better choice of hiding places to dmt compared to the clathrates. Which aliphatics do not. In a situation where there's loads of dmt around, some will inevitably find a hiding place in the non-polar solvent, whether the solvent is aromatic or aliphatic. But in low dmt amounts, aliphatics just don't give dmt a better hiding place choice than the clathrates, whereas aromatics do. Hence aliphatics can pull that much whereas aromatics keep on pulling from where aliphatics have stopped.

Now, it MUST be mentioned that all these explanations with chelations, putative dmt clathrates and the kinetics of dmt extraction are purely theoretical. Sort of a mental masturbation and an attempt to rationalise on what might be happening. To my or SWIM's knowledge no such things have been demonstrated, they are not far fetched however!

 

[Gir]

I was always under the influence that heptane made preeeeeeeetttttyyyy glass shardy crystals when slow evapped. Other than that I always also thought it was just up to whoever was using it, whatever solvent they wanted.

Don't you think it is somewhat unscientific approach? It seems to be a simple question that has a simple answer.

"Shot through the heart.... and your to blame... "

That was my simple answer to the "simple" question.

 

[mandelbrot]

Well, I said above. Aromatics "break" the chelation by giving a better choice of hiding places to dmt compared to the clathrates. Which aliphatics do not. In a situation where there's loads of dmt around, some will inevitably find a hiding place in the non-polar solvent, whether the solvent is aromatic or aliphatic. But in low dmt amounts, aliphatics just don't give dmt a better hiding place choice than the clathrates, whereas aromatics do. Hence aliphatics can pull that much whereas aromatics keep on pulling from where aliphatics have stopped.

Now, it MUST be mentioned that all these explanations with chelations, putative dmt clathrates and the kinetics of dmt extraction are purely theoretical. Sort of a mental masturbation and an attempt to rationalise on what might be happening. To my or SWIM's knowledge no such things have been demonstrated, they are not far fetched however!

Excellent explanation, Infundibulum. Sorry I missed the explanation before.

Can I ask what more precise term/phrase for "giving a better choice of hiding places" would be so I may research more?

 

[Infundibulum]

Can I ask what more precise term/phrase for "giving a better choice of hiding places" would be so I may research more?

Ah, this is what I get for using too much layman's terms!

Well, freebase dmt is basically not soluble in water, and as a lipophilic molecule it feels uncomfortable in an aqueous environments. It tries to "protect" itself somehow from the aqueous environment. This is a very general principle, e.g hydrophobic amino acid side-chains in proteins tend to bury in the inside of the protein so that they do not come in contact with water; hydrophobic fatty acid chains of soap molecules tend to bury inside the fatty stains (and inadvertently cleaning them); or the lipid chains of other molecules form micelles or liposomes when in aqueous solutions; the hydrophobic molecule THC accumulates in the fatty tissues of people who smoke weed; there are numerous examples around.

Since dmt does not like having water around it, it tries to protect itself. The non polar solvent is one place, and some hypothetical chelating structure in the bark extract. The latter is the default choice if there's no non-polar solvent around. If there is, then dmt makes a choice between the chelating hiding places and the NP solvent. In the situation where there is plenty of dmt some will inevitably end up in the aliphatic solvent. But if there is not much, then the dmt finds that the chelating pockets are better at providing a hydrophobic environment than the aliphatic solvent, hence they are preferred and not really much goes in the aliphatic solvent. However, if aromatic is used, then it provides a better hydrophobic protective environment and dmt is willing to leave the chelating hiding places and go into the solvent. Hence the phrase that the aromatics provide a better choice of hiding places (compared to the clathrates.

 

[mandelbrot]

Ah, this is what I get for using too much layman's terms!

Hahah.. Sorry. I know you must speak in layman's terms to get the point across. It's just hard for me to personify a hydrophobic molecule looking for a hiding place without asking "WHY?".

I assume that there is some conservation of energy or electron swapping that ties this all together? As in: number of electrons available in aromatic solvent vs. hypothetical chelating structure.

Or am I way out in left field.

 

[Infundibulum]

I assume that there is some conservation of energy or electron swapping that ties this all together? As in: number of electrons available in aromatic solvent vs. hypothetical chelating structure.

Or am I way out in left field.

No, you're right - it is all about conservation of energy, or more favourable energy states to be more precise.

And being a lazy-ass, I copy-paste from this wikipedia article:

According to thermodynamics, matter seeks to be in a low-energy state, and bonding reduces chemical energy. Water is electrically polarized, and is able to form hydrogen bonds internally, which gives it many of its unique physical properties. But, since hydrophobes are not electrically polarized, and because they are unable to form hydrogen bonds, water repels hydrophobes, in favour of bonding with itself. It is this effect that causes the hydrophobic interaction—which in itself is misleadingly named as the energetic force comes from the hydrophilic molecules. Thus the two immiscible phases (hydrophilic vs. hydrophobic) will change so that their corresponding interfacial area will be minimal. This effect can be visualized in the phenomenon called phase separation.

 

[benzyme]

gibbs free energy
equilibrium tends to favor lowest free energy states. the same holds true for protein-folding.
nonpolar molecules will aggregate when present in a polar solvent, like oil droplets in water.

 

[fraterS.O.L.]

What are some brand names for hex in the US? I am intrigued and want to try a re-x with some.

 

[fraterS.O.L.]

also would like to try methylen chloride for pulls so some info on that would be much appreciated as well. thx

 

[Infundibulum]

also would like to try methylen chloride for pulls so some info on that would be much appreciated as well. thx

Well, you know;

There is no better solvent than methylene chloride, or DCM. Basically:

-It virtually pulls all the alkaloids under the sun. And it is very well at doing so, dmt, bufotenine, 5-meo, psilocin, dmt n oxide, bufotenine oxide(?), jungle, harmine-harmaline-THH freebase, LSA freebase, LSD freebase, mescaline freebase, you name it. It is the choice of any (semi) professional who really wants to pull all of the good stuff

-it pulls efficiently at low pH, so one can make dmt pulls at pH of, say, as low as 9 - this is important when one pulls alkaloids that are very pH sensitive - this is why one should for instance use dcm to pull freebase psilocin that is normally unstable at basic pH

-It boils at 40 degrees centigrade, so it can be easily distilled off and forever reused. Many alkaloids will not boil at this temperature

-It is not flammable so it can be very safely distilled

-It sinks to the BOTTOM, that is it does not flow on top, so a separatory funnel is a saviour here

-it cannot be thus used for an STB, which is good since STB teks suck ass anyway

-It smells far far better than the trendy hippie limonene. It smells like the REAL STUFF.mmmm!

 

[Trickster]

There is no better solvent than methylene chloride, or DCM.

Wow!

Excuse my ignorance, but why would people continue using heptane, hexane, limonene, etc?

Is it because DCM is somewhat toxic?