Beta Carboline MAOIs - towards a more effective e-liquid

[kardenm]

"have you tried extracting tobacco with water? You gotta do it at least once, to really appreciate the non polar first step! "


Yes. I did do one water extraction. Seemed pretty effective although it gets all the baddies to. What is the problem that you see with it tceight? It seems to me easier to filter the water only mix rather than a mix with oil in it. Mainly for that reason i like the approach of getting rid of all the solids before purifying with acid/base extractions. I realize that's defeating the built in saftey of the method to some degree but may not be necessary to evap all of the water and you would also have alot of garbage still. But i still might try it if there is a way to get the alkaloids to then go into the oil.

By the way, I think kina mentioned that olive or vegatable oil might be better than mineral oil. Is that true? I really don't like this (heavy) mineral oil. Doesn't look like it works very well but I haven't done enough to really say one way or the other.

 

[kardenm]

Put the emulsion on your Christmas card list, cuz' it'll still be around come December...

This is actually something I've been thinking about and have fooled with in the past, but I shy away from it due to the experience with an absolutely horrid emulsion.

Yeah. I guess that could be a problem.

 

[hgielm1]

Don't I remember some thing from about 2 years ago about how the SIZE of the nicotine particles in the ejuice was part of the problem with not getting "sufficient" lung and/or brain "hit". Has anything more been learned about that? Or, is "beta carboline" the answer to making a more effective liquid? I don't really know what I'm talking about here, so forgive me. Just curious.

 

[tceight]

Re-reading some past posts, and found that DVAP edited this one. Must have missed it, and by the timestamp it was quite a ways back when it was posted.
Some good info, better than my 'sugar/salt solution' explanation, so reposting in case it was missed.
DVAP, don't do that! I hate to miss your posts. Always food for thought.

must... Hunt... Down... Kin... And... Slap... Him... Upside... Head... With... Codex... twice.
It doesn't really work like that... it's not like a crowded bar. I can think off-hand of what's known as the 'common ion effect' affecting the solubility of say sodium chloride in a solution of potassium chloride...the common chloride anion plays a part, probably won't have a lot of luck getting a lot of sodium chloride to dissolve in a saturated solution of potassium chloride..(and given time, I'd bet the equilibriums at play would end up with a balance of dissolved and precipitated sodium and potassium chloride) and that's a bit like a crowded bar... but you could probably get a bunch of sucrose into that same solution because the non-ionic sucrose really doesn't give a flip about chloride, sodium, or potassium. In the context of what's going on here.

There are a lot of factors in play.. I can't recall meaningfully a lot of them, intermolecular fiddling, energy, kinetics, etc. (Being a spectroscopist, I forget all kinds of things that are off the straight and narrow of what I do day to day!)

Alkaloids probably won't give a 2nd thought to the presence of these compounds.

Best best is to read up on solubility to help get past the analogous thinking that seems to be knocking you off course. Solutions are weird.

 

[tceight]

......................................I feel pretty safe figuring a partition coefficient of at least 4 (solid evidence) and perhaps as high as 6. As partition coefficients go, these are pretty similar in the big picture.

This is firmly in the "good enough" range, though not ideal for too much fooling around with isolation. Other tricks/solvent systems needed for that.

the "good" news about this is also, that if the partition co-efficient to oil is that 'poor', then we should be able to safely make the assumption that going the other direction is great. If the oil doesn't grab them up, it won't hold on to them either.

looking at the 'original recipe' and making some assumptions,
assuming 20 grams of tobacco will give you 200mg of alkaloids in 40ml of oil,
assuming a partition coefficient of say 4:1...
wash 1 time with 1/2 volume of basic water, for a loss of about 25mg.

leaving 175 mg to move to the acidic water, and the water does not need to be very acidic,
assume 98% transfer (out of my hat)
to 2.5ml water/7.5ml glycerin
for 10ml of 17.5 mg/ml final product.

if this sounds reasonable, then it would explain why
http://www.e-cigarette-forum.com/fo...s-more-effective-e-liquid-40.html#post1775588
worked.

 

[tceight]

Yes. I did do one water extraction. Seemed pretty effective although it gets all the baddies to. What is the problem that you see with it tceight? It seems to me easier to filter the water only mix rather than a mix with oil in it. ..............................................................
By the way, I think kina mentioned that olive or vegatable oil might be better than mineral oil. Is that true? I really don't like this (heavy) mineral oil. Doesn't look like it works very well but I haven't done enough to really say one way or the other.

I hate messing with water extractions. the tobacco soaks up 5 times it's volume like a sponge, and then turns into a mush that can't be worked with. Maybe I'm doing it wrong?
If interested, there is a good writeup in the "Lorillard" papers on water extraction, including a multistep partitioning approach that greatly increases initial concentration. Someone have the link? I lost my bookmarks when I changed OS.

I've used heavy mineral oil with great success. the SG and viscosity difference isn't huge.
Vegetable oils may be better. I left them alone to try to eliminate variables.... which there are a lot of in vegetable oils.
All the extra stuff in vegetable oils may make it a more aggressive solvent, but not necessarily for the stuff we want.
DVap has confirmed the alkaloids miscibility in mineral oil.

 

[tceight]

Don't I remember some thing from about 2 years ago about how the SIZE of the nicotine particles in the ejuice was part of the problem with not getting "sufficient" lung and/or brain "hit". Has anything more been learned about that? Or, is "beta carboline" the answer to making a more effective liquid? I don't really know what I'm talking about here, so forgive me. Just curious.

there are studies that disagree.
my own take.... I know I get nicotine, period. From an aerosol medicine pov, E-Cig's are a great delivery tool. Optimal droplet size, slow speed, and long duration.

 

[kinabaloo]

the "good" news about this is also, that if the partition co-efficient to oil is that 'poor', then we should be able to safely make the assumption that going the other direction is great. If the oil doesn't grab them up, it won't hold on to them either.

Not quite. The reverse depends on a different partition ratio - that for the protonated alkaloids (salts). Though you are right that will be much more on our favor.

The fact that the freebase alkaloids are polar enables our mehod, but also makes the partition for the freebase alkaloids poor. C'est la vie. That is, it is not only that the oil is a poor solvent for polar organics but that the water is a quite good solvent of polar organics too. Polar organics fall in the middle zone in this way (hence the 'poor' partition).

But with careful volume choices, we could perhaps get 90%+ of the alkaloids into the oil.

~~~

I agree that a circa 20mg/ml end product should be possible. And hopefully we can have that confirmed one day (probably by titration).

 

[hgielm1]

Don't I remember a discussion over a year ago about the reason that ecigs didn't have the throat/lung/and brain "hit" as analogs, was because the ejuice wasn't absorbed properly, due to the size of the nicotine particles - they were either too large or too small - I can't remember. Do you think that modifying the eliquid by changing the size of the particles would cause the way it is absorbed to be more effective? It doesn't feel like the ecigs provide a "hit" to the brain the way that analogs did. I'm still sticking with ecigs - no analogs for over one and 1/2 years - but it still does seem like "something is missing". Maybe it is the beta carboline MAOs. I really don't know what I'm talking about, but I'm curious so I thought I'd ask what you guys think. Thanks. (is there a better place where this should be posted?)

 

[Bagazo]

I hate messing with water extractions. the tobacco soaks up 5 times it's volume like a sponge, and then turns into a mush that can't be worked with. Maybe I'm doing it wrong?
If interested, there is a good writeup in the "lobilard" papers on water extraction, including a multistep partitioning approach that greatly increases initial concentration. Someone have the link? I lost my bookmarks when I changed OS.

I think this is the water extraction you are talking about:

Investigations Into the Extraction of Nicotine From Tobacco

Says they got 80-85% nicotine reduction from the leaf. The idea was to get the nic out and still leave the leaf smokable and that is why they went with water instead of solvents.

There is also this:
The Form of Nicotine in Tobacco. Thermal Transfer of Nicotine and Nicotine Acid Salts to Nicotine in the Gas Phase

Which says

These results suggest that nicotine is mostly protonated in tobacco leaf.

which would explain why a water extraction would work.

 

[kinabaloo]

Don't I remember a discussion over a year ago about the reason that ecigs didn't have the throat/lung/and brain "hit" as analogs, was because the ejuice wasn't absorbed properly, due to the size of the nicotine particles - they were either too large or too small - I can't remember. Do you think that modifying the eliquid by changing the size of the particles would cause the way it is absorbed to be more effective? It doesn't feel like the ecigs provide a "hit" to the brain the way that analogs did. I'm still sticking with ecigs - no analogs for over one and 1/2 years - but it still does seem like "something is missing". Maybe it is the beta carboline MAOs. I really don't know what I'm talking about, but I'm curious so I thought I'd ask what you guys think. Thanks. (is there a better place where this should be posted?)

The missing MAOIs make the response both less intense and less long.

Plus the fact that the alkaloids are in a carrier liquid might slow absrobtion somewhat (particularly with VG I'd say), but this ight be minimal.

The particle size can't easily be changed (it's just the physics of recondensing vapor and ejected droplets. And probably it would'nt make much difference anyway. It was a topic of interest at one time.

 

[kinabaloo]

[...] which would explain why a water extraction would work.

It certainly works. But one gets much more than just alkaloids. One also gets sugars, tannins, gums, etc., things that we don't want to inhale, even assuming they leave the atomiser. To the extent that droplets are ejected, they would be in the 'vapor', but a lot would gum up the wicking and some 'burn' on the heater coil.

 

[Bagazo]

But the acid/base work afterwards gets rid of the other junk. I know that I have done it a couple of times and once I bring the Ph up and mix with the non-polar solvent nothing seems to come over into the solvent but in theory (because it can't be seen) the deprotonated alkaloids should be moving over into the polar solvent. I have even shaken for a couple of seconds and I have never gotten more than a couple of mm of emulsion where the water and solvent meet.

Only bad thing is that I don't have the materials available to check how much nic I have gotten.

 

[tceight]

I think this is the water extraction you are talking about:

Investigations Into the Extraction of Nicotine From Tobacco

Yes, that's the exact paper I was thinking of. Thanks!
The same multi step process could also be done using oil, to maximize yield.

 

[kinabaloo]

But the acid/base work afterwards gets rid of the other junk. I know that I have done it a couple of times and once I bring the Ph up and mix with the polar solvent nothing seems to come over into the solvent but in theory (because it can't be seen) the deprotonated alkaloids should be moving over into the polar solvent. I have even shaken for a couple of seconds and I have never gotten more than a couple of mm of emulsion where the water and solvent meet.

Only bad thing is that I don't have the materials available to check how much nic I have gotten.

I understand, but doing it in 2 steps like this means more water relative to the oil (or too much oil) - for a good yield from the partition. So what is the advantage ? Just that can filter the water more easily first? Yes, but the extra water volume has a serious downside.

~~~

ps : welcome to the team

 

[Bagazo]

Well the paper showed that they got 40-45% extraction from a single extraction. I actually used alot of water and then evaporated alot of it to reduce the amount of solvent needed. Extra step but at this point it's just a weak tea and I haven't even opened anything to worry about (acids, lye). Next I raised the Ph and used thinner as the non-polar solvent (above I typed polar but it was non, edited). I know that it may not be a good idea to use this solvent but I had no intention of vaping the results.

Follwing step involved lowering the Ph and extracting into water. The following should never be done but I just had to know if I had gotten anything at all. I placed the water/nic mixture in a jar and allowed all the water to evaporate in a locked cabinate. I ended up with about 1.5 mm of crystals at the bottom of the jar. Without even touching the jar I poured plain water into the jar (about 250ml), locked the cabinate and let it sit overnight. In the morning the salts had almost all dissolved I took the jar out and stirred until everything was dissolved I dumped the contents out and washed everything up.

 

[slopes]

Out of interest, can anyone say why this simple kitchen method should or shouldn't work?

Salt n' Vinegar Method.
1) Soak crushed tobacco in white vinegar.
2) Press the mush to extract the liquid.
3) Repeat steps 1) and 2) and discard tobacco.
______________________________________
4) Heat liquid, stir in table salt and chill.
5) Syringe off and discard the liquid.
6) Add hot water to residue
7) Repeat steps 4) and 5).
______________________________________
8) Filter residue and add to PG.

 

[kinabaloo]

Out of interest, can anyone say why this simple kitchen method should or shouldn't work?

Salt n' Vinegar Method.
1) Soak crushed tobacco in white vinegar.
2) Press the mush to extract the liquid.
3) Repeat steps 1) and 2) and discard tobacco.
______________________________________
4) Heat liquid, stir in table salt and chill.
5) Syringe off and discard the liquid.
6) Add hot water to residue
7) Repeat steps 4) and 5).
______________________________________
8) Filter residue and add to PG.

gonna pass

 

[slopes]

gonna pass

I'm gonna try it and see. It's a good opportunity to test out my pollen press

 

[kinabaloo]

I'm gonna try it and see. It's a good opportunity to test out my pollen press

Any link to this idea ?

I'd use as little tobacco as possible