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These are my personal notes on developing a kitchen safe method of concentrating and cleaning up tobacco alkaloids.
100% of the credit, and reason I am attempting this, goes to those that went before me, and discovered the entire WTA vs nicotine alone limitations.
read about here, on DVAP's blog.

this is a 'poor mans' attempt to duplicate his results, in effectiveness, if not efficiency.

I hope that blogging as I go will be of benefit to others, and will motivate me to continue my experiments. Questions, comments are welcome.
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  1. by flash boiling the absorbed water in the tobacco, I have seen increases in total yield from the tobacco of greater than 25%. But, even more importantly, the elimination of H2O from the oil, and subsequent fine filtration/settling of the oil to remove (now) undissolved sodium carbonate, greatly improves reliable and repeatable extraction to even mildly acidic water.
    I've repeated the process 3 times, with results within 5% of each other, and measuring out to ~ 24mg/ml, and no need to 'augment' the final product with commercial juice.

  2. I have taken one new sideline 'experiment' with the initial tobacco preparation that I hope will dramatically increase the extraction efficiency of the alkaloids from the tobacco matrix.
    discusses the Microwave-assisted extraction of solanesol from tobacco leaves.... the electron photographs show cell wall degradation from moderate amounts of microwave radiation.

    by the mechanism of action, we should be able to achieve the same results without using a microwave.

    Basic premise, would be to
    1. add sufficient basic solution to cause sufficient cellular turgidity.
    2. pre-heat the mineral oil to slightly greater than 100C.
    3. slowly add the tobacco to the oil, and the oil would flash boil the water in the tobacco

    This would cause cell wall rupturing, and expel the cell products with enough energy to escape the tobacco matrix, and dissolve into the oil.

    4. The excess water would be boiled off, maximizing the partition co-efficient.

    * limitation would be that the excess carbonate would have to be carefully filtered to prevent it from neutralizing the acidic water step. ​
  3. I added an additional 50ml of basic water to the 'already extracted' tobacco, and let it sit for 5 days. Partly to ensure that the water was taken up, through the oil coating everything, but mostly because of lack of time to get back to it.
    The water was taken up quite readily, and the tobacco swelled up considerably.
    I then did a further extraction with the mineral oil, copying the steps as before, doing 3 extraction with oil, letting each one sit for a full day.

    Extracted the resultant mineral oil with acidic water, and then attempted to isolate any remaining alkaloids. There was a trace, but not enough to measure.

    Next, I attempted a quick extraction from the tobacco using a more far more aggressive non-polar. After washing and isolating, I did end up with some additional alkaloids, with a much darker colour than the original ones. Very low volume, less than 0.05 ml as best as I can measure them. I can't titrate the result without knowing exactly what they are. It might be worth doing a much larger batch to get a more accurate measurement.

    Next steps, are to dissolve the isolated alkaloids back into the mineral oil, and extract using a kitchen friendly process, to measure the efficiency of various methods.
  4. I finally got around to extracting and concentrating the alkaloids from the 20g of tobacco.
    I used a nonpolar solvent with a known high partition co-efficient 3 times on the tobacco, washed the resulting solution 3 times with 1/2 volume of basic water, then extracted to acidic water, washed with the non-polar once, basified the acidic water and moved the alkaloids back to the non-polar solvent.
    I ended up with ~0.2ml of alkaloids which equates to ~200mg. I still need to titrate to confirm the quantity, as I don't have a scale accurate enough.
    If one assumes 1.2% available alkaloids in the tobacco, this amounts to a recovery efficiency of 83%
    Next, I will add more basic water to the tobacco and let it sit for a day.
    I will then do a second extraction to see if there are more recoverable alkaloids that were missed due to insufficient deprotonation.
  5. doh, should read "de"protonation throughout, not protonation. That comes later.
  6. a couple days ago, I added 10ml of basic water (78g/l sodium bicarbonate solution pH 12.3) to 25grams of finely ground tobacco and left it in an enclosed container.
    Today, on opening the container the entire mass was barely moist with a strong earthy smell of ammonia, and the tobacco has gone from a golden brown to a very dark colour, almost like soil.
    I'm confident that there was more than enough -OH to fully protonate all the alkaloids in the tobacco, while maintaining an absolute minimum water volume.

    Next step, is to see just how much I can extract from this.
  7. my reasoning to reduce the initial basic water volume is to maximise the transfer at a 'poor' partition coefficient of 4:1, thereby increasing overall yield.

    if you use 40 ml of water and 40 ml of oil, then the most you will get is 75% transfer.
    if you use 20 ml of water and 40ml of oil, then your potential increases to 88%
    if you use 10 ml of water, and 40ml of oil, then it increases again to 94%

    very little water is needed, as water molecules and the -OH ions highly mobile.
    I would normally add the water a little at a time to ensure uniform distribution, but as a test of mobility, I added 10ml of basic water on top of 25grams of finely powdered dry tobacco. The water 'pooled' on the top due to surface tension, with little being absorbed. I'll leave it and see how long it takes to uniformly saturate the tobacco.
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