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Ethanol Extract - Full Strong Buzz & Moderate flavor

Discussion in 'Liquid Extraction From Tobacco' started by Lastlokean, Dec 13, 2013.

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  1. Lastlokean

    Lastlokean Senior Member Verified Member ECF Veteran

    Mar 12, 2010
    Red Wing, MN
    That is such a far cry from a scientific or sound conclusion. This person did multiple washes and transfers back and forth through a variety of organic solvents. Not to mention the link you posted does not even mention the solvent/methodology used. How can you logically deduce this is some kind of standard of 100% efficiency WTA?

    Here is a much more legitimate link.
    http://pages.towson.edu/jsaunder/Saunders%20Publications/13.Quantitation%20of%20Major%20Tobacco%20Alkaloids%20by%20High%20Performace.pdf

    chart.jpg

    As can be seen it is reasonable to expect 17 mg/gram nicotine, 22mg/gram Nornicotine, .7mg/gram Anatabine not to mention the harman and other alkaloids. This research article seems to imply tobacco contains at least 40mg alkaloids per gram dry tobacco, or a 4% yield. This allows me to draw serious question to the efficiency and methodology of others supposed claims of 'wta'.

    Not to mention the huge potential variance among tobacco grades. The Drum tobacco I used is quite potent. When I used to roll my own of them they would give pack a day smokers that bummed one a serious head rush.

    Finally in the quoted link is talking about a yield of '.5ml' from 100 grams of tobacco. This is VERY far from qualitative. That measurement could easily be .8 mls of a substance that weighs 3 grams/ml leaving him with a yield similar to mine. I'm not saying that is the case. Just that volume and weight just don't relate in the way you are trying to relate them.

    One last point, harman and harmine alkaloids are very water soluble. If one were to do a polar/nonpolar rinse to collect alkaloids it is very possible they may wash away the harman in the nps/water rinse back and forth process.

    Sorry to rant back so hard, but please lets be reasonable and scientific about our conclusions.

    Sorry if this is threatening to someone who makes a huge fortune selling overpriced ejuice... But I am going to start calling this whole tobacco alkaloids via ethanol. WTAE.

    There I didn't even mention significant figures or appropriate units relative to quantity.:evil:
     
  2. PLANofMAN

    PLANofMAN Signature Guru Verified Member ECF Veteran

    Dec 9, 2012
    Woodburn, OR
    That was a summary. A lot of technical stuff was left out of that particular write-up. As for calling it WTAE, you can put a crown on a pig and call it a princess, but that does not make it so.

    Since Dvap is following this thread and has already posted in it, I'll let him explain why you are wrong.
     
  3. Lastlokean

    Lastlokean Senior Member Verified Member ECF Veteran

    Mar 12, 2010
    Red Wing, MN
    High-performance liquid chromatography does not lie. I have provided scientific evidence that my yield is reasonable.

    I am quite simply stating the basis of scientific methodology.

    You can not take experiment and methodology A, and use there result to set an unbreakable 'fact'. That is simply unsound. It does not become 'truth' without mass reproduction and verification. The data in the link I gave is a published scientific document clearly demonstrating tobacco contains at least 4% alkaloids by weight of dry tobacco. Also yields that high can be achieved with a simple solvent soak and filter.

    Where your argument is one person who in his basement did an acid/base multi-phase extraction. That clearly has loses at EVERY stage. Then used it to say anything that yields more isn't as pure. That is simply unfounded gibberish.

    Please clarify for me.... What does this '.5 ml' of end product weigh in grams? I hope you understand how liters and grams are not quantifiable without more information... aka density.

    .5 ml water = 500 mg at room temperature.
    .5 ml of VG = 630 mg
    .5 ml of lead = 5,675 mg
     
  4. Lastlokean

    Lastlokean Senior Member Verified Member ECF Veteran

    Mar 12, 2010
    Red Wing, MN
    Where exactly did I say anything about semi-solid plant matter? I got clean amber oil. Why are you attacking this experiment from an unfounded standpoint? I appreciate input, but you could at least read the thread before you comment.
     
  5. Chinook

    Chinook Super Member ECF Veteran

    Sep 16, 2013
    OR, USA
    Thanks a lot for the detailed clarification. I got it, I think. This is more for the alkaloid extraction vs flavor.

    Is there any way to extend this method to increase the flavor production for robust NETs with less unwanted plant material compared to hot or cold VG/PG macerations?

    Thanks!
     
  6. Lastlokean

    Lastlokean Senior Member Verified Member ECF Veteran

    Mar 12, 2010
    Red Wing, MN
    Doubling up on the tobacco amount into one bottle may be enough flavor to offset the losses from being cold extracted. So make a NET with a cold 1-2 hour soak, to get a little flavor and minimize plant matter / oils. Then combine this with a WTA via cold ethanol to your desired/needed alkaloid strength. Then pray it has as much flavor as your looking for.

    You could always process more tobacco less time with a NET. Say do a cold 3 hour soak on 100 grams of tobacco. Filter it off. Then add the NET to a fresh 100 grams of tobacco and soak for another 3 hours cold. Doing this should allow one to get very strong flavors without pulling lots of nasty crap from long hot soaks.

    Edit: This is obviously not tobacco efficient.
     
  7. Veritas Obscurum

    Veritas Obscurum Full Member

    Dec 20, 2013
    United States
    All we need is a % nicotine per mill range from a specific solvent like EtOH or PG and we're golden.
     
  8. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    Retired
    The 0.5 grams per 100 grams was an early effort. Depending on the tobacco, I can get several times that amount of purified alkaloids.

    3.5 grams from 110 grams of tobacco gives me enough information to get my head around this.

    The amount of available alkaloids from the typical RYO tobacco is around 1.2%. Getting those 1.2% alkaloids isn't easy and steps must be taken to assure thorough cell disruption. I'd guess about 25% alkaloid recovery using cold ethanol. This means that 110 grams of tobacco would yield 0.33 grams of alkaloids. The harder you work to improve the alkaloid recovery, the more crud is going to be co-extracted.

    Ethanol is going to pull out a lot of crud, even ice cold. Purified tobacco alkaloids are not semi-solid or even viscous, they are a free flowing liquid. If we take the 3.5 gram figure and combine it with 0.33 grams of alkaloids, then the alkaloid percentage in the semi-solid can be gotten from 0.33/3.5 or around 10%. WTA is a purified alkaloid isolate, so a material that is only 10% pure should not be referred to as WTA.

    If I understand the dilution correctly, the semi-solid was diluted to 2.4% of it's initial strength. This is equivalent to diluting 1 gram of the semi-solid to around 40 mL or all 3.5 grams to 140 mL. Since the 3.5 grams of semi-solid likely contains around 330 mg of alkaloids, and the final volume for vaping is 140 mL. This gives us 330 mg / 140 mL or around 2.4 mg/mL of tobacco alkaloids.

    2.4 mg/mL strikes me as a pretty good alkaloid content for a NET type extraction. The use of cold ethanol might well provide an advantage over more aggressive extractions.

    Getting a highly efficient alkaloid extraction unfortunately requires aggressive conditions. Sort of a "twice the alkaloids equals twice the crud" situation.
     
  9. Chinook

    Chinook Super Member ECF Veteran

    Sep 16, 2013
    OR, USA
    Very interesting idea indeed! So from what I understand, the shorter cold ethanol soaks will put out the tobacco "flavor" compounds first. Is this why you are suggesting 2 x 3 hour soaks with fresh tobacco for the 2nd soak?

    Why not then 2 x 6 hour soaks with fresh tobacco for the 2nd soak? I assume this would be a stronger NET but also with plenty of alkaloids in it?

    Sorry if I'm asking too many questions but this topic really intrigued me :)
     
  10. LucentShadow

    LucentShadow Super Member ECF Veteran

    Dec 28, 2011
    Michigan, USA
    I'm not sure why there is so much bristling going on here by some.

    Lastlokean is being quite reasonable in his methods, from my point of view. I don't see him touting this as a 'purified' WTA extraction, either. Simply 'assuming' such for safety is reasonable, and was stated as such. I don't see any evidence of him putting any of the testers in any danger.

    On the other hand, assumptions of motives and such just leads to chaos, IMO. I think Dvap's skepticism is non-threatening in manner, and his input could well be productive, given his experience.

    I'd love to see reasonable discussion on this, even if it's slow-going.
     
  11. holy_handgrenade

    holy_handgrenade Senior Member ECF Veteran

    May 20, 2013
    Phoenix, AZ, USA
    I'll have to agree with lucent shadow; barring an actual stated amount of "golden clear alkaloid syrup" I had assumed, and for that I apologize. I'm still very interested in discussion and seeing how this turns out. :D
     
  12. Aheadatime

    Aheadatime Ultra Member Verified Member ECF Veteran

    Feb 20, 2013
    USA
    Couldn't agree more.
     
  13. PLANofMAN

    PLANofMAN Signature Guru Verified Member ECF Veteran

    Dec 9, 2012
    Woodburn, OR
    Did you happen to notice, when you ordered your nicotine test kit from Wizard Labs, that last little line at the bottom of the description?
    Nicotine Test Kit

    "Special thanks to ECF's resident chemistry professor, DVap, for publishing his original methodology and labwork on titrating for nicotine content."
     
  14. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    Retired
    Relax folks. I happen to like the cold ethanol extraction as compared to other soak procedures when it comes to not making complete gunk.

    As for alkaloid content, I already have a solid expectation of what the test will show and have warned against being overly optimistic, but we'll let the test have it's say.
     
  15. hittman

    hittman ECF Guru Verified Member ECF Veteran

    Supporting member
    Thanks for the good read.
     
  16. Lastlokean

    Lastlokean Senior Member Verified Member ECF Veteran

    Mar 12, 2010
    Red Wing, MN
    I did notice that Dvap is an acknowledged chemist in these parts. That does not make him infallible or any experiment executed by him a standard, especially not if it is in conflict with published literature. (No offense Dvap, its just the nature of scientific process) :toast:

    Got any analytic sources on that information? All detailed information I can find yield in the range of 3-5% alkaloids / gram dried leaf. That is with simple agitative soak of ethanol,methanol,acetone, water, HCL, etc. SOURCE page 7

    Sorry if I went off on a defensive rant. I just don't want conclusions drawn on the purity of this resulting substance one way or the other until there is some concrete evidence. I think we can all agree to move on and say what exactly this is is up in the air. If anyone has the connections to a lab capable of HPLC (at reasonable prices) I would certainly send off a sample.

    Before I even begin testing the nicotine content of oil resulting from evaporating cold washed ethanol I would like to get some clarification on the test kit itself. I can find very limited information on Nornicotine or how it would respond to such a test. Being as a full spectrum alkaloid extract is expected to be very roughly, 49% nicotine 49% Nornicotine 1% Anatabine 1% variety of other alkaloids, (2,2'-Bipiperidine; 2,3'-Bipyridine; 2,2'-Bipyridine; Anabasine; Nicotelline; N-Methylanabasine; Anatalline), would it be reasonable to assume that a pure WTA extract may test 50% pure via such procedures? Or would it be more reasonable to expect nornicotine to have equal impact on the solutions acidity, or even somewhere between the two? About the only thing I can find out, is the glaring obvious, it is nicotine without a methyl group. It seems difficult to determine much accurately from such a titration without clearly understanding the details of all the alkaloids at play. But, I am an electrical engineer that pursues an interest in organic chemistry, and some of the finer details of chemistry yet elude me.

    On a side note: I have recently run into evidence that 50% ethanol 50% water, in other words 100 proof vodka, may be even more efficient than 100% ethanol for this process.
     
  17. holy_handgrenade

    holy_handgrenade Senior Member ECF Veteran

    May 20, 2013
    Phoenix, AZ, USA
    So I guess the next question I have, while waiting for purity testing :)

    How fragile/volatile are these extra alkaloids? I mean, if we get a pure WTA extract, DVaps numbers seemed to indicate 95% nicotine to about 4.5% other alkaloids (I dont have any more than just what DVap suggested in his WTA thread/blog)

    At what dosage are those remaining alkaloids actually ingested by the smoker? While I'm all for a good way to get all smokers off the analogs to vaping, I'm curious if we aren't introducing new alkaloids to some folks or if not new, at a larger dose than would otherwise be received from combustion.

    That being said; how pure does the extract really need to be to be effective? Assuming this process turns out good but less than pure, does it need to be more pure than what this process results in? That being said, I'm sure purity has it's place for consistent dosaging and perhaps making non-tobacco flavored juices.


    Lastlokean: If 50% ethanol 50% water may be more effective at extraction, wouldnt the water make it more difficult to wash down to the resultant alkaloid soup? Ethanol seems to be effective because it evaporates pretty quickly at room temperature, however, water is slower - and I would suspect that adding heat may disrupt or damage some of the alkaloids in the process - could be wrong though. :) <edit> the assumption being that one were to add heat to speed up the evaporation process</edit>
     
  18. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    Retired
    The nicotine test kits are tuned for nicotine.

    They can be used for WTA type mixes to obtain an accurate result since nicotine is the dominant alkaloid present. It all comes down to the molecular weight, the basic extent of the nitrogens, and the pH behavior of the indicator. The test relies on the protonation of the nicotine pyrollidine nitrogen. The pyridine nitrogen does not come into play.

    Nornicotine also has this pyrollidine ring while anabasine and anatabine have a piperidine ring. All are more basic than the pyridine ring which they all have and with BTB indicator, the pyridine nitrogen again doesn't matter. It protonates at pH levels below the range of the indicator. With a molecular weight of approx 162 for nicotine, the math used with the test will work perfectly for any base with this same molecular weight (again, with the understanding that it effectively acts as a mono base with respect to the indicator). At 148, nornicotine is a bit off. At 162 anabasine is right on, and at 160 anatabine is pretty close. In practice, when I produce at WTA liquid at 24 mg, the test will nail it.

    I advise a large dose of caution when Googling for sources. In most cases, a specific reference tobacco is being used, and these reference tobaccos can contain significantly more alkaloid content than the tobaccos that we actually encounter at the tobacco shop.

    "Nicotine Psychopharmacology" (Henningfield) is a good read as it provides a good amount of real world data on alkaloid content of tobacco. I'm more than willing to offer advice, caveats, and opinions based upon my own research and results, but I'm not particularly interested in reproducing a paper trail within the context of this thread. It's interesting but not so much that I feel compelled to prove myself here. You can take what I say as sage advice or you can take it with a grain of salt. I'm fine either way. We'll look forward to the test results.
     
  19. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    Retired
    For sake of duplication and also curiosity, I've gone ahead and obtained the same Drum Halfzware Shag and some 190 proof ethanol.

    The alcohol and 100 grams of tobacco were chilled to -5C. 0.75L of alcohol was added to the tobacco. The tobacco was compacted sufficient to allow the alcohol to cover the tobacco. The mixture is being allowed to sit at -5C for 6 hours with a gentle stir of the tobacco every hour. Upon completion of the extraction, the ethanol will be filtered, measured, and stripped. The residue will be processed to remove non-alkaloidal components such that the remainder will be purified free base tobacco alkaloids. The alkaloids will be diluted in PG and determined by titration. Total mg of recovered alkaloids will be calculated.

    Comparison of alkaloid recovery to the OP's recovery should provide results roughly consistent.
     
  20. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    Retired
    Similar volatility to nicotine. Boiling points are around 250°C or nearly 500°F.
    The combustion process actually destroys much of the alkaloid material present in a cigarette. You could view the alkaloid delivery as a distillation process where the heat of the advancing coal liberates alkaloids from the tobacco matrix into the inhaled smoke stream.
    It doesn't really have to be pure, just at a concentration sufficient for efficacy. Folks who respond to WTA seem to prefer it in the 12 - 24 mg range. Of course, purity is a good thing as it precludes non-alkaloidal tobacco material from being inhaled.
    50% water will cause a great deal more gunk to be extracted from tobacco (One may take my word for this or not). The alkaloids are actually quite robust in solution at the temperatures you're talking about.
     
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