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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. holy_handgrenade

    holy_handgrenade Senior Member ECF Veteran

    May 20, 2013
    Phoenix, AZ, USA
    Awesome! Thanks for the info Dvap.

    Really interesting thread, lots to glean. Looking forward to seeing more, Lastlokean! :D
  2. Aheadatime

    Aheadatime Ultra Member Verified Member ECF Veteran

    Feb 20, 2013
    The one thing that's throwing me off here it the measurements used, er.. well I guess it's moreso about dilution. Nicotine works at weight/volume (mg/ml), and we dilute a concentrated base (60, 100mg) to our preferred strength (6, 12, 18). That's easy enough to understand.

    What's confusing me is the 'base' strength of the alkaloid extract vs consumer levels. I suppose as I'm typing this my mind is making sense of it. The extract that the OP obtained is questionable in it's purity/strength, yet for safety reasons he/she has assumed 100% strength. Thus, he/she has weighed it in gram form and proceeded to dilute accordingly.

    So if, for example, I had .5 grams of extract assumed to be 100% strength, I would need to dilute this into 5mLs PG to get 100mg/mL alkaloid strength correct? Which I would then use the same way I use nic base, which is to dilute into preferred 12-24 range per use.

    Dvap, have you done any measurements on the alkaloid content/strength being picked up when people do VG/PG NETs? This intrigues me as it seems like if there was a measurable amount being extracted, than vendors should be advising people to proceed with caution when buying one of their NETs.
  3. Chinook

    Chinook Super Member ECF Veteran

    Sep 16, 2013
    OR, USA
    Sorry to sidetrack here somewhat... DVap and others, do you have any comments regarding cold ethanol extraction for robust NET flavoring with minimized gunk relative to the usual PG/VG maceration methods?
  4. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    Due to the strong and viscous nature of NET extractions, the material must be diluted to a vapeable (not overpowering) level. Due to the viscosity of the material, we know that most of what's there are not alkaloids. I would say that once diluted, there should be no danger of over-dosage. However, I would also consider an abundance of caution to be a good thing such that NET vendors should be at least titrating their products to determine alkaloid content.
  5. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    I've got my test batch down to nearly dryness now, and the material is not displaying the characteristic sharp alkaloid odor. I'm leaving open the possibility and probability that much of the alkaloid content of the tobacco is in alkaloid salt form such that the odor of the extract might not be what I expect from an alkaloid extract since I purify to free base alkaloids. The procedure I will be applying to the residue will convert any alkaloid salts present to free base alkaloids. This brings up the possibility that a NET extraction will contain more alkaloid salts than free base alkaloids. As a result, a titration would miss these alkaloid salts while determining alkaloid content.
  6. kinabaloo

    kinabaloo Vaping Master ECF Veteran

    The ~1mg / g nicotine content listed on cigarettes / tobacco is that received from the smoke. There's ~10x more than that available in the tobacco for extraction (~1%).

    If I am right that vaping is more mist than vapor, some fraction of the alkaloid salts would be inhaled; but what 'benefit' these might give I'm not sure (relative to free-base). Perhaps slower in effect ?

    Looking forward to measurements, and an answer to the above.

    My experience was that I could detect little in the way of nicotine, but a pronounced relaxing effect after a few minutes (maybe 5 or more - it was quite a while ago). And satiation.

    So at least some of the alkaloids get into the 'vapor' and do have physiological effect.

    Soaks are a form of WTA, just not that great. Do a dry residue test to get an indication - put some on a teaspoon and boil dry over a flame to see how much dry stuff remains on the spoon.


    For a superior method, that takes only a day (mostly waiting time), with a high yield and no contaminants (or minimal), see:

    Heat the oil only to 100C if you like, or don't heat it at all - simpler but a bit less efficient (less yield).

    See :

    for the enhancement.

    No concentration beyond typical e-liquid; still needs some care - wash it off if anything gets on your skin.

    It's a base-acid method in which tceight worked out how to maximise the solubility partition transfers using simple equipment and a well-designed approach.

    Don't worry about the temp here, because while many organics will be extracted in step 1, only the alkaloids pass in step 2. Alkaloids are unique in being both organic and polar (*) - hence the 2 step base-acid method finally extracts only these. This is why it is the superior method. Coldness is only important absent second step (and that would require a non-polar organic solvent for step one, not ethanol).

    Commercially they might use an organic solvent such as ether rather than mineral oil but it is essentially the same approach, with similar purity to be expected. That ultimately depends most on careful and patient handling.

    * (Of the two, alkaloids prefer a polar solvent. In step one they migrate to the oil because it is more voluminous, and the water content diminished further by being turned to steam (if hot oil is used).)


    I'd say that WTA, no matter how extracted, is different in alkaloid profile from that in smoke (combusted toacco). It is more 'other' and might well be good blended with just nicotine liquid for that reason. All depends on what one prefers.
  7. PLANofMAN

    PLANofMAN Signature Guru Verified Member ECF Veteran

    Dec 9, 2012
    Woodburn, OR
    Dvap, did you perform a titration on the test batch before beginning the process to convert alkaloid salts to free base alkaloids?
    Edit: Nevermind. I just realized that you haven't filtered it yet, so testing would be pointless at this stage.
  8. kinabaloo

    kinabaloo Vaping Master ECF Veteran

    I expect DVap will do so - it would be a good indicator of the split - freebase to salts.

    ps: must leave now. But wanted to note that many who do the ethanol extraction do it for 6 weeks, r.t. 6 hours. Neverthless, the experiment and resultsare most welcome. I'll check back later.

    pps: tceight confirms what I found : 5mg/ml WTA is better than 20+mg/ml just nicotine e-liquid. At least for those who 'need' WTA. The synergy thing is powerful. So a low alkaloid figure is not neccesarily 'bad' - just 20% of the total alkaloid strength of 'normal' e-liquid would be good (because it's WTA).
  9. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    Here are the results I obtained.

    First, a summary of what was done.

    100 grams of Drum Halfzware Shag tobacco was chilled to -5C. 0.75L of 190 proof ethanol chilled also to -5C was added to the tobacco and the tobacco compacted to allow the ethanol to cover the solid. The mixture was allowed to sit at -5C for six hours with the tobacco being stirred once per hour.

    While still cold, the ethanol extract was filtered. The volume of extract recovered was 475 mL. No attempt was made to squeeze additional ethanol from the tobacco solids in order to minimize aggressive handing of the tobacco solids.

    The ethanol was stripped and the residue processed to isolate tobacco alkaloids in free base form (proprietary methodology). The isolated tobacco alkaloids were diluted to a final volume of 10 mL in propylene glycol. The alkaloid content was determined via titration.


    Tobacco alkaloids obtained from 100 grams of tobacco processed under the conditions outlined above: 305 mg

    This 305 mg figure should be considered the recovery only under the conditions outlined above. Since 475 mL out of 750 mL of ethanol was recovered, it is reasonable to assume that some alkaloids remained in the tobacco-bound ethanol. Using the 475 mL out of 750 mL of recovered ethanol, the percentage of recovered ethanol is 63%. We can then look at the 305 mg of recovered alkaloids and assume that this represents 63% of the total extracted alkaloids, or 484 mg of extracted alkaloids either recovered or bound up in the tobacco solids. Getting at the alkaloids in this tobacco-bound ethanol could be accomplished via a wash of the drained tobacco with additional cold ethanol.

    In the context of an extraction to be purified to WTA isolate, additional time and additional heat might be appropriate to increase the alkaloid recovery since any co-extracted gunk will be eliminated later. In the context of a NET extraction, additional time/heat would serve to increase the alkaloid recovery but also the co-extraction of undesirable gunk.

    Allowing the additional rinse of the drained tobacco with cold ethanol, we come up with an absolute extracted amount of alkaloids using this procedure of 484 mg.

    It must be noted that the extracted alkaloids are apparently in the form of alkaloid salts as the raw extract displayed no discernible basic character. This means that attempting to titrate a NET liquid will not give a true alkaloid result since a titration will not respond to alkaloid salts.

    The OP used 110 grams of tobacco, 10 percent more tobacco than I used. Adjusting the 484 mg figure upward by 10% increases the extracted alkaloid amount to 532 mg. For sake of argument, I'll use this best case alkaloid amount.

    This means that however much oil is obtained from this extraction, it will contain alkaloid salts equivalent to 532 mg of free base alkaloids.

    We can now look at some NET eliquid figures using the data above. There are sufficient alkaloids present to produce a NET liquid with relatively high alkaloid content, however, the limitation of needing to produce a non-overpowering liquid is present. It will do one no good to produce a NET liquid with a high alkaloid concentration if vaping the stuff rips out the lungs. I'll put up some numbers and it is up to the reader to determine what is vapeable and what is over-powering. The numbers below represent diluting the entire volume of recovered oil to the specified volume in propylene glycol (or whatever).

    20 mL: 26.6 mg/mL
    40 mL: 13.3 mg/mL
    50 mL: 10.g mg/mL
    75 mL: 7.1 mg/mL
    100 mL: 5.3 mg/mL
    150 mL: 3.5 mg/mL
    200 mL: 2.7 mg/mL


    [Edit: This all being said, I do not endorse or encourage the use of NET's. There does appear to be strong desire among some forum users to get a handle on the alkaloid content of NET extractions, and my intention is simply to help satisfy this curiosity. Vape them if you want to, I'll pass.]
  10. PLANofMAN

    PLANofMAN Signature Guru Verified Member ECF Veteran

    Dec 9, 2012
    Woodburn, OR
    And with that, the finest NET extraction the world has ever seen...was probably flushed down the toilet by Dvap.

    Very interesting results. Especially the part that explains why a titration won't work (or shows skewed results) on NETs.
  11. Lastlokean

    Lastlokean Senior Member Verified Member ECF Veteran

    Mar 12, 2010
    Red Wing, MN
    Just got in my titration kit... I'm not sure its going to do much good. I am going to launch a retake of this experiment with detailed documentation and photos. I currently intend on running the same Drum tobacco and American Spirit at 50%, 75%, 95% at 6,12 and 24 hour soak times. Nearly all the resulting extract from post #1 has been consumed/shared...

    It is an interesting point that tobacco may naturally contain many salts. In my experiences with curing/processing raw tobacco into something consumable I can attest that raw sun cured tobacco is quite a bit different from most consumer available tobaccos. I am certain some commercially available tobacco has been treated with ammonia to freebase the nicotine allowing it to enter the blood faster. I can not seem to find if all tobacco is treated in this manner or not.

    A surprising statement from the journal of Chemical Research in Toxicology, January 2003.
    "American Spirit cigarettes, for example, had 36 percent freebase nicotine, compared to 1 percent in a benchmark cigarette, 2.7 percent in Camel, 5-6.2 percent in Winston, and 9.6 percent in Marlboro."

    This is most surprising as American Spirit claims to be 'additive free' and organic. How exactly are they freebasing 36% of the nicotine? Urine?
    Anyway it is sufficient to deduce that most the nicotine present commercially available tobacco will be in the form of various salts. There is quite a bit of documentation suggesting that freebase nicotine is much more bio-available than various salts.

    IMO I am after emulating the 'natural tobacco' alkaloid profile in order to get effects similar to those I enjoyed from tobacco. Converting the alkaloids to freebase changes that alkaloid spectrum into something that absorbs much more readily into the blood. Such action also implicates potential for breakdown / side-reactions among the multitude of alkaloids present. 2,3'-Bipyridine and N-Methylanabasine and other oxidative compounds can be shown to be formed during curing up to 3% of alkaloids and may not survive harsh conditions such as the strong alkaline necessary for converting nicotine to freebase. Or various oxidative/additive compounds may form from nicotine under various conditions such as nicotelline and anatalline forming from acidic nicotine condensation.

    I don't know to the extent of any of this is or is not occurring, but I certainly do not feel impelled to dump ammonia,lye or any other caustic additive into my ejuice. But to each there own.

    Being as the titration test for nicotine is testing for freebased alkaloids and any alkaloids that are already salted will pretty much be unaccounted... The test seems worthless relative to this ethanol extraction. It would seem feasible and worthwhile to develop a titration test for alkaloids in the natural salt-form.
  12. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    Actually, the NET extraction residue was processed to get rid of anything that isn't an alkaloid. Those materials were dumped unceremoniously into a waste bottle.
  13. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    To take this a bit further, attempting to convert NET alkaloid salts to base by the addition of alkali to a NET liquid doesn't stop at foolish. It would be plain idiotic.

    I've got a saying, "There are ten ways to do anything, and most of them are wrong". Be careful. folks.
  14. PLANofMAN

    PLANofMAN Signature Guru Verified Member ECF Veteran

    Dec 9, 2012
    Woodburn, OR

    So NET vendors have been over nic'ing themselves and their customers without anyone being the wiser?

    I would change that from "feasible and worthwhile" to "necessary" if I were a NET vendor reading this.

    Edit: They extract for flavor, not flavor + alkaloids, though. Would that make a difference?
  15. Lastlokean

    Lastlokean Senior Member Verified Member ECF Veteran

    Mar 12, 2010
    Red Wing, MN
    I must have left behind some water... :oops: In terms of efficiency it would obviously be best to due multiple small washes.

    Couldn't agree more, and actually that should have been expected.

    The entire point of this thread is to get a clean & natural tobacco extraction representing tobaccos natural alkaloid spectra without creating a nasty PG maceration or the addition of any chemical additive. Soaking tobacco in cold ethanol should allow the pulling of alkaloids with minimal pulling of plant waxes/oils. This has yet to be fine tuned, but that is just further experiment. After filtering, evaporating and diluting you can achieve a 'NET' that is of a ~known strength without having the overpowering flavor / volume issues you are describing.

    Try diluting your resulting 500 mg crude extract to a reasonable 16-24 mg/ml and tell me its not delicious&satisfying. Or Just flush it, I don't really care what other people do... As of right now I am pretty certain I will never vape anything other than a natural tobacco extract I make for myself again.

    Edit: No matter what you want to call the resulting product from a cold ethanol soak & evaporation I enjoy it. The entire argument whether this is a WTA or a NET seems pointless as it is a natural tobacco extract that contains the whole natural alkaloid spectra of tobacco that is soluble in ethanol(which I currently believe to be all of them.)

    Edit2: Does anyone know if the commercially available ejuice nicotine concentrate vendors sell is in freebase form or a salt?
  16. PLANofMAN

    PLANofMAN Signature Guru Verified Member ECF Veteran

    Dec 9, 2012
    Woodburn, OR
    I got this info from post #22 of this old thread: It might help you with the water problem.

    Ethanol might be getting the tobacco specific nitrosamines (carcinogens) too, and if you are using American tobacco which is likely fermented, those are in elevated amounts. That's something of less concern in WTA because WTA vendors (or at least Aroma E-Juice) source tobacco that is low in nitrosamines. You might want to do the same.

    But WTA is as pure as the nicotine sold to e-juice vendors. NET is full of organic detrius, some of which are known carcinogens.
    It's freebase, otherwise you wouldn't be able to measure it with a titration kit. ;)
  17. Lastlokean

    Lastlokean Senior Member Verified Member ECF Veteran

    Mar 12, 2010
    Red Wing, MN
    I am personally not that concerned with the trace nitrosamines. Obviously I'm in no position to tell other people they are 'safe', however for me it has been smoking combustion bi-products from analogs or a WTA. That's good to know that fermentation increases nitrosamines as its not good to actively consume them.

    Nitrosamines are unfortunately in cosmetics, latex, plastic, pesticides have them. Searing your steak - not such a good idea forming them. Not to mention, significant levels of nitrosamines in many foodstuffs, especially beer, fish, and fish byproducts, and also in meat and cheese products preserved with nitrite pickling.

    I do actually own a variety of sieves, unfortunately, in 100% pure ethanol nicotine is only marginally soluble. There are a few differences between isopropyl and ethanol, from a chemical standpoint, I am not certain what is occurring, but in experiment have observed such: an extraction as described with cold 99% isopropyl. The product you get a dark resinous solid that smells kinda nasty. Then dissolve the resulting crude extract into room temperature ethanol, it will fully dissolve. Then freeze it. All the chlorophyll and plant oils / waxes will precipitate out to the bottom. Such methodology is a technique commonly practiced in cleaning up tinctures. In practice I have found ice cold ethanol azeotrope to be quite selectively soluble in various extractions for this reason.

    I personally don't mess with isopropyl... While it is a lot cheaper than ethanol, it is a not food safe, doesn't extract as selectively and the concern for consumption of residual solvent does not really exist if your solvent is tasty vodka.

    The water problem is easily solved by being patient, or oven drying/dehydrating at the lowest temperature possible.
  18. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    A few comments.

    Though I'm no fan of NET's, I know many folks are, so any NET extraction procedure that can produce a cleaner NET is a good thing for those interested in this sort of thing. (As an aside, what the hell does "naturally extracted tobacco" mean? A buzz-term if you ask me, and meaningless).

    Short of abstaining from any and all forms of tobacco derived materials, my focus is on getting as much of the tobacco out of the picture as possible while retaining the active ingredients. None of this stuff, alkaloids included, are likely particularly good for us (no interest here in getting into a discussion about the positive mental acuity aspects of nicotine, etc). I endorse the harm reduction strategy of "X versus smoking" so a NET is probably better than smoking, but it's still a pretty complex brew, so how much better is quite unknown. Just as going from nicotine only liquid to a WTA liquid is probably a step in the wrong direction, going to a NET liquid represents perhaps a much larger step in the wrong direction. But, I'll acknowledge again that a cleaner NET will likely reduce the size of that wrongly-directed step.

    Anyway, I've presented the data I have to present, so take it, leave it, or do what you all want with it. You're welcome.
  19. kinabaloo

    kinabaloo Vaping Master ECF Veteran

    As any extraction takes only the soluble constituents, and use of involves no combustion, all extracts will be a big step forward in terms of safety, imo.

    At ~50% extraction, the cold ethanol soak is reasonably productive. Knowing that figure (will vary according to method details and tobacco used) is a reasonable guide as to alkaloid content in a NET, so useful info.

    Salt form alkiloids do seem to work in vaping, but there's likely at least some loss involved. And there is the malates, tartrates, citrates etc, that one gets along with the alkaloids. Maybe no problem in the lungs, maybe not; I don't know.

    For only a little more work one can do base-acid extraction to (free-base) alkaloids only, so that's what I do (see an earlier post link for method; no alkalis left in the final product!).

    I disagree with DVap on WTA being a step backwards; I know what he means - more ingredients - but one must remember that WTA will enable more people to give up smoking. And more, people typically consume less WTA. So I see it as a step forward. The advice would be to try just nicotine first and WTA only if about to return to smoking (but I don't see this as a big issue; WTA might work better for everyone, in terms of reduced consumption - i.e. more satiation). WTA (incl. NETs) also work at lower strengths.


    Rough reference guide:

    A typical soak / NET - 100g tobacco in 200ml - will give a final alkaloid content (in organic salt form) in the range 1.5 mg / ml to 5 mg / ml.

    Because it has a range of alkaloids that work synergistically, it will feel a lot more potent than that, relative to nicotine only e-liquid.
  20. Chinook

    Chinook Super Member ECF Veteran

    Sep 16, 2013
    OR, USA
    Dvap, you mentioned that "the material is not displaying the characteristic sharp alkaloid odor". So does that mean as a NET extract just for the flavor and aroma of tobacco, this would be kind of weak?
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