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Removal of nicotine from tobacco.

Bauhaus

Greenlighter
Joined
Jul 12, 2014
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Looking for a way to remove nicotine from tobacco.
From wiki:

It is miscible with water in its base form between 60 ?C and 210 ?C. As a nitrogenous base, nicotine forms salts with acids that are usually solid and water-soluble. Its flash point is 95 ?C and its auto-ignition temperature is 244 ?C.

So as far I understand it I should first boil it with a base and then add an acid to get the salt which should be readily solved in the aqueous solution.
What base should I use, something like Na2CO3, NaHCO3, NaOH, .... ?
And which acid to use, would something like citric acid or vinegar suffice or do you need a stronger acid ?
I could also use a solvent like ether instead, but then I prolly remove most other substances too, which I don't want to.
Any advice ?
 
What is it you're trying to do?

Making nicotine-free tobacco for smoking? (although that would be pretty pointless, because the nicotine isn't the most harmful thing about tobacco smoke).

Or are you trying to isolate the nicotine and use it as a cheap way to make vape juice?
 
I think he is trying to isolate the nicotine because he is trying to get the salt and mentioned not wanting to "remove most other substances."

I am curious as to why and am now a bit interested.
 
One will first require to defat the tobacco. Acidification to render the nicotine in salt form, followed by several extractions with dichlor or chloroform, TCE or whatever similar chlorinated hydrocarbon floats your boat. DCM is nice for the low BP.

Plant parts often have a ton of waxes, fats, etc. in leaves, stems, seeds, rootbarks are sometimes extractable, or dried barks, with straight-to-base techniques, but aerial portions of most plants you need to defat first.

If you don't, you can and likely will end up with an unholy emulsion and a load of saponified shite to deal with. Which trust me, you really would rather never have to deal with either.

Don't forget, if you make a total alkaloidal isolate from tobacco, there are things like beta-carbolines (harmala alkaloids in fact, the MAOIs we know and love, harmine for example) in there, as well as, aside from the main pyridine alkaloid, nicotine itself, smaller amounts of anatabine, cotinine, desmethylnicotine and anabasine. Also depending on the tobacco species, with tree tobacco, Nicotiana glauca, IIRC containing significantly more anabasine.

Furthermore, I have a conjecture to offer, based on my experience with both smoking tobacco, and using a nicotine-only fag juice.

The fag juice is based on a propylene glycol base (I do not allow glycerin to be present in mine, nor will I use off the shelf ones containing it, because of the dehydration of glycerin to acrolein, a most unpleasant substance, which has the nature of a tear-gas, only far more toxic than the military or filth-issue tear agents, but a noxious-smelling, noxious tasting, highly toxic, violently irritant unsaturated aldehyde, that can be formed by dehydration of glycerin. Indeed that, in my first, and up until the present day, only deliberate act aimed at it's synthetic preparation.

In that case, I employed the sodium bisulfate from my first ever kiddie's chemistry set plus some glycerin from a local pharmacy; can't remember exact age, but under 10, running it on a test tube scale, purification via distillation from tube to tube, after mixing bisulfate and glycerine, heating, and collecting the distillate, redistillation under welding argon to prevent oxidation during the distillation, and more or less, doing it because it was a novel experiment, and those in the booklet that came with the chem set, and it's highly limited resources, were for the most part boring, like watching cobalt chloride and CuSO4 change color between hydrate and anhydrous forms. Not really fodder for my young and enquiring mind, and besides, nothing I hadn't already known and in the copper sulfate case already done with a blowtorch (the set was actually my first supply of cobalt resources, but once you've seen one coloured crystal hydrate turn to another colour with a blowtorch, and you know whats going to happen, what's the point? to me, not very much, so I found something else to do, that was more intriguing than the proposed experiments the set had guides to.

Make, distill and bioassay dilute concentrations of atmospherically dispersed lachrymatory agents, extremely dilute in the case of acrolein knowing the toxicity. Not on anyone else, or animals, mind you. I'm no animal abuser, never have been, never will be, and neither do I tolerate it in others if I can get within range to act upon such an individual.

All went swimmingly, and choking, spluttering, coughing, eye-streamingly once a sample was tested in an enclosed space and allowed to vaporise.

However not knowing any better, and considering the small quantity prepared, once done with it, and I hang my head in shame at this, but it went down the kitchen sink. And flushed with a lot of water. Unfortunately, and to teach me a lesson for dumping it in such an irresponsible manner, I'd turned the tap the wrong way, and flooded the U-bend with steaming hot water. Whilst standing at the sink.

You can guess the rest, after the entire remainder of the batch was exposed to hot water causing the sink plug hole to vomit forth the most noxious miasma back up into the kitchen, and right back at me. Pretty funny looking back at some of the crap I got up to as a wee'un, but I wasn't nearly as amused at the time.

Anyhow, amusement for your consumption aside, I use propylene glycol, commercial flavourings and nicotine dissolved in PG to make a calibrated volumetric dilution.

The nicotine, is not a tobacco extract of whole composition, and it has quite different properties when administered in an e-fag or transdermally, than does smoking tobacco.

The e-fag sourced nicotine alone, is to me, pretty devoid of compulsivity and ultra-notorious-grade addictive potential. I've been a smoker since age 9, of tobacco fags, long before e-fags were all the rage, although the nicotine alone has let me cut down to the point where I only enjoy occasional cigars, particularly as the icing on an opioid injectable-shaped 'cake', so to speak. It just fits, smoking tobacco. the nicotine from an E-fag lacks this particular reinforcing, satisfactory pleasure enhancement when delivered as an inhaled dose via the E-fag (obviously transdermal is a bit slower, so was aiming for rapid delivery to compare.

Tobacco does, it really makes things a lot more satisfying, addictive, but nicotine, without tobacco constituents, does not, in me, act thusly in the same fashion.

I have hunches, but the primary one, is, knowing the presence of harmala type beta-carboline alkaloids with MAOI properties, that these, in tobacco smoke, dramatically increase both addictive tendencies of the product used without opioids in context or at least, when using only at the doses I must maintain to remain free of withdrawal and to have the chronic pain in my knee joint, patellar tendon, and the trochanteric bursitis I have bilaterally not scream in red hot howling agony, such as nasal lower dose oxy, or plugged morphine rather than IM or IV or subcut morphine.

In short, I believe the harmala alkaloids present, are modulating the effect of the delivered nicotine when tobacco smoke is intaken, and doing so in such a manner as to render the end result far more compulsive and addictive.

So, I postulate, and it's only, I should make clear, a theory of mine as of the present, as I have yet to prepare a beta-carboline MAOI-spiked sample of fag juice nicotine and compare it for addictive, reinforcing, compulsive tendencies, both whilst at baseline, and after the administration of intravenous doses, or IM doses if the vein-gods won't smile on the endeavour, to then test PG/flavouring/nicotine spiked with known concentrations of harmine, harmaline and tetrahydroharmine alone and in combinations with one another; that the result of using tobacco as a source for extracted nicotine, would likely pull along with it, quantities of these MAOI beta-carboline harmala alkaloids. And make the fag juice more addictive than it otherwise would be due to their presence.

I feel it would be irresponsible if I were not to share this hypothesis, despite not yet having performed the bioassays on myself, since I'll have to either perform a Pictet-Spengler, on appropriate tryptophan derivatives to prepare the harmala alkaloids in single pure forms, or, to extract Banisteriopsis caapi liana, or syrian rue seed and remove the likes of vasicine, vasicinone, peganine and what have you, for the reason that if this were done, using tobacco to make fag liquid, it could end up being just as addictive, as cigarette smoking is and in a sly, underhanded, unexpected guise.

At this, I will leave you to draw your own conclusions from the reported results of the bioassay of tobacco smoking vs delivery of inhaled nicotine, both alone, and with the highly divergent effects upon opioid bolus dosing via injection type routes. VERY, very different animals.
 
Nicotine is an uncontrolled commodity. It seems like a lot of unnecessary work to try to isolate it from tobacco if you mean to use it. If you are doing it out of intellectual curiosity, or for a challenge, by all means carry on!

EDIT: I see you are in fact looking to make nicotine-free tobacco, so never mind.
 
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Macerate tobacco in slighlty acidic water, strain, make water basic and then steam distil the freebase nicotine out is the proper way. kudos to Gattermann.
The freebase will need to be salified with sulfuric or tartaric acid for storage as the freebase is unstable and oxidises.
Be aware nicotine is very toxic, and is toxic by skin contact.
 
Making nicotine-free tobacco for smoking? (although that would be pretty pointless, because the nicotine isn't the most harmful thing about tobacco smoke).

Yes, that's what I want. Instead of "remove" I should have said "get rid of". It's a complicated story but in short, I suffer from severe insomnia because of a compromised immune system while immunity plays a CRUCIAL role in generating deep sleep through raising inflammatory substances (cytokines, interleukins, etc....) which activate NF-kB and sets a whole cascade in motion to give you that nice, deeep quality sleep;
And tobacco contains substances that elevate certain proinflammatory substances like IL-6, TNFalpha, IL-1beta which is the reason why smoking half a cig. or even taking a few puffs makes me more relaxed and a bit sleepy but when smoking more, then the nicotine kicks in and has a countereffect.

And it's hard to find sources (drugs, plants,...) to raise these subs., I did a lot of research to find ways to activate NF-kB in particular, but it's hard to find literature about activating proinflammatory subs., cos all research focuses on the opposite:
In the 60s we had the vitamin hysteria, then came the antibiotics hype and nowadays it's all about anti-inflammatory/antioxydants. Any substance that may be inflammatory is considered *EVIL*. But what people don't seem to realize is that these subs. also have vital roles, it's not like your body makes them to pester you.... It's a typical example of extremes, either a subs. is "good" or it's "bad".
As usually the truth lies somewhere in between, these subs can act both beneficial and harmful, depending on the situation.
And it's also true that simply ingesting such a sub. will prolly have adverse effects, unlike natural sleep where your immune system produces specific subs. in specific brain regions at specific times.
Unfortunately sleep research is still in it's infancy and it will take science a very, very long time to decipher this sleep puzzle.
I wish I was born several centuries later.

(On a side note, I would have answered earlier but I didn't get notified of replies to this thread even though I checked the "instantly get email" when someone replies to your thread)
 
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Do you have any idea about the nature of these pro-inflammatory substances?

From a cursory Google search, it looks like benzo[a]pyrene and other polycyclic aromatic hydrocarbons are major contributors to the pro-inflammatory effects of tobacco smoke.

In that case, you might as well smoke any random plant material instead of going through the trouble of "de-nicotinating" your tobacco, because such pyrolysis products will form in pretty much any sort of organic matter when heated.

Not that inhaling any of these highly cancerogenic substances in order to achieve what might very well be a placebo effect would necessarily be a good idea.
 
if I were isolating nicotine from n. tabacum I would just steam distill the shit

presumably if you play with direct solvent extraction you could make "nicotine free" tobacco but I fail to see why it would be something you'd want to consume... might as well be burning the oregano from your spice jars

which is the reason why smoking half a cig. or even taking a few puffs makes me more relaxed and a bit sleepy but when smoking more, then the nicotine kicks in and has a countereffect.

you do know nicotine has different effects at differing dosages?
 
Yeah, you'd be starting with addictive reinforcing carcinogenic poison, then taking out what little there is to make it pleasurable in the least, to end up with just carcinogenic poison.
 
if I were isolating nicotine from n. tabacum I would just steam distill the shit
Interesting, I will try it out.

Regarding all other comments, everything was explained in my post but comprehensive reading seems to be a lost art.
 
Regarding all other comments, everything was explained in my post but comprehensive reading seems to be a lost art.

Or maybe your request was just a bit ...odd?
When someone says they want to remove a psychoactive substance from a drug known to cause cancer, the logical assumption would be that they're trying to purify the psychoactive part (and that maybe the odd wording in their post is because of English not being their first language), not to assume that you want to throw away the nicotine so you can inhale those sweet, sweet pro-inflammatory carcinogens (that would automatically form in any other kind of plant smoke, anyway). This is why I asked for a clarification before.

Oh, by the way: Nicotine is also one of the major pro-inflammatory factors in tobacco smoke:
https://www.ahajournals.org/doi/abs/10.1161/01.atv.0000193510.19000.10

Sounds more like you might want to try "microdosing" small amounts of nicotine from a vape instead (as Sekio said, the effects of nicotine can be highly dose-dependent).
 
As far as I'm aware, nicotine is stimulating (NE, DA) in low doses, and sedating (S, Mu) in high doses. But I never knew why/how that could be. I could see how it would make cigarettes that much more addictive: tailoring your buzz for the desired effect in the amount of smoke breathed in and time the smoke spends in the lungs per hit.

Son't mean to derail the thread. Just thought sekmaster or another who knows more would pose a quick, logical hypothesis on this...
 
Or maybe your request was just a bit ...odd?
When someone says they want to remove a psychoactive substance from a drug known to cause cancer, the logical assumption would be that they're trying to purify the psychoactive part (and that maybe the odd wording in their post is because of English not being their first language), not to assume that you want to throw away the nicotine so you can inhale those sweet, sweet pro-inflammatory carcinogens (that would automatically form in any other kind of plant smoke, anyway). This is why I asked for a clarification before.
Ok, fair enough I guess, though I did mentioned that subs. in tobacco are harmfull.
Oh, by the way: Nicotine is also one of the major pro-inflammatory factors in tobacco smoke:
https://www.ahajournals.org/doi/abs/10.1161/01.atv.0000193510.19000.10
As far as I'm aware, nicotine is stimulating (NE, DA) in low doses, and sedating (S, Mu) in high doses.
Even if nicotine has proinflammatory properties it still is a potent stimulant, and not only activates parasympathetic NS, but also releases catecholamines:
That ingesting more nicotine is sedating doesn't make sense. And I assume with 'S' you mean serotonin which is stimulating. Dunno what Mu stands for.
Sounds more like you might want to try "microdosing" small amounts of nicotine from a vape instead (as Sekio said, the effects of nicotine can be highly dose-dependent).
Yes it's dose dependant, but the other way round: more smoking means more nicotine which means more stimulation. Take out the nicotine from tobacco and there won't be any stimulation (or addiction for that matter).

I might sound like a smart ass but I have be dealing with severe insomnia for some 20 years now, I tried 101 things and did a lot of research and know what could help and what not. The big problem now is when your immunity is compromised and you actually feel never sleepy then traditional sleep meds will barely have an effect anymore. To put it in other words: sleeping meds don't make you actually sleepy but they enhance sleepiness, so basically they work like catalysers.
But if you never feel really sleeepy and stay awake, they won't do anything, in fact they have ironically a paradoxical effect and make me more awake/alert/anxious !
So that's the reason why I now focus on proinflammatory subs. Even if these subs. may be harmfull and might cut of a few years of my life, I gladly take them if I can get a good night of sleep and have a more or less normal life.
But you need to suffer severe insomnia to understand this.

I really regret I didn't kept a diary when my sleep problems started, I could have written a book by now. I learned a lot of the (severely underestimated) role of sleep. But I have a hard time writing down everything I discovered, it's like you rmind goes blank at the moment I need to write it down.
 
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I've always found that ingesting more nicotine definitely leads to sedation. I get very tired and will often vape before bed to help fall asleep if I'm restless. If I get any stimulation from nicotines it's only with with coffee.
 
I have a vapor pen but it's unfortunately not suitable for e-liquids (nicotine).
Perhaps I might buy an e-liquid pen for nicotine to see if it really makes a difference.
 
depending on the subtype/5-HT3, serotonin can act is both stimulating and sedating ways, i thought.

"Mu" is not using the actual Greek letter. It's pronounced "mew". It's mostly responsible for the euphoria of opioids.

As a thought experiment, take dipping vs. smoking. Dipping is a much heavier hit of nicotine, causing many people to sit down to to imbalance.
 
depending on the subtype/5-HT3, serotonin can act is both stimulating and sedating ways, i thought.
Well, it depends with what you mean with serotonergic: SSRI's and 5-HTP supplements are stimulating, I once took fluoxetine and it looked like I took someting like speed or amphetamine.
5-HT2 & 5-HT3 antagonists OTOH can be beneficicial.
I take regurlary mirtazapine, which helps for "winterdepression" (dark weather) and also insomnia because of it's strong antihistamine effect. It's also a 5-HT2 & 5-HT3 antagonist which help with the nauseating feeling of chronic sleep deprivation. The downside is it also make you hungry and I need to eat a meal with it.
 
Furthermore, I have a conjecture to offer, based on my experience with both smoking tobacco, and using a nicotine-only fag juice.

The fag juice is based on a propylene glycol base (I do not allow glycerin to be present in mine, nor will I use off the shelf ones containing it, because of the dehydration of glycerin to acrolein, a most unpleasant substance, which has the nature of a tear-gas, only far more toxic than the military or filth-issue tear agents, but a noxious-smelling, noxious tasting, highly toxic, violently irritant unsaturated aldehyde, that can be formed by dehydration of glycerin. Indeed that, in my first, and up until the present day, only deliberate act aimed at it's synthetic preparation.
Slightly off topic so my apologies, but Limpet_Chicken, I would be very interested if you would care to elaborate on this a little, specifically your thoughts on the differences between glycerin (presumably "Vegetable Glycerin", since that's usually what's advertised in vape liquids?) and propylene glycol.

I've never been a big smoker but I've started to dabble in vapes recently, I would prefer to do this the healthiest way that I can but I can't find much on the difference between PG and VG, from a health perspective. In fact I haven't seen a single source that said they were anything but equivalent. I'm a little unclear from your story if this is just a life-long aversion to VG because of your previous bad experience, or if you think there is a genuine health risk in using VG over PG.

Can it happen that acrolein can be formed even during normal use of a vape and VG-containing vape liquid? Surely if this was the case and it is as unpleasant as you say, then no-one would use it...
 
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