Extracting nicotine from tobacco

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TropicalBob

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A few further thoughts on this:

Remember those liquid burn tests done by knutselpeter and posted on the Dutch e-cig site (Ruyan came out great and E-Cig stuff looked dreadful, convincing knutselpeter that E-Cig e-liquid ruins atomizers). How? Tar deposits.

When I cooked down my homebrewed tobacco liquid, attempting to distill a clear liquid that I hoped might contain some nicotine, what I got was shocking. The pot was coated with black tar. When it was cool enough, I ran a finger around the bottom of the pot and came up with gobs of pure, carcinogenic tar.

It was so thick that I had to use a chemical product called Goo Gone to get it off the countertop, sink and pot. And how much liquid produced this? One 10ml vial of cooked tobacco juice!

Had I smoked that vial, much of that tar would have moved into my lungs, I'm sure. Some would have stopped in the filter, turning it brownish, but some would make it through with the vapor, ending up inside me. Not a happy thought. I love e-smoking precisely because it's healthier than cigarette smoking, minus the tars produced by combusting tobacco.

In making my own liquid, I had succeeded only in thwarting the very reason I think e-smoking is superior. Ironic, huh?

And know that E-Cig still uses tobacco extract, an oil, in its e-liquid. It produces tar, and you see it as the brownish stain on the cartridge after short use. Ruyan stopped using the real tobacco absolute last November.

So where does this leave me? I'll think about it some more, but I sure hope I can find happiness with pure Bickford and glycerine. It's not nicotine I'm fleeing, however; it's the tar I cooked for myself in home experiments and the knowledge that it's there in the liquids I ordered from E-Cig many months ago.
 
I think you're right. If it were easy to get nicotine, the whole world would know how to do it. Instead, distillation needs to be done with chemicals in a lab setup. Not for me.

BUT .. the gummy stuff I did distill smells great! Just like pipe tobacco. It kept the aroma and probably the taste. But ... it's gum and I can't smoke that.

TB, One of the methods I use is Steam Distilling. I like this because it uses no chemicals but actually draws a very pure amount of the natural 'oils' from the tobacco leaf. One of the best distillation methods but expensive and a little dangerous.
Also, I did in fact mean to ask you, are you using Pipe tobacco? One thing to bear in mind is that most pipe tobacco is Cavendish which is naturally oily. Add to that the fact that they usually load it with sugars and extracts (hence the heavy, sweet feel) that may not come out to well when 'cooked'. Just a thought.
Anyway, I heard you like Kahlua, TB?
 

TropicalBob

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Actually, this was a pretty good thread, with some good info. Since the last post, Drew Estate announced it was discontinuing Kahlua cigars, so I got my tobacco shop to order me two tins. I'm puffing one cigar a day now, after dinner. The unsmoked .... ends will become the next home cooked brew! I plan to use my coffee bean grinder on them, put them in refillable tea bags and cook 'em for smoke juice flavor.

Someone on another thread talked about having to throw away the tobacco. Heavens, no. After it's been cooked, remove it and let it dry. When it's mostly dry, spray it with your favorite Bickford flavor. The PG will attract moisture to the tobacco at exactly the right 70% humidity level and the Bickford flavor will remain when you actually puff it in your pipe.

Strange but true: Many commercial pipe tobaccos are sprayed with propylene glycol for its humectant qualities. It prevents the tobacco from drying out.
 

Denni

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Argh, I just had a look at the spreadsheet. If you start with 15mg/g tobacco (medium: my zware shag has about 25, I think even cigars aren't much higher) and use 20g tobacco then you'll end up with just over 10mg/ml in the final reduced volume (20ml) assuming 85% efficiency (double wash and all, so assume less).

Given that you want to have a final volume of at least 80% PG/VG, you'll end up with 2mg/ml which is just not worth bothering :(

Stockpile the xx-strong liquid while you can!
 

Zach

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Yeah but... there's really no way to tell exactly how much nicotine is in whatever tobacco you buy. Tobacco is a natural product and therefore based on small variations in things like sunlight, available water, curing method, and fertilizer could vary wildly from one specimen to the next.

As far as i can tell, the only way to dose your home-made fluid with nicotine effectively would be to extract pure nicotine crystal, measure with digital scale, and dilute in the appropriate amount of water/pg or vg.
The problem with this is, until you get the nicotine crystal dissolved in the appropriate amount of water, you're in great danger because you're dealing with an extremely concentrated, extremely deadly poison.
 

jbbishop

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Supposedly, if it is pure nicotine there are no carcinogens so despite speculation concerning the possibility of carcinogens being produced by vaporizing e-liquid due to impurities, flavoring or other additives most people conclude that at least the majority of the carcinogens found in tobacco products are probably not present.

For extracting nicotine from tobacco, again see:

Sciencemadness Discussion Board

AND for cheep bulk tobacco:

http://tobaccotalk.itgo.com

A couple of ideas. Consider getting a nylon fine mesh straining bag at a brew shop. I actually have a beekeeper's screen here which has worked just as well for home brewing. Pour the liquid and powdered tobacco that you've been brewing into the straining bag and squeeze as much of the juice out of it as you can. As I recall, what I did was to suspend the straining bag over the stockpot and after the initial straining I poured a volume of boiling water over the filtrate, stirring the leaf particles to expose the maximum surface area to the leaching process, before squeezing out as much of the liquid as I could and then filtering and condensing. I highly recommend brewing and condensing it outdoors over a hot plate because the evaporating steam will stain your walls if I am not mistaken. Also, you should use a stainless steel or enameled pot, not aluminum which is reactive. You might try progressively filtering the remaining liquid with steel wool or cotton balls in a plastic funnel and finally filter paper... a hand pumped or powered filter process would probably work best but I think a gravity filtration is plausible and I believe this is what I endeavored, with ordinary filter paper. Most of the gunk forms a sediment and since the majority of the nicotine is in solution it may be just as good an idea to let it settle and dump the last fraction. But be aware: "[Nicotine] is miscible with water, alcohol, ether, chloroform, and fatty oils, the solutions being strongly alkaline. Nicotine is heavier than water, and forms salts with acids, which do not easily crystallize."

I'm not even sure of how necessary it is to get it very clean if you're going to extract with ether. While it would be most appropriate to follow some of the methodologies discussed in the first link (above) for purified yields, various forms of relatively purified extracts can be produced by a variety of more simplified methods. I'll quote from here:

http://www.e-cigarette-forum.com/forum/diy-e-liquid/1687-isopropyl-alcohol-tobacco-extraction.html
"Extraction with volatile solvents
so im soak 50g of cherry pipe tobacco chop into powder in 500ml of water for 24 hours then filter and put 25ml of DIETHYLETHER, shake sometimes for another 24 hours then gently separate the upper layer, evaporate the DIETHYLETHER and get around 500mg yellow substance witch have identical smell and after mixing with 50ml of VG identical taste of the cherry tobacco when u smoke it..."

Any chemists want to comment on what this is going to produce if not employing an acid/base extraction method? Again, it has been suggested that this can be accomplished by simply adding drops of battery acid (dilute sulfuric acid) during the water extraction and then basifying with ordinary powdered lime before washing with ether.

[From: Black Leaf 40, an environmentally safe and biodegradable agricultural insecticide used around the world, is 40 percent nicotine sulfate. Farmers have been using nicotine sulfate insecticide since the early 1800s. To make it, all you do is boil tobacco leaves in water with a little sulfuric acid (the same acid as in a car battery). If you mix the resultant nicotine sulfate extract with a common alkali such as lime, then add a solvent such as ether, pure nicotine alkaloid - or free-base "crack" nicotine - will float to the top dissolved in the solvent.]

I honestly don't think any extract that isn't washed with a solvent is going to produce anything you want near your vaporizer because of all the tar.

TB, wondering if your attempt at refluxing wouldn't benefit from a more elaborate setup. There is a description of a refluxing and soxhleting extractor made from pots and pans around here somewhere.

If you're boiling solvents you need to do the whole thing in a water bath so you have a tub with wooden spacers that the contraption sits in. Also because of the plastic bag you're going to need to use this double boiler method to avoid melting the plastic unless you can think of something better. The contraption is a large stew pot (steam canner) with the lid inverted as you've suggested, but it is covered in a piece of plastic garbage bag and secured with rubber bands to keep the vapor in and the ice cubes are piled on top of that. Your tobacco and solvent or water is not put directly in the stew pot because the condensing surface area (the ice cooled lid) must be larger than the surface area of the boiling solution which is instead contained in a stainless steel pot set in the bottom of the stew pot. Variations include placing a metal strainer over the stew pot containing the previously refluxed soaked material and "soxhleting" to perform a thorough extraction, and in the case of extraction with solvents a collecting pan is placed in the metal strainer to recollect the solvent and to separate it from the collected oils.

While this might be a particularly efficient method, I personally don't see where this would be a particularly desirable method of extraction in that it is so elaborate. A simple water based infusion extraction used as the starting point should yield sufficient results if done correctly.

When I attempted this I did not proceed past the ether extraction step but this is what I observed: The nicotine becomes suspended in the fatty ether/emulsion layer and through repeated agitation over a 24 hour period is gradually eluted by the petroleum ether. When allowed to sit, what appears to be liquid nicotine occurs as a clear or yellowish oily layer suspended above the clear ether. Because of the relatively small volume of the final yield, actually working with larger quantities may be easier than smaller ones. In my case I believe I had started with at least 16 ounces of tobacco. Depending on the volumes worked with, this layer of liquid nicotine may be somewhat thin, but by tipping the bottle at an angle a deeper pool was observed against the side of the jug. One should be able to siphon this off using a pipette and evaporate any remaining ether from that. Finally, one would want to recapture and recycle the remaining ether. Here's another method of separating the ether/oil layer from the ether/emulsion layer and the water, tar and resins that are not soluble in petroleum ether (if you don't have a separatory funnel). Use a cork and simply tip the bottle upside down and extract the cork just enough to capture the water and emulsion layers as they flow into a collecting pot, quickly reinserting the cork so you don't lose much of the ether... (of course you're wearing rubber gloves). Or you can use a rubber stopper with two holes and glass tubes in the top of a gallon jug. One glass tube penetrates just to the bottom of the ether layer and the other just enters into the atmosphere of the bottle and rubber tubing is inserted over the two glass tubes that protrude from the stopper. Blowing into the short tube will cause the ether solution to flow through the other tube and into a collecting jar, so it's just like siphoning gas without a mouthful of something potentially lethal.

Here's some interesting clarification:

From: The Smoker's Club, Inc. Encyclopedia 16

"Nicotine" is a chemical component of many related compounds, such as nicotine citrate, nicotine sulfate, nicotine malate, nicotine oxide (cotinine) and nicotinic acid (vitamin B3, niacin). Pure, free base, nicotine is a deadly poison, an addictive drug and also a good explosive.

Freebase nicotine is highly poisonous and is sometimes used as an insecticide. It makes a good insecticide because it only lasts about half an hour in the environment, being so unstable in the presence of air. In very small amounts, freebase nicotine can be injected into a person's bloodstream and has an effect almost identical to ........

When you burn tobacco, you don't get any freebase nicotine. What you get is an assortment of harmless, stable chemicals that result from the oxidation of nicotine. Visit a drug store and read the ingredients of "nicotine" gum, lozenges and patches. You will find that most of them contain no nicotine, but rather nicotine sulfate or nicotine oxide, or even good old vitamin B3 (nicotinic acid)."

Also: Cotinine is the primary nicotine based chemical absorbed when smoking a cigarette there is no actual nicotine as it boils off when the tobacco burns. Cotinine is produced when the tobacco is heated as nicotine has a much lower boiling point than water you will produce plenty of that when making the tea.

Nicotine is water soluble (miscible) and has a boiling point of 247* C - much higher than water. Therefore, you should be able to steep tobacco in water, strain out the plant matter, and boil most of the water off the tea. This should leave you with a crude nicotine extract, along with a few other things.

See: How to Grow Tobacco ::

"Here are the 2 most commonly used nicotine extraction methods although neither is safe to do outside of a laboratory environment & neither gives you the required forms of nicotine. You would still have to convert it to nicotine polacrilex or cotinine."

While I'm no expert, I'm guessing that a simple aqueous extract of nicotine solution that was extracted in ether as Izx appears to have done with his cherry pipe tobacco should produce a product that, while impure, is still smokable, flavorful and satisfying.

I would start with some known premises regarding the ratios of the final mixture by estimating maximum potential yields of any nicotine. Thus, 50 grams of tobacco is equal to about 4 packs of cigarettes or an estimable maximum 80 milligrams of potential nicotine yield. Combine the product with the other ingredients in the indicated proportions to produce a total fluid volume with the desired strength per milliliter (if feasible). So much for theoretical considerations. From a practical viewpoint: if Blackleaf 40 is given as 40% nicotine (and we assume we have produced a comparable solution with the concentrated aqueous infusion) then further refinement with a solvent extraction should yield a product with a very high percentage of nicotine content. If we yielded 500 milligrams of the resulting compound as Izx has reported, then this would reasonably become a component of a total volume of 20 milliliters of vaporizing liquid with a target potency of approximately 25 mg/ml of nicotine. The actual truth may lie somewhere in between these estimates and the results Izx obtained may be subject to various interpretations.

Also see: Tabacum (U. S. P.)?Tobacco. | Henriette's Herbal Homepage

Nicotine may be obtained by adding to a concentrated tobacco extract, solution of caustic soda or lime, distilling with steam, extracting the distillate with ether, and carefully evaporating the solvent. (For another method, that of Schloesing, see this Dispensatory, preceding edition.) R. Kissling (Fresenius' Zeitschrift f. Analyt. Chem., 1882, pp. 64-90) assays tobacco by agitating 20 grammes, in powder form, with alcoholic caustic soda, exhausting the mixture with ether, carefully distilling off the greater part of the solvent, adding diluted caustic soda to the residue, distilling off the nicotine with steam, and titrating each 100 Cc. of the distillate with volumetric sulphuric acid solution, using rosolic acid for indicator. (For other methods, see Archiv der Pharm., 1893, p. 658; and Jour. Amer. Chem. Soc. Proc., 1899, p. 32.)
 
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jbbishop

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See this useful discussion of solvents and extraction methods here:

http://www.e-cigarette-forum.com/forum/diy-e-liquid/1687-isopropyl-alcohol-tobacco-extraction-3.html

I had been attempting to find a source which cited the actual nicotine content of cigarettes. According to this source, a smoker may ingest between say 1 and 2 mg. of nicotine from smoking a single cigarette, but each cigarette can actually contain up to 7-24mg. of nicotine:

http://books.google.com/books?id=G0...X&oi=book_result&resnum=1&ct=result#PPA504,M1

The fact sheets for purified nicotine make it clear that a person needs a HAZMAT suit to handle it so take every precaution.

I'm not here to call for censorship or to lecture those amateur chemists who are obsessed with finding the 'holy grail' of nicotine.
Just to say, holding an open 100ml bottle of pure nicotine in your hands is not the most comfortable feeling, even in strict laboratory conditions.
Playing with it at home is potentially lethal to yourself and others as you don't just have to drink it or spill it on your skin to be poisoned.
If you have an accident, make sure you've read the checklist below and made suitable emergency preparations, or funeral arrangements.
You can buy pure nicotine, but I will not tell you where or how, leave it to the chemists.

* In case of contamination, wash skin by flooding with water and scrubbing vigorously with soap.
* Emesis - patient may already be vomitting. Emesis is not advisable because it may be dangerous. If possible, give activated charcoal orally to adsorb any remaining nicotine. Administer charcoal slurry, aqueous or mixed with saline cathartic or sorbitol. The FDA suggests 240 ml of diluent/30 g of charcoal. Usual charcoal dose is 30 to 100 g in adults and 15-30 g in children (1-2 g/kg in infants).
* Administer one dose of a cathartic, mixed with charcoal or given separately.
* Gastric lavage - may be indicated if performed soon after ingestion, or in patients who are comatose or at risk of convulsing. Protect airway by placement in Trendelenburg and left lateral decubitus position or by cuffed endotracheal intuba tion. Use tap water containing activated charcoal, if available.
* After control of any seizures present, perform gastric lavage. Volume of lavage return should approximate fluid given.
* Initiate artificial respiration using oxygen, is available.

Specific Drugs and Antidotes

* Mecamylamine is a specific antagonist of nicotine actions; however since it is only available in tablets, therefore it is not suitable for a patient who is vomiting, convulsive or hypotensive.
* either give atropine sulphate, (adult 0.4-2 mg; child 0.01 mg/kg, not to exceed 0.4 mg per dose) i.m. or i.v. and repeat every 3-8 min. until signs of parasympathetic toxicity are controlled. Repeat atropine frequently to maintain control o f symptoms. As much as 12 mg of atropine has been given safely in the first 2 hours in adult. Ensure proper oxygenation to avoid arrythmias associated with hypoxia. Interruption of atropine therapy may be rapidly followed by fatal pulmonary edema or respiratory failure.
* or give phentolamine 1-5 mg i.m. or i.v. to control signs of sympathetic hyperactivity, such as hypertension.

General Measures

* Control convulsions: Administer diazepam i.v. bolus (adult, 5-10 mg initially which may be repeated every 15 minutes PRN up to 30 mg; child, 0.25-0.4 mg/kg dose up to 10 mg/dose) or lorazepam i.v. bolus (adult, 4-8 mg; child, 0.05-0.1 mg/kg).
* Do not administer antacids since nicotine is better absorbed in an alkaline media.
* Monitor ECG and vital signs carefully.

Chronic Poisoning
Remove from further exposure to dust or smoke. Prognosis
Survival for more than 4 hours is usually followed by complete recovery.
 
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