Synthetic Nicotine - Is there really such a thing?

[Outlander]

xtraelf,

likewise I am a long time smoker, albeit not as heavy. 1 pack a day since 1962. I have also tried all the alternatives to quit and found none of them to be effective until I tried the e-cig.

I gave each try a real effort and even managed to have stayed away from the analogs for over a year twice. The problem was, it was and "EFFORT".

I got my first e-cig 60 days ago, as did my oldest son. We put down the analogs and neither of us has even had the slightest desire to pick them back up. I didn't even miss the nic, yes I went no-nic on the git-go. Sure, I'll do some nic maybe once or twice a day I'll do a single drop and then several days or even a week I won't. That is one thing I really like about the PV, I decide if, when and how much, but if I want I can still vape all day and not intake any nic if I so desire.

I enjoy the act of smoking/vaping, it is relaxing to sit back and watch the vapors rise and swirl, twisting and winding their way along in a blissful dance, carrying away my troubles and anxieties with them. Well, I can hope can't I? Anyway it's a stress reliever and stress is the biggest killer of them all.

Let's face it cigarettes actually taste like crap. With vaping you can enjoy the action and also the variety of flavors.

I wish you the best and hope that your transition from the analog to the PV will be as effortless and effective as mine was.

Fred

 

[warbdan]

Fred, You put it beautifully. That pretty well sums it up.

 

[rolygate]

Synthetic nicotine

Here are a couple of points that have come our way at ECF. I have no way of verifying these statements, so please take them as hearsay until otherwise proven.

1. Chemist "X" stated that if presented with a sample of liquid with nicotine of a reasonable strength, he could determine whether it was synthetic or natural simply with a light source and viewing apparatus of the correct type. At the time I wasn't interested enough to pursue it but I'm assuming he was referring to a laser source and some way to view the resulting light dispersion safely. In other words, you can tell by looking at it which type it is (or if it's a mixture, presumably). It seems that differentiation is fairly simple.

2. Chemist "Y" stated that synthetic nicotine has 50% of the effect on humans compared to natural nicotine.

3. Apparently there are no published clinical trials that determine the effect of synthetic nicotine on humans as far as the safety aspect goes. So we don't know what the implications are. We know it affects the body in a different way to natural nic but we don't know to what extent. Therefore it would not seem proven safe at this time to use it.

4. We know of one supplier who claims to use only synthetic nicotine in their cartos. They pay $1,800 per barrel for their nic, when standard natural nic of very high purity is $300 per barrel or less. The reason they use it is apparently to ensure it is of the highest quality and contains no pesticides, carcinogens or any other contaminants.

It is of course very expensive. However this supplier (a major name) only sells cartomizer ecigs, and to the 'new buyer' market. Their product is very expensive indeed, around $150 or more for a starter kit - you know the type. Therefore I guess the nic cost is not a huge factor; also like many suppliers in that market their 'high strength' cartos are what others would consider medium or low. I can easily see that whatever the cost of their nic, it would be absorbed without issue, due to the price of the end product. The ability to claim ultra-high purity, and for that to be provable on analysis, would be a good selling point especially in that market.

This was unfortunately told me in confidence so I can't say any more on the subject.

These points, again, are just what I've been told or read so are not 'facts'.

 

[Mister]

There are two "optical isomers" of the nicotine molecule.

The nicotine in tobacco consists primarily of just one of those isomers, and that isomer is known to have much more effect on the mammalian body.

Chemist "X" is assuming that the synthetic nicotine would be "racemic", i.e. would contain equal proportions of both isomers. If it does then what chemist "X" says is all true.

But, it is possible to synthetically produce each isomer of nicotine separately. And anyone synthesizing nicotine for e-liquid ought to know enough about all of this to realize that this is what they must do, even though it will almost certainly be much more expensive than synthesizing a racemic mix. Assuming the manufacturer understands all this (and if they don't they are crazy to be doing this at all) then Chemist "X" is wrong on all counts.

 

[DVap]

There are two "optical isomers" of the nicotine molecule.

The nicotine in tobacco consists primarily of just one of those isomers, and that isomer is known to have much more effect on the mammalian body.

Chemist "X" is assuming that the synthetic nicotine would be "racemic", i.e. would contain equal proportions of both isomers. If it does then what chemist "X" says is all true.

But, it is possible to synthetically produce each isomer of nicotine separately. And anyone synthesizing nicotine for e-liquid ought to know enough about all of this to realize that this is what they must do, even though it will almost certainly be much more expensive than synthesizing a racemic mix. Assuming the manufacturer understands all this (and if they don't they are crazy to be doing this at all) then Chemist "X" is wrong on all counts.

Expanding on Misters' explanation:


There are indeed only two substances that can be called "nicotine".

1) Naturally occurring (-)-nicotine
2) Non-naturally occurring (+)-Nicotine.


Nicotine can be produced synthetically as:

1) (-)-Nicotine
2) (+)-Nicotine
3) (±)-Nicotine (a 50:50 mixture of (-)-nicotine and (+)-nicotine referred to as a "racemic" mixture).


Any form of nicotine synthetically produced is more costly to produce than simply extracting (-)-nicotine from tobacco and purifying it.

Synthesis is exacting and specialized work, extraction not nearly so.


The potency of synthetically produced nicotine versus natural (-)-nicotine extracted and purified from tobacco is:

synthetic (-)-nicotine: Equally potent vs natural (-)-nicotine.
synthetic (+)-nicotine: About half a potent as natural (-)-nicotine
synthetic (±)-nicotine: About 75% as potent as natural (-)-nicotine (due to being a 50:50 mix of equal-potent and half-potent enantiomers.


Relative expense of purified nicotine:

Natural (-)-nicotine: low
synthetic (±)-nicotine: high
synthetic (-)-nicotine: very high
synthetic (+)-nicotine: extrememly high

The reason that the synthetic (±)-nicotine is rated "high" while the synthetic (-)-nicotine and (+)-nicotine are rated very high and extremely high is due to a combination of chemistry and demand. It is much easier to produce synthetic (±)-nicotine than synthetic (-)-nicotine or synthetic (+)-nicotine. In practice, it is probably no more difficult to produce synthetic (+)-nicotine than it is to produce synthetic (-)-nicotine. (and actually, the two are probably separated from an initial (±)-preparation. The reason I rate the expense of synthetic (+)-nicotine higher than synthetic (-)-nicotine is that the demand for synthetic (+)-nicotine is pretty low compared to synthetic (-)-nicotine. I could obtain 1 gram of synthetic (±)-nicotine for $413.50, while I could obtain 5 mL (approx 5 grams) of presumably natural (-)-nicotine for $64.00 (or $12.80 per gram). Gram per gram, the synthetic (±)-nicotine is around 32 times more expensive than the natural (-)-nicotine. I can't even find a source for synthetic (+)-nicotine.


Do I personally believe the supplier mentioned by RG believes he is getting synthetic (-)-nicotine?

Yes.


Do I personally believe the supplier mentioned by RG is actually getting synthetic (-)-nicotine?

No.


If it were practical from a cost-basis to use synthetic (-)-nicotine, would it offer any advantage over using natural (-)-nicotine.

I don't think so. Just because (-)-nicotine can be synthetically produced, it doesn't make it pure. Cleanup and purification is still required to remove un-reacted intermediaries and possible side-reaction products. Obtaining highly purified (-)-nicotine from natural sources takes some work, but isn't that hard, especially compared to synthesizing it (one example here). Techniques such as multiple vacuum distillations and isolation of the nicotine/water azeotropic mixture come to mind.


Could I be wrong?

Yes, but it would take some thorough convincing to make me believe that I am.

 

[DVap]

1. Chemist "X" stated that if presented with a sample of liquid with nicotine of a reasonable strength, he could determine whether it was synthetic or natural simply with a light source and viewing apparatus of the correct type.

Chemist "X" is correct to a point, after which he muddies the water.

The device he refers to is known as a "polarimeter". It could easily distinguish between (-)-nicotine, (+)-nicotine, and (±)-Nicotine.

Could a polarimeter distinguish between natural (-)-nicotine and synthetic (-)-nicotine. No, it could not. Doesn't matter how a chemical is produced, if two samples of (-)-nicotine produced naturally and synthetically are pure, they are identical. It does not matter the source, they cannot be distinguished.

 

[DVap]

4. We know of one supplier who claims to use only synthetic nicotine in their cartos. They pay $1,800 per barrel for their nic, when standard natural nic of very high purity is $300 per barrel or less. The reason they use it is apparently to ensure it is of the highest quality and contains no pesticides, carcinogens or any other contaminants.

Just as a note, I'm sure some folks are quite aware of which supplier is being discussed here. I've looked at the laboratory data, and the nicotine is indeed quite pure, there's no mistaking that fact. In this sense, quality-wise, the stuff is quite good.

Depending on the thoroughness of the purification, naturally derived (-)-nicotine can be purified free of TSNA's, pesticides, etc (I.E. pure to the point where these impurities, if present, could not be detected).

 

[Kurt]

I am 100% in agreement with DVap. The idea that synthetic (-)-nic is being sold is really hard to believe for a trained organic chemist. Just too expensive and not necessary at all...extraction will make just as pure (-)-nic as synthesis at a small fraction of the cost.

And the idea that other vendors are pushing (+)-nic is frankly beyond belief. It is WAY expensive, and about half as potent. Synthesis to make even a racemic mixture of the two enantiomers is still very expensive compared to extraction.

Unfortunately, the vast majority of people do not have knowledge of these chemistry details, and can be fooled by words like "enantiomer". For someone in the field, this is pretty much open and shut, and something is not at all right with this picture. I PMed said supplier a while back to warn him that I thought he was being had, as I was concerned that he was being ripped off, and I don't want our good suppliers, and he is good, to be duped. But I didn't hear back, and the issue seems to be the same as it was some months ago.

To be honest, someone is going to have to come up with some pretty hard evidence that this is synth (-)-nic. Polarimetry will only say it is (-), not synthetic. Extracted pharm grade (-)-nic is every bit as pure as synthetic (-)-nic, and orders of magnitude cheaper...unless said supplier has his own chemist who has a big lab and a recipe better than what is used by pharm/chem houses. And I doubt that. You do not need to be a trained chemist to find this info, just look up the prices at Sigma.

But I think you DO have to be a trained chemist to argue that this is synthetic (-)-nic being sold. I'm afraid to DVap and me this is like arguing that the earth is flat, and without references for the actual synthesis and cost analysis, or a lengthy conversation with the chemist, this just seems impossible.

That said, I am also with DVap that the supplier is not being deceptive, he has just likely been fooled by someone supplying him. Just my opinion, but it is a professional one.

 

[PoliticallyIncorrect]

Ok, now I'm really getting confused.

To begin with, I read somewhere--that somewhere would be the internet, of course, although I can't recall the website--that the type of nicotine found in all e-liquids (where there's any at all) is synthetic.

This was previous to reading that the issue was moot, at least if one were to believe the findings of one Professor Thomas Eissenberg, who conducted a study regarding the effectiveness of e-cigarettes--i.e., their nicotine-delivery performance.

This site won't allow me to post links just yet, but here's the pertinent snippets from one of the web pages reporting the findings:

"...the smokers started off with very low nicotine blood levels (around 2 ng/ml) and went up to around 17 and 20 ng/ml after smoking the usual cigarettes. However, when the smokers used 2 E-cigarettes their blood nicotine levels hardly budged, peaking at 3.5 ng/ml (i.e. not significantly different from before they used the E-cigarette or puffing on an unlit cigarette). Similarly, unlike smoking real cigarettes, the E-cigarettes did not affect heart rate and had a relatively small (but observable) effect of reducing craving for a smoke.

"What this suggests is that regardless of how much nicotine is supposed to be contained in the E-cigarette cartridge, almost none of it is transferred via the vapor and absorbed in the human body. As I have previously suggested, the E-cigarettes appear to be a good idea, with intuitive appeal, but ultimately have the status of a neat theatre prop which mimics rather well the appearance of smoking."

Now, the notion that PVs are essentially placebos flies in the face of everything I've heard anecdotally from the vaporizers here and elsewhere--especially those that have weaned themselves off analogs.

A theory occurs to me, however: I'm not a chemist, but if it were true that the active ingredient in e-liquids are synthetic, is it possible that only organic nicotine is detected by whatever means Eissenberg was using to look for it? If the synthetic variety flew under his radar equipment, that would explain matters neatly.

There's a whole lotta ifs there.

 

[rolygate]

PoliticallyIncorrect - To begin with, I read somewhere--that somewhere would be the internet, of course, although I can't recall the website--that the type of nicotine found in all e-liquids (where there's any at all) is synthetic.

This was previous to reading that the issue was moot, at least if one were to believe the findings of one Professor Thomas Eissenberg, who conducted a study regarding the effectiveness of e-cigarettes -- i.e., their [lack of] nicotine-delivery performance.

The nicotine used in all eliquids is organic and can be traced back to suppliers of organic nicotine. Organic is used because:

1. There's nothing wrong with it and it is available at such high purity that there is zero risk of any contaminants.
2. Synthetic nicotine is at least 6 times more expensive and there would be no reason to use it.
3. Synthetic nicotine only has 50% of the effect on the human body, so you would need twice as much to get the same effect.
4. It is obviously different as the effects are clearly different - but to date there are no published trials of its safety or other implications, so that it would seem unwise to use it at this point in time.

However it appears there are one or two suppliers with personnel who have claimed at one time or another that their nicotine is partly or completely synthetic. For various reasons this seems unlikely, but cannot be disproved without testing. As far as most of us are concerned it's a non-issue that for some reason keeps being revived, although given the (non) results of all ecig trials published to date, this is perhaps understandable.

Prof. E's trial, like others, was conducted by people who had zero knowledge of how to specify, prepare or test the equipment, and with new users with no experience of ecigarettes, and who were instructed to "use the ecigarette exactly as a tobacco cigarette is used".

This is virtually a blueprint of how to get no measurable result, since every single factor is the opposite of that which should prevail. However in the current regulatory environment it does us no harm at all.

The fact that in order to test a car, you would not choose a tribesman from Papua New Guinea as he wouldn't know how to put the gas in never mind how to drive it, does not seem to have been factored in to the methodology in these trials - which, as stated, is a good thing as far as we are concerned. If government is going to ban cars that exceed 50mph, then if you are a car owner, from your perspective the ideal person to test them is someone who can't even figure out how to put the gas in - all models will pass...

We aren't complaining about the results of these tests at all, since they may be used in legal proceedings. From that perspective they are the ideal results from our point of view. Just so you understand that.

This has nothing whatsoever to do with the fact that they work for experienced users, or that if human life or public health were a factor, the moral obligation of government would be to fast-track ecigarettes to wider public use and even to advertise them with government funds. These points are irrelevant.

 

[PoliticallyIncorrect]

For whatever it's worth, I found the page I mentioned from Medscape.com that made the following claim:

"E-cigarettes contain no tobacco products; even the nicotine is synthetic."

The page it at medscape.com/viewarticle/706362, and it's the last bullet point under the sub-heading, "How E-Cigarettes Work."

It's a reputable-looking site, but they're evidentally guilty of at least one piece of very bad information.

 

[DVap]

The nicotine used in all eliquids is organic and can be traced back to suppliers of organic nicotine. Organic is used because:

1. There's nothing wrong with it and it is available at such high purity that there is zero risk of any contaminants.
2. Synthetic nicotine is at least 6 times more expensive and there would be no reason to use it.
3. Synthetic nicotine only has 50% of the effect on the human body, so you would need twice as much to get the same effect.
4. It is obviously different as the effects are clearly different - but to date there are no published trials of its safety or other implications, so that it would seem unwise to use it at this point in time.

However it appears there are one or two suppliers with personnel who have claimed at one time or another that their nicotine is partly or completely synthetic. For various reasons this seems unlikely, but cannot be disproved without testing. As far as most of us are concerned it's a non-issue that for some reason keeps being revived, although given the (non) results of all ecig trials published to date, this is perhaps understandable.

Prof. E's trial, like others, was conducted by people who had zero knowledge of how to specify, prepare or test the equipment, and with new users with no experience of ecigarettes, and who were instructed to "use the ecigarette exactly as a tobacco cigarette is used".

This is virtually a blueprint of how to get no measurable result, since every single factor is the opposite of that which should prevail. However in the current regulatory environment it does us no harm at all.

The fact that in order to test a car, you would not choose a tribesman from Papua New Guinea as he wouldn't know how to put the gas in never mind how to drive it, does not seem to have been factored in to the methodology in these trials - which, as stated, is a good thing as far as we are concerned. If government is going to ban cars that exceed 50mph, then if you are a car owner, from your perspective the ideal person to test them is someone who can't even figure out how to put the gas in - all models will pass...

We aren't complaining about the results of these tests at all, since they may be used in legal proceedings. From that perspective they are the ideal results from our point of view. Just so you understand that.

This has nothing whatsoever to do with the fact that they work for experienced users, or that if human life or public health were a factor, the moral obligation of government would be to fast-track ecigarettes to wider public use and even to advertise them with government funds. These points are irrelevant.

As out of place to this discussion as it is, I can consistently max out a nicalert strip vaping nothing but approx 10 mg eliquid. Eissenberg himself acknowledged/admitted to getting a 5 out 6 on a nicalert strip after spending only a couple hours the previous evening with a halfway decent ecig. The cotinine detected has to come from somewhere.

 

[DVap]

"E-cigarettes contain no tobacco products; even the nicotine is synthetic."

Seems to be a simple case of poor research by someone not qualified to notice the red flag such a statement throws up. If you Google for "even the nicotine is synthetic", you'll see that this statement has been picked up and spread far and wide, and it is, unfortunately, incorrect.

The quality of nicotine offered by vendors varies from insecticidal crud to pharmaceutical grade. The former, is fortunately rare, and the latter is rare as well.

If I were concerned about knowing my nicotine is absolutely the purest pharmaceutical nicotine, I would pay the premium for proven pharma grade nicotine (such as TW's Platinum Ice).

 

[rolygate]

What we do know:

- Ecigarettes are the most important discovery since antibiotics
- Ecigarettes will eventually replace tobacco cigarettes

What we don't know:

- How long that will take
- Exactly what the long-term health implications are

Presumably there will be some health implications, though perhaps on a microscopic scale compared with those of tobacco smoking.

OK, you can start in now...

 

[hairball]

Okay, I'm far from being a chemist. For gosh sakes, I'm a factory worker/housewife/mother. Here is my question to all the chemists: Is the nicotine that we use, the stuff derived from tobacco plants, clean? I mean, just how much of the "junk" is actually removed and that what we vape is clear of carcinogens?

 

[warbdan]

Should it be noted that the main difference in pesticide grade nicotine and pharmaceutical grade is the purity? When we talk about pesticide grade it sounds like we're vaping 7 dust or something. Would it be fair to say that any nicotine grade below 99% purity is considered pesticide grade and to be pharma grade it has to be over 99% pure? Personally I'm more afraid of the flavorings than whether or not the nicotine in my liquid is cloudy. Correct me if I'm wrong, this is just my train of thought at the moment.

 

[Toritha]

This discussion is intriguing. My personal experience with the other nicotine alternatives is as follows;

patch - Weirdest dreams I've ever had in my life... I'm talking vivid, realistic, make you wet the bed, nightmares.

gum - tasted nasty no matter what flavor i used and the long term side effects were cavities along the upper and lower sides of of my teeth

Now vaping causes no symptoms unless you want to call breathing deeper, a return to my smelling and tasting senses symptoms.

I wonder how cost effective it would be to extract nicotine from non-tobacco plants ie: tomatoes. Perhaps then we could avoid the whole "tobacco product" argument.
I think that is a part of why some places want to say they use synthetically derived nicotine, to survive the so-called fall out when/if the FDA screws us vapers.

If their nicotine is synthetic then they don't fall under the tobacco product heading b/c they don't utilized tobacco to get the nicotine.

Just my thoughts on the matter and i don't have any hardcore evidence just my observations.

 

[jerrydon10]

Let me set you guys straight.......HAHA just kidding, throw me out and I'll run...LOL. I do have a BA in environmental chemistry. Of course, that degree pales in comparison to a couple of chemists who are posting in this thread, at least one of which I know to be an organic chemist (much more training in the field).

I have planned to become a registered supplier of nicotine products on here for about a year now and have researched it all, including this.

How cool would it be, to be able to honestly state that NONE of my nic products come from tobacco, it is all synthetic and made in the lab. Yep, that would be icy cool and might cause the FDA to scratch their beloved heads.

But it would be a lie. And everyone who tells you that their nic is synthetic is scamming you.

Let's look at the details and Mister nails it:

There are only two distinct things named nicotine. Both of them have the chemical formula C10H14N2, and the molecular structure described by the IUPAC name 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine.

The only difference between the two is the "optical" arrangement in the molecule. It can be either levorotatory or dextrarotatory.

OK, what does this mean? They are the same molecules but they are not? Yup.

Look at your hands. Don't they look the same? Four fingers and a thumb. Wow they both have a palm, nails, a pinky and a back with age spots. They are the same structures.

But here is the truth, they look the same but they are not!

Place one hand over the other and you will discover that although they are the same structures, the thumbs stick out on opposite sides. In fact, they are not the same, they are mirror images of one another.

This is the optical arrangement that Mister is referring to. It's all mirrors. And do the opposites work the same? Nope.

I challenge you right handers to start signing your checks with your left. It doesn't work. And it's the same when we look at chemistry.

Yes, of course nicotine has been synthesized in the lab. But it simply does not work in the body the same as it's opposite hand does, even though it has the same chemical formula. And it would be so expensive to produce that I don't think anyone would pay $200.00 for a 30 ml bottle which will not satisfy their cravings in the first place.

"Natural nicotine" is all that works for us and in it's common modern usage, this is a word used to refer to a a variety of chemical compounds, which are derivatives of a specific base chemical: freebase nicotine. The "nicotine" found in tobacco is actually a mixture of two "salts" of nicotine, nicotine citrate and nicotine malate. The "nicotine" found in gum and patches is usually nicotine sulfate. The most common form of nicotine found in nature is its oxide, nicotinic acid (usually abbreviated niacin).

So what are we getting when we a vape? A combination of all the above.

Is it contained in tomatoes? Yes. All green plants contain nicotine, as the chemical is necessary in the process called photosynthesis whereby the plant feeds itself partially via sunlight. However, some plants have higher nicotine content than others--and chief among them, of course, is tobacco.

The latter (pass the tomatoes), unfortunately, is all you will ever vape and enjoy. If anyone tells you anything else, they are scamming you.....

 

[VictoryNotVengence]

A google search while listening to the Winston Cowboy on VP-Live led me to this thread.
Is the nicotine in the patch and gum derived from tobacco?
I ask because the fda has to regulate ecigs as tobacco products BECAUSE the nicotine is derived from tobacco.
Where else could it be derived from?
Does that mean the gum and the patch are tobacco products as well?

 

[deusXmchna]

Is the nicotine in the patch and gum derived from tobacco?

yes.

I ask because the fda has to regulate ecigs as tobacco products BECAUSE the nicotine is derived from tobacco.

You'd think that ecigs might fall under ATF, not FDA, but most of that is tax related- so aside from that, a synthetic nicotine would still end up falling under the regulation of FDA, because it would still be nicotine (a drug), regardless where it came from.

For instance, naturally occurring opiates (morphine) still falls under the FDA just as the synthetic opiates (methadone) do, and the semi-synthetic opiates (thebaine derivs) do. It doesn't matter where the opiate is derived from, it falls under FDA regs. (and DEA controls, but thats a separate issue).

Did that make sense? I'm awfully tired....communication skills not at 100% efficiency