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Different nicotine salts - synthesis and discussion

Synaps3

Synaps3

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Joined
Sep 14, 2011
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I'm not sure whether this is within the rules or not here, but I can't think of a better place to post this with more knowledgeable people. Reddit would not be good. Even vape forums don't seem to cover this (nobody seems to care for some reason - amazing to me).

So I've gotten pretty annoyed with e-juice recently. It's all going synthetic and it sucks. It also seems like they are using many different salts under black box terms like, smooth, hit, or signature blend.
I've been thinking about the potential differences and health effects of the different salts. I'm mostly interested in tartrate, malate, and the OG - benzoate.
It looks like making salts is not hard at all.

Different salts description: https://letsupload.cc/nbufF2T6y3/Salts_pdf

I found this patent here: https://patentimages.storage.googleapis.com/57/f8/7e/2db69f396801d5/US20150020824A1.pdf

In it, they discuss many salts (unfortunately not tartrate :(
Here's the benzoate:
Nicotine benzoate salt formulation can also be
made by adding 0.15g benzoic acid to a beaker followed
by adding 0.2 g nicotine and 9.65 g PG/VG (3:7) solu
tion to the same beaker. The mixture was then stirred at
55° C. for 20 minutes until a visually homogenous for
mulation solution was achieved with no undissolved
chemicals.
Click to expand...
They seem to add the PG/VG separate from the nicotine (like they are using nic powder), but I don't see why a standard widley available 100mg/mL freebase nicotine solution couldn't be used instead.

Now how about the tartrate (it's not in there and can't find the synth anywhere). I've seen both nicotine tartrate and nicotine di-tartrate on the market (for business). I'm not sure which I'd want. Looking at the other salts in that patent though, I can say that the synths are all very similar and so I think I'd just have to account for the different molecular weight, but otherwise perform the same procedure, correct?
 
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Synaps3 said:
I'm not sure whether this is within the rules or not here, but I can't think of a better place to post this with more knowledgeable people. Reddit would not be good. Even vape forums don't seem to cover this (nobody seems to care for some reason - amazing to me).

So I've gotten pretty annoyed with e-juice recently. It's all going synthetic and it sucks. It also seems like they are using many different salts under black box terms like, smooth, hit, or signature blend.
I've been thinking about the potential differences and health effects of the different salts. I'm mostly interested in tartrate, malate, and the OG - benzoate.
It looks like making salts is not hard at all.

Different salts description: https://letsupload.cc/nbufF2T6y3/Salts_pdf

I found this patent here: https://patentimages.storage.googleapis.com/57/f8/7e/2db69f396801d5/US20150020824A1.pdf

In it, they discuss many salts (unfortunately not tartrate :(
Here's the benzoate:

They seem to add the PG/VG separate from the nicotine (like they are using nic powder), but I don't see why a standard widley available 100mg/mL freebase nicotine solution couldn't be used instead.

Now how about the tartrate (it's not in there and can't find the synth anywhere). I've seen both nicotine tartrate and nicotine di-tartrate on the market (for business). I'm not sure which I'd want. Looking at the other salts in that patent though, I can say that the synths are all very similar and so I think I'd just have to account for the different molecular weight, but otherwise perform the same procedure, correct?
Click to expand...

As you yourself said. Figure out the molar weight of tartaric acid and benzoic acid, then just swap out one for the other.

-GC
 
G_Chem said:
As you yourself said. Figure out the molar weight of tartaric acid and benzoic acid, then just swap out one for the other.

-GC
Click to expand...
Ok, but would it make the tartrate or di-tartrate? Is it basically just adding 2 molar equivalents, makes the di-tartrate? And if I do just one, then I'd have a blend of tartrate and di-tartrate?
 
Skorpio said:
What health effects are you worried about from different counterions?
Click to expand...
It's probably not a big deal, but I don't know if some of those are bad to be inhaled.
I think a lot of vape juice manufacturers don't understand the difference between inhaling a substance and eating it. They think if you can safely eat it, then it's OK to inhale, NO.
Like they put sucralose in juice and it caramelizes the coils. Sucralose is a chlorinated derivative of sucrose sugar and upon heating to caramelizing temperature, it releases carcinogens.
Basically I'm just trying to make juice that is as healthy as possible. And I want to document the effects of the different salts - nobody is doing it and I think it will be fun.

Right now I'm trying super hard to get the different acids in the highest purity and not Chinese.
 
I just found this video on youtube. Surprised I didn't see it earlier. This guy is doing exactly what I'm thinking about and he's super detailed:
 
Holy crap you were right @Synaps3

Synthetic nicotine has been making me sick!

Headaches, anxiety, chest pain, breathing difficulties, scratchy throat, brain zaps & exaggerated startle response, and more recently seems to be the cause of my liver problems. It was also exacerbating previous psychiatric issues and interacting with other drugs in a very negative way.

As soon as I stopped using synthetic juice all of these problems stopped. I kept blaming these symptoms on other things because I didn't think it could be my vape, but it was.

There is something very sketchy with synthetic nicotine... at least the brand I was using called "Baton".

Wow... I feel SO much better since stopping 4 days ago. I can now enjoy kratom and cannabis again without feeling awful. What the hell was this shit doing to me??
 
So from what I've gathered nicotine from tobacco is >99% (S) nicotine, it produces virtually no (R) nicotine enantiomer.

Synthetic nicotine is racemic. I also doubt the average company bothers to separate them for cost effectiveness.

There is basically no research on (R) nicotine, other than suggestive stuff like it is less psychoactive and less addictive. The health consequences are unknown.

All my symptoms have disappeared after ceasing my vape... lots of people on reddit reporting similar symptoms. Headaches, heart palpitations, anxiety, breathing problems, etc.

I suspect it may be that isomer, or possibly a metabolic product of whatever salt base they were using. Still not sure.
 
Snafu in the Void said:
So from what I've gathered nicotine from tobacco is >99% (S) nicotine, it produces virtually no (R) nicotine enantiomer.

...

All my symptoms have disappeared after ceasing my vape... lots of people on reddit reporting similar symptoms. Headaches, heart palpitations, anxiety, breathing problems, etc.

I suspect it may be that isomer, or possibly a metabolic product of whatever salt base they were using. Still not sure.
Click to expand...
Correct.
Yeah, and I had similar issues.

I'm now beginning to doubt the healthiness of vape overall - synthetic or not. Although, it is clear that the natural is much better.
I did make the tartrate salt myself BTW. It was alright. Not as much of a head rush as the benzoate though. It's more similar to a cigarette at the end of the day whereas I actually find benzoate to be stronger, but much more fleeting. It does seem to have a slight tart taste on the exhale, but not much. It was a cool experiment.

Anyway, I've now linked some health effects I have to vaping, so I'm not going to experiment with any more salts. I think I have liver problems and have lost a lot of weight. I talked about this in your other thread I think. I feel hungry all the time and no matter how much I eat, my weight stays the same and I can't get it back up to where I was several months ago. Mild itchiness and liver pain too. I've now read some studies that vaping is linked to liver problems.
I may switch to cigs or just stop, I don't know.

I had also been wondering whether the salt effects the properties and toxicology of nicotine. If the salt detaches from nicotine in the body, then vaping nic salt should be no different than vaping a higher potency freebase, but this appears to not be the case. The salt stays attached under most bodily PH conditions. So what does this mean? I don't know exactly, however, it tells me that there might be different health effects between the different salts (given that you don't have nicotine AND benzoic acid moving around your body, instead you have nicotine-benzoate the whole time).
The point is: the health effects of pure nicotine have been studied, BUT nobody studies the toxicology of the different salts.

Overall, the idea of dry herb vaporization is starting to seem the healthiest to me.
 
Synaps3 said:
Ok, but would it make the tartrate or di-tartrate? Is it basically just adding 2 molar equivalents, makes the di-tartrate? And if I do just one, then I'd have a blend of tartrate and di-tartrate?
Click to expand...
Just double the amount needed to make tartarate and you get di-tartate.
Why it’s not possible to make “di” of some salts but not for other?
 
Bitartrate usually refers to the tartrate. I think it's one of the -OH moieties binding to the water of crystallization. Look at MW of hydrocodone, tartaric acid and water. That's referred to as 'bitartrate' but the MW and formula suggest 1... but it's early, so don't listen to me.
 
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Again, the patent would suggest that you are forming the dihydrogen phosphate salt which is where I'm guessing the 'di' comes from. A lot of this is because the chemistry is so old that strict IUPAC naming didn't trouble the makers. I believe some Russians on Hyperlab rediscovered the patent which is why amphetamine phosphate (dihydrogen phosphate) turns up in Eastern Europe.
 
Snafu in the Void said:
@Synaps3 how long were you using synthetic stuff for?

The pain I was having around my liver are gone, but I'm still getting chills after eating food and using kratom.
Click to expand...
Only two to three days, but that was plenty of time to tell the difference. I could tell there was something off after only half a day (lots of anxiety), but the headaches came later.
I know it's been a while, but how you been doing? Have you quit vaping completely or?

I'm doing alright. Still using juul though (instead of my old box mod). At this point I'm not even sure if the liver condition was real or just my imagination. Things have improved a fair bit since quitting kratom and not using my high power mod.
I've been using hydromorphone instead though. I still get this weird situation where after the hydro wears off, I get itchy and slight pain in liver area. I might be over-analyzing though cause it's way better than when I was on the kratom. It's weird that the itchy sensation comes after the hydro is wearing off, but not during. That makes me think it's not just the normal itching associated with opioids (which I don't seem to experience anyway).
 
I've been doing better. I stopped vaping and switched to tobacco, cigarettes and oral, which is not what I want to do. I intend to go back to vaping tobacco derived nicotine I've just been lazy.

Still having those liver issues. Sporadic pain in my liver but infrequent. More frequently I get pain about 6 inches below my liver, right where my appendectomy scar is, which is odd. But the worst symptom I still have are weird body chills I get in my torso after eating food. My body is producing too much bile (?). Opioids and kratom can dilate the bile ducts which may be the explanation.

I don't know, overall I do feel a lot better than when I was using the synthetic nic, but these liver issues are lingering.
 
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The salt stays attached under most bodily PH conditions.
Click to expand...
Incorrect. In solution nicotine and its salt-forming acid are fully dissociated.
In a mixed salt solution nicotine can "trade" its counterion. For instance dissolving nicotine sulfate in salt water will produce nicotine hydrochloride in solution (and sodium sulfate).

And at physiological pH both nicotine freebase and nicotine as a salt are present in blood.

That being said, the salt form should not really matter too much.
 
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