Chemistry of Nicotine

[kinabaloo]

A thread to discuss the chemistry of nicotine.

First, some basic facts:

Chemical Formula C10H14N2
Aqueous solubility Slightly soluble
Boiling Point477°F (247°C)
Density Liquid: 1.01 g/cm3 at (68°F/39°F) (20°C/4°C)
Gas: 5.6 (air = 1)
Flammability Combustible liquid
Flashpoint203°F (95°C)
Molecular Mass162.23
Soluble In Alcohol, chloroform, ether, petroleum ether, kerosene, and oils. Specific Gravity1.01
Vapor Pressure0.08 mm Hg at 68°F (20°C) 0.038 mm Hg at 77°F (25°C)
Volatility Not established/determined
Auto-Ignition Temperature: 240 degrees Celsius
Explosive Limits: 0.7 - 4 percent, by volume, in air

 

[kinabaloo]

The high boiling pont (247C) makes me wonder if all of the nicotine gets into the vapor; some may be simply degraded on the heater coil (this needs investigating).

In a thread about running attys on 6v people report an unpleasant sharp burning taste. Decomposition of VG could be one reason for that taste. Increased release of nicotine could be another.

 

[kinabaloo]

Freebase nicotine in smoke or vapor impossible?

See The Smoker's Club, Inc. Encyclopedia 16

Down a little is the artcle "Nicotine: What is it, and where does it come from?" Start reading from the paragraph starting "Freebase nicotine is ..."

Where this reasoning might be wrong is that free-base nicotine might not self-destruct when well diluted.

Thoughts ?

 

[Harry Crazington]

Freebase nicotine in smoke or vapor impossible?

See The Smoker's Club, Inc. Encyclopedia 16

Down a little is the artcle "Nicotine: What is it, and where does it come from?" Start reading from the paragraph starting "Freebase nicotine is ..."

Where this reasoning might be wrong is that free-base nicotine might not self-destruct when well diluted.

Thoughts ?

Great find/read there Kinabaloo.
Well I'm happy so see that I'm not addicted to nicotine, and never have been. Question is why can't almost anyone quit smoking, vaping, or thinking that they need nicotine when it's actually cotinine (harmless & non addictive) that we inhale? I wonder what causes the cravings to smoke or vape after not doing it for a period of time, along with withdrawl symptoms. I know that I can sleep for 8 to 10 hours and not crave a smoke, until just after waking up, then it's the first thing on my mind. So it just may well be psychological after all. Amazing information from that link!!

 

[kinabaloo]

Great find/read there Kinabaloo.
Well I'm happy so see that I'm not addicted to nicotine, and never have been. Question is why can't almost anyone quit smoking, vaping, or thinking that they need nicotine when it's actually cotinine (harmless & non addictive) that we inhale? I wonder what causes the cravings to smoke or vape after not doing it for a period of time, along with withdrawl symptoms. I know that I can sleep for 8 to 10 hours and not crave a smoke, until just after waking up, then it's the first thing on my mind. So it just may well be psychological after all. Amazing information from that link!!

I don't know that the info there is true; but there some reasons to think it might be at least part true. Even if the main thrust is completely wrong, it does at least include some useful information (and some dodgy analogies).

 

[Harry Crazington]

I don't know that the info there is true; but there some reasons to think it might be at least part true. Even if the main thrust is completely wrong, it does at least include some useful information (and some dodgy analogies).

Yes VERY useful information. I've been browsing through that Smokers Club website The Smokers Club, Inc. I think it may become as addictive as this ECF forum !

 

[kinabaloo]

A different take on what freebase nicotine is and some other interesting info: Researcher publishes measurements of 'free-base' nicotine in cigarette smoke | Science Blog

Excerpt: "Nicotine enters a smoker's body mostly carried on the billions of particles in cigarette smoke, Pankow said. In common with street drugs like ......., he said, nicotine's molecular structure can appear in both free-base ("unprotonated") and non-free-base ("monoprotonated") forms. The difference is that the free-base form is missing a hydrogen ion, and this allows it to vaporize easily into a gas during smoking. "During smoking, only the free-base form can volatize from a particle into the air in the respiratory tract. Gaseous nicotine is known to deposit super-quickly in the lungs. From there, it's transported rapidly to the brain."

So the non freebase form has an extra hydrogen atom - as part of a bond to other atoms (as say nicotine citrate) or what does this mean exactly?

Other forms of nicotine could reach the lungs and release nicotine once there? If so, they get there by being carried on particles of ash. In vaping they just burn up on the heater coil (hence a reduced bodily nicotine intake)?

 

[kinabaloo]

In this article it is suggested that secondhand nicotine can linger for months!: Neuroscience for Kids - Nicotine, Second Hand Smoke, Infants

Although it's about smoking, suggests that nicotine lingers for months. But are they really measuring nicotine or the harmless compounds of nicotine found widely in vegetables, such as vitamin B3. I believe that freebase nicotine wouldn't last more than a minute without reacting/oxidising to something benign, but don't have the info at hand. The Smokers Club article suggests this.

This is important to understand because this argument is one likely to made for banning vaping.

 

[kinabaloo]

Online book: Nicotine Psychopharmacology - Google Book Search

Among many many other things, suggests freebase nicotine is more associated with ventilation than pH.

Searching that book could yield lots of useful info.

Chemistry / forms of nicotine: p30 onwards; cotinine etc.
p31 discuuses pH wrt absorbtion and the different types of tobacco (ppe, cig, chew etc.).

 

[dedmonwakin]

According to the info that you have provided, the nicotine can reach and withstand 477 degrees ferinheight before breaking down. I'm not sure how hot the nichrome gets with in the atty, but my assumption is that a majority of the vapor is produced long before the nichrome could ever reach that temperature.

The fact that the nicotine is slightly water soluble, leads me to believe that much of it is carried by the vapor, maybe more so than a cigarette, since there is no filtration in our ecig and we lack the surface area of a burning cherry, which has reports of 1700 degrees fahrenheit, that would definitely destroy any remaining nicotine that hasn't been carried by ash particles.

Essentially, we already are free basing.

 

[kinabaloo]

According to the info that you have provided, the nicotine can reach and withstand 477 degrees ferinheight before breaking down. I'm not sure how hot the nichrome gets with in the atty, but my assumption is that a majority of the vapor is produced long before the nichrome could ever reach that temperature.

The fact that the nicotine is slightly water soluble, leads me to believe that much of it is carried by the vapor, maybe more so than a cigarette, since there is no filtration in our ecig and we lack the surface area of a burning cherry, which has reports of 1700 degrees fahrenheit, that would definitely destroy any remaining nicotine that hasn't been carried by ash particles.

Essentially, we already are free basing.

Perhaps; we just don't know for sure.

But people, and some studies, show that the absorbtion is both slow and low when vaping.

My possible explanation for this is that VG / PG (VG in particular) dissolves the nicotine and it is held by the VG in droplets; VG is extremely reluctant to evaporate; not sure about skin/lung absorption.

 

[kinabaloo]

Came across a new source today on the chemistry of nicotine.

I was primarily interested in the possibilities for synthesis, but there are some other interesting things on this site.

Worryingly, the author states quite boldly that nicotine is a carcinogen in it's own right, through a mechanism that can create a strong radical.

Nicotine

 

[DVap]

Came across a new source today on the chemistry of nicotine.

I was primarily interested in the possibilities for synthesis, but there are some other interesting things on this site.

Worryingly, the author states quite boldly that nicotine is a carcinogen in it's own right, through a mechanism that can create a strong radical.

Nicotine

Water is explosive in it's own right through a mechanism that can liberate free hydrogen.

My point being, unless the author can show that the mechanism is actually significantly present in smoking related activities, it isn't going to create the radical, and thus his assertion may become a practical non-starter.

Oh.. on your comment earlier in the thread on folks vaping at 6 volts getting a sharp, burning taste.. I never ever want to vape VG at 6 volts. They're quite possibly describing acrolein.