Bonded vs Non Bonded Nicotine

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texmexpipe

Part of the Furniture Now
Oct 20, 2014
998
246
I read on here the other day a comment by someone that said pipe tobaccos have non bonded nicotine, and cigarettes have bonded nicotine. I googled it and came up flat. Can anyone point me to something that can substantiate this? My curiosity is getting the better of me.

 

cobguy

Lifer
Oct 18, 2013
3,742
15
This is a pretty good Nicotine "primer" and explanation of how pH plays a role

in bound vs un-bound nicotine and it's absorption:
http://www.bernd-mayer.com/nicotine-the-basics/

 

texmexpipe

Part of the Furniture Now
Oct 20, 2014
998
246
Thanks, I wish I understood more than about half of it, but I did find it a little helpful in explaining the absorption.

 

cobguy

Lifer
Oct 18, 2013
3,742
15
I think the jist is that Nicotine is more available to the body in an alkaline smoke.
Sugars in Virginia leaf tend to keep the smoke more acidic and thus lower in available nicotine.
It's obviously more complex than this but that's the basic idea.

 

cobguy

Lifer
Oct 18, 2013
3,742
15
It's not only the leaf but the curing processes as well.

Curing, fermentation and aging have a significant effect on nicotine.

Ropes and twists are strong in nicotine largely because they are less processed than pressed, stoved tobaccos.
Then, there is the consideration of the soil it was grown in, the rainfall that year, etc ...

For example, GH uses a lot of African Virginia. The soil there is nitrogen poor, and produces a low sugar.
So many variables ... so little time to smoke more! :puffy:

 

jitterbugdude

Part of the Furniture Now
Mar 25, 2014
993
8
Nic absorption is dependent on the pH of the leaf. Fermenting, processing has no affect on nix absorption. Fermenting can very slightly change the pH though. The type of tobacco matters. A dark air is typically high in nix whereas a Turkish is low. The issue you might have had with. Your search is you used the wrong word. Try " bound nicotine" for a search word.

 

mso489

Lifer
Feb 21, 2013
41,210
60,433
Corporate or municipal bonds? I knew there was some reason I took physics instead of

chemistry in high school.

 
Cobguy, didn't you mean to say that the acidity of Virginias makes it more readily absorbed, and the alkalinity of the burley makes it slower to absorb?
The low levels of nicotine found in the Virginias are offset by its easily absorbed nature; whereas, Burleys have a lot of nicotine, but because of it's combustion rate and high PH, it doesn't readily absorb through the small membranes.

We tend to waste the nicotine from Burleys into the air, but because there is so much smoke and nicotine, that we get the fix, regardless. And, the low level of nicotine found in Virginias is offset by its more acidity, which makes it pass more readily through the membranes, thus Virginia smokers don't need to make billowing clouds of smoke to get the fix.
Burleys are like a shotgun blast of nicotine, some pellets hit and some gets wasted. Whereas, Virginias are a rifle shot, hitting the target with a sniper's accuracy, ha ha.

 
I know that he said the reverse, but that didn't make sense, nor did it seem to coordinate with what the article was saying, with way more jargon that I am familiar.
Burley keeps getting reported as having more nicotine, but yet, burley blends outside of Dark Fired some African Burleys, just don't do it for me. And, almost all of the cheap topped aromatics are burley blends. Sutliff and Lane might as well be marketed to kids. But, yet Virginia flakes deliver the goods for me, even bright Virginias.
So, the reverse makes more sense from a rubber meets the road perspective.

 

cobguy

Lifer
Oct 18, 2013
3,742
15
From the article:
"The following main species are present at the following ranges of pH values:

(i) pH 8: fully deprotonated (also referred to as “unbound” nicotine)"
... high pH values shifting the equilibrium towards fully deprotonated (unbound) nicotine that is resorbed by passive diffusion along its concentration gradient.
From another good article here at PM:
http://pipesmagazine.com/blog/put-that-in-your-pipe/burley-the-rodney-dangerfield-of-tobacco/
"Burley is alkaline by nature, meaning that the smoke will tend to have a pH above 7, and one of the things that will cause the body to absorb nicotine more readily is an alkaline (or basic) matrix, which makes sense if you realize that nicotine belongs to a group called alkaloids."

 

jitterbugdude

Part of the Furniture Now
Mar 25, 2014
993
8
I do not know of any Burley that is actually alkaline. Burleys have a higher pH than Virginias. It's all relative (like people in West Virginia.. :wink: ). A typically Burley might have a pH of closer to 6.8. Keep in mind that the pH scale is logarithmic so a 1 point drop from a pH of 6.8 would mean it (nicotine) is 10 times more bound but a 2 point drop means it would be 100 times more bound.
I think a more correct wyt to discuss pH as it relates to tobacco is to say that Virginias "tend" towards an acidic pH and Burleys "tend" toward an alkaline pH.
Additionally, inhaled nicotine from a cigarette is absorbed quicker than nicotine from a pipe that is not inhaled. I believe inhaled nicotine reaches the brain within 20 seconds but I do not know the time period for non inhaled smoke, just that it is slower to reach the brain.

 

cobguy

Lifer
Oct 18, 2013
3,742
15
Thermodynamics%20Presentation.017-001.png

As I mentioned earlier, it's not just about the original leaf content either.

The curing, fermenting and processing methods all play a role in the final outcome.

In fact, every time tobacco leaf dries out, it loses some degree of its original chemistry.

Volatile oils evaporate. Nicotine content degrades. Natural leaf sugars break down.

There are many factors which enter the arena prior to reaching the consumer.

 

jitterbugdude

Part of the Furniture Now
Mar 25, 2014
993
8
Nice chart!, Noticed the pH of Burley? Like I said before I do not know of any Burley that is actually alkaline. I'm sure there is.. somewhere. Not sure where this "fact" got started that Burleys are alkaline and Virginias are acidic.

 
Hmmm, I guess I'm not communicating well. Or, I am just perplexed by the idea (verses what I feel when I smoke). FVF or a McClelland red Virginia give me the sensation of just having had nicotine, not inhaled, but a good nic buzz. Yet, almost any burley blend, like Dark Fired by Stokkebye, which is the pure Kentucky, and some GH blends that are full burleys, don't effect me (as much), unless there is a Virginia component. So, while less nicotine is in the Virginia blends, I feel them more readily in my system than I would a pure burley. Unless the burleys have a different type pf nicotine or effect that is more subtle.
My hypothesis was that the "more" acidic Virginias were utilizing the acidity to get the nicotine through membrane walls faster. Whereas, burleys have more nicotine, it seemed to not get absorbed as fast (or at all).
Blends that tend to hit me the hardest are a mix of Virginia and burley, where the burley has a brighter flavor, assuming this means more acidic. This is just based on my experience as evidence.
I've read in a few places that Canada requires cigarettes to be of the Virginia variety, and even in the US, while I don't know what the tobacco leaf is specifically, the brands that I used to smoke were more acidic tasting, like Camels.

 

cobguy

Lifer
Oct 18, 2013
3,742
15
The values posted in the chart are for dried leaf, "after aging, moisture free".
What happens next is a myriad of possibilities:
Which sugars will be added, which leaves from which locations around the world will be combined,

will they have been grown in nitrogen rich or poor soils, are they to be heated, pressed, steamed, fire cured, etc ... the way it is processed, fermented and cured plays a HUGE role.
By the time pipe tobacco hits the shelves the pH may be on the acidic side but the nicotine content

itself is relatively high. This is due to the way it's processed.

From another recent study, it was interesting to note the actual average pH and nicotine content:
Pipe tobacco presents the lowest observed pH 4.7-4.9, while nicotine content averaged around 17 mg/g.

Cigars present pH levels between 6 and 7 while nicotine contents are low, between 7 and 12 mg/g.

So, with pipe tobacco, the amount of nicotine available is high.

The pH of cigars is more alkaline so the rate of absorption will be faster.
The next phase is when it enters your body. That starting pH is "out the window".

Nicotine will be broken down and metabolized at a starting body pH of around 7.4

FYI, nicotine accumulates in saliva ... do you spit or swallow? :wink:
Lastly, there are a multitude of factors that intervene at this point:
Physiological Influences - Diet & exercise ... smoke some Triple Play on an empty stomach!

Age, Gender, Race all influence absorption rates

Medications - both inducers and inhibitors exist (a common blood thinner, coumarin, is an inhibitor)
There's a lot to it and I find it pretty fascinating ... positively a three bowl topic! :puffpipe:

 
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