So - are we getting it or are we not - nicotine

[DVap]

It's hard to believe that reading this and a few other threads that 50yrs of testing didnt reveal this to the FDA.

An understanding of scientific paradigm change is relevant here. When one scientific paradigm is in force, observations that don't fit the predefined borders of the paradigm tend to be discounted as anomaly. In the meantime, the scientists who turn their attention to these anomalies are persecuted and marginalized. See the seminal work of Thomas Kuhn, "The Structure of Scientific Revolutions". I took a course in the philosophy of science back in college that was basically a study of this book, and this work has influenced me greatly throughout my career. And yes, Kuhn's work neatly predicts the actions of the anti's, though not as neatly the most radical of them.

It wasn't until 1835 that the Catholic Church removed the original manuscripts of Copernicus' De revolutionibus orbium coelestium and Galileo's Dialogo sopra i due massimi sistemi del mondo from their Index Librorum Prohibitorum. It took the church until 1966 to revoke the Index entirely, which according to some, represented the last gasp of the Inquisition. (no, I didn't have those titles on the top of my head, had to look them up!)

 

[Caesarea]

'Nother thought paraphrased from Carl Jung:

Mores = what is customarily accepted. Innovation is by definition immoral.

 

[Vaporer]

DVap,
The zealots would actually prepuncture the lifeboats so they could say "we told you so".

 

[a2dcovert]

For myself, I'm pretty sure I'm getting it. I have a good indicator that currently plagues me called GERD, and withdrawal. If I get too much nicotine my acid reflux goes beyond the control of conventional medication. If I get too little my smoking withdrawal symptoms return and it becomes something very hard to deal with emotionally.

My acid reflux problem originally surfaced in 1986 after a failed attempt to quit smoking. My doctor put me on Doxepin and the problem was imediately corrected. I remained reflux free until in 2004. After open heart surgery I was convinced that I needed to quit smoking. I was off cigarettes for 3 months and almost went out of my mind. I resumed smoking. The reflux returned and I was given an additional drug, Nexium, and again the problem was under control. Believe me, GERD for someone who has had a heart attack, is very scarry.

Fast forward to May 2009 when I quit smoking again after gradually increasing e-cig vaping since March. Once again the reflux and GERD have returned. I am now taking the maxium dose of Doxepin and Zegerid and still barely have the situation under control. I don't know which is worse, withdrawal symptoms or GERD, but they seem to be my only two choices.

Kevin

 

[Mister]

DVap, you are doing fantastic work here, words fail me!

I feel the absence of the X factor. I'm now into my fourth month of vaping and I'm still having one or two cigarettes a day. The crazy thing is that they taste a bit foul now, and I no longer enjoy smoking them. But they satisfy (minimally) a need for something I'm not getting in the vapor. It sounds likely that you have found it. Wow!

On a separate (or is it separate? I wonder) subject, I'm still finding the Platinum Ice noticeably stronger than two unflavored Chinese liquids I have, when all are diluted with PG to the same strength. I can't blind test myself (e.g. ask wife to select and label carts) because I can readily taste a difference too. The Platinum Ice has a more peppery hit on the back of my mouth. The Platinum Ice does NOT have any better X factor result, if anything it is less satisfying. Might less purified liquids be carrying some of the alkaloids?

 

[Kurt]

Well they did have some Rhodelia

Now that's in interesting thought: vaping rhodiola. I don't think it would be calming though. It does increase focus and cut down on negative thought chatter, but it is more on the stimulant side than calming side. Sort of like espresso or red bull. The alkaloids are large polyphenols, though, high molecular weight. So maybe not vapable due to high bp and possible decomp.

No kava?? I haven't looked for it in some time, but it is certainly useful (see my nerve-pain tea recipe in Nicotine and nerve pain thread in the Health and Safety forum). I find it to be mildly sedating and peaceful. The kava lactones would be ok to vape, IMHO. They are not MAOI's, though. They work more as an SSRI.

It would not surprise me that they would just quietly remove it from the shelves. So many people are on SSRIs now that it is possibly in their interest to avoid any fallout from synergistic effects with said SSRIs, which is actually a real danger, from serotonin syndrome.

 

[Kurt]

DVap, you are doing fantastic work here, words fail me!

I feel the absence of the X factor. I'm now into my fourth month of vaping and I'm still having one or two cigarettes a day. The crazy thing is that they taste a bit foul now, and I no longer enjoy smoking them. But they satisfy (minimally) a need for something I'm not getting in the vapor. It sounds likely that you have found it. Wow!

On a separate (or is it separate? I wonder) subject, I'm still finding the Platinum Ice noticeably stronger than two unflavored Chinese liquids I have, when all are diluted with PG to the same strength. I can't blind test myself (e.g. ask wife to select and label carts) because I can readily taste a difference too. The Platinum Ice has a more peppery hit on the back of my mouth. The Platinum Ice does NOT have any better X factor result, if anything it is less satisfying. Might less purified liquids be carrying some of the alkaloids?

I have been thinking about the same thing with respect to the chinese juices. But I was actually thinking about components other than the spectrum of alkaloids, such as pesticides sprayed on the plants in the field. The darker in color of the juice, the more tobacco plant ingredients are in the juice, perhaps both good and bad. Seems reasonable that pesticides would also come out in the extraction process, but without a high-res mass spec, we simply do not know what is in them. And the chinese are not very forthcoming about it. Stands to reason that tobacco for juice is not as high quality at that chosen for smoking. Why should it be if you are not going to reveal components?

 

[IANAN]

Now that's in interesting thought: vaping rhodiola. I don't think it would be calming though. It does increase focus and cut down on negative thought chatter, but it is more on the stimulant side than calming side. Sort of like espresso or red bull. The alkaloids are large polyphenols, though, high molecular weight. So maybe not vapable due to high bp and possible decomp.

No kava?? I haven't looked for it in some time, but it is certainly useful (see my nerve-pain tea recipe in Nicotine and nerve pain thread in the Health and Safety forum). I find it to be mildly sedating and peaceful. The kava lactones would be ok to vape, IMHO. They are not MAOI's, though. They work more as an SSRI.

I wasn't going to vape it... I was thinking more like as a supplement 2-3 times a day or as a tea (Tisane)... Keep a nice steady level in the system. I wouldn't even try to figure what the efficacy, if any, of these would be if we tried to vape them at PV vaping temps and then tried to absorb them in the upper respiratory tract/mouth lining.

The more recent research on Nicotine compared MOA-B inhibitors and MOA-A inhibitors. The MOA-B inhibitors didn't have the effect in the test subjects(Rodents)- While the MOA-A inhibitors did. In particular the [SIZE=-1]beta-carbolines(Harmala alkoloids); Harman (Harmane is a synonym) , [/SIZE][SIZE=-1]1-methyl-beta-carboline [/SIZE][SIZE=-1] and Norharman (beta-carboline) are present in tobacco smoke.

Syrian Rue, Pasion Flower Extract, Caapi (Yage or [/SIZE]Ayahuasca[SIZE=-1]), and Puke Weed (Indian Tobacco or [/SIZE]lobelia[SIZE=-1]) all have beta-carbolines alkaloids as well. The herbal stores also report Cat's Claw having beta-carbolines (Harman to be exact) in them[/SIZE]


Like I said I didn't want the Valerian as it has ingredients that work on the GABAA receptor but purchased the supplement because it also contained Passion Flower Extract (Which contains low levels of Harmine- exactly what I am looking for) ... Have some pure Passion flower Extract and Some Cat's Claw coming via mail order to test them.

Part of the problem, well not really a problem for me as I wouldn't care as it worked one way or the other for me, is by trying them myself they may work simply because I want them to work. This is slightly different than placebo effect.

It doesn't shock me that most of the mood enhancing herbs have been removed from the store shelves... I seem to recall the news media having cows over "Natural" Prozac -- Quality assurances , efficacy, terrible side effects (No seriously every pharmaceutic has side-effects and the herbs at herbal remedy dosing levels side-effects tend to be less severe than the BP equivalent) etc etc.


The eaxct citation on Cat's Claw;

CO-OCCURRENCE OF HARMAN AND BETA-CARBOLINE-TYPE MONOTERPENOID GLUCOINDOLE ALKALOIDS IN UNA DEGATO (UNCARIA TOMENTOSA). KITAJIMA,M: YOKOYA,M: TAKAYAMA,H: AIMI,TN: NATURAL MED 55 6: 308-310 (2001) (FAC PHARM SCI CHIBA UNIV CHIBA 260 JAPAN)

www.rain-tree.com/cats-claw-references.pdf

 

[kinabaloo]

First, the worry that overdosing of the other alkaloids could occur: it doesnt happen with smoking, and the presence of the nicotine will ensure people 'cut-off'; in all likelihood, better satiation will lead to less consumption; and DVap has indicated that this can indeed occur. In short, it will more probably work the other way. At the moment, many vape more and more looking for something that isn't there.

TSNAs in e-liquid are some 7000 times less than in malboro cigs; so a lot of leeway here for the possibility (and it is only that) that WTA liquid might have increased TSNA levels.

Btw, few compounds have the same property as alkaloids that allow them to pass through successive acid-alkali phases as used to extract the alkaloids.

Doesn't really matter that e-liquid is 'addictive' - or that not everyone wants to quit nicotine/alkaloids; why should they? The point is to quit smoking; that's where the harm is. And for a smoking alternative to be the most successful, it has to be effective. E-liquid is easily diluted as required, to satisfy all requirements. Some of the anti-smoking people do understand this. To make the biggest impact on reducing smoking requires safer alternatives that are as effective as possible (keep people off smokes). NRT needs to renamed something like SSA (safer smoking alternatives).

Not 'nicotine plus other ingredients', but 'purified tobacco extract'; the message being that this is 'no additives and no messing with the psychoactive ratios'. No designer drug, just purified tobacco extract.

~~~

On the tar increase as one smokes nearer to the but: by making cigs so expensive with tax, they are ensuring that peop0le will be more likely to smoke right down to the but, and even the but itself. And that manufacturers will try to offset the price by cutting costs - by using cheaper, lower quality ingredients. Simpleton, knee-jerk, populist policies do not make good health promoting policies; just the appearance of.

~~~
　
"The zealots would actually prepuncture the lifeboats so they could say "we told you so"." - Yes, studies can be designed to fail, and sometimes are.

 

[TWISTED VICTOR]

Dvap, just catching up here and noticed this:

Here's the problem, the worst of you are puritanical radicals. You cannot be reasoned with.

and this:
"It makes your little brains explode, and you'll twist logic and facts to your agenda, spouting noble words out of one side of your mouths, while spreading lies out the other side"

and this:
You market lie upon lie, with the intention that if one lie doesn't get traction, maybe another will. Ultimately you fail because what you are selling is bull****."

and this:
"It's a good thing you people don't have it in for automobiles. Seat belts, air-bags, and crash-test safety ratings would really piss you guys off."

and this:
" only a car that explodes into a hellish fireball on the slightest impact would be grudgingly tolerated."

and finally, this:
"Hell needs a special place for .......s like you."

(chuckle, chuckle) 'Nuff said, pass the WTA, please.

Rrr matey. Ye've the gist o' their gibs now ya have an tha's sure. R'ttle the sabres loud n' long bucko

I don't know, it just came out...

Mornin', friend. Strange, but, my wife says I say that in my sleep, sometimes. Beyond me, I haven't seen Glenn Beck for a long time. By the way, where's Igor?

 

[June]

From what I have read nicotine dissipates in the blood very quickly. As in about an hour it would be pretty low. So, if I had a blood test at my Dr.'s office and it took an hour between the waiting time and the visit I could be pretty low prior to having the lab test done downstairs. With this scenario, I figure I would have to be vaping in the elevator on the way down to the lab to ensure my normal level of nicotine was in my system. Might have to ride the elevator up and down a couple of times and sit with a coat over my head in the lab area vaping to ensure I was at normal vaping levels.

Since I have a life to maintain, and crazy doesn't go over so well, a home test kit might be the best solution. I was thinking of urine test to test for cotinine? This kit states that the test will provide the quantitative level of cotinine. The other kits that I found only tested for the presence of cotinine.

NicAlert - Quantitative Instant Urine Professional Nicotine Test + Second Hand Smoke

Any thoughts on this method?

 

[TWISTED VICTOR]

First, the worry that overdosing of the other alkaloids could occur: it doesnt happen with smoking, and the presence of the nicotine will ensure people 'cut-off'; in all likelihood, better satiation will lead to less consumption; and DVap has indicated that this can indeed occur. In short, it will more probably work the other way. At the moment, many vape more and more looking for something that isn't there.

TSNAs in e-liquid are some 7000 times less than in malboro cigs; so a lot of leeway here for the possibility (and it is only that) that WTA liquid might have increased TSNA levels.

Doesn't really matter that e-liquid is 'addictive' - or that not everyone wants to quit nicotine/alkaloids; why should they? The point is to quit smoking; that's where the harm is. And for a smoking alternative to be the most successful, it has to be effective. E-liquid is easily diluted as required, to satisfy all requirements. Some of the anti-smoking people do understand this. To make the biggest impact on reducing smoking requires safer alternatives that are as effective as possible (keep people off smokes). NRT needs to renamed something like SSA (safer smoking alternatives).

Not 'nicotine plus other ingredients', but 'purified tobacco extract'; the message being that this is 'no additives and no messing with the psychoactive ratios'. No designer drug, just purified tobacco extract.

~~~

On the tar increase as one smokes nearer to the but: by making cigs so expensive with tax, they are ensuring that peop0le will be more likely to smoke right down to the but, and even the but itself. And that manufacturers will try to offset the price by cutting costs - by using cheaper, lower quality ingredients. Simpleton, knee-jerk, populist policies do not make good health promoting policies; just the appearance of.

~~~
　
"The zealots would actually prepuncture the lifeboats so they could say "we told you so"." - Yes, studies can be designed to fail, and sometimes are.

kin, on the over dosing issue I agree. In my case, and, I'd assume alot of us, nic satisfaction with an analog was the "turn-off" point. Didn't smoke another until it was time to ward off another craving. This would explain why someone like myself would be able to to switch to PV only, vape high nic mg to the point of o.d., still not feel satisfied, but not go back to analogs. Also, the idea of cigarette cost promoting more tar intake is a good one. I know I always made sure to get my money's worth.

 

[kinabaloo]

There is also the question of why these MAOIs are in tobacco in the first place. It may be that they keep nic from being oxided to cotinine, thus allowing the plant to retain its vital nicotine. Is it known that these MAOIs have dopamine/norepi activity? Or do they just get into us and keep nic from oxidizing to cot, thus allowing us to have the amount of nic needed to maintain the addiction?

Kin, shout out to you too! Excellent literature work and insights! Question: what is the enzyme in your avitar?

Just seen your post: the pic is the enzyme MAO

Of your many points, the one that stands out for me is whether the extra alkaloids, in particular, those with MAOI activity, works at least partly by reducing the conversion of nicotine to cotine in its journey to the brain, as well as maintaining dopamine once in the brain (why so named). Could well be. Though there is likely more to WTA than just acting as a nic support act; as there is a mellowness involved, as with analogs, that cannot be accounted for by nic alone.

 

[kinabaloo]

kin, on the over dosing issue I agree. In my case, and, I'd assume alot of us, nic satisfaction with an analog was the "turn-off" point. Didn't smoke another until it was time to ward off another craving. This would explain why someone like myself would be able to to switch to PV only, vape high nic mg to the point of o.d., still not feel satisfied, but not go back to analogs. Also, the idea of cigarette cost promoting more tar intake is a good one. I know I always made sure to get my money's worth.

I suspect I've been more harmed by burning filters than burning tobacco. Tests may have stopped at the last 1/4, but in real-life, many consumed cigs to the bitter end.

On the other point: yes, to reverse that oft used phrase, for once, 'more is less' - if you see what i mean.

 

[IANAN]

From what I have read nicotine dissipates in the blood very quickly. As in about an hour it would be pretty low. So, if I had a blood test at my Dr.'s office and it took an hour between the waiting time and the visit I could be pretty low prior to having the lab test done downstairs. With this scenario, I figure I would have to be vaping in the elevator on the way down to the lab to ensure my normal level of nicotine was in my system. Might have to ride the elevator up and down a couple of times and sit with a coat over my head in the lab area vaping to ensure I was at normal vaping levels.

Since I have a life to maintain, and crazy doesn't go over so well, a home test kit might be the best solution. I was thinking of urine test to test for cotinine? This kit states that the test will provide the quantitative level of cotinine. The other kits that I found only tested for the presence of cotinine.

NicAlert - Quantitative Instant Urine Professional Nicotine Test + Second Hand Smoke

Any thoughts on this method?

Others in the forum are using this method.

 

[Kurt]

Just seen your post: the pic is the enzyme MAO

Of your many points, the one that stands out for me is whether the extra alkaloids, in particular, those with MAOI activity, works at least partly by reducing the conversion of nicotine to cotine in its journey to the brain, as well as maintaining dopamine once in the brain (why so named). Could well be. Though there is likely more to WTA than just acting as a nic support act; as there is a mellowness involved, as with analogs, that cannot be accounted for by nic alone.

I think in another post I did guess MAO, but I certainly recognized it after looking at some of the external pages about the topics in this thread. It was luck though...I'm not that good with recognizing most enzymes.

I'm changing my thinking about the nic to cot thing. Nic is a secondary amine, not a primary, which is what gets oxided to an aldehyde plus peroxide. So maybe MAOI's do inhibit this, but if MAO did oxidize nic it would not form cot, which is a lactam. But given the ease that nic is oxidized, and how central nic is to many of the plant's needs, it seems something in the plant would inhibit this, but I clearly need to read more about it.

I'm also thinking now that DVap's WTA is essentially the same spectrum that is in the plant, just more concentrated. And in an analog the hot cherry vaporizes everything now stream from it, so even if some is pyolized, which it is, the smoke is likely to have the same balance of alkaloids.

I must say that it is a supreme pleasure to be part of this board and to know you all. DVap's work here, and the intense discussions about it, are reinvigorating my faith in the intelligence and innovation of man. How far we have come from the early days about a year ago (I wasn't vaping then, but the threads are still here). Then it was all about the new vaping vehicle VG, and possible PG allergies. Now look at us!!! Trying to analyze the relative activities of natural monoamine oxidase inhibitors in hopes of better mimicking the actual activities of cigarette smoke.

This is the power of the internet right here. This is hive-mind at its best. It feels like we are a single organism with various appendages, rapidly and effectively solving one of the biggest problems our species faces.

DVap, in response to your PM. When I got it, and I kid you not, I was in the process of sending you another stating that what you have is indeed a thing of beauty, and I was going to use that phrase. Certainly the WTA is a thing of beauty, and so is this place here, and what is being accomplished. Brings a tear to the eye. This is all that good.

 

[TWISTED VICTOR]

Kurt, I'm glad you're back into the "Meeting of the Great Minds" on this thread. I can barely understand anything you just posted ( I got "is", "are", "was", stuff like that), and in the future I'll need someone else to dumb it down for me, but to underscore the last part of your post, I feel that no one in this forum, except maybe this thread's moderator understands the utter significance of what is taking place here. Revolutionary. I'll watch on in anticipation as you fellas do what you do.

 

[Kurt]

Kurt, I'm glad you're back into the "Meeting of the Great Minds" on this thread. I can barely understand anything you just posted ( I got "is", "are", "was", stuff like that), and in the future I'll need someone else to dumb it down for me, but to underscore the last part of your post, I feel that no one in this forum, except maybe this thread's moderator understands the utter significance of what is taking place here. Revolutionary. I'll watch on in anticipation as you fellas do what you do.

TV, yeah, sometimes this place can get pretty hairy for those that haven't had years of chemistry. But kudos to you for at least trying to hang in there! Fact: vaping is ALL chemistry. From extraction of nic, to viable vaping vehicles (the chemical term for in our case PG or VG, the liquids that vaporize and carry the nic), to safe flavors, to atty temps and decomposition, to battery electrochemical reactions that allow strong loads, and now to this topic...all the other chemicals we are missing with PVs. I have never had a "hobby" that utilized all of my chemistry education like vaping does. So it is my supreme pleasure to be able to help out the little that I have. This is all kinds of fun! I feel that I am not doing any of the heavy work here, Kin and Dvap are, and I'm just sort of presenting comments and queries that my training bring up. If I wasn't involved in trying to get a paper published with my own research before a Nov. 30 deadline, I would be doing much more.

But here is the gist of some of what I was saying about nic and cot.

MAOs oxidize monoamines, such as dopamine:

http://upload.wikimedia.org/wikipedia/commons/6/6c/Dopamine2.svg

and norepinephrine:

http://upload.wikimedia.org/wikipedia/commons/8/8c/Norepinephrine_structure_with_descriptor.svg

Both of these are "monoamines" which are also primary amines. The NH2 amino group is attached to only one carbon.

The reaction of MAO is:

http://upload.wikimedia.org/wikipedia/en/5/56/GabeTheNerd_01_in_2008.png

Notice how the amine shown is also just attached to one carbon (primary, monoamine).

Nicotine is a secondary amine:

http://upload.wikimedia.org/wikipedia/commons/c/c7/Nicotine-2D-skeletal.png

The NH is attached to 2 carbons, in a ring. The other N is in a pyridine ring 6-membered ring, double and single bonds, which like benzene is very stable. The five-membered ring does the oxidizing to form cotinine:

http://upload.wikimedia.org/wikipedia/commons/d/d4/Cotinine_Structural_Formulae.png

But the final product cotinine is nothing like the final products of MAO on a monoamine, which is essentially blasted apart entirely. Thus my reasoning that MAO was not involved with nic to cot oxidation, so the MAOIs would not be doing anything one way or another to affect the oxidation of nic to cot (although I am wondering if SOMETHING in tobacco is doing this).

To those outside of chemistry, this sort of stuff can sound like crazy talk. To those in chemistry, this is the true language of the real world. Its just that we are still trying to understand it!!

Oh, and DVap, your protonation comment about which N is more basic. The amine N has an sp3 lone pair, the pyridine N has an sp2 lone pair. sp3 has more p-character than sp2 (3/4 vs 2/3) and so reaches out more, like a p, and grabs protons more. pKb of amines are around 4, pyridine is I think around 10. So it is right in line with what I would expect as far as which is going to salt first. Plus alkyl groups tend to donate e- character, making the N even more basic than ammonia.

 

[BillF]

Now that's in interesting thought: vaping rhodiola. I don't think it would be calming though. It does increase focus and cut down on negative thought chatter, but it is more on the stimulant side than calming side. Sort of like espresso or red bull. The alkaloids are large polyphenols, though, high molecular weight. So maybe not vapable due to high bp and possible decomp.

Hi, I'd love to vape R. rosea, but alas . . .no dice. I would like to comment that not all Rhodiola is like a Red Bull or an espresso. That's just some Rhodiola, those with a bit of a raggedy edge to them. There's one that was designed to help addictions and it has none of the over-stimulation you get from others. I can take it at night. Verde Botanica designed two Rhodiola supps, one with no stimulating factor but all the good stuff that Rhodiola is known for -- that's called Mind Body & Spirit. The other, full of energy and stimulation (Red Bull for sure, but no caffeine!) is called Energy Reserves. I've tried both -- they each have their place.

I like Kava too, but because I drink (sometimes heavily) I know that there's possible liver damage with Kava, so I stick to Rhodiola. Sometimes Lemon Balm.

BF

 

[TWISTED VICTOR]

TV, yeah, sometimes this place can get pretty hairy for those that haven't had years of chemistry. But kudos to you for at least trying to hang in there! Fact: vaping is ALL chemistry. From extraction of nic, to viable vaping vehicles (the chemical term for in our case PG or VG, the liquids that vaporize and carry the nic), to safe flavors, to atty temps and decomposition, to battery electrochemical reactions that allow strong loads, and now to this topic...all the other chemicals we are missing with PVs. I have never had a "hobby" that utilized all of my chemistry education like vaping does. So it is my supreme pleasure to be able to help out the little that I have. This is all kinds of fun! I feel that I am not doing any of the heavy work here, Kin and Dvap are, and I'm just sort of presenting comments and queries that my training bring up. If I wasn't involved in trying to get a paper published with my own research before a Nov. 30 deadline, I would be doing much more.

But here is the gist of some of what I was saying about nic and cot.

MAOs oxidize monoamines, such as dopamine:

http://upload.wikimedia.org/wikipedia/commons/6/6c/Dopamine2.svg

and norepinephrine:

http://upload.wikimedia.org/wikipedia/commons/8/8c/Norepinephrine_structure_with_descriptor.svg

Both of these are "monoamines" which are also primary amines. The NH2 amino group is attached to only one carbon.

The reaction of MAO is:

http://upload.wikimedia.org/wikipedia/en/5/56/GabeTheNerd_01_in_2008.png

Notice how the amine shown is also just attached to one carbon (primary, monoamine).

Nicotine is a secondary amine:

http://upload.wikimedia.org/wikipedia/commons/c/c7/Nicotine-2D-skeletal.png

The NH is attached to 2 carbons, in a ring. The other N is in a pyridine ring 6-membered ring, double and single bonds, which like benzene is very stable. The five-membered ring does the oxidizing to form cotinine:

http://upload.wikimedia.org/wikipedia/commons/d/d4/Cotinine_Structural_Formulae.png

But the final product cotinine is nothing like the final products of MAO on a monoamine, which is essentially blasted apart entirely. Thus my reasoning that MAO was not involved with nic to cot oxidation, so the MAOIs would not be doing anything one way or another to affect the oxidation of nic to cot (although I am wondering if SOMETHING in tobacco is doing this).

To those outside of chemistry, this sort of stuff can sound like crazy talk. To those in chemistry, this is the true language of the real world. Its just that we are still trying to understand it!!

Oh, and DVap, your protonation comment about which N is more basic. The amine N has an sp3 lone pair, the pyridine N has an sp2 lone pair. sp3 has more p-character than sp2 (3/4 vs 2/3) and so reaches out more, like a p, and grabs protons more. pKb of amines are around 4, pyridine is I think around 10. So it is right in line with what I would expect as far as which is going to salt first. Plus alkyl groups tend to donate e- character, making the N even more basic than ammonia.

????? wheeww, can't bluff myself through this one. I think I was almost comprehending something when I got to your note to Dvap. First, my eyes started to water, drooled a little, then my head exploded. Not sure what happened while blacked out, but my left eyelid is quivering and all the neighbors' lights are all on. ?? Thanks, though.