Nicotine vs. nicotinic acid (niacin).

Can nicotine be turned into niacin? There are those who declare there is no relationship between the two, that it is a mere accident of nomenclature. Well, let’s see.

Here is the molecular structure of nicotine.

nicotine_structureFor those unfamiliar with the shorthand in these diagrams, every unlabelled  ‘corner’ is a carbon atom and the single-hydrogen-atoms poking out all over the place are routinely omitted for clarity. Lines represent bonds, double lines represent double-bonds. Carbon makes four bonds so any corner with three bonds showing has a hydrogen tacked on the outside of the ring. Nitrogen makes three bonds, oxygen two, hydrogen one… oh hell, I’m not getting into lecture mode at this time of night!

Now, here is the molecular structure of nicotinic acid – niacin – vitamin B3:

nicotinic_acid_structure

Take the five-atom ring off nicotine by breaking just one bond and replace it with a COOH group and you’re there. In biochemical terms, this is known as ‘a piece of piss’.

The two molecules are not unrelated. A simple oxidation reaction is all you need to turn nicotine into nicotinic acid. It’s not an accident of nomenclature at all.

Much as the Righteous would like to have us believe.

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33 thoughts on “Nicotine vs. nicotinic acid (niacin).

  1. Pingback: Nicotine vs. Nicotinic Acid (niacin). | VapeHal...

  2. LI, I don’t think the Righteous knew.

    The Righteous had to be reassured before Public Health could go ahead and save thousands of lives by enriching the bread. Pellagra was a nasty disease “diarrhea, dermatitis, dementia and death” that was plaguing the United States. The pictures of sufferers aren’t pretty.

    The Journal of the American Medical Association – 1942

    “A poor name is a handicap to the promotion of a meritorious product. The name “nicotinic acid” for the vitamin so important in the prevention of pellagra has been doubly unfortunate. To the general public the word “nicotinic” implies too strongly the relationship of this vitamin to nicotine, the chief alkaloid of tobacco often used as an insecticide. The term “acid” denotes a corrosive substance such as the liquid used in automobile storage batteries. The vitamin called “nicotinic acid” was first produced in the laboratory in 1867 by the oxidation of nicotine with potassium chromate and sulfuric acid. Later the compound was named nicotinic acid because it had been made from nicotine and it had the ability to form salts. As a laboratory curiosity, which it remained for over seventy years, nicotinic acid was adequately named.
    From the point of view of those interested in furthering the distribution of foods enriched with this dietary essential the name has proved unsuitable.”

    Following the announcement of proposed regulations for enriched bread by the Food and Drug Administration, a well known trade publication announced the event with the heading “Tobacco in your Bread”
    http://jama.jamanetwork.com/article.aspx?articleid=254218

    The Jama article goes on to point out that the nicotinic acid is being made from a derivative of coal tar as it is today.

    “Commercially, niacin is obtained from beta -picoline or from quinoline, which are both obtainable from coal tar.”
    http: //www.chemicalland21.com/lifescience/foco/NIACIN.htm

    The Righteous thus satisfied, Public Health went ahead and saved thousands if not millions of people by the simple expedient of putting the vitamins back in white bread.

    Effectiveness of food fortification in the United States: the case of pellagra
    http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1446222/pdf/10800421.pdf
    With lots of charts.

    Apart from which the Righteous could have had no knowledge that the scientists at Lorillard had already done the experiments and had their findings confirmed by Conrad A. Elvehjem at the University of Wisconsin, those industry documents containing the experiments were only made public in 1998.

    I hadn’t even heard of nicotinic acid in 2007, I was just sitting on the back step wondering what happened to nicotine when it burned, when I noticed that a candle holder in the garden had gone rusty and suddenly remembered from school that rust is iron slowly burning in air and that the keyword I had been looking for was “oxidized”.

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      • It turns out that I far exceed the RDA for niacin in coffee and cigarettes alone.

        But there’s always someone out to spoil it.

        Opinion of the Scientific Committee on Food on the Tolerable Upper Intake Level of Nicotinic Acid and Nicotinamide (Niacin) – 2002

        “A tolerable upper intake level for nicotinic acid of 10 mg/day is based on the available data indicating occasional flushing at 30 mg per day, using an uncertainty factor of 3 to allow for the fact that a slight effect was reported, and that the study was performed in a small number of subjects, but taking into account the steep dose-response relationship. This upper level is 300-fold below the dose frequently used clinically for the treatment of hypercholesterolaemia (3 g/day) and which is associated with a high incidence of
        serious adverse reactions.

        The only reports of flushing associated with the ingestion of nicotinic acid with food have occurred following the addition of free nicotinic acid to food
        prior to consumption. Although flushing might be considered a minor health effect, it has been used as the basis for setting the upper level for nicotinic acid, because of concerns about the possibility of a transient hypotensive episode, especially in the elderly”
        http://ec.europa.eu/food/fs/sc/scf/out80j_en.pdf

        Niacin is said to be a vasodilator and in combination with the inhaled nitric oxide which is said to be a vasodilator too,is presumably why lighting a cigarette while you are waiting at the bus stop on a frosty morning makes you feel just that little bit warmer.
        In days long gone by, I thought that was just a product of my imagination.

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    • “…the Righteous could have had no knowledge that the scientists at Lorillard had already done the experiments and had their findings confirmed…”

      Experimental evidence? Then confirmed or refuted?
      I can’t help but wonder what the outcome would have been if the MSM-pushed ‘progressive’ computer modelling or unthinking politically obvious*(!) health policies had held as much sway then as they do now.

      *obvious, as in the sun circling the earth!

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    • Well, nothing is straightforward.

      I have the old Sigma map of biochemistry and have been trying to track back from NAD to see where that ring structure originates. Unfortnuately mine is old, faded and the small version so it’ll take a bit of time. I might have to bite the bullet and open Lehninger. It’s been a long time since I delved into that tome!

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      • LI, may I show my ignorance of chemistry by saying that I have seen pyridine mentioned more than once and nicotine, like trigonelline in coffee referred to as a pyridine alkaloid, trigonelline also turns to nicotinic acid when roasted.
        If that was what you were talking about

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  3. I’ve been saying for ages that the things they say are bad for us…well, we should join together in joyful rebellion by making sure we eat more of them. For instance, they say we should all be on low fat diets, cos apparently fat is bad for us. Well, it’s coming out now that studies show we need these fats and without them our health suffers. We need more Omegas! In fact, we are suffering from a lack of Omegas, especially here in the West.

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  4. In my search for “what’s the missing ingredient in e-juice” I looked at vit B3 and searched for a liquid version. I was side tracked and never did get around to trying this.

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    • It’s soluble, but I don’t know if it’s inhalable. If it is, Electrofag could be a delivery device for water-soluble vitamins! They are vapourised, not burned, so it is a possibility.

      Making an asthma inhaler look like an Electrofag should be easy too. That would stop a few Righteous hearts!

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      • Nicotinic acid – 1941

        page 2

        “We find that the smoke from ordinary Ripple cigarettes contains the anti-pellagra vitamin or nicotinic acid in fairly substantial amounts. However, the quantity is probably too low for a man to rely upon this source alone for his nicotinic acid requirement.At least to do so he would find it necessary to smoke an unreasonable number”

        “You will recall that in our letter of March 11th we doubted that vitamins could be absorbed from tobacco smoke by the throat and lung tissues. However, we have now found that nicotinic acid is disolved in the saliva of the smoker when smoking ordinary oigarettes, and even in greater amounts when smoking cigarettes made from the enriched tobacco. Thus, the vitamin does not have to be absorbed thru the lungs, but will be swallowed in the approved manner. These conclusions are based on actual analysis of saliva, collected from a smoker while smoking.

        “In other words, we analyzed the saliva, which would have otherwise been swallowed. No Nicotinic Acid occurred in the smoker’s saliva before smoking. We feel that we have made this report sufficiently long to cover the discoveries, which we regard as quite remarkable”

        http://tobaccodocuments.org/product_design/04365489-5491.html

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  5. Pingback: Various Headlines | Frank Davis

  6. “Making an asthma inhaler look like an Electrofag should be easy too”

    Or the other way round ie an e-cig that looks like an inhaler. That would be great for Waiting Room/Departure Lounge Cold Turkey in these days of e-cig bans (to save the fluffy kittens of course).

    Something for you to get on with in those long dark Scotch winter nights, laddie. Put your modeling skills to good use and you can sign me up for the first ones .

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    • The only thing would be the out-puff of steam. Although a small condenser could make that vanish.

      Once this book’s done I must get back to modelling and fiddling. There are several things in line, including the tiny sub with a smoking captain.

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  7. LI, as a chemist, please can you give a definitive answer to these questions.
    1. How would 7.2% nicotine in pg degrade if kept for longer than the recommended 2 years in a cool dark place.
    2. Many people apparently store nicotine/pg in the freezer. Does it actually freeze solid and, if so, does that slow its degradation?

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  8. I have a brilliant idea: Razor Blades for Righteous!

    Some are coated with nicotine and some are coated with niacin…

    If you’re lucky, your anemia is cured. If not, well, not so good…

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  9. Pingback: Health, food, booze and smoking | underdogs bite upwards

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