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Encyclopedia Page: Nicotine

 

Newsletter articles about nicotine.



Nicotine

 

Good Tobacco
There's not a lot of good chewing tobacco or smoking cigarettes can do for your health. But, as this ScienCentral News video reports, one researcher says genetically modified tobacco may do some good by cleaning up some polluted military sites.

June 14, 2005  http://www.sciencentral.com/

 


 

Nicotine: What is it, and where does it come from?

Time to clear the air.

The best way to understand nicotine, if you don't have a lot of chemistry background is to understand table salt.

The chemical name for table salt is "sodium chloride". It is made up of two chemical elements named "sodium" and "chlorine".

Sodium is a soft, dull grey metal that looks a lot like aluminum or lead. Unlike aluminum or lead however, metallic sodium is rather unstable. Drop some of it into water and it immediately bursts into flames. Expose it to air and it reacts with oxygen and water vapor to form white, powdery crystals. It has to be stored in an oxygen free atmosphere to retain its pure, metallic form. Usually, it is stored in oil.

Chlorine is a highly toxic gas. When concentrated, it has a pale, yellowish green color. Like sodium, chlorine reacts quickly with just about everything. Chlorine bleach, which has chlorine dissolved in water, allows the water to dissolve wood, paper, cotton, fat, human skin, and just about every living tissue. This is why chlorine kills you pretty quickly if you inhale the stuff. Chlorine gas was one of the first chemical weapons invented and used in World War I.

However, mix sodium and chlorine together and the two neutralize each other to form sodium chloride, a harmless, stable chemical compound that we call "table salt". Small to moderate amounts of sodium chloride are found in every living thing on earth. In fact, without the stuff, a person would get sick and die.

Nicotine has a chemical nature much like sodium. In its pure form, which is called "freebase nicotine", it reacts chemically with oxygen in the air, with water, and most other living tissues, destroying them instantly.

Freebase nicotine is highly poisonous and is sometimes used as an insecticide. It makes a good insecticide because it only lasts about half an hour in the environment, being so unstable in the presence of air. In very small amounts, freebase nicotine can be injected into a person's bloodstream and has an effect almost identical to cocaine.

All green, living plants produce and store nicotine. They use the nicotine to produce another chemcal compound called NADP (nicotinic acid adenine dinucleotide phosphate). NADP is what breaks apart water molecules during photosynthesis. Plants make NADP from nitrates and phosphates found in the soil. The common name for nitrates and phosphates is "fertilizer".

The secret to how plants store nicotine, without the nicotine killing them, is that they combine it with other things to make more stable compounds. The common forms of nicotine stored in plants are nicotine citrate, nicotine malate, nicotine sulfate, nicotine oxide (cotinine), and nicotinic acid (vitamin B3, niacin). Like table salt, these compounds formed from nicotine are stable, are not poisonous, are not addictive drugs, and are essential to good human health and nutrition.

The tobacco plant stores its nicotine as a mixture of nicotine citrate and nicotine malate. The tobacco plant happens to produce a lot off nicotine because it grows quickly. Corn and hemp (marijuana) also produce and store nicotine at roughly the same rate as tobacco, because they also can grow six to ten feet in one season.

To give a clear picture of just how unstable freebase nicotine is, let's look at a few facts about it. According to the International Programme on Chemical Safety (IPCS), freebase nicotine has the following physical properties:

Melting Point: -80 degrees Celsius
Boiling Point: 247 degrees Celsius
Flash Point: 95 degrees Celsius
Auto-Ignition Temperature: 240 degrees Celsius
Explosive Limits: 0.7 - 4 percent, by volume, in air
Vapor Pressure at Room Temperature: 0.006 kPa


The interesting thing to note here is that the auto-ignition temperature is lower than the boiling point. This means that, if you heat freebase nicotine in an air free container, it will detonate (explode) before it boils.

Nicotine is so unstable that it does not need to react chemically with anything to have an explosion occur. Its low vapor pressure tells us that nicotine does not evaporate on its own. If you heat it, nicotine will decompose chemically before it boils. Furthermore, in the presence of air, nicotine bursts into flames at a temperature just below the boiling point of water.

For a reference on the physical properties of nicotine, you can check the IPCS:
http://www.inchem.org/documents/icsc/icsc/eics0519.htm

In summary, what the above physical properties are saying is that there is no possible way in this universe, or any other, that a nicotine vapor can exist.
You can not get nicotine by burning tobacco. The nicotine will chemically decompose before a vapor of it is formed. Furthermore, if any nicotine vapor did form by burning tobacco, it would burst into flames before any residual moisture in the tobacco leaves is boiled away.

Now, I realize that the stuff I just said is going to stomp hard on the religion that you have been taught since childhood, but there is no nicotine in tobacco smoke. Never has been and never will be.

When "scientists" study tobacco smoke to measure "nicotine content", they do not actually look for nicotine. They look for a different chemical named "cotinine", which is nicotine oxide.

Cotinine is neither harmful, nor addictive, nor psycho-active.

A great deal of research has been done on cotinine because it blocks the effects of cocaine on the human nervous system and is used medically for detoxification from cocaine addiction.

"Nicotine" is a chemical component of many related compounds, such as nicotine citrate, nicotine sulfate, nicotine malate, nicotine oxide (cotinine) and nicotinic acid (vitamin B3, niacin). Pure, free base, nicotine is a deadly poison, an addictive drug and also a good explosive. The above mentioned compounds containing nicotine however, bear as much resemblance to nicotine as table salt does to metallic sodium, or as water does to hydrogen.

Now, you may ask, if nicotine is so unstable, how do scientists get it to use as a pesticide? The method used to extract freebase nicotine from dried tobacco leaves was discovered in 1828, and can best be summarized by this quote from a 1911 encyclopedia:

NICOTINE, Ci0H14N2, an alkaloid, found with small quantities of nicotimine, C,9H14N2, nicoteine, Ci0Hl2N2, and nicotelline, CioH8N2, in tobacco.

The name is taken from Nicotiana, the tobacco plant, so called after Jean Nicot (1530-1600), French ambassador at Lisbon, who introduced tobacco into France in 1560. These four alkaloids exist in combination in tobacco chiefly as malates and citrates. The alkaloid is obtained from an aqueous extract of tobacco by distillation with slaked lime, the distillate being acidified with oxalic acid, concentrated to a syrup and decomposed by potash.

The free base is extracted by ether and fractionated in a current of hydrogen. It is a colorless oil, which boils at 247 C. (745 mm.), and when pure is almost odorless. It has a sharp burning taste, and is very poisonous.

It is very hygroscopic, dissolves readily in water, and rapidly undergoes oxidation on exposure to air. The free alkaloid is strongly laevo-rotatory. F. Ratz (Mounts., 1905, 26, p. 1241) obtained the value [o]u = 169-54 at 20; its salts are dextro-rotatory. It behaves as a di-acid as well as a di-tertiary base.

Here is a link to the web page of that enclopedia article:
http://77.1911encyclopedia.org/N/NI/NICOTINE.htm

In other words, to get nicotine from tobacco, you would have to soak your dried tobacco leaves in water to produce an "aqueous extract". Then, mix that aqueous extract with slaked lime (calcium hydroxide). Then, mix the distillate with oxalic acid. Then concentrate it into a syrup. Then mix that syrup with some potash (potassium hydroxide). Then distill it again in an atmosphere of flowing ether and hydrogen. Do you take the time to do all this when you smoke a cigarette? Highly doubtful.

Stop to think, the next time you read some b.s. on "nicotine addiction" and realize that all this crap has been based on 75 years of pure "junk science" and propaganda. Who was it that said, "Tell a lie enough times and it becomes the truth?" I believe that the author of this strategy was a certain high ranking officer in the Nazi Party of Germany in the 1930s, which Party was also the origin of today's anti-tobacco religion.

When you burn tobacco, you don't get any freebase nicotine. What you get is an assortment of harmless, stable chemicals that result from the oxidation of nicotine. Visit a drug store and read the ingredients of "nicotine" gum, lozenges and patches. You will find that most of them contain no nicotine, but rather nicotine sulfate or nicotine oxide, or even good old vitamin B3 (nicotinic acid).

The fallacy that makes "nicotine addiction" junk science is that: Yes, if you make freebase nicotine in a chemical laboratory and inject it intravenously, it will act as a potent, addictive drug, and do every evil thing ascribed to nicotine. However, burning the tobacco does not produce any freebase nicotine.

Many double blind studies have already shown that "nicotine" patches, gum and lozenges are no more effective than placebos at stopping a smoking habit. Strictly, scientifically speaking, there is no (freebase) nicotine in tobacco smoke; never has been and never will be.

If you really want to nail the health-nazis to the wall in court, get the research scientists on the witness stand, under oath and penalty of perjury, and ask, "Did you actually measure 1.5 mg of pure, freebase, nicotine in the smoke from that cigarette, or was it actually cotinine that you measured?" The infamous FTC method devised in the 1960's for measuring the "nicotine" content of different brands of cigarettes is a test for cotinine (nicotine oxide). At the time, the researchers said they had to do it that way because it "is not possible to measure nicotine in tobacco smoke because nicotine decomposes too rapidly." A good library or even the web might have a paper telling exactly how the "FTC Method" is done. Do a Google search on "FTC Method" and I bet you find the word "cotinine" in the same paragraph.

Patrick J. Gleason


 

NIDA InfoFacts: Cigarettes and Other Nicotine Products

 


 

 

Heading down a new tobacco road

 

By Arthur Hirsch Sun Staff Originally published July 29, 2005

 

A University of Maryland research project seeks to juice up the familiar plant and develop it as a source of proteins for numerous uses by other industries

 

UPPER MARLBORO - The tobacco thriving here on the University of Maryland's research farm looks like the plant that dominated state agriculture for centuries, the leaves mint green, fuzzy to the touch, long and wide as the blades of a ceiling fan.

 

These plants have been to college, though, and might be nearing the threshold of a future that generations of tobacco farmers would scarcely recognize.

 

For one thing, this vision of Maryland tobacco's future is stamped "NO SMOKING." Think, instead, of tobacco as a component of cosmetics, diet supplements, medicine or shampoo. Consider high-protein fluids for kidney dialysis patients, and drugs that might someday be used to treat, of all things, cancer and heart disease.

 

It all seems at least as unlikely as the idea that Maryland tobacco has a future at all. Growing on a testing ground here no bigger than a Major League Baseball diamond, this tobacco might help resurrect a Maryland business shrunk to a fragment of its old self since the 1980s, most recently by a program that has paid farmers millions to stop growing tobacco for smoking.

 

Since the buyouts, a question has been hanging in the air, said Gary V. Hodge, a Southern Maryland regional planner who helped run the tobacco program that began in 1998, cutting Maryland tobacco sales from 9.58 million pounds to 1.4 million this year.

 

"Now what?" Hodge said. "We're trying to answer that question."

 

He was standing under a hazy sky on the test patch off Route 202 recently with a group of men involved in the University of Maryland's Alternative Uses of Tobacco Project. These men have doctoral degrees and business experience. They are schooled less in the arduous work of bringing tobacco to local auctions year after year than in chemical extraction technology and multibillion-dollar markets in pharmaceuticals.

 

The future of Maryland tobacco and the state's agricultural landscape might lie there.

 

Because along with the aroma, taste and nicotine buzz smokers crave, tobacco offers proteins. Extracted in pure form, the protein might compete with milk, egg and soy proteins used in sundry ways by industry.

 

The hope, said Hodge, is to restore the economic impact of Maryland tobacco, which in 1997 accounted for two-thirds of Southern Maryland's farm income while growing on less than 5 percent of farmland in those five counties.

 

Neil A. Belson, president of Pharmacognetics Inc., a biotechnology company in Port Tobacco and a member of the project team, called the effort part of a larger shift from petroleum-based to plant-based industrial materials, "from a hydrocarbon to a carbohydrate economy."

 

All plants produce proteins and other compounds, but the reason scientists are so enthusiastic about tobacco in particular is evident even to the untrained observer visiting the research farm. In a word: volume.

 

"Bulk is a key appeal of tobacco," Belson said.

 

The plants can be grown in dense thickets, sprouting leaves nearly as long as your arm and a couple hands across. Crop science people call all this green stuff "biomass," and tobacco produces more of it per acre than any other crop.

 

That matters when the compounds you're trying to extract constitute very small percentages of the whole plant. The more mass you start with, the more of any given material you might get.

 

This means treating Maryland tobacco in a new and rather brutal way. For much of its centuries-long history, the plant has been babied step by step.

 

The Maryland tobacco farmer typically transplants about 6,000 seedlings per acre in spring and harvests once in late summer. The stalks are raised in roomy rows, chopped by hand and hung in barns to air dry through the fall and winter, the dried reddish-brown leaves then carefully stripped off by hand, tied in fan-like clusters and bundled off to market in spring. Maryland tobacco farmers could hardly take more care if they were raising orchids.

 

Tobacco's steady decline here beginning in the 1980s had much to do with the difficulty of finding labor to raise it. The Alternative Uses project suggests a new, mechanized and high-volume tobacco crop that would demand less labor.

 

The researchers have devised direct seeding methods to raise about 90,000 plants per acre, harvesting two or three times a year. Leaves harvested by machine on the research farm recently have been trucked to the University of Maryland's College Park campus and unloaded at the old creamery, where the school once made ice cream.

 

Lately, professors and graduate students working there have run a few tests on a noisy configuration of conveyors, hammer choppers and a screw press, cutting about 200 pounds of tobacco leaves into particles as fine as "McCormick spices," said Y. Martin Lo, an associate professor in the University of Maryland's Department of Nutrition and Food Science.

 

Some of the juice has been taken to a laboratory and run through an elaborate series of spinnings, filtrations, washings, chemical treatments and cooling to produce a pure protein crystal: colorless, odorless, tasteless.

 

Lo said they have produced maybe a couple teaspoons of two different proteins. It's a small start at a stage of the game where quantity matters if you are trying to attract investors.

 

Crop scientist Ray Long knows that only too well from his research at North Carolina State University in Raleigh, where work on protein extraction and bio-engineered tobacco began in the 1970s.

 

Long ruefully recalled a day in the 1990s when a representative of a chemical company that supplies the cosmetics industry called him asking about tobacco protein.

 

"He said they would like to have 50 pounds to do formulations and test in a market," Long said. "I didn't have 50 grams. ... That has been the Catch-22."

 

That is, the research on how to produce large amounts of this pure protein costs money, which might be available from industry representatives if they could get large amounts of the material.

 

The difficulty of inducing the plant to produce significant amounts of a particular protein by genetic manipulation should "not be trivialized," said Long's N.C. State colleague, Arthur Weissinger. He estimates it could be 20 years before human vaccines based on tobacco proteins will be produced.

 

The Maryland research, which does not include genetic engineering, anticipates results sooner.

 

By the end of 2006, Lo wrote in an e-mail, researchers hope to have a blueprint for a protein-producing operation. Such a design on paper would then be offered "to interested parties such as tobacco farmers or investors to establish a commercial processing facility adjacent to tobacco farmlands," Lo said.

 

Researchers here hope to attract investors while there are farmers around who know how to grow tobacco, and before too much more farmland is transformed into subdivisions and shopping centers.

 

More than 80 percent of Maryland tobacco farmers took the buyout, meaning they agree never to grow tobacco again for smoking and what the state calls "similar personal consumption."

 

That would not include sipping a soft drink that has been given a nutritional boost with a shot of tobacco protein, or foaming up your hair with a tobacco-protein shampoo, washing out the smell of a night in some smoky bar.

 

http://www.baltimoresun.com/