A Better Buzz Through Science: Chemical Manipulation of Nicotine Throughout History

For smokers and casual observers alike, it is a fascinating exercise to examine the ways in which tobacco companies have manipulated the tobacco plant and the chemical structure of nicotine throughout history. In fact, in terms of altering the chemistry of a plant, tobacco must be one of history’s most manipulated plants after wheat.

A technique that began as a strategy for improving the yield of tobacco harvests inadvertently allowed the tobacco giant Philip Morris to create the world’s most popular cigarette – and today, the makers of nicotine-infused e liquid are reversing that work. It’s all in the name of providing a better buzz through science.

This is the story of what the world’s companies have done – and are continuing to do – to provide you the best possible nicotine buzz.

Ammonia: Tobacco’s Favorite Chemical

When a company sells a plant-based product, the fastest way to increase profitability is by increasing the volume of materials yielded from the plants. During the 1930s and 1940s, that’s where tobacco companies like Philip Morris focused much of their research. Making cigarettes from tobacco leaves involved a great deal of waste. The soft portions of the tobacco leave were easiest to work with and had the best flavor. The ribs and stems also contained nicotine, but it was difficult to make cigarettes from those parts of the tobacco leaf. The ribs and stems also didn’t taste as good as the soft portions of the leaf.

Around 70 years ago, Philip Morris developed the perfect answer to the question of how to use tobacco ribs and stems rather than throwing them away. The answer was ammonia. Philip Morris discovered that they could grind the undesirable portions of the tobacco leaf, add water to make a liquid slurry and infuse the slurry with ammonia to get the plant material to release pectin. The result of that process was reconstituted tobacco, a paper that could then be shredded and used to fill cigarettes. The “recon” process improved profitability for Philip Morris. Today, virtually all cigarettes contain reconstituted tobacco.

Philip Morris Continues Its Ammonia Investigations

In exploring the interactions between ammonia and tobacco, Philip Morris discovered that ammonia didn’t just increase the yield from tobacco leaves; it was also a potent flavor enhancer. Philip Morris researchers described the flavor of cigarettes with ammonia as “milder,” “sweeter” and “more aromatic.” So, the ammonia didn’t just increase yields; it also made the cigarettes taste better, so people didn’t mind the fact that they were smoking ribs and stems.

Philip Morris also experimented with using ammonia as a catalyst for increasing the volume of reconstituted tobacco sheets, eventually patenting a procedure for that purpose in 1973. Philip Morris found that, by exposing the sheets to dry ice and gaseous ammonia – and then heating the sheets – the reconstituted tobacco became “puffy.” It was then possible to use less tobacco to fill cigarettes. Today, tobacco companies typically use dry ice alone to puff up the tobacco sheets, because it is cheaper than using ammonia.

Philip Morris’s greatest discovery, however, had nothing to do with increasing yields or improving flavor.

The Discovery of Freebase Nicotine

By the 1970s, Philip Morris used ammoniated tobacco in many of its cigarette brands. The ammonia used in the production of reconstituted tobacco sheets also had the pleasant side effect of improving flavor, so Philip Morris brands like Merit became hits with consumers.

However, ammonia also had another benefit: It increased the pH of the nicotine. As far back as the 1970s, researchers at Philip Morris were aware of the effect that pH had on nicotine delivery. At higher pH levels, they found, nicotine becomes more volatile and is therefore more readily absorbed by the central nervous system.

By the 1980s, internal documents show that Philip Morris was well aware of what they were doing. By adding ammonia to tobacco, they were creating freebase nicotine. By increasing the physiological effect of the nicotine, it was possible for the company to release cigarettes that were lower in tar and nicotine but just as satisfying as the “full-flavored” brands.

Thanks to freebase nicotine, the Philip Morris low-nicotine Merit brand delivered as much nicotine to the body as the Marlboro brand, even though the actual nicotine content of Merit was half that of Marlboro.

Philip Morris eventually began using ammoniated tobacco in the Marlboro brand, of course, and that – combined with the legendary “Marlboro Man” ad campaigns – helped to make Marlboro the world’s best-selling cigarette. It retains that title today.

Philip Morris kept their discoveries secret and carefully monitored the pH levels of competing cigarette brands. Eventually, though, competitors discovered Marlboro’s secret, and today, most cigarettes contain ammonia. That’s even true of “additive-free” cigarette brands like American Spirit.

The Vaping Industry Looks Forward by Looking Back

Ammonia is a powerful solvent that, today, is almost universally used in the extraction of nicotine from tobacco because it increases yields. Nicotine extracts are used in the production of nicotine replacement products like gums and patches. Extracted nicotine is also necessary for the production of e-liquid for vaping. Effectively, that means almost all e-liquid contains freebase nicotine.

Based on what you’ve read in this article so far, you might assume that the presence of freebase nicotine in e-liquid is a good thing for smokers who are trying to quit. However, freebase liquid nicotine also has a problem. It is alkaline, so people find it difficult to inhale in high concentrations because it irritates the throat.

To deliver around the same nicotine per puff as a tobacco cigarette, a cigarette-shaped vaping device needs to have an e-liquid with a nicotine strength around 50 mg/ml. With freebase nicotine e-liquid, though, the highest strength that most people can tolerate is about 18 mg/ml, which is available at 180Smoke. At higher strengths, the vapor becomes too harsh and unpleasant. Until recently, any smoker who switched to vaping would have to adjust to lower blood-nicotine levels during the transition.

In the mid-2010s, e-liquid makers found a solution to that problem by adding acid to vape juice. The most commonly used reagent is benzoic acid, which converts the nicotine from freebase nicotine to nicotine acid benzoate – a salt. Nicotine salt e-liquid has a lower pH than freebase nicotine e-liquid, and it is therefore less harsh on the throat. It has enabled the creation of higher-strength e-liquids, which have helped more smokers than ever transition to vaping.

Effectively, the vaping industry looked forward by looking back. While the conversion of nicotine salt to freebase nicotine was an advancement that took the tobacco industry decades to achieve and to understand, the vaping industry reversed the process in the first few years of its young history.

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