Nicotiana, a duality of realities

The first time Tobacco was introduced to the Western world was in the 15th century as a gift to the explorer Christopher Columbus by Native Americans in his explorations. The plant immediately gained popularity in the Western Communities as it was believed to be medicine with mystical healing powers from the Natives. This popular belief extended until the early 17th century when scientists and philosophers began reporting difficulty breathing and addiction, in 1632, the state of Massachusetts, stated a law making smoking in public illegal. However, the true boom of Tobacco-related products was dated in the 1900s, approximately 3.5 billion cigarettes were sold in the U.S only, and various Tobacco companies were founded.

Less than a century after the popularization of cigarettes, lung cancer has become the number one cause of death in women, lung cancer rates were higher than breast cancer during this time. Today, various campaigns to anti-smoking are being advertised, the advertising of tobacco related products in television broadcasts have been banned in several countries, the correlation between lung cancer and tobacco has been accentuated.

Today, various campaigns to anti-smoking are being advertised, the advertising of tobacco-related products in television broadcasts have been banned in several countries, the correlation between lung cancer and tobacco has been accentuated, as well as the commercialization of alternative tobacco products, such as e-cigarettes and heated tobacco products, however, these products have become restricted in some situations, being considered a public display of addiction and of not being a good pedagogical example.

Several species of the genus Nicotiana can be found growing natively in South American soil, the most common being Nicotiana Tabacum, the species mainly used in cigarettes sold by enterprises globally, Nicotiana Glauca and Nicotiana Rustica, unlike the previous species, these plants are used solemnly for ritualistic purposes in the Native American tribes, the plants are seen as sacred and used for their spiritual and mental guidance.

Nicotiana Rustica, or Mapacho, is often used by shamans for its high percentage of nicotine and beta-carboline alkaloids, the smoke of these plants plays an important role in the healing, and it’s considered a medicine itself. The shaman blows the smoke of the Mapacho cigarette over the head, hands, and body of the participant to cleanse the negative energy from their body, this practice is also done for the shaman to visualize the messages from the mother tobacco, by reading and studying different patterns formed by the smoke, by creating snuffs or Rapé with the objective of protection, energy activation, removal of blockages, heart-opening, the use of tobacco is a complementary ritual to plants such as San Pedro and Ayahuasca.

Nicotiana Glauca on the other hand was used for Hunting ceremonies, as medicine, and several dermatological diseases, such as cuts, swellings, bruises. The shamans also used the plant to communicate with the divine in order to control rains, increase crop production, and improve the health of the community by blowing the smoke into the ears of patients for earaches, removing pus from boils, and create an infusion from the leaves for rheumatism.

The leaves of Nicotiana species contain a series of alkaloids in between them the psychoactive compound Nicotine, which was first isolated by Posselt and Reimann in 1828, as well as pyrrolidine, N-methyl-pyrroline, N-methylpyrrolidine, l-nornicotine, dl-nornicotine, nicotyrine, anabasine, N-methyl-anabasine.

  Nicotiana Rustica midrib and veins shot with Macro

In the year 1895, the German chemist Adolf Pinner elucidated the formula,  the direct oxidation of the base with chromic acid gives estinic acid. One-half of the nicotine molecule is consequently elucidated. If nicotine-py-mono-methyl iodide(py meaning the CH₂ is attached at the N of the pyridine) treated with potassium ferricyanide and alkali is oxidized to N-Methyl-nicotone. Allowing the entrance of oxygen into the idine nucleus, N-methyl-nicotine can be decomposed to 1-hygrinic the pyridine radical becomes more sensitive to chromic acid than the pyrrol aid. Following in the nicotine a pyridine ring is linked in the ß-position of a N-methyl-pyrrolidine molecule represented in the following image:

The decomposition of l-nicotine to l-hygrinic acid shows that the alkaloid has the same configuration as l-stachydrine and l-proline. The first total synthesis of nicotine was directed by A.Pictet, starting with heating B-aminopyridine compound of mucic acid giving N-ß-pyridyl-pyrrole. 

The B-pyridyl compound is converted into a C-pyridyl derivative, B-pyridyl-a-pyrrole, once it goes thru a red-hot tube. The methylation of the latter is converted into methyl iodide compound of B-pyridyl-N-methyl-a-pyrrole, and it’s converted by quicklime to nicotyrine.

The last step of the synthesis is the reduction of the pyrrole half of nicotyrine. Iodo-nicotyrine is reduced to dihydro-nicotyrine. The mixture is monobrominated and reduced again. This way, dl-nicotine is formed which can later be turned into its enantiomorphic form by means of the tartrate.      


Later, a straightforward synthesis by Späth was published, this synthesis starts from nicotinic ester and N-methyl-pyrrolidone.                

Nicotine is a colorless oil and the salts are dextrorotatory, the alkaloid dissolves in water as well as in most of the organic solvents. This compound acts in the central and peripheral nerves, stimulating them and causing increased glandular secretion, consequently contracting the intestines, and particularly the blood vessels, increasing blood pressure, and giving the feeling of euphoria, reason of why the substance has gone so popular, especially once it’s used as a snuff and/or chewed, for this same reason personalities such as Dr. Johnson to the novelist Philip K.Dick have benefited from snuffs for their writing, as well as several people have benefited from Nicotine gum for their attentive activities, however, this effect can be negated by atropine, which exerts a paralyzing effect on the peripheral nerve. Unlike the most common way to consume tobacco, smoking, the alternatives have been proved to be less damaging to one’s health as the lungs don’t get damaged by the percentage of tar presented in cigarettes after combustion.

This duality of realities between the Western communities and the indigenous tribes is a factor to be considered, the method of utilization of the plant may decrease the harming factor, as well as the dosage and the times that the substance is administrated, as cigarettes have been abused and part of our history of addiction in various aging groups.

Could we be misusing Nicotiana species while we could be taking advantage of its benefits?

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