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Using "Basic Principles" To Understand Complex Science: Nicotine Smoke Chemistry and Literature Analogies
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Section:Abstract
The Henderson–Hasselbalch equation calculates the equilibrium distribution of 50:50 for nicotine in its nonprotonated (free base form), relative to its monoprotonated form, at pH of 8 in dilute aqueous solution. This ratio has then been used in the literature to predict the effect of ammonia compounds in tobacco and in smoke on nicotine pyrolysis and smoke chemistry. Experiments demonstrate that neither the thermal chemistry of tobacco alkaloids nor the transfer of nicotine from tobacco to smoke can be explained by the position of the nonprotonated versus monoprotonated form equilibrium in aqueous extracts of tobacco. The high thermal stability of nicotine in air allows nicotine salts to be converted to nonprotonated nicotine and volatilize during heating prior to any substantial decomposition of the nicotine moiety. In contrast, cocaine hydrochloride is thermally unstable and will rapidly decompose upon heating; cocaine hydrochloride must first be converted to its nonprotonated form prior to heating and volatilization.
Keywords (Audience):
General PublicKeywords (Domain):
Public Understanding / OutreachKeywords (Pedagogy):
Analogies / TransferKeywords (Subject):
Acids / BasesCiting Articles
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This article has been cited by 1 ACS Journal articles (1 most recent appear below).
Possible Role of Ammonia on the Deposition, Retention, and Absorption of Nicotine in Humans while Smoking†
Jeffrey I. SeemanChemical Research in Toxicology2007 20 (3), 326-343Possible Role of Ammonia on the Deposition, Retention, and Absorption of Nicotine in Humans while Smoking†
Jeffrey I. SeemanChemical Research in Toxicology2007 20 (3), 326-343This perspective presents an overview of the properties of tobacco smoke aerosol and the possible effect of ammonia on the deposition location, retention and the amount and rate of nicotine absorption during cigarette smoking. Three main mechanisms ...
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- Received: August 03, 2009
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