NICOTINE - (54-11-5)

Introduction

Name: nicotine; 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
* IUPAC
CAS Number: 54-11-5
Chemical Formula: C10H14N2
Molar Mass: 162.23156 g
Mass Percent: C 74.034 %; H 8.6981 %; N 17.267 % 

Classification

• organic • aromatic

Uses/Function

• "This stimulant hits acetylcholine receptors in the nervous system, leading to improved alertness. It also promotes dopamine release, which is associated with pleasure-seeking behavior." 1

• "Nicotine and the neurotransmitter acetylcholine, which acts on maintenance neurons, have similar structures...Nicotine molecules are therefore able to bind to acetylcholine receptor sites and trigger many of acetylcholine's effects, including relaxation and increased digestion, which explains the tendency of smokers to smoke after eating meals. In addition, acetylcholine is used for muscle contraction, and so the smoker may also experience some muscle stimulation immediately after smoking. After these initial responses, however, nicotine molecules remain inertly bound to the acetylcholine receptor sites, thereby blocking acetylcholine molecules from binding. The result is that the maintenance neurons are no longer stimulated - in other words, the activity of these neurons is depressed...as nicotine depresses the maintenance neurons, it favors the stress neurons, thereby raising the smoker's blood pressure and stressing the heart.

Up in the brain, nicotine effects the stress system directly by enhancing the release of stress neurotransmitters, such as norepinephrine. Nicotine also increases the levels of dopamine in the reward center. Furthermore, when inhaled, nicotine is a fast-acting drug. All these factors give nicotine a high level of addictiveness. Animal studies show inhaled nicotine to be about six times more addictive than injected heroin. Because nicotine leaves the body quickly, withdrawal symptoms begin about 1 hour after a cigarette is smoked, which means the smoker is inclined to light up frequently." 2

• "...a poisonous compound found in tobacco leaves" 3

Bonding

Double Bonds: 3
Triple Bonds: 0
Sigma Bonds: 27
Pi Bonds: 3
Total: 30
Carboxyl Groups: 0
Hydroxyl Groups: 0

Thermochemistry

ΔHf° (ℓ): 9.4 kcal/mol 4 = 39.33 kJ/mol

For More Information

Sources

(1) - Ehrenberg, Rachel. Chemists Pin Down Poppy's Tricks for Producing Narcotic Painkiller. Science News, April 10, 2010, p 6.
(2) - Suchocki, John. Conceptual Chemistry: Understanding Our World of Atoms and Molecules; Addison Wesley: San Francisco, California, 2001; p 463.
(3) - Kotz, John C. and Purcell, Keith F. Chemlstry and Chemlcal Reactivity, 2nd ed.; CBS College Publishing: New York. NY, 1987; p 98.
(4) - Dean, John A. Lange's Handbook of Chemistry, 12th ed.; McGraw-Hill Book Company: New York, NY, 1979; p 9:85.
(5) - Dean, John A. Lange's Handbook of Chemistry, 12th ed.; McGraw-Hill Book Company: New York, NY, 1979; p 9:85.
(6) - Dean, John A. Lange's Handbook of Chemistry, 12th ed.; McGraw-Hill Book Company: New York, NY, 1979; p 9:85.