Disposition Kinetics of Nicotine and Cotinine Enantiomers in Rabbits and Beagle Dogs

Jacob, Peyton; Benowitz, Neal L.; Copeland, James R.; Risner, Marcus E.; Cone, Edward J.

doi:10.1002/jps.2600770508

Cited by 36 publications

(19 citation statements)

References 32 publications

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“…This compound also is used as a pesticide, 2 as an experimental drug, 3,4 and is FDA-approved as an active agent in smoking cessation therapy. [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] It should be noted that many of the reported differences very likely result from the fact that different animal and/or cell systems were used in the studies. 1 The less common enantiomer of nicotine, (R)-(+)nicotine, also is pharmacologically active; although there are conflicting reports as to its effects and potency.…”

Section: Introductionmentioning

confidence: 99%

“…5 Most commercial sources of nicotine are an extraction by-product of the tobacco industry. [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] However, there is no doubt, that (R)-(+)-nicotine is biologically active and can differ from (S)-(−)-nicotine in potency, effect, and metabolism. [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] It should be noted that many of the reported differences very likely result from the fact that different animal and/or cell systems were used in the studies.…”

Section: Introductionmentioning

confidence: 99%

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Enantiomeric composition of nicotine in smokeless tobacco, medicinal products, and commercial reagents

1998

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The enantiomeric composition of nicotine in 18 smokeless tobaccos, 3 strains of tobacco leaf, 8 pharmaceutical products, and 4 commercial reagents was determined. The relative amount of the minor enantiomeric component, (R)‐(+)‐nicotine, ranged from ∼0.1% to ∼1.2% of the total nicotine in all samples. In some cases it appears that (R)‐(+)‐nicotine may be considered one of the five most common alkaloids in tobacco products. The highest level of (R)‐(+)‐nicotine was found in a commercial transdermal patch. The extraction and purification processes used in obtaining commercial (S)‐(−)‐nicotine supplies from tobacco do not appear to decrease the amount of (R)‐(+)‐nicotine present. Chirality 10:587–591, 1998. © 1998 Wiley‐Liss, Inc.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantiomeric composition of nicotine in smokeless tobacco, medicinal products, and commercial reagents

1998

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“…Studies by Yildiz [2] and other investigators [8,13] have shown that the nicotine enantiomers elicit significant stereoselective differences in their lethality, pharmacology, and behavioural and physiological effects. Other researchers [14] reviewed the effects produced by nicotine enantiomers on the central nervous system, and pharmacokinetic studies of (1)-and (À)-nicotine have shown that biotransformation pathways are influenced by stereochemistry factors [15,16]. These effects will be reflected in NBA as nicotine represents the main part of the molecule and the target binding site.…”

Section: Introductionmentioning

confidence: 96%

Determination of trace amount of enantiomeric impurity in therapeutic nicotine derivative using capillary electrophoresis with new imaging technology detection

Dahab

Smith

2011

J of Separation Science

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One of the many attempts to stop the danger of tobacco smoking is the development of an anti-smoking vaccine using nicotine butyric acid (NBA) linked to a carrier protein to produce anti-nicotine antibodies. NBA is a chiral molecule and there is a need to obtain a high degree of enantiomeric purity. The aim of this work is to develop a novel method for the enantioseparation of NBA and the determination of trace amounts of enantiomeric impurity required by regulatory authorities. This was achieved successfully using high-performance capillary electrophoresis combined with label-free intrinsic imaging as new imaging technology. A 50 μm id fused-silica capillary was used with UV detection at λ(214 ) nm and label-free intrinsic imaging. The background electrolyte consisted of highly sulphated β-cyclodextrin 10% m/V as a chiral selector in 75 mM phosphoric acid-triethylamine at pH 7.0. Baseline separation and detection of 0.1% and possibly less of the unwanted impurity (R-enantiomer) were achieved. Also, the detection limits were calculated for both enantiomers. The use of label-free intrinsic imaging has improved the sensitivity, enabling us to detect trace amounts of enantiomeric impurities.

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“…Nicotine has one asymmetric centre and, as a result, exists as a pair of optical isomers (enantiomers) (Figure 10.2). In addition, it is known that the enantiomers are metabolized differently (Martin et al, 1983;Jacob et al, 1988a). Small amounts of the (R)-isomer (up to 5% of the total nicotine) are found in tobacco smoke, presumably formed by racemization during combustion .…”

Section: Synthesis Of Labelled Nicotine and Metabolitesmentioning

confidence: 99%

Nicotine and Related Alkaloids

Gorrod¹,

Wahren²

1993

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Disposition Kinetics of Nicotine and Cotinine Enantiomers in Rabbits and Beagle Dogs

Cited by 36 publications

References 32 publications

Enantiomeric composition of nicotine in smokeless tobacco, medicinal products, and commercial reagents

Enantiomeric composition of nicotine in smokeless tobacco, medicinal products, and commercial reagents

Determination of trace amount of enantiomeric impurity in therapeutic nicotine derivative using capillary electrophoresis with new imaging technology detection

Nicotine and Related Alkaloids

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