Extraction of nicotine

Molecularly imprinted polymers in solid phase extractions 

Transferring the procedure to an off-line mode, quantification by reversed phase HPLC showed that all analytes except -nicotyrine were quantitatively recovered. Due to the enhanced stability of the nicotine MIP, achieved by thermal annealing, and the reusability of the MIP, the procedure may be suited for automation. 

---

Aqueous extraction procedures for water-soluble molecules are especially advantageous in CE. For example, toluene extraction of nicotine from tobacco prior to gas chromatography gives low recoveries compared to aqueous extraction and CE [39],... 

Although CO2 is the most commonly used supercritical fluid for extraction, the solubility of certain solutes in CO2 is usually low and causes an inconvenience. The remedy for this problem is to add some entrainers such as water to facilitate the extraction. In this background, the MD simulations were carried out to study the supercritical extraction of nicotine by CO2 in the presence and absence of water as entrainer[40]. In the tobacco leaf, nicotine molecule is bonded to other organic molecules and forms organic acid salts. The malic salts of nicotine was chosen as the model with nicotine bonded to two malic molecules by hydrogen bonds[41]. It is assumed that when malic salts of nicotine are extracted from tobacco leaf, supercritical CO2 or entrainer molecule attacks the hydrogen bonds and decomposes the salt into three molecules. 

The role of water as entrainer in the extraction of nicotine by supercritical CO2 fluid was studied by MD simulation. The following three systems were studied in detail ... 

A new photometric determination of volatile bases in tobacco and tobacco smoke in terms of nicotine, which compares quantitatively with mass spectral and g.c. methods, has been developed.27 A colorimetric method for the estimation of nicotine alkaloids in tobacco by reaction with cyanogen bromide and 4,4 -di-aminostilbene-2,2 -disulphonic acid has also been reported.28 Dilute sulphuric acid extraction of nicotine and anabasine from autopsy tissue appears to be a more efficient method than extraction with acidified ethanol, aqueous oxalic acid, and steam distillation.29 Thin-layer chromatography has been effective in the analysis of nicotine and other alkaloids and drugs.30 Two reports on the isolation of anabasine from anabasine-lupinine mixtures have appeared.31 The P a values of some nicotine-type compounds have been determined.32... 

Extraction of nicotine from tobacco using supercritical fluid is carried out in a manner quite similar to the decaffeination of roasted coffee described in U.S. 3,843,824. Tobacco is first contacted with dry supercritical CO2 which extracts the aroma constituents. The C02-aroma stream is expanded to subcritical conditions via expansion across a valve the aromas precipitate from soludon. The CO2 vapor is recompressed, is adjusted in temperature to supercritical conditions via heat exchangers, and is recycled to the extractor via a compressor. The aromas extracdon step condnues until the aroma constituents are removed from the tobacco. 

Nicotine in a water solution containing 2% nicotine is to be extracted with kerosene at 293 K. Water and kerosene are essentially insoluble. Determine the percentage extraction of nicotine if 100 kg of the feed solution is extracted in a sequence of four batch ideal extractions using 49.0 kg of fresh, pure kerosene each. The equilibrium data are as follows (Claffey et al., 1950) ... 

T.l.c. characteristics of nicotine on alumina sintered glass plates have been reported." Extraction of nicotine alkaloids using water vapour distillation" and fatty acids" has been studied. 

EXAMPLE 12.7-3. Extraction of Nicotine with Immiscible Liquids. 

Analytical Equation for Number of Stages. Example 12.7-3 gives data for extraction of nicotine from water by kerosene where the two solvents are immiscible. A total of 3.8 theoretical stages were needed. Use the analytical equations (10.3-21)- 10.3-26) to calculate the number of theoretical stages and compart with the valufc obtained graphically. 

Find the minimum kerosene rate for countercurrent extraction of nicotine from a nicotine-water solution (1 percent nicotine) to reduce nicotine content to 0.1 percent. The feed rate of nicotine-water is 0.1263 kg/sec. Also determine stages needed if kerosene rate is 0.1452 kg/sec. Equilibrium data is given in Problem 13-42. 

Tobacco and its alkaloids have long ceased to have any therapeutic importance, but their extensive use as insecticides and the demand for nicotine for the manufacture of nicotinic acid have stimulated interest in processes of extraction and methods of estimation. On the latter subject there is a voluminous literature, of which critical resumes have been published by various authors.Recent work on this subject has been specially concerned with (1) the development of miero- and semi-miero-methods suitable for estimating nieotine in tobacco smoke and the distribution of nieotine on sprayed garden produce, in treated soils and in tobaeeo leaves,(2) the study of conditions necessary to ensure satisfactory results in using particular processes, " and (3) methods of separation and estimation of nicotine, nomicotine and anabasine in mixtures of these bases. ) In the United States and in Russia considerable interest is being shown in the cultivation of types of tobacco rich in nicotine, in finding new industrial uses for tobacco and its alkaloids, and in possible by-products from tobacco plants such as citric and malic acids, i " Surveys of information on tobacco alkaloids have been published by Jackson, i Marion and Spath and Kuffner. ... 

A TLC method was developed for the estimation of nieotinie aeid and nicotinamide (Fignre 10.7) in phatmacentical preparations containing other vitamins, enzymes, herbs, and drugs, etc. [16]. The percentage recoveries for nicotinic acid and nicotinamide were 100.1 + 1.9 and 100.2 1.5, respectively, with this system. Each alcohol extract of samples or standard was pnt on sihca gel TLC plates, which were developed with distilled water. Each silica gel spot visualized under UV lamp was collected and extracted with 0.1 mol/1 HCl. The optical density of each clear extract was measured at 262 run. 

Extraction of foods and pharmaceuticals Caffeine from coffee and tea Flavors, cholesterol, and fat from foods Nicotine from tobacco... 

The use of plant extracts for insect control dates into antiquity the use of Paris green as an insecticide for control of the Colorado potato beetle in 1867 probably marks the beginning of the modern era of chemical control of injurious insects. The development of lead arsenate followed later in the nineteenth century for gypsy moth control. The commercial production of nicotine insecticides, the production of calcium arsenate at the time of the first world war, and the use of fluorine, arsenical, and cyanide compounds, as well as other inorganic chemicals for insect control, were important steps in pest control. These chemicals were applied largely by dilute high pressure sprays or dusts. 

In a further application of MI-SPE, theophylline could be separated from the structurally related caffeine by combining the specific extraction with pulsed elution, resulting in sharp baseline-separated peaks, which on the other hand was not possible when a theophylline imprinted polymer was used as stationary phase for HPLC. A detection limit of 120 ng mb1 was obtained, corresponding to a mass detection limit of only 2.4 ng [45]. This combination of techniques was also used for the determination of nicotine in tobacco. Nicotine is the main alkaloid in tobacco and is the focus of intensive HPLC or GC analyses due to its health risk to active and passive consumers. However, HPLC- and GC-techniques are time-consuming as well as expensive, due to the necessary pre-purification steps required because the sample matrices typically contain many other organic compounds besides nicotine. However, a simple pre-concentration step based on MI-SPE did allow faster determination of nicotine in tobacco samples. Mullett et al. obtained a detection limit of 1.8 jig ml 1 and a mass detection limit of 8.45 ng [95]. All these examples demonstrate the high potential of MI-SPE to become a broadly applicable sample pre-purification tool. 

FIGURE I A reconstructed extracted ion chromatogram of nicotinic acid and its six metabolites under HILIC conditions. Column Hypersil silica (4.6 X 50 mm) at a flow rate of 4 mL/min. Mobile phase A is water, mobile phase B is acetonitrile, both containing 1% formic acid. Gradient is 0.01-0.25 min 90% B to 65% B 0.25-0.90 min 65% B to 50% B. NA nicotinic acid NAM nicotinamide NUA nicotinuric acid 2-PY l-methyl-2-pyridone-5-carboxamide l-MNAM I-methyl-nicotinamide NAMO nicotinamide-N-oxide 4-PY l-methyl-4-pyridone-5-carboxamide. (Reprinted with permission from Reference 20.)... 

The rate of metabolism of nicotine can be determined by measnring blood levels after administration of a known dose of nicotine (Table 1) (Hukkanen et al. 2005c). Total clearance of nicotine averages about 1200 ml min . Nonrenal clearance represents about 70% of liver blood flow. Assuming most nicotine is metabolized by the hver, this means that about 70% of the drug is extracted from blood in each pass through the hver. 

An implication of the high degree of hepatic extraction is that clearance of nicotine should be dependent on liver blood flow. Thus, physiological events, such as meals, posture, exercise, or drugs perturbing hepatic blood flow, are predicted to affect the rate of nicotine metabolism. Meals consumed during a steady state infusion of nicotine result in a consistent decline in nicotine concentrations, the maximal effect seen 30-60 min after the end of a meal (Gries et al. 1996 Lee et al. 1989). Hepatic blood flow increases about 30% and nicotine clearance increases about 40% after a meal. 

Several natural products have been evaluated in rodent models of nicotine withdrawal. An extract of Hypericum perforatum (St. John s Wort, a putative antidepressant, and inhibitor of serotonin reuptake) reversed somatically expressed withdrawal behaviors and locomotor depression in spontaneous withdrawal (Catania et al. 2003). A benzoflavone compound isolated from Passiflora incarnata, interfered with the induction of physical dependence. Coadministration with chronic nicotine prevented various subsequent indicators of withdrawal syndrome in the mouse, including jumping, locomotor inactivity, immobility in the swim test and naloxone-precipitated escape jumping (Dhawan et al. 2002). 

---