nicotine

nicotine uses and its effects

1. Alkaloids prepared by Sonia knawel Nicotine

2. contents ALKALOIDS NICOTINE Historical Awareness Forms 0f tobacco Common Food with Nicotine Content Biosynthesis of nicotine Extraction of nicotine structure elucidation Pharmacokinetics Pharmacodynamics Determinants of Tobacco Use Treatment options

3. ALKALOIDS Alkaloid,  are naturally occurring organic nitrogen-containing bases. Alkaloids have divers and important physiological effects on humans and other animals. Well-known alkaloids include morphine, quinine, ephedrine, and nicotine. Alkaloids are found primarily in plants and are especially common in certain families of flowering plants. More than 3,000 different types of alkaloids have been identified in a total of more than 4,000 plant species. https://www.britannica.com/science/alkaloid

4. Both opium poppy and fungus argot contain about 30 different types of alkaloids All Parts e.g. Datura. Barks e.g. Cinchona Seeds e.g. Nux vomica Roots e.g. Aconite Fruits e.g. Black pepper Leaves e.g. Tobacco Latex e.g. Opium Distribution in Plant:

5. NICOTINE Nicotine is soluble in water and in non polar solvents. Nicotine is an pyridine pyrrolidine alkaloid found naturally in tobacco plants, constitutes aproximately 0.6- 3.0 percent of dry weight of tobacco Ncotiana tabacum , the type of nicotine found in tobacco plants, comes from the nightshade family( solanaceae ). Nicotine is a brown liquid and Volatile in nature https://en.wikipedia.org/wiki/Nicotine

6. Nicotine is synthesized in the roots of tobacco plants and it is then carried to the leaves, where it is stored in concentrations of between 2 to 8 percent by weigh. nicotine is also an antiherbivore chemical, specifically for the elimination of insects - it extensively used as an insecticide. " Nicotine is as addictive as heroin Causes physical dependence Highly hydrophobic, so can cross blood brain barrier. http://www.encyclopedia.com/science-and-technology/chemistry/organic-chem/nicotine

7. Historical Awareness 1560 - Marked as 1 st yr tobacco officially introduced to Europe Proponents of tobacco Sir Francis Drake Sir Walter Raleigh Led to the fashionability of pipe smoking of tobacco 2 , 000 years ago (maybe 6,000) - natives of the Americas used tobacco as a medicine, in religious ceremonies, and as offerings to spirits. 1492 - Christopher Columbus introduce tobacco and nicotine to Spain http://www.toxipedia.org/download/attachments/6003685/Chpater%206%20Slides%2

8. 1612 - British colony at Jamestown, Virginia, exporting tobacco to England – became an essential source of money 1700-1800’s - Farms used slaves to cultivate tobacco Historical Awareness 1828 - Nicotine was isolated from the tobacco plant by German chemists posselet and Reimann formally introduced to Europe as a medicinal herb over 60 species of nicotiana but only 2 major ones; 1850s , Cigarettes first appeared , but chewing still more popular

9. Forms 0f tobacco smokebal tobacco cigar or pipes Tight rolls of tobacco leaves. Flue-curing - process of heating tobacco leaves to cure them, make a milder smoke. Cigarettes Rolls of shredded tobacco wrapped in paper The smoke is than drawn through the stem and mouthpiece and inhaled. Pipes are often reusable Pipe smoking has been shown to cause gum disease and tooth loss, is a pipe used to smoke Shisha , a combination of tobacco and fruit or vegetable that is heated and the smoke is filtrated through water. The tobacco or Shisha is heated in the hookah usually using charcoal. Hookah www.ct.gov/dph/lib/dph/hems/tobacco/tobacco_products.pdf

10. snuff Grind tobacco into fine powder Pinch into nose & exhale with sneeze. Started in France & spread through rest of Europe In U.S., snuffing replaced by chewing Free hands for working Low cost - Chewing The two main types of smokeless tobacco are chewing tobacco and snuff. Chewing tobacco comes in the form of loose leaf, plug, or twist Smokeless tobacco

11. Common Food with Nicotine Content few common vegetables and plants, mostly from the Solanaceae (nightshade) family, shown to have nicotine content. Tomato belongs to the solanaceae family ,found to posses a nicotine alkaloid called tomatine It has an average of 7.1- 7.3 ng /g wet weight. It means there is a 7.1 ng of nicotine in every 1 gram of tomato Potato Potatoes also contain a nicotine alkaloid called solanine, which is highly concentrated on its skin . abouttesting.testcountry.com/.../6-common-food-with-nicotine-content.h

12. Eggplant Eggplants have a concentration of 100  ng /g ,of nicotine. It is second highest next to tobacco among the nightshade family where nicotine alkaloids are commonly present . In simple terms, 10 kg of eggplant have the same nicotine content as stick of cigarette. Tea green and black teas also contain small amounts of nicotine whether regular or decaffeinated Common Food with Nicotine Content

13. Cauliflower is another food source of nicotine. The nicotine concentration contained in cauliflower is 16.8 ng /g. cauliflower is also an excellent dietary source of vitamin K ,vitamin C, and fiber. Regular consumption of cauliflower will promote some health benefits such as protection against some forms of cancer, detoxification in the body Peppers and Capsicums . Peppers and capsicums also contain solanine and solanadine , nicotine alkaloids, just like the other nightshade family plants. Common peppers have a solanine concentration of 7.7 – 9.2 mg per 100 grams of serving Cauliflower

14. Biosynthesis of nicotine The biosynthetic pathway of nicotine involves a coupling reaction between the two cyclic structures that compose nicotine. Metabolic studies show that the pyridine ring of nicotine is derived from  niacin(nicotinic acid) while the pyrollidine is derived from  N -methyl pyrrollidium cat ion Biosynthesis of the two component structures proceeds via two independent syntheses , the NAD pathway for niacin and the tropane pathway for  N -methyl- - pyrrollidium cation

15. The NAD pathway in the genus  nicotiana  begins with the oxidation of aspartic acid into α- imino succinate by aspartate oxidase (AO). This is followed by a condensation with glyceraldehyde-3-phosphate and a cyclization catalyzed by quinolinate synthas (QS) to give  quinolinic acid. Quinolinic acid then reacts with Phosphoribosyl pyrophosphate catalyzed by quinolinic acid phosphoribosyl transferase (QPT) to form niacin mononucleotide ( NaMN ). The reaction now proceeds via the NAD salvage cycle to produce niacin via the conversion of  nicotinamide  by the enzyme  nicotinamidase

16. The  N -methyl- - pyrrollidium cation used in the synthesis of nicotine is an intermediate in the synthesis of tropane -derived alkaloids. Biosynthesis begins with  decarboxylation  of  ornithine by ornithine decarboxylase (ODC) to produce  putrescine . Putrescine is then converted into  N -methyl putrescine via  methylation  by SAM catalyzed by putrescine   N - methyltransferase (PMT). N - methylputrescine then undergoes  deamination into 4-methylaminobutanal by the  N - methylputrescine oxidase (MPO) enzyme, 4-methylaminobutanal then spontaneously cyclize into  N -methyl- - pyrrollidium cation  

17. The final step in the synthesis of nicotine is the coupling between  N -methyl--pyrrollidium cation and niacin Although studies conclude some form of coupling between the two component structures, the definite process and mechanism remains undetermined. The current agreed theory involves the conversion of niacin into 2,5-dihydropyridine through 3,6-dihydronicotinic acid. The 2,5-dihydropyridine intermediate would then react with N -methyl- pyrrollidium cation to form enantiomerically  pure (–)-nicotine.

18. Extraction of nicotine from tobacco leaves Solvent extraction 10 gm of tobacco leaves were dipped in 100ml of NaoH Solution was stirred and filter. Then filtrate was diluted in 30ml of distilled water filter the solution again to remove impurities solution was transfer into the separating funnel and extracted with 25ml ether. extraction was repeated for 3 times. Ether was evaporate on water bath (avoid extra heat because nicotine is hydrolyzed by extra heating ) After that nicotine oil is obtained Nicotine is liquid that is miscible in water. Nicotine form salt with acids that are usually solid and water soluble.

19. steam distillation . Plant material + water + Fixed alkali Heat steam contain alkaloids received in acidic solution.

20. structure elucidation Infra red spectrum of nicotine http://www.chm.bris.ac.uk/motm/nicotine/E-propriete.html

21. pnmr spectra of nicotine

22. C-13 spectrum of nicotine

23. Mass spectrum of nicotine

24. Smoking Nicotine in a cigarette – 8 to 10 mg Smoking – delivers about 1 mg to the smoker Technique of smoker can increase nicotine in Lungs (nicotine enters brain in 7 seconds) Skin; (slower absorption, more constant blood levels) Stomach poor ; (nicotine is strong base – stomach is acid) Intestine better. Cigarettes were invented by beggars in Seville, Spain (from scrap of cigars

25. Pharmacokinetics Readily absorbed from all over the body, including Lungs (smoked) Mucosa (cigar, chewing tobacco) Skin (patch) Gastrointestinal tract (uncommon) Pharmacokinetics refers to what the body does to a substance

26. Nicotine Absorption The most common way to get nicotine into your bloodstream is through inhalation Your lungs are lined by millions of alveoli, which are the tiny air sacs where gas exchange occurs These alveoli provide an enormous surface area, 90 times greater than that of your skin, and thus provide ample access for nicotine and other compounds Nicotine taken in by cigarette or cigar smoking takes only 10-15 seconds to reach the brain but has a direct effect on the body for only ~30 minutes

27. It can be absorbed by the body from smoke that has been taken into the lungs, or through the skin. It rapidly crosses the blood-brain barrier, appearing in brain tissue; minutes after its absorption into capillaries lining the alveoli of the lungs. The presence of nicotine in the body stimulates nicotinic-cholinergic receptors of the nervous system, resulting in increased attention span, increased heart rate and blood pressure, and increases in the concentrations of some hormones.

28. Metabolism & Elimination About 80 percent of nicotine is broken down to cotinine by enzymes in your liver Nicotine is also metabolized in your lungs to cotinine and nicotine-N-oxide Cotinine . and the remaining nicotine is filtered from the blood by your kidneys and excreted in the urine

29. Pharmacodynamics Nicotine is a direct agonist for nicotinic ACh receptors Nicotine initially causes a rapid release of adrenaline, the "fight-or- flight“hormone by binding with nAch resepter nicotine increse the level of several neurotransmeters pharmacodynamics refers to what a substance does to the body.

30. Pharmacodynamics nAChRs found in limbic system( hypothallamus ) , midbrain , various cortical areas (frontal lobes) Nicotine also increases release of various neuro hormones Has powerful effects on peripheral nervous system, heart, and other organs

31. Physiological effects in large doses, nicotine is highly toxic Symptoms of nicotine poisoning are Sweating ,vomiting, mental confusion , diminished pulse rate, and breathing difficulty ,Respiratory failure Stimulus effect - release of norepinephrine Norepinephrine   Iworks by constricting (narrowing) the blood vessels and increasing blood pressure and blood glucose (sugar) level. nicotine mood altering effects are different by report it is both a stimulant and relaxent . first causing a release of glucose from the liver and epinephrine ( aderaline ) from the adrenal meduula it cause stimulation user report feeling of relaxation . By reducing the appetite and raising the metabolism some smoker may lose weight as a consequence. Depression - caused by blocked nerve activity

32. Nicotine effects Constricts blood vessels in skin, producing cold, thin, wrinkles (faster aging). Inhibits stomach secretions, stimulates bowel (laxative in nontolerant person). May increase metabolism of fat; dull taste buds. Slows stomach contractions; increases blood sugar. May improve attention/memory; although high doses may increase nervousness, seizures, panic attack. May have an antidepressant effect (i.e., are smokers self-medicating?).

33. cancer Cancer related to nicotine include Mouth kidney Larynx bladder Esophagus throat Stomach lungs pancreas

34. Determinants of Tobacco Use Socioeconomic status Cultural characteristics Biological elements Stress Advertising (for and against) Price of tobacco products Peer pressure

35. Why should I treat tobacco use ? I in 5 deaths in the US are due to smoking 1 in 3 cancer deaths are caused by smoking 70% of smoker want to quit 64% of New Yorkers who smoke tried to quit; NYCommunity Health Survey 2001 Less than 10% succeed without assistance A 35-year-old male who smokes two packs a day has a life expectancy that is 8.1 years shorter than his nonsmoking counterpart Based on data collected in the late 1990s, the US Centers for Disease Control and Prevention (CDC) estimated that adult male smokers lost an average of 13.2 years of life and female smokers lost 14.5 years of life because of smoking.

36. Treatment options Behavior modification Nicotine lozenges Nicotine gum Nicotine patches Nicotine inhaler Nicotine nasal spray Bupropion (non-nicotinic pharmacological agent) NRT ( n icotine r eplacement t herapy) https://aidsetc.org/sites/default/files/resources_files/nynj_nicotine

37. Zyban ( buproprion ) – approved in 1997 for smoking cessation originally an antidepressant. weak inhibitor of dopamine ( Dopamin e is a neurotransmitter that helps control the brain's reward and pleasure centers regulate movement and emotional responses ),  and nor adrenaline reuptake, and has also been shown to antagonize nicotinic acetylcholine receptor function.