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Nicotine
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==Natural occurrence== Nicotine is a [[secondary metabolite]] produced in a variety of plants in the family [[Solanaceae]], most notably in tobacco ''[[Nicotiana tabacum]]'', where it can be found at high concentrations of 0.5 to 7.5%.<ref>{{cite web |url=http://www.tis-gdv.de/tis_e/ware/genuss/tabak/tabak.htm |title=Tobacco (leaf tobacco) |publisher=Transportation Information Service}}</ref> Nicotine is also found in the leaves of other tobacco species, such as ''[[Nicotiana rustica]]'' (in amounts of 2–14%). Nicotine production is strongly induced in response to wounding as part of a [[jasmonate]]-dependent reaction.<ref>{{cite journal | vauthors = Baldwin IT | title = An ecologically motivated analysis of plant-herbivore interactions in native tobacco | journal = Plant Physiology | volume = 127 | issue = 4 | pages = 1449–1458 | date = December 2001 | pmid = 11743088 | pmc = 1540177 | doi = 10.1104/pp.010762 | jstor = 4280212 }}</ref> Specialist insects on tobacco, such as the tobacco hornworm (''[[Manduca sexta]]''), have a number of adaptations to the detoxification and even adaptive re-purposing of nicotine.<ref>N.d. Natural history-driven, plant-mediated RNAi-based study reveals CYP6B46's role in a nicotine-mediated antipredator herbivore defense | PNAS.</ref> Nicotine is also found at low concentrations in the nectar of tobacco plants, where it may promote [[outcrossing]] by affecting the behavior of hummingbird pollinators.<ref>{{cite journal | vauthors = Kessler D, Bhattacharya S, Diezel C, Rothe E, Gase K, Schöttner M, Baldwin IT | title = Unpredictability of nectar nicotine promotes outcrossing by hummingbirds in Nicotiana attenuata | journal = The Plant Journal | volume = 71 | issue = 4 | pages = 529–538 | date = August 2012 | pmid = 22448647 | doi = 10.1111/j.1365-313X.2012.05008.x }}</ref> Nicotine occurs in smaller amounts (varying from 2–7 [[microgram|μg]]/[[kilogram|kg]], or 20–70 millionths of a percent wet weight<ref name=SiegmundLeitner1999/>) in other [[Solanaceae]]ous plants, including some crop species such as [[potato]]es, [[tomato]]es, [[eggplant]], and [[capsicum|peppers]],<ref name=SiegmundLeitner1999/><ref name=Domino1993>{{cite journal | vauthors = Domino EF, Hornbach E, Demana T | title = The nicotine content of common vegetables | journal = The New England Journal of Medicine | volume = 329 | issue = 6 | page = 437 | date = August 1993 | pmid = 8326992 | doi = 10.1056/NEJM199308053290619 | doi-access = free }}</ref> as well as non-crop species such as ''[[Duboisia hopwoodii]]''.<ref name="metcalf">{{citation| vauthors = Metcalf RL |contribution=Insect Control|title=Ullmann's Encyclopedia of Industrial Chemistry|edition=7th|publisher=Wiley|year=2007|page=9| title-link = Ullmann's Encyclopedia of Industrial Chemistry }}</ref> The amounts of nicotine in tomatoes lowers substantially as the fruit ripens.<ref name=SiegmundLeitner1999/> A 1999 report found "In some papers it is suggested that the contribution of dietary nicotine intake is significant when compared with exposure to ETS [environmental tobacco smoke] or by active smoking of small numbers of cigarettes. Others consider the dietary intake to be negligible unless inordinately large amounts of specific vegetables are consumed."<ref name=SiegmundLeitner1999/> The amount of nicotine eaten per day is roughly around 1.4 and 2.25 [[microgram|μg]]/day at the 95th percentile.<ref name=SiegmundLeitner1999/> These numbers may be low due to insufficient food intake data.<ref name=SiegmundLeitner1999>{{cite journal | vauthors = Siegmund B, Leitner E, Pfannhauser W | title = Determination of the nicotine content of various edible nightshades (Solanaceae) and their products and estimation of the associated dietary nicotine intake | journal = Journal of Agricultural and Food Chemistry | volume = 47 | issue = 8 | pages = 3113–20 | date = August 1999 | pmid = 10552617 | doi = 10.1021/jf990089w | bibcode = 1999JAFC...47.3113S }}</ref> The concentrations of nicotine in vegetables are difficult to measure accurately, since they are very low (parts per billion range).<ref name=MoldoveanuScott2016>{{cite journal | vauthors = Moldoveanu SC, Scott WA, Lawson DM |title=Nicotine Analysis in Several Non-Tobacco Plant Materials |journal=Beiträge zur Tabakforschung International/Contributions to Tobacco Research |date=April 2016 |volume=27 |issue=2 |pages=54–59 |doi=10.1515/cttr-2016-0008 |doi-access=free }}</ref> Pure nicotine tastes "terrible".<ref name=":4" />
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