Caffeine Aaron Warning and Megan Anderson
Caffeine: The Most Popular Nutraceutical • Use dates back to the stone age • Popular: easy access and few documented negative side effects • Effects: ↑ heart rate, ↑ respiration rate, psychotropic effects • http://blog.timesunion.com/healthyprofessor/is-more-coffee-in-your-genes/1814/ • Nehlig, Astrid; Daval, JL.; Debry, G. Effects of Coffee on the Central Nervous System. Brain Res Rev. 1992, Volume 17, 139-170.
1,3,7-trimethylxanthine or 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione ChemDraw (convert name to structure)
Mode of Action • Caffeine stimulates the nervous system • It binds to adenosine receptors on neurons in the brain • Adenosine receptors: normally causes you to feel tired and slows down the nervous system • If caffeine binds to them = opposite effect Fisone, G; Borgkvist, A; Usiello, A. Caffeine as a psychomotor stimulant: mechanism of action. CMLS2003, Volume 61, 857-867
How much is too much? • No RDA for caffeine • UL is 300-400 mg/day • No Adequate Intake established • Negative side effects: heart rate, anxiety, depression, insomnia, nausea, and vomiting • Lethal dose is 10g http://johngushue.typepad.com/blog/coffee/ Lindskog, M; Svenningsson, P; Pazzi, L; Kim, Y; Fienberg, A; Bibb, J; Fredholm, B; Nairn, A; Greengard, P; Fisone, G. Involvement of DARPP-32 phosphorylation in the stimulant action of caffeine. Nature2002, Volume 418, 774-778.
1H NMR Spectral Database for Organic Copounds SBDS. http://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_disp.cgi?sdbsno=1898 (accessed March 5, 2014).
13C NMR • WinChembase. http://www.chemicalbook.com/SpectrumEN_58-08-2_13CNMR.htm (accessed March 5, 2014)
UV-Vis Caffeine: max wavelength: 272nm Solvent: water http://www.onsalesupplements.com/product/59-caffeine-powder Spectral Database for Organic Copounds SBDS. http://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_disp.cgi?sdbsno=1898 (accessed March 5, 2014).
IR 1 2 3 1 2 3 2 1 Spectral Database for Organic Compounds SBDS. http://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_disp.cgi?sdbsno=1898 (accessed March 5, 2014).
Caffeine Consumption • Biosynthesis v. Synthetic Synthesis • Synthetic more in energy drinks • Synthetic is cheaper and faster • Natural: found more in tea and coffee • Natural is buffered with over 500 plant molecules • Slower acting • More expensive http://www.mohrresults.com/mohr-results-weight-loss-2/the-worst-energy-drinks/ http://www.salisburyarea.com/TheChamberVoice/TabId/179/ArtMID/603/ArticleID/183/Coffee-with-your-Council.aspx Ashihara, Hiroshi; Purine metabolism and the biosynthesis of caffeine in mate leaves. Phytochemistry1993, Volume 33, 1427-1430.
Biosynthesis Ashihara, Hiroshi; Montiero, Ana Maria; Gillies, Fiona M; Crozier, Alan; Biosynthesis of Caffeine in Leaves of Coffee. Plant Physiol. 1996, 111, 747-753.
Removing the Sugar N-methyl nucleosidase (catalyst) Xanthosine
Methylating on Methylating SAM SAH
Product! Why is caffeine produced in plants? -Caffeine is a naturally occurring pesticide • http://whyfiles.org/2011/coffee-drink-of-the-gods/ • Looser, Elizabeth; Baumann, T.W; Wanner, H; The biosynthesis of caffeine in the coffee plant. Phytochemistry1974, Volume 13, 2515-2518.
The Future for Caffeine • Continued abuse • Potential use in fighting cancer • Market will shift toward synthetic caffeine