CaffeineAaron 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

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Caffeine

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. CMLS 2003, 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. Nature 2002, Volume 418, 774-778.

1H NMR

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Caffeine 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

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CaffeineWinChembase. http://www.chemicalbook.com/SpectrumEN_58-08-2_13CNMR.htm (accessed March 5, 2014)

UV-Vis

Solvent: water

Caffeine: max wavelength: 272nm

http://www.onsalesupplements.com/product/59-caffeine-powderSpectral 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

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Caffeine

1

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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).

1

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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

o Slower actingo 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.aspxAshihara, Hiroshi; Purine metabolism and the biosynthesis of caffeine in mate leaves. Phytochemistry 1993, 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

SAMSAH

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Caffeine

Product!

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Caffeine

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. Phytochemistry 1974, Volume 13, 2515-2518.

The Future for Caffeine

Continued abuse

Potential use in fighting cancer

Market will shift toward synthetic caffeine

The End