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27600 Sigma-Aldrich

Caffeine

purum, anhydrous, ≥99.0% (HPLC)

Synonym: 1,3,7-Trimethylxanthine

  • CAS Number 58-08-2

  • Empirical Formula (Hill Notation) C8H10N4O2

  • Molecular Weight 194.19

  •  Beilstein Registry Number 17705

  •  EC Number 200-362-1

  •  MDL number MFCD00005758

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Properties

Related Categories Alkaloid, Cell Biology, Nutrition Research, Phytochemicals by Chemical Classification
grade   purum
assay   ≥99.0% (HPLC)
mp   233-238 °C
  234-236.5 °C(lit.)
Gene Information   human ... ADORA1(134), PDE4B(5142)

Description

Other Notes

Pharmacology and toxicology1

Same product — same quality — now Sigma-Aldrich brand

Biochem/physiol Actions

A central nervous system stimulant believed to act through adenosine receptors and monoamine neurotransmitters. It is an adenosine receptor antagonist and adenosine 3′,5′-cyclic monophosphate (cAMP) phosphodiesterase inhibitor. Thus, levels of cAMP increase in cells following treatment with caffeine. It has been reported to affect cellular calcium levels, releasing calcium from intracellular stores. It overrides the cell cycle effects of various chemicals such as protease inhibitors, preventing apoptosis; and it has been shown to inhibit cellular DNA repair mechanisms.

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Safety Information

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GHS07  GHS07
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Warning
Hazard statements 
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RIDADR 
UN 1544 6.1/PG 3
WGK Germany 
1
RTECS 
EV6475000

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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Caffeine and the olfactory bulb. Hadfield, M.G. Mol. Neurobiol. 15, 31-39, (1997)

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Adenosine-dopamine receptor-receptor interactions as an integrative mechanism in the basal ganglia. Ferre, S., et al. Trends Neurosci. 20, 482-487, (1997)

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p53-independent anisomycin induced G1 arrest and apoptosis in L1210 cell lines. He, A.W., and Cory, J.G. Anticancer Res. 19, 421-428, (1999)

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DNA damage-associated cell cycle and cell death control is differentially modulated by caffeine in clones with p53 mutations. Takagi, M., et al. Leukemia 13, 70-77, (1999)

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QSAR study on permeability of hydrophobic compounds with artificial membranes. Masaaki Fujikawa et al Bioorg. Med. Chem. 15, 3756-67, (2007)

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Tacripyrines, the first tacrine-dihydropyridine hybrids, as multitarget-directed ligands for the treatment of Alzheimer's disease. José Marco-Contelles et al J. Med. Chem. 52, 2724-32, (2009)

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Biomarker measurements in a coastal fish-eating population environmentally exposed to organochlorines. Ayotte P, Dewailly E, Lambert GH, et al. Environ. Health Perspect. 113(10), 1318-24, (2005)

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Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. R Scott Obach et al Drug Metab. Dispos. 36, 1385-405, (2008)

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Caffeine suppresses homologous recombination through interference with RAD51-mediated joint molecule formation. Zelensky AN, Sanchez H, Ristic D, et al. Nucleic Acids Res. 41(13), 6475-89, (2013)

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Control of cognition and adaptive behavior by the GLP/G9a epigenetic suppressor complex. Schaefer A Neuron 64(5), 678-91, (2009)

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Pharmacogenetics of CYP1A2 activity and inducibility in smokers and exsmokers. Dobrinas M, Cornuz J, and Eap CB Pharmacogenet. Genomics 23(5), 286-92, (2013)

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Physicochemical determinants of human renal clearance. Manthena V S Varma et al J. Med. Chem. 52, 4844-52, (2009)

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Use of caffeinated substances and risk of crashes in long distance drivers of commercial vehicles: case-control study. Sharwood LN, Elkington J, Meuleners L, et al. BMJ 346, f1140, (2013)

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Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination. Manthena V S Varma et al J. Med. Chem. 53, 1098-108, (2010)

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Toward an optimal blood-brain barrier shuttle by synthesis and evaluation of peptide libraries. Morteza Malakoutikhah et al J. Med. Chem. 51, 4881-9, (2008)

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Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Sreekumar A, Poisson LM, Rajendiran TM, et al. Nature 457(7231), 910-4, (2009)

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Too much of a good thing. Consum. Rep. 78(3), 7, (2013)

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Simultaneous in vivo phenotyping of CYP enzymes. Ghassabian S and Murray M Methods Mol. Biol. 987, 261-7, (2013)

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Boiled or filtered coffee? Effects of coffee and caffeine on cholesterol, fibrinogen and C-reactive protein. Rodrigues IM and Klein LC Toxicol. Rev. 25(1), 55-69, (2006)

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Anesthesia concerns for children with tuberous sclerosis. Septer S, Thompson ES, and Willemsen-Dunlap A AANA J. 74(3), 219-25, (2006)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Neuroprotective and cholinergic properties of multifunctional glutamic acid derivatives for the treatment of Alzheimer's disease. Mariana P Arce et al J. Med. Chem. 52, 7249-57, (2009)

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The Japanese toxicogenomics project: application of toxicogenomics. Takeki Uehara et al Mol. Nutr. Food. Res. 54, 218-27, (2010)

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Intake of caffeinated, carbonated, or citrus beverage types and development of lower urinary tract symptoms in men and women. Maserejian NN, Wager CG, Giovannucci EL, et al. Am. J. Epidemiol. 177(12), 1399-410, (2013)

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Hologram QSAR model for the prediction of human oral bioavailability. Tiago L Moda et al Bioorg. Med. Chem. 15, 7738-45, (2007)

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Acetaminophen-induced acute liver failure: results of a United States multicenter, prospective study. Larson AM, Polson J, Fontana RJ, et al. Hepatology 42(6), 1364-72, (2005)

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Discovery of potent and selective inhibitors of ataxia telangiectasia mutated and Rad3 related (ATR) protein kinase as potential anticancer agents. Charrier, J.-D.; et al. J. Med. Chem. 54, 2320, (2011)

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Caffeine in floral nectar enhances a pollinator's memory of reward. Wright GA, Baker DD, Palmer MJ, et al. Science 339(6124), 1202-4, (2013)

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Biophysical mapping of the adenosine A2A receptor. Andrei Zhukov et al J. Med. Chem. 54, 4312-23, (2011)

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Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Lourdes Santana et al J. Med. Chem. 51, 6740-51, (2008)

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Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies. Xiaoan Wen et al J. Med. Chem. 51, 3540-54, (2008)

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1-alkyl-8-(piperazine-1-sulfonyl)phenylxanthines: development and characterization of adenosine A2B receptor antagonists and a new radioligand with subnanomolar affinity and subtype specificity. Thomas Borrmann et al J. Med. Chem. 52, 3994-4006, (2009)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Evaluation of a published in silico model and construction of a novel Bayesian model for predicting phospholipidosis inducing potential. Dennis J Pelletier et al J. Chem. Inf. Model. 47, 1196-205, (2007)

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A small chemical library of 2-aminoimidazole derivatives as BACE-1 inhibitors: Structure-based design, synthesis, and biological evaluation. Gianpaolo Chiriano et al Eur. J. Med. Chem. 48, 206-13, (2012)

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How well can the Caco-2/Madin-Darby canine kidney models predict effective human jejunal permeability? Alex Avdeef et al J. Med. Chem. 53, 3566-84, (2010)

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Developing structure-activity relationships for the prediction of hepatotoxicity. Nigel Greene et al Chem. Res. Toxicol. 23, 1215-22, (2010)

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High coffee intake, but not caffeine, is associated with reduced estrogen receptor negative and postmenopausal breast cancer risk with no effect modification by CYP1A2 genotype. Lowcock EC, Cotterchio M, Anderson LN, et al. Nutr. Cancer 65(3), 398-409, (2013)

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N-acylaminophenothiazines: neuroprotective agents displaying multifunctional activities for a potential treatment of Alzheimer's disease. Gema C González-Muñoz et al Eur. J. Med. Chem. 46, 2224-35, (2011)

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Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Gronwald W, Klein MS, Zeltner R, et al. Kidney Int. 79(11), 1244-53, (2011)

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Novel peptidomimetics containing a vinyl ester moiety as highly potent and selective falcipain-2 inhibitors. Roberta Ettari et al J. Med. Chem. 52, 2157-60, (2009)

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Neuroprotective efficacy of quinazoline type phosphodiesterase 7 inhibitors in cellular cultures and experimental stroke model. Miriam Redondo et al Eur. J. Med. Chem. 47, 175-85, (2012)

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Interactions of skin thickness and physicochemical properties of test compounds in percutaneous penetration studies. Wilkinson SC, Maas WJ, Nielsen JB, et al. Int. Arch. Occup. Environ. Health 79(5), 405-13, (2006)

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Relationship between brain tissue partitioning and microemulsion retention factors of CNS drugs. Hong Wan et al J. Med. Chem. 52, 1693-700, (2009)

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Studies on the interaction of caffeine with bovine hemoglobin. Yan-Qing Wang et al Eur. J. Med. Chem. 44, 2100-5, (2009)

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Intrauterine metabolic programming alteration increased susceptibility to non-alcoholic adult fatty liver disease in prenatal caffeine-exposed rat offspring. Wang L, Shen L, Ping J, et al. Toxicol. Lett. 224(3), 311-8, (2014)

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Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class. Canan Ku? et al Bioorg. Med. Chem. 16, 4294-303, (2008)

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Coffee and caffeine intake and breast cancer risk: an updated dose-response meta-analysis of 37 published studies. Jiang W, Wu Y, and Jiang X Gynecol. Oncol. 129(3), 620-9, (2013)

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Hybrids of oxoisoaporphine-tacrine congeners: novel acetylcholinesterase and acetylcholinesterase-induced ?-amyloid aggregation inhibitors. Huang Tang et al Eur. J. Med. Chem. 46, 4970-9, (2011)

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Restriction of dopamine signaling to the dorsolateral striatum is sufficient for many cognitive behaviors. Darvas M and Palmiter RD Proc. Natl. Acad. Sci. U. S. A. 106(34), 14664-9, (2009)

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A role for Chk1 in blocking transcriptional elongation of p21 RNA during the S-phase checkpoint. Beckerman R Genes Dev. 23(11), 1364-77, (2009)

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Simian virus 40 large T antigen disrupts genome integrity and activates a DNA damage response via Bub1 binding. Hein J J. Virol. 83(1), 117-27, (2009)

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Prediction of drug intestinal absorption by new linear and non-linear QSPR. Alan Talevi et al Eur. J. Med. Chem. 46, 218-28, (2011)

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Dual inhibition of monoamine oxidase B and antagonism of the adenosine A(2A) receptor by (E,E)-8-(4-phenylbutadien-1-yl)caffeine analogues. Judey Pretorius et al Bioorg. Med. Chem. 16, 8676-84, (2008)

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Rynaxypyr: a new insecticidal anthranilic diamide that acts as a potent and selective ryanodine receptor activator. George P Lahm et al Bioorg. Med. Chem. Lett. 17, 6274-9, (2007)

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Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure. Larry J Jolivette et al J. Pharm. Pharm. Sci. 94, 1467-83, (2005)

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Caffeine and adenosine A(2A) receptor inactivation decrease striatal neuropathology in a lentiviral-based model of Machado-Joseph disease. Gonçalves N, Simões AT, Cunha RA, et al. Ann. Neurol. 73(5), 655-66, (2013)

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Distinctive anatomical and physiological features of migraine aura revealed by 18 years of recording. Hansen JM, Baca SM, Vanvalkenburgh P, et al. Brain 136(Pt 12), 3589-95, (2013)

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A predictive ligand-based Bayesian model for human drug-induced liver injury. Sean Ekins et al Drug Metab. Dispos. 38, 2302-8, (2010)

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Occurrence and fate of PPCPs and correlations with water quality parameters in urban riverine waters of the Pearl River Delta, South China. Yang X, Chen F, Meng F, et al. Environ. Sci. Pollut. Res. Int. 20(8), 5864-75, (2013)

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Internal standard application to dried blood spots by spraying: investigation of the internal standard distribution. Zimmer D, Hassler S, Betschart B, et al. Bioanalysis 5(6), 711-9, (2013)

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Pentacyclic triterpenes. Part 3: Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase. Jun Chen et al Bioorg. Med. Chem. Lett. 16, 2915-9, (2006)

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Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors. Xiaoan Wen et al Bioorg. Med. Chem. Lett. 16, 722-6, (2006)

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New prognostic scoring model for liver transplantation in patients with non-acetaminophen-related fulminant hepatic failure. Miyake Y, Sakaguchi K, Iwasaki Y, et al. Transplantation 80(7), 930-6, (2005)

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Changes in taste neurons support the emergence of an adaptive behavior in cockroaches. Wada-Katsumata A, Silverman J, and Schal C Science 340(6135), 972-5, (2013)

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Insights into binding modes of adenosine A(2B) antagonists with ligand-based and receptor-based methods. Feixiong Cheng et al Eur. J. Med. Chem. 45, 3459-71, (2010)

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Pentacyclic triterpenes. Part 1: the first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases. Xiaoan Wen et al Bioorg. Med. Chem. Lett. 15, 4944-8, (2005)

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Novel oxoisoaporphine-based inhibitors of acetyl- and butyrylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation. Huang Tang et al Bioorg. Med. Chem. Lett. 22, 2257-61, (2012)

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Regulatory T-cell modulation by green tea in chronic lymphocytic leukemia. D'Arena G, Simeon V, De Martino L, et al. Int. J. Immunopathol. Pharmacol. 26(1), 117-25, (2013)

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Practical synthesis of bredemolic acid, a natural inhibitor of glycogen phosphorylase. Keguang Cheng et al J. Nat. Prod. 71, 1877-80, (2008)

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A nonsense mutation in the ERG6 gene leads to reduced susceptibility to polyenes in a clinical isolate of Candida glabrata. Patrick Vandeputte et al Antimicrob. Agents Chemother. 52, 3701-9, (2008)

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Caffeine does not increase the risk of atrial fibrillation: a systematic review and meta-analysis of observational studies. Caldeira D, Martins C, Alves LB, et al. Heart 99(19), 1383-9, (2013)

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Pentacyclic triterpenes. Part 5: synthesis and SAR study of corosolic acid derivatives as inhibitors of glycogen phosphorylases. Xiaoan Wen et al Bioorg. Med. Chem. Lett. 17, 5777-82, (2007)

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Effect of smoking and caffeine consumption on polybrominated diphenyl ethers (PBDE) and polybrominated biphenyls (PBB). Jain RB J. Toxicol. Environ. Health A 76(8), 515-32, (2013)

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Urinary inflammatory mediators and inhalation of hypertonic saline in children. Mai XM, Böttcher MF, Bruhammar M, et al. Allergy 60(1), 60-4, (2005)

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Urinary 3-bromotyrosine and 3-chlorotyrosine concentrations in asthmatic patients: lack of increase in 3-bromotyrosine concentration in urine and plasma proteins in aspirin-induced asthma after intravenous aspirin challenge. Mita H, Higashi N, Taniguchi M, et al. Clin. Exp. Allergy 34(6), 931-8, (2004)

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Synthesis of 3-deoxypentacyclic triterpene derivatives as inhibitors of glycogen phosphorylase. Pu Zhang et al J. Nat. Prod. 72, 1414-8, (2009)

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Determination of log D via automated microfluidic liquid-liquid extraction. Muhammad Alimuddin et al J. Med. Chem. 51, 5140-2, (2008)

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Novel N-methylated 8-oxoisoguanines from Pacific sponges with diverse neuroactivities. Tsuyoshi Sakurada et al J. Med. Chem. 53, 6089-99, (2010)

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2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists. Anja B Scheiff et al Bioorg. Med. Chem. 18, 2195-203, (2010)

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Screening for long-lived genes identifies Oga1, a guanine-quadruplex associated protein that affects the chronological lifespan of the fission yeast Schizosaccharomyces pombe. Ohtsuka H, Ogawa S, Kawamura H, et al. Mol. Genet. Genomics 288(5-6), 285-95, (2013)

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Predicting hERG activities of compounds from their 3D structures: development and evaluation of a global descriptors based QSAR model. Nandita Sinha et al Eur. J. Med. Chem. 46, 618-30, (2011)

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The effect of black tea and caffeine on regional cerebral blood flow measured with arterial spin labeling. Vidyasagar R, Greyling A, Draijer R, et al. J. Cereb. Blood Flow Metab. 33(6), 963-8, (2013)

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Computational modeling of novel inhibitors targeting the Akt pleckstrin homology domain. Lei Du-Cuny et al Bioorg. Med. Chem. 17, 6983-92, (2009)

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Impairment of mitochondrial calcium handling in a mtSOD1 cell culture model of motoneuron disease. Jaiswal, MK BMC Neurosci. 10, 64, (2009)

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Synthesis of hybrid molecules of caffeine and eudistomin D and its effects on adenosine receptors. Kengo Ohshita et al Bioorg. Med. Chem. 15, 3235-40, (2007)

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Graphene matrix for signal enhancement in ambient plasma assisted laser desorption ionization mass spectrometry. Chang C, Li X, Bai Y, et al. Talanta 114, 54-9, (2013)

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Acute effects of tea consumption on attention and mood. Einöther SJ and Martens VE Am. J. Clin. Nutr. 98(6 Suppl), 1700S-1708S, (2013)

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Plasmalemmal sodium-calcium exchanger shapes the calcium and exocytotic signals of chromaffin cells at physiological temperature. Padín JF, Fernández-Morales JC, Olivares R, et al. Am. J. Physiol. Cell Physiol. 305(2), C160-72, (2013)

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Intake of coffee, caffeine and other methylxanthines and risk of Type I vs Type II endometrial cancer. Uccella S, Mariani A, Wang AH, et al. Br. J. Cancer 109(7), 1908-13, (2013)

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Prospective study of the relationship between coffee and tea with colorectal cancer risk: the PLCO Cancer Screening Trial. Dominianni C, Huang WY, Berndt S, et al. Br. J. Cancer 109(5), 1352-9, (2013)

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Determination of permeability and lipophilicity of pyrazolo-pyrimidine tyrosine kinase inhibitors and correlation with biological data. Elena Dreassi et al Eur. J. Med. Chem. 44, 3712-7, (2009)

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Inhibition of monoamine oxidase by (E)-styrylisatin analogues. Elizna M Van der Walt et al Bioorg. Med. Chem. Lett. 19, 2509-13, (2009)

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Synthesis of eudistomin D analogues and its effects on adenosine receptors. Haruaki Ishiyama et al Bioorg. Med. Chem. 16, 3825-30, (2008)

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Tea catechins and flavonoids from the leaves of Camellia sinensis inhibit yeast alcohol dehydrogenase. Md Maniruzzaman Manir et al Bioorg. Med. Chem. 20, 2376-81, (2012)

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Increases in cerebrospinal fluid caffeine concentration are associated with favorable outcome after severe traumatic brain injury in humans. Sachse KT, Jackson EK, Wisniewski SR, et al. J. Cereb. Blood Flow Metab. 28(2), 395-401, (2008)

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Hepatic veno-occlusive disease due to tacrolimus in a single-lung transplant patient. Shah S, Budev M, Blazey H, et al. Eur. Respir. J. 27(5), 1066-8, (2006)

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Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. Zydroń M, Baranowski J, and Baranowska I J. Sep. Sci. 27(14), 1166-72, (2004)

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Chronological effects of rifampicin discontinuation on cytochrome P450 activity in healthy Japanese volunteers, using the cocktail method. Inui N, Akamatsu T, Uchida S, et al. Clin. Pharmacol. Ther. 94(6), 702-8, (2013)

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Binding thermodynamics as a tool to investigate the mechanisms of drug-receptor interactions: thermodynamics of cytoplasmic steroid/nuclear receptors in comparison with membrane receptors. Paola Gilli et al J. Med. Chem. 48, 2026-35, (2005)

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Caffeine and modafinil promote adult neuronal cell proliferation during 48 h of total sleep deprivation in rat dentate gyrus. Sahu S, Kauser H, Ray K, et al. Exp. Neurol. 248, 470-81, (2013)

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Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models. Naomi L Kruhlak et al Toxicol. Mech. Methods 18, 217-27, (2008)

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First-principle, structure-based prediction of hepatic metabolic clearance values in human. Haiyan Li et al Eur. J. Med. Chem. 44, 1600-6, (2009)

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N9-benzyl-substituted 1,3-dimethyl- and 1,3-dipropyl-pyrimido[2,1-f]purinediones: synthesis and structure-activity relationships at adenosine A1 and A2A receptors. Anna Drabczyńska et al Bioorg. Med. Chem. 15, 5003-17, (2007)

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Long-term alcohol and caffeine intake and risk of sudden cardiac death in women. Bertoia ML, Triche EW, Michaud DS, et al. Am. J. Clin. Nutr. 97(6), 1356-63, (2013)

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Collision-induced dissociation studies of caffeine in positive electrospray ionisation mass spectrometry using six deuterated isotopomers and one N1-ethylated homologue. Bier D, Hartmann R, and Holschbach M Rapid Commun. Mass Spectrom. 27(8), 885-95, (2013)

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Neural computational prediction of oral drug absorption based on CODES 2D descriptors. A Guerra et al Eur. J. Med. Chem. 45, 930-40, (2010)

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Selected health and behavioral effects related to the use of caffeine. Lamarine RJ J. Community Health 19(6), 449-66, (1994)

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QSAR-based permeability model for drug-like compounds. Rafael Gozalbes et al Bioorg. Med. Chem. 19, 2615-24, (2011)

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Identification of small molecule compounds with higher binding affinity to guanine deaminase (cypin) than guanine. José R Fernández et al Bioorg. Med. Chem. 18, 6748-55, (2010)

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Phenylethyl-substituted pyrimido[2,1-f]purinediones and related compounds: structure-activity relationships as adenosine A(1) and A(2A) receptor ligands. Anna Drabczyńska et al Bioorg. Med. Chem. 15, 6956-74, (2007)

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Efficacy of activated charcoal administered more than four hours after acetaminophen overdose. Spiller HA, Winter ML, Klein-Schwartz W, et al. J. Emerg. Med. 30(1), 1-5, (2006)

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Inhibition of CTP synthase from Escherichia coli by xanthines and uric acids. Alexander C Roy et al Bioorg. Med. Chem. Lett. 20, 141-4, (2010)

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Prediction of volume of distribution values in human using immobilized artificial membrane partitioning coefficients, the fraction of compound ionized and plasma protein binding data. Xiaofan Sui et al Eur. J. Med. Chem. 44, 4455-60, (2009)

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Impaired mutagenic activities of MPDP(+) (1-methyl-4-phenyl-2,3-dihydropyridinium) and MPP(+) (1-methyl-4-phenylpyridinium) due to their interactions with methylxanthines. Katarzyna Ulanowska et al Bioorg. Med. Chem. 15, 5150-7, (2007)

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Activation and inhibition of CTP synthase from Trypanosoma brucei, the causative agent of African sleeping sickness. Craig H Steeves et al Bioorg. Med. Chem. Lett. 21, 5188-90, (2011)

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Caffeine reduces myocardial blood flow during exercise. Higgins JP and Babu KM Am. J. Med. 126(8), 730.e1-8, (2013)

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Detection of caffeine in tea, instant coffee, green tea beverage, and soft drink by direct analysis in real time (DART) source coupled to single-quadrupole mass spectrometry. Wang L, Zhao P, Zhang F, et al. J. AOAC Int. 96(2), 353-6, (2013)

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Terpenoids. III: Synthesis and biological evaluation of 23-hydroxybetulinic acid derivatives as novel inhibitors of glycogen phosphorylase. Peiqing Zhu et al Bioorg. Med. Chem. Lett. 19, 6966-9, (2009)

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Glycogen phosphorylase inhibitory effects of 2-oxo-1,2-dihydropyridin-3-yl amide derivatives. N David Karis et al Bioorg. Med. Chem. 17, 4724-33, (2009)

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Synthesis of hybrid analogues of caffeine and eudistomin D and its affinity for adenosine receptors. Haruaki Ishiyama et al Bioorg. Med. Chem. 17, 4280-4, (2009)

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Molecular imaging of the ATM kinase activity. Williams TM, Nyati S, Ross BD, et al. Int. J. Radiat. Oncol. Biol. Phys. 86(5), 969-77, (2013)

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The MP65 gene is required for cell wall integrity, adherence to epithelial cells and biofilm formation in Candida albicans. Sandini S BMC Microbiol. 11, 106, (2011)

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Design and synthesis of novel photoaffinity probes for study of the target proteins of oleanolic acid. Liying Zhang et al Bioorg. Med. Chem. Lett. 22, 1036-9, (2012)

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A method for the measurement of plasma hydroxyeicosatetraenoic acid levels. Chavis, C., et al. Anal. Biochem. 271, 105-108, (1999)

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Efficient synthesis and biological evaluation of epiceanothic acid and related compounds. Pu Zhang et al Bioorg. Med. Chem. Lett. 21, 338-41, (2011)

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Development of an in silico model for human skin permeation based on a Franz cell skin permeability assay. Pil H Lee et al Bioorg. Med. Chem. Lett. 20, 69-73, (2010)

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Determination of catechins and caffeine in camillia sinensis raw materials, extracts, and dietary supplements by HPLC-uv: single-laboratory validation. Roman MC J. AOAC Int. 96(5), 933-41, (2013)

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An RP-HPLC-UV method with SPE for cefotaxime in all-in-one total parenteral nutritional admixtures: application to stability studies. Iqbal MS, Bahari MB, Darwis Y, et al. J. AOAC Int. 96(2), 290-4, (2013)

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Simultaneous determination of L-tyrosine and caffeine based on their electrocatalytic oxidation at a 4-tert-butylcalix[6] arene-modified carbon paste electrode. Srivastava AK and Gaichore RR J. AOAC Int. 96(1), 133-41, (2013)

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N-acylhydrazone improves exercise intolerance in rats submitted to myocardial infarction by the recovery of calcium homeostasis in skeletal muscle. da Silva JS, Pereira SL, Maia Rdo C, et al. Life Sci. 94(1), 30-6, (2014)

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Caffeinated-beverage consumption and its association with socio-demographic characteristics and self-perceived academic stress in first and second year students at the University of Puerto Rico Medical Sciences Campus (UPR-MSC). Ríos JL, Betancourt J, Pagán I, et al. P. R. Health Sci. J. 32(2), 95-100, (2013)

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Caffeine gum minimizes sleep inertia. Newman RA, Kamimori GH, Wesensten NJ, et al. Percept. Mot. Skills 116(1), 280-93, (2013)

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Actual treatment of overactive bladder and urge urinary incontinence. Cornu JN Minerva Urol. Nefrol. 65(1), 21-35, (2013)

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[Vasobral in the treatment of brain lesions: views of physicians and patients]. Kamchatnov PR Zh. Nevrol. Psikhiatr. Im. S. S. Korsakova 113(1), 23-5, (2013)

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Genetics of drug-induced hepatotoxicity toxicity in Gilbert's syndrome. Raza A, Vierling J, and Hussain KB Am. J. Gastroenterol. 108(12), 1936-7, (2013)

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Caffeine-induced rhabdomyolysis. Golcuk Y, Ozsarac M, Golcuk B, et al. Am. J. Emerg. Med. 32(1), 100, (2014)

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Energy drinks: cause for concern or scaremongering? Roehr B BMJ 347, f6343, (2013)

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Caffeine overdose resulting in severe rhabdomyolysis and acute renal failure. Campana C, Griffin PL, and Simon EL Am. J. Emerg. Med. 32(1), 111.e3-4, (2014)

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Energy drinks and alcohol: research supported by industry may be downplaying harms. Miller P BMJ 347, f5345, (2013)

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Caffeine and atrial fibrillation: friends or foes? Bhave PD and Hoffmayer K Heart 99(19), 1377-8, (2013)

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The toxicity of energy drinks: myth or reality? Hoyte C Clin. Toxicol. (Phila.) 51(8), 729-30, (2013)

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Protective effects of subchronic caffeine administration on cisplatin induced urogenital toxicity in male mice. Nasri H Indian J. Exp. Biol. 51(5), 406, (2013)

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Merck 14,1636

Beil. 26,461 / Beil. 26,IV,2338

Aldrich MSDS 1, 343:A / Corp MSDS 1 (1), 664:C / FT-IR 1 (2), 710:B / FT-IR 2 (3), 3668:B / IR-Spectra (2), 1120:B / IR-Spectra (3), 1287:D / NMR-Reference 2 (2), 586:A / RegBook 1 (2), 2467:A / Sax 6, 615 / Sigma FT-IR 1 (1), 581:A / Structure Index 1, 390:E:3

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