Caffeine

Papers

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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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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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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Parallel artificial membrane permeability assay: a new membrane for the fast prediction of passive human skin permeability. Giorgio Ottaviani et al J. Med. Chem. 49, 3948-54, (2006)

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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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Identifying off-target effects and hidden phenotypes of drugs in human cells. Marnie L MacDonald et al Nat. Chem. Biol. 2, 329-37, (2006)

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In silico and in vitro filters for the fast estimation of skin permeation and distribution of new chemical entities. Giorgio Ottaviani et al J. Med. Chem. 50, 742-8, (2007)

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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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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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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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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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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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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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Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds. Bram Baert et al Bioorg. Med. Chem. 15, 6943-55, (2007)

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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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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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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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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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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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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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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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Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1. Gustav Ahlin et al J. Med. Chem. 51, 5932-42, (2008)

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

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Pyrano[3,2-c]quinoline-6-chlorotacrine hybrids as a novel family of acetylcholinesterase- and beta-amyloid-directed anti-Alzheimer compounds. Pelayo Camps et al J. Med. Chem. 52, 5365-79, (2009)

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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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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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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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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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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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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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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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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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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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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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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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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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N-methyl phenylalanine-rich peptides as highly versatile blood-brain barrier shuttles. Morteza Malakoutikhah et al J. Med. Chem. 53, 2354-63, (2010)

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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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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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Structure-activity relationship and mechanism of action studies of manzamine analogues for the control of neuroinflammation and cerebral infections. Peng, J.; et al. J. Med. Chem. 53, 61, (2010)

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

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

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

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

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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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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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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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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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Translating Clinical Findings into Knowledge in Drug Safety Evaluation - Drug Induced Liver Injury Prediction System (DILIps). Zhichao Liu et al PLoS Comput. Biol. 7, e1002310, (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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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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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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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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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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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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Reduced DNA synthesis and cell viability in small cell lung carcinoma by treatment with cyclic AMP phosphodiesterase inhibitors. Shafer, S.H., et al. Biochem. Pharmacol. 56, 1229-1236, (1998)

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In situ activation of the type 2 ryanodine receptor in pancreatic beta cells requires cAMP-dependent phosphorylation. Islam, M.S., et al. Proc. Natl. Acad. Sci. U. S. A. 95, 6145-6150, (1998)

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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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Caffeine modulates heat shock induced apoptosis in the human promyelocytic leukemia cell line HL-60. Poe, B.S., and O'Neill, K.L. Cancer Lett. 121, 1-6, (1997)

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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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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