Theophylline

• Formula: C₇H₈N₄O₂
• Molecular weight: 180.1640
• IUPAC Standard InChI: InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9) Copy

  
• IUPAC Standard InChIKey: ZFXYFBGIUFBOJW-UHFFFAOYSA-N Copy
• CAS Registry Number: 58-55-9
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: 1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-; Elixophyllin; Elixophylline; Lanophyllin; Liquophylline; Optiphyllin; Parkophyllin; Pseudotheophylline; Solosin; Teofyllamin; Theocin; Theofol; Theograd; Theophyllin; 1,3-Dimethylxanthine; Acet-theocin; Aerolate III; Diphyllin; Doraphyllin; Elixex; GS 2591A; Maphylline; Medaphyllin; Nuelin; NSC 2066; Purine-2,6(1H,3H)-dione, 1,3-dimethyl-; Respbid; Synophylate-L.A. Cenules; Tefamin; Teolair; Theacitin; Theo-11; Theocontin; Theolair; Theophyl-225; Theophylline, anhydrous; Theovent; X 115; Xanthine, 1,3-dimethyl-; Xantivent; 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione; Elixicon; Euphylline; Slo-phyllin; Teofilina; Theal tabl.; Theo-Dur; Theolix; Theophyline; Theona P; Theodel; Unifyl; Uniphyl; Uniphyllin; Xanthium; Unicontin CR; Quibron T/SR; 1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-; Physpa; PulmiDur; Accurbron; Aerobin; Diffumal; Duraphyl; Telbans; Teocen 200; Teonova; Theopek; Slo-Bid; component of Bronkotabs (Salt/Mix); component of Dicurin Procaine (Salt/Mix); component of Hecadrol (Salt/Mix); component of Primatene (Salt/Mix); component of Quibron (Salt/Mix); component of Quibron Plus (Salt/Mix); component of Tedral (Salt/Mix); component of Theo-Organidin (Salt/Mix); component of Mudrane GG elixir (Salt/Mix); component of Primatene tablets (Salt/Mix); component of Quibron-T/SR (Salt/Mix); component of Slo-phyllin GG (Salt/Mix); component of Theo-organdin (Salt/Mix); component of Theolair plus (Salt/Mix); 1,3-Dimethylxanthine (theophylline)
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• Information on this page:
  • Phase change data
  • IR Spectrum
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
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Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Enthalpy of fusion

IR Spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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Additional Data

UV/Visible spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Bruns, Reichelt, et al., 1984
Bruns, S.; Reichelt, J.; Cammenga, H.K., Thermochemical investigation of theophylline, theophylline hydrate and their aqueous solutions, Thermochim. Acta, 1984, 72, 31. [all data]

Fokkens, van Amelsfoort, et al., 1983
Fokkens, J.G.; van Amelsfoort, J.G.M.; de Blaey, C.J.; de Kruif, C.G.; Wilting, J., A thermodynamic study of the solubility of theophylline and its hydrate, International Journal of Pharmaceutics, 1983, 14, 1, 79-93, https://doi.org/10.1016/0378-5173(83)90116-3 . [all data]

Emmenegger and Piccand, 1999
Emmenegger, F.; Piccand, M., Organometallics, 1999, 57, 1, 235-240, https://doi.org/10.1023/A:1010100531350 . [all data]

Good and Rodriguez-Hornedo, 2009
Good, David J.; Rodriguez-Hornedo, Nair, Solubility Advantage of Pharmaceutical Cocrystals, Crystal Growth & Design, 2009, 9, 5, 2252-2264, https://doi.org/10.1021/cg801039j . [all data]

Gondová, Králik, et al., 1989
Gondová, T.; Králik, P.; Gonda, J., Determination of some thermodynamic characteristics of melting of 8-alkyltheophyllines by the DSC method, Thermochimica Acta, 1989, 156, 1, 147-155, https://doi.org/10.1016/0040-6031(89)87180-1 . [all data]

SUZUKI, SHIMOMURA, et al., 1989
SUZUKI, Etsuko; SHIMOMURA, Kikuko; SEKIGUCHI, Keiji, Thermochemical study of theophylline and its hydrate., Chem. Pharm. Bull., 1989, 37, 2, 493-497, https://doi.org/10.1248/cpb.37.493 . [all data]

Fuchs, Gottlieb, et al., 1978
Fuchs, H.; Gottlieb, M.; Pfleiderer, W., Uber die cyclisierung von 4-alkylamino-5-nitrosouracilen und die synthese von 8-substituierten xanthinen und bis(theophyllin-8-yl)-alkan-derivaten, Chem. Ber., 1978, 111, 982-995. [all data]

Japp, Gill, et al., 1987
Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 1987, 32, 6, 1574-1586. [all data]

Lora-Tamayo, Rams, et al., 1986
Lora-Tamayo, C.; Rams, M.A.; Chacon, J.M.R., Gas Chromatographic Data for 187 Nitrogen- or Phosphorus-Containing Drugs and Metabolites of Toxicological Interest Analysed on Methyl Silicone Capillary Columns, J. Chromatogr., 1986, 374, 73-85, https://doi.org/10.1016/S0378-4347(00)83254-5 . [all data]

Schepers, Wijsbeek, et al., 1982
Schepers, P.; Wijsbeek, J.; Franke, J.P.; de Zeeuw, R.A., Applicability of capillary gas chromatography to substance identification in toxicology by means of retention indices, J. Forensic Sci., 1982, 27, 1, 49-60. [all data]

Berninger, Grunnagel, et al., 1975
Berninger, H.; Grunnagel, R.; Mall, S.; Moller, M.R., Gas chromatographic identification of unknown substances from body fluids by menas of retention indices, Beitr. Gerichtl. Med., 1975, 33, 185-191. [all data]

Oyama, Sano, et al., 1987
Oyama, N.; Sano, T.; Syoyama, M.; Maeda, K., Studies on systematic analysis of poisonous compounds in forensic chemistry. II. Application of capillary column gas chromatography to substance identification by means of retention indices, Eisei Kagaku, 1987, 33, 5, 342-348, https://doi.org/10.1248/jhs1956.33.342 . [all data]

Perrigo, Peel, et al., 1985
Perrigo, B.J.; Peel, H.W.; Ballantyne, D.J., Use of Dual-Column Fused-Silica Capillary Gas Chromatography in Combination with Detector Response Factors for Analytical Toxicology., J. Chromatogr., 1985, 341, 81-88, https://doi.org/10.1016/S0378-4347(00)84011-6 . [all data]

Perrigo, Ballantyne, et al., 1984
Perrigo, B.J.; Ballantyne, D.J.; Peel, H.W., Condierations in developing a data base for drugs on a DBI capillary column, J. Can. Soc. Forensic Sci., 1984, 17, 2, 41-49, https://doi.org/10.1080/00085030.1984.10757360 . [all data]

Stowell and Wilson, 1987
Stowell, A.; Wilson, L.W., A simple approach to the interlaboratory transfer of drug retention indices determined by temperature programmed capillary gas chromatography, J. Forensic Sci., 1987, 32, 5, 1214-1220. [all data]

Anderson and Fuller, 1987
Anderson, W.H.; Fuller, D.C., A simplified procedure for the isolation, characterization, and identification of weak acid and neutral drugs from whole blood, J. Anal. Toxicol., 1987, 11, 5, 198-204, https://doi.org/10.1093/jat/11.5.198 . [all data]

Sharp, 1987
Sharp, M.E., A rapid screening procedure for acidic and neutral drugs in blood by high resolution gas chromatography, J. Anal. Toxicol., 1987, 11, 1, 8-11, https://doi.org/10.1093/jat/11.1.8 . [all data]

Stowell and Wilson, 1985
Stowell, A.; Wilson, L., Use of retention indices in drug screening by capillary gas chromatography, Rep. # CD 2362, Department of Scientific and Industrial Reseach, Chemistry Division, Lower Hutt, NZ, 1985, 32. [all data]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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