Theophylline
- Formula: C7H8N4O2
- Molecular weight: 180.1640
- IUPAC Standard InChIKey: ZFXYFBGIUFBOJW-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - 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)
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Options:
Phase change data
Go To: Top, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Subscription Links, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 544.7 | K | N/A | Bruns, Reichelt, et al., 1984 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 135. | kJ/mol | N/A | Fokkens, van Amelsfoort, et al., 1983 | See also Emmenegger and Piccand, 1999.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
126. | 421. | ME,TE | Fokkens, van Amelsfoort, et al., 1983 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
19. | 546.8 | DSC | Good and Rodriguez-Hornedo, 2009 | AC |
28.2 | 544. | N/A | Gondová, Králik, et al., 1989 | AC |
28.2 | 542.3 | N/A | SUZUKI, SHIMOMURA, et al., 1989 | AC |
31.2 | 543.7 | N/A | Fokkens, van Amelsfoort, et al., 1983 | AC |
IR Spectrum
Go To: Top, Phase change data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Subscription Links, References, Notes
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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
View spectrum image in SVG format.
Download spectrum in JCAMP-DX format.
Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
Mass spectrum (electron ionization)
Go To: Top, Phase change data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, NIST Subscription Links, References, Notes
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
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118946 |
UV/Visible spectrum
Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Subscription Links, References, Notes
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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
View spectrum image in SVG format.
Download spectrum in JCAMP-DX format.
Source | Fuchs, Gottlieb, et al., 1978 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 4832 |
Instrument | Cary Model 1115/15 |
Melting point | 273 |
Gas Chromatography
Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, NIST Subscription Links, References, Notes
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | BP-1 | 200. | 1909. | Japp, Gill, et al., 1987 | 25. m/0.22 mm/0.25 μm, N2 |
Capillary | DB-1 | 200. | 1904. | Japp, Gill, et al., 1987 | 30. m/0.53 mm/1.5 μm, N2 |
Capillary | BP-1 | 200. | 1923. | Japp, Gill, et al., 1987 | 25. m/0.53 mm/1. μm, N2 |
Capillary | SPB-1 | 250. | 1962. | Lora-Tamayo, Rams, et al., 1986 | He; Column length: 25. m; Column diameter: 0.20 mm |
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 1947. | Schepers, Wijsbeek, et al., 1982 | 25. m/0.49 mm/1.14 μm, 100. C @ 2. min, 8. K/min, 275. C @ 15. min |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | OV-1 | 1990. | Berninger, Grunnagel, et al., 1975 | N2, Chromosorb G, AW-DMCS; Column length: 2. m; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CBP-1 | 1900. | Oyama, Sano, et al., 1987 | N2, 6. K/min; Column length: 12. m; Column diameter: 0.53 mm; Tstart: 120. C; Tend: 250. C |
Capillary | DB-1 | 1917. | Perrigo, Peel, et al., 1985 | 15. m/0.32 mm/0.25 μm, He, 8. K/min, 280. C @ 5. min; Tstart: 120. C |
Capillary | DB-1 | 1917. | Perrigo, Ballantyne, et al., 1984 | 15. m/0.25 mm/0.25 μm, He, 8. K/min, 280. C @ 5. min; Tstart: 120. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BP-1 | 1917. | Stowell and Wilson, 1987 | 12. m/0.22 mm/0.25 μm, He; Program: 120C => 8C/min => 270C => 25C/min => 300C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 1900. | Anderson and Fuller, 1987 | 10. m/0.53 mm/2.65 μm, He, 5. K/min; Tstart: 130. C; Tend: 230. C |
Capillary | DB-1 | 1921. | Sharp, 1987 | 15. m/0.25 mm/0.25 μm, He, 130. C @ 1. min, 10. K/min, 290. C @ 10. min |
Capillary | BP-1 | 1917. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He, 8. K/min; Tstart: 120. C; Tend: 280. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BP-1 | 1917. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: 120 0X 8 0C/min -> 270 0C 25 0C/min -> 300 0C (5 min) |
References
Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Subscription Links, Notes
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
Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Subscription Links, References
- 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.