Phenobarbital

Formula: C₁₂H₁₂N₂O₃
Molecular weight: 232.2353
IUPAC Standard InChI: InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)
IUPAC Standard InChIKey: DDBREPKUVSBGFI-UHFFFAOYSA-N
CAS Registry Number: 50-06-6
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: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-phenyl-; Barbituric acid, 5-ethyl-5-phenyl-; Adonal; Agrypnal; Amylofene; Barbenyl; Barbiphenyl; Barbipil; Barbita; Barbivis; Blu-phen; Cratecil; Dormiral; Doscalun; Duneryl; Eskabarb; Etilfen; Euneryl; Fenemal; Gardenal; Gardepanyl; Hysteps; Lepinal; Lepinaletten; Liquital; Lixophen; Lubergal; Luminal; Neurobarb; Noptil; Nunol; Phenaemal; Phenemal; Phenobarbitone; Phenobarbituric acid; Phenoluric; Phenonyl; Phenylethylbarbituric acid; Phenylethylmalonylurea; Phenyral; Phob; Sedonal; Sevenal; Somonal; Stental Extentabs; Teolaxin; Triphenatol; Versomnal; 5-Ethyl-5-phenylbarbituric acid; 5-Phenyl-5-ethylbarbituric acid; Aephenal; Aphenylbarbit; Aphenyletten; Barbilehae (barbilettae); Barbinal; Barbiphen; Barbonal; Barbophen; Bardorm; Bartol; Bialminal; Cabronal; Calmetten; Calminal; Cardenal; Chinoin; Codibarbita; Coronaletta; Damoral; Dezibarbitur; Dormina; Ensobarb; Ensodorm; Epanal; Epidorm; Epilol; Episedal; Epsylone; Fenbital; Fenobarbital; Fenosed; Fenylettae; Glysoletten; Haplopan; Haplos; Helional; Hennoletten; Henotal; Hypnaletten; Hypnette; Hypno-Tablinetten; Hypnogen; Hypnolone; Hypnoltol; Lefebar; Leonal; Lephebar; Linasen; Lubrokal; Lumen; Lumesettes; Lumesyn; Lumofridetten; Luphenil; Luramin; Molinal; Nirvonal; Nova-Pheno; Parkotal; Pharmetten; Phen-Bar; Phenemalum; Phenobal; Phenobarbitol; Phenobarbyl; Phenolurio; Phenomet; Phenoturic; Phenylethylbarbiturate; Phenyletten; Polcominal; Promptonal; Seda-Tablinen; Sedabar; Sedicat; Sedizorin; Sedlyn; Sedofen; Sedonettes; Solfoton; Solu-Barb; Sombutol; Somnolens; Somnoletten; Somnosan; Spasepilin; Starifen; Starilettae; Stental; Talpheno; Teoloxin; Thenobarbital; Theoloxin; Triabarb; Tridezibarbitur; Zadoletten; Zadonal; 5-Ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione; Mephobarbital M (nor); Methylphenobarbital, M(nor-); Fenemal recip; Phenobar; Sedophen; Sedonal (sedative); component of Antrocol; component of Bronkotabs; component of Hecadrol; component of Hydantal; component of Primatene P; component of Slowten; component of Tedral; component of Valpin 50-PB; Dormital; SK-Phenobarbital; Sinoratox; component of Barbidonna; component of Chardonna-2; component of Donnatal; component of Donnazyme; component of Kinesed; component of Levsin pb drops and tablets; component of Quadrinal; Solfoton talpheno; Primidone, M (phenobarbital); Antrocol (Salt/Mix); Barbidonna (Salt/Mix); Bronkotabs (Salt/Mix); Chardonna-2 (Salt/Mix); Donnatal (Salt/Mix); Donnazyme (Salt/Mix); Hydantal (Salt/Mix); Kinesed (Salt/Mix); Quadrinal (Salt/Mix); Tedral (Salt/Mix); Levsin PB Drops and Tablets (Salt/Mix); component of Primatene P (Salt/Mix); component of Valpin 50-PB (Salt/Mix)
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Phase change data

Go To: Top, Gas Chromatography, References, Notes

Data compiled by: Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director

Quantity	Value	Units	Method	Reference	Comment
T_fus	449.	K	N/A	Kuffner, Bush, et al., 1957	Uncertainty assigned by TRC = 4. K; not clear that this was measured by author

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Gas Chromatography

Go To: Top, Phase change data, References, Notes

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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	DB-5	220.	1984.	Phillips, Logan, et al., 1990	15. m/0.25 mm/0.2 μm, He
Capillary	BP-1	200.	1932.	Japp, Gill, et al., 1987	25. m/0.22 mm/0.25 μm, N2
Capillary	DB-1	200.	1931.	Japp, Gill, et al., 1987	30. m/0.53 mm/1.5 μm, N2
Capillary	BP-1	200.	1937.	Japp, Gill, et al., 1987	25. m/0.53 mm/1. μm, N2
Capillary	SPB-1	250.	1995.	Lora-Tamayo, Rams, et al., 1986	He; Column length: 25. m; Column diameter: 0.20 mm
Packed	SE-30	200.	1934.	Stead, Gill, et al., 1982
Packed	OV-1	200.	1955.	Berninger and Möller, 1977
Packed	OV-101	200.	1950.	Möller, 1976	N2, Chromosorb G AW DMCS (80-100 mesh); Column length: 2. m
Packed	OV-101	200.	1955.	Möller, 1976	N2, Chromosorb G AW DMCS (80-100 mesh); Column length: 2. m
Packed	OV-101	200.	1955.	Möller, 1976	N2, Chromosorb G AW DMCS (80-100 mesh); Column length: 2. m
Packed	OV-101	200.	1960.	Möller, 1976	N2, Chromosorb G AW DMCS (80-100 mesh); Column length: 2. m

Kovats' RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Packed	SE-30	1965.	Maurer, 1990	N2, 100. C @ 3. min, 30. K/min, 310. C @ 5. min
Packed	SE-30	1965.	Maurer, 1990	N2, 100. C @ 3. min, 30. K/min, 310. C @ 5. min
Packed	OV-101	1965.	Maurer, 1990, 2	N2, Chromosorb G HP, 100. C @ 3. min, 30. K/min, 310. C @ 5. min; Column length: 0.6 m
Packed	OV-101	1965.	Maurer, 1990, 2	N2, Chromosorb G HP, 100. C @ 3. min, 30. K/min, 310. C @ 5. min; Column length: 0.6 m
Packed	OV-101	1965.	Maurer, 1990, 2	N2, Chromosorb G HP, 100. C @ 3. min, 30. K/min, 310. C @ 5. min; Column length: 0.6 m
Capillary	SE-30	1939.	Schepers, Wijsbeek, et al., 1982	12. m/0.22 mm/0.45 μm, He, 120. C @ 2. min, 8. K/min, 300. C @ 12. min
Capillary	SE-30	1938.	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

View large format table.

Column type	Active phase	I	Reference	Comment
Packed	OV-101	1990.	McLinden and Stenhouse, 1979	N2, Chromosorb W; Column length: 2. m; Program: not specified
Packed	OV-1	1975.	Berninger, Grunnagel, et al., 1975	N2, Chromosorb G, AW-DMCS; Column length: 2. m; Program: not specified
Packed	OV-1	1970.	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

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Column type	Active phase	I	Reference	Comment
Capillary	SPB-1	1944.	Christ, Noomano, et al., 1988	30. m/0.75 mm/1.0 μm, He, 10. K/min, 280. C @ 12. min; T_start: 160. C
Capillary	DB-1	1928.	Perrigo, Peel, et al., 1985	15. m/0.32 mm/0.25 μm, He, 8. K/min, 280. C @ 5. min; T_start: 120. C
Capillary	Methyl Silicone	1921.5	Newton and Foery, 1984	12. m/0.2 mm/0.33 μm, He, 50. C @ 1. min, 20. K/min, 300. C @ 3. min
Capillary	5 % Phenyl methyl siloxane	1995.0	Newton and Foery, 1984	12. m/0.2 mm/0.33 μm, He, 50. C @ 1. min, 20. K/min, 300. C @ 3. min
Capillary	DB-1	1928.	Perrigo, Ballantyne, et al., 1984	15. m/0.25 mm/0.25 μm, He, 8. K/min, 280. C @ 5. min; T_start: 120. C
Packed	SE-30	1975.	Perrigo and Peel, 1981	N2, Chromosorb W, 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 1.8 m

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	BP-1	1924.	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, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	OV-101	180.	1964.	Dubsky, Hána, et al., 1978	Nitrogen, Chromosorb G (100-120 mesh); Column length: 2. m
Packed	OV-101	200.	1950.	Dubsky, Hána, et al., 1978	Nitrogen, Chromosorb G (100-120 mesh); Column length: 2. m
Packed	OV-101	200.	1955.	Dubsky, Hána, et al., 1978	Nitrogen, Chromosorb G (100-120 mesh); Column length: 2. m
Packed	OV-101	200.	1950.	Möller, 1976	N2, Chromosorb G AW DMCS (80-100 mesh); Column length: 2. m

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	BP-1	1934.	MHA, 9999	T_start: 100. C; T_end: 300. C
Capillary	SE-54	1996.	Friel, Logan, et al., 1997	30. m/0.32 mm/0.25 μm, He, 80. C @ 1. min, 15. K/min, 295. C @ 8. min
Capillary	OV-1	1957.	Schutz and Wollrab A., 1988	16. K/min; T_start: 200. C; T_end: 280. C
Capillary	DB-1	1926.	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	1928.	Stowell and Wilson, 1985	12. m/0.22 mm/0.25 μm, He, 8. K/min; T_start: 120. C; T_end: 280. C
Capillary	BP-1	1922.	Stowell and Wilson, 1985	12. m/0.22 mm/0.25 μm, He, 20. K/min; T_start: 50. C; T_end: 300. C
Packed	SE-30	1935.	Marozzi, Gambaro, et al., 1982	Gas Chrom P, 2.5 K/min; Column length: 2. m; T_start: 120. C; T_end: 200. C
Packed	SE-30	1975.	Peel and Perrigo, 1976	Nitrogen, Chromosorb W AW DMS (80-100 mesh), 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 2. m
Packed	SE-30	1975.	Peel and Perrigo, 1975	N2, Chromosorb W AW DMS, 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 2. m

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	CP Sil 5 CB	1980.	Bogusz, Bialka, et al., 1986	10. m/0.53 mm/5.2 μm; Program: 100 0C (2 min) 20 0C/min -> 180 0C 7.5 0C/min -> 280 0C (6 min)
Capillary	CP Sil 5 CB	1957.	Bogusz, Bialka, et al., 1986	10. m/0.53 mm/5.2 μm; Program: not specified
Capillary	BP-1	1924.	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)
Capillary	BP-1	1950.	Stowell and Wilson, 1985	12. m/0.22 mm/0.25 μm, He; Program: not specified
Other	Methyl Silicone	1957.	Ardrey and Moffat, 1981	Program: not specified
Packed	OV-101	1954.	Dubsky, Hána, et al., 1978	Nitrogen, Chromosorb G (100-120 mesh); Column length: 2. m; Program: not specified
Packed	OV-101	1950.	Dubsky, Hána, et al., 1978	Nitrogen, Chromosorb G (100-120 mesh); Column length: 2. m; Program: not specified

References

Go To: Top, Phase change data, Gas Chromatography, Notes

Kuffner, Bush, et al., 1957
Kuffner, R.J.; Bush, M.T.; Bircher, L.J., Studies on the surface tension of aqueous barbituric acid solutions, J. Am. Chem. Soc., 1957, 79, 1587-1589. [all data]

Phillips, Logan, et al., 1990
Phillips, A.M.; Logan, B.K.; Stafford, D.T., Further applications for capillary gas chromatography in routine quantitative toxicological analyses, J. Hi. Res. Chromatogr., 1990, 13, 11, 754-758, https://doi.org/10.1002/jhrc.1240131106 . [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]

Stead, Gill, et al., 1982
Stead, A.H.; Gill, R.; Evans, A.T.; Moffat, A.C., Predictions of gas chromatographic retention characteristics of barbiturates from molecular structure, J. Chromatogr., 1982, 234, 2, 277-283, https://doi.org/10.1016/S0021-9673(00)81866-X . [all data]

Berninger and Möller, 1977
Berninger, H.; Möller, M.R., Retentionsindices zur gaschromatographischen Identifizierung von Arzneimitteln, Arch. Toxicol., 1977, 37, 4, 295-305, https://doi.org/10.1007/BF00330821 . [all data]

Möller, 1976
Möller, M.R., Comparability of retention indices of polar substances at elevated temperatures, Chromatographia, 1976, 9, 7, 311-314, https://doi.org/10.1007/BF02268832 . [all data]

Maurer, 1990
Maurer, H.H., Identification and differentiation of barbiturates, other sedative-hypnotics and their metabolites in urine integrated in a general screening procedure using computerized gas chromatography-mass spectrometry, J. Chromatogr., 1990, 530, 307-326, https://doi.org/10.1016/S0378-4347(00)82334-8 . [all data]

Maurer, 1990, 2
Maurer, H.H., Detection of anticonvulsants and their metabolites in urine within a general unknown analysis procedure using computerized gas chromatography-mass spectrometry, Arch. Toxicol., 1990, 64, 7, 554-561, https://doi.org/10.1007/BF01971834 . [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]

McLinden and Stenhouse, 1979
McLinden, V.J.; Stenhouse, A.M., A chromatography system for drug identification, Forensic Sci. Int., 1979, 13, 71-79, https://doi.org/10.1016/0379-0738(79)90265-2 . [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]

Christ, Noomano, et al., 1988
Christ, D.W.; Noomano, P.; Rosas, M.; Rhone, D., Retention indices by wide-bore capillary gas chromatography with nitrogen-phosphorus detection, J. Anal. Toxicol., 1988, 12, 2, 84-88, https://doi.org/10.1093/jat/12.2.84 . [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]

Newton and Foery, 1984
Newton, B.; Foery, R.F., Retention indices and dual capillary gas chromatography for rapid identification of sedative hypnotic drugs in emergency toxicology, J. Anal. Toxicol., 1984, 8, 3, 129-134, https://doi.org/10.1093/jat/8.3.129 . [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]

Perrigo and Peel, 1981
Perrigo, B.J.; Peel, H.W., The use of retention indices and temperature-programmed gas chromatography in analytical toxicology, J. Chromatogr. Sci., 1981, 19, 5, 219-226, https://doi.org/10.1093/chromsci/19.5.219 . [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]

Dubsky, Hána, et al., 1978
Dubsky, H.; Hána, K.; Komárková, M.; Rittich, B., Pouzití kovatsovych indexu pri toxikologickych analysách, Chem. Listy, 1978, 72, 980-984. [all data]

MHA, 9999
MHA, Directorate of ForensicScience., Forensic Toxicology, 9999. [all data]

Friel, Logan, et al., 1997
Friel, P.N.; Logan, B.K.; Formoso, E.J., GC-MS analysis and post-mortem distribution of felbamate in humans, J. Epilepsy, 1997, 10, 6, 283-286, https://doi.org/10.1016/S0896-6974(97)00063-7 . [all data]

Schutz and Wollrab A., 1988
Schutz, H.; Wollrab A., The significance of the retention index in toxicologic analysis II, Pharmazie in unzerer Zeit, 1988, 17, 4, 97-101. [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]

Marozzi, Gambaro, et al., 1982
Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F., Use of the retention index in gas chromatographic studies of drugs, J. Anal. Toxicol., 1982, 6, 4, 185-192, https://doi.org/10.1093/jat/6.4.185 . [all data]

Peel and Perrigo, 1976
Peel, H.W.; Perrigo, B., A practical gas chromatographic screening procedure for toxicological analysis, Can. Soc. Forens. Sci. J., 1976, 9, 2, 69-74, https://doi.org/10.1080/00085030.1976.10757247 . [all data]

Peel and Perrigo, 1975
Peel, H.W.; Perrigo, B., A practical gas chromatographic screening procedure for toxicological analysis, Can.Soc.Forens.Sci.J., 1975, 9, 2, 69-74, https://doi.org/10.1080/00085030.1976.10757247 . [all data]

Bogusz, Bialka, et al., 1986
Bogusz, M.; Bialka, J.; Gierz, J.; Klys, M., Use of short, wide-bore capillary columns in GC toxicological screening, J. Anal. Toxicol., 1986, 10, 4, 135-138, https://doi.org/10.1093/jat/10.4.135 . [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Notes

Go To: Top, Phase change data, Gas Chromatography, References

Symbols used in this document:

T_fus Fusion (melting) point
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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