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
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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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IR Spectrum

Go To: Top, Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

SOLID (NUJOL MULL); PERKIN-ELMER 21 (GRATING); 2 cm^-1 resolution

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

gas; HP-GC/MS/IRD

Gas Chromatography

Go To: Top, IR Spectrum, 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

View large format table.

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

View large format table.

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, IR Spectrum, Gas Chromatography, Notes

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, IR Spectrum, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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