Doxepin

Formula: C₁₉H₂₁NO
Molecular weight: 279.3761
IUPAC Standard InChI: InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11-
IUPAC Standard InChIKey: ODQWQRRAPPTVAG-BOPFTXTBSA-N
CAS Registry Number: 1668-19-5
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: 1-Propanamine, 3-dibenz[b,e]oxepin-11(6H)-ylidene-N,N-dimethyl-; Dibenz(b,e)oxepin-δ11(6H),γ-propylamine, N,N-dimethyl-; 11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz(b,e)oxipin; 3-Dibenz[b,e]oxepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine; NSC 108160; Doxepine; N,N-Dimethyldibenz(b,e)oxepin-δ11(6H),γ-propylamine
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Other data available:
- Mass spectrum (electron ionization)
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Gas Chromatography

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
Packed	SE-30	220.	2239.	Musumarra, Scarlata, et al., 1987	N2, 1% se-30 on Anachrom ABS(80-100mesh); Column length: 2. m
Packed	OV-1	200.	2215.	Berninger and Möller, 1977

Kovats' RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	SE-30	2226.	Schepers, Wijsbeek, et al., 1982	25. m/0.49 mm/1.14 μm, 100. C @ 2. min, 8. K/min, 275. C @ 15. min

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	2231.	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	2210.	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	DB-1	2210.	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
Capillary	SE-30	2194.	Anderson and Stafford, 1983	15. m/0.25 mm/0.25 μm, He, 5. K/min; T_start: 100. C; T_end: 295. C
Packed	SE-30	2210.	Perrigo and Peel, 1981	N2, Chromosorb W, 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 1.8 m

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Packed	SE-30	2217.	MHA, 9999	Nitrogen, Chromosorb G AW DMCS (80-100 mesh); Column length: 2. m; T_start: 100. C; T_end: 300. C
Capillary	DB-5	2196.	Phillips, Logan, et al., 1990	15. m/0.25 mm/0.2 μm, He, 10. K/min; T_start: 185. C; T_end: 270. C
Packed	OV-1	2220.	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	2235.	Marozzi, Gambaro, et al., 1982	Gas Chrom P, 2.5 K/min; Column length: 2. m; T_start: 120. C; T_end: 200. C

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

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Column type	Active phase	I	Reference	Comment
Packed	OV-101	2242.	Maurer and Pfleger, 1984	Program: not specified
Other	Methyl Silicone	2217.	Ardrey and Moffat, 1981	Program: not specified

References

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Musumarra, Scarlata, et al., 1987
Musumarra, G.; Scarlata, G.; Romano, G.; Cappello, G.; Clementi, S.; Giulietti, G., Qualitative organic analysis. Part 2. Identification of drugs by principal components analysis of standardized TLC data in four eluent systems and of retention indices on SE 30, J. Anal. Toxicol., 1987, 11, 4, 154-163, https://doi.org/10.1093/jat/11.4.154 . [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]

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]

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]

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]

Anderson and Stafford, 1983
Anderson, W.H.; Stafford, D.T., Applications of capillary gas chromatography in routine toxicological analyses, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1983, 6, 5, 247-254, https://doi.org/10.1002/jhrc.1240060506 . [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]

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

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]

Maurer and Pfleger, 1984
Maurer, H.; Pfleger, K., Screening procedure for detection of antidepressants and their metabolites in urine using a computerized gas chromatographic-mass spectrometric technique, J. Chromatogr., 1984, 305, 309-323, https://doi.org/10.1016/S0378-4347(00)83345-9 . [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

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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