Imipramine
- Formula: C19H24N2
- Molecular weight: 280.4073
- IUPAC Standard InChI: InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3
- IUPAC Standard InChIKey: BCGWQEUPMDMJNV-UHFFFAOYSA-N
- CAS Registry Number: 50-49-7
- 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: 5H-Dibenz[b,f]azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-; 5H-Dibenz[b,f]azepine, 5-[3-(dimethylamino)propyl]-10,11-dihydro-; Antideprin; Melipramine; N-(γ-Dimethylaminopropyl)iminodibenzyl; N-(3-Dimethylaminopropyl)-o-iminodibenzyl; Prazepine; Berkomine; Censtim; Censtin; Dimipressin; Dyna-Zina; Dynaprin; DPID; Imidobenzyle; Imiprin; Impramine; Intalpram; Iramil; Irmin; Melipramin; Nelipramin; Promiben; Timolet; Tofranil (free base); Tofranil, base; 1-(3-Dimethylaminopropyl)-4,5-dihydro-2,3,6,7-dibenzazepine; 2,2'-(3-Dimethylaminopropylimino)bibenzyl; 2,2'-(3-Dimethylaminopropylimino)dibenzyl; 5-(3-(Dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine; 5-(3-Dimethylaminopropyl)-10,11-dihydro-5H-dibenzo(b,f)azepine; 5H-Dibenz(b,f)azepine, 10,11-dihydro-5-(3-(dimethylamino)propyl)-; Imipramina; 10,11-Dihydro-5-(3-(dimethylamino)propyl)-5H-dibenz[b,f]azepine; Declomipramine; 5,6-Dihydro-N-(3-(dimethylamino)propyl)-11H-dibenz(b,e)azepine; NSC 169866; 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine; Tofranil; Eupramin; G-22355; Imavate; Surplix; Imizin; Imizine; Imizinum; Psychoforin; SK-Pramine
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Gas phase ion energetics data
Go To: Top, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.21 ± 0.07 | CTS | Poltorakov, Pirnazarova, et al., 1973 | LLK |
| 7.35 ± 0.05 | CTS | Fulton and Lyons, 1968 | RDSH |
| 8.03 | CTS | Slifkin and Allison, 1967 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, UV/Visible spectrum, Gas Chromatography, 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
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Additional Data
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| 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 | Virginia Division of Forensic Science |
| NIST MS number | 250696 |
UV/Visible spectrum
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Download spectrum in JCAMP-DX format.
| Source | Lang (editor), 1965 |
|---|---|
| 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. 19647 |
| Instrument | Hilger Uvispek |
| Melting point | 172-173 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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 | DB-1 | 275. | 2262. | Japp, Gill, et al., 1987 | 30. m/0.53 mm/1.5 μm, N2 |
| Packed | SE-30 | 220. | 2212. | Musumarra, Scarlata, et al., 1987 | N2, 1% se-30 on Anachrom ABS(80-100mesh); Column length: 2. m |
| Capillary | SPB-1 | 250. | 2262. | Lora-Tamayo, Rams, et al., 1986 | He; Column length: 25. m; Column diameter: 0.20 mm |
| Packed | OV-1 | 200. | 2210. | Berninger and Möller, 1977 |
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-30 | 2222. | 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-101 | 2240. | McLinden and Stenhouse, 1979 | N2, Chromosorb W; 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 | VF-5MS | 2282.3 | Tretyakov, 2014 | 30. m/0.25 mm/0.25 μm, He; Tstart: 60. C; Tend: 270. C |
| Capillary | SPB-1 | 2226. | Christ, Noomano, et al., 1988 | 30. m/0.75 mm/1.0 μm, He, 10. K/min, 280. C @ 12. min; Tstart: 160. C |
| Packed | Methyl Silicone | 2205. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2219. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2218. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2220. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2220. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2220. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2222. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2225. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2225. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2225. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2225. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2228. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2228. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2230. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2220. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2220. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2222. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2223. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2223. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2223. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2223. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2223. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2225. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2233. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2230. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2230. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2230. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2232. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2232. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2232. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2232. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2235. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2235. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2235. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2240. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Packed | Methyl Silicone | 2242. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
| Capillary | DB-1 | 2205. | 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 | 2205. | Perrigo, Ballantyne, et al., 1984 | 15. m/0.25 mm/0.25 μm, He, 8. K/min, 280. C @ 5. min; Tstart: 120. C |
| Capillary | SE-30 | 2190. | Anderson and Stafford, 1983 | 15. m/0.25 mm/0.25 μm, He, 5. K/min; Tstart: 100. C; Tend: 295. C |
| Packed | SE-30 | 2215. | 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, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | OV-101 | 180. | 2208. | Dubsky, Hána, et al., 1978 | Nitrogen, Chromosorb G (100-120 mesh); Column length: 2. m |
| Packed | OV-101 | 200. | 2210. | Dubsky, Hána, et al., 1978 | Nitrogen, Chromosorb G (100-120 mesh); Column length: 2. m |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 2192. | Phillips, Logan, et al., 1990 | 15. m/0.25 mm/0.2 μm, He, 10. K/min; Tstart: 185. C; Tend: 270. C |
| Packed | OV-1 | 2260. | Marozzi, Gambaro, et al., 1982 | Gas Chrom P, 5. K/min; Column length: 2. m; Tstart: 150. C; Tend: 300. C |
| Packed | SE-30 | 2240. | Marozzi, Gambaro, et al., 1982 | Gas Chrom P, 5. K/min; Column length: 2. m; Tstart: 150. C; Tend: 300. C |
| Packed | SE-30 | 2215. | 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 | 2215. | 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
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | OV-101 | 2214. | Maurer and Pfleger, 1984 | Program: not specified |
| Other | Methyl Silicone | 2223. | Ardrey and Moffat, 1981 | Program: not specified |
| Packed | OV-101 | 2212. | Dubsky, Hána, et al., 1978 | Nitrogen, Chromosorb G (100-120 mesh); Column length: 2. m; Program: not specified |
| Packed | OV-101 | 2220. | Dubsky, Hána, et al., 1978 | Nitrogen, Chromosorb G (100-120 mesh); Column length: 2. m; Program: not specified |
References
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Poltorakov, Pirnazarova, et al., 1973
Poltorakov, A.P.; Pirnazarova, F.N.; But, P.G.; Piruzyan, L.A.; Chibrikin, V.M.; Vikjlyaev, Yu.I.; Ul'yanova, O.V.,
Ionization potentials of phenothiazine derivatives and their correlation with the parmacologic effect,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1973, 22, 2050, In original 2106. [all data]
Fulton and Lyons, 1968
Fulton, A.; Lyons, L.E.,
The ionization energies of some phenothiazine tranquillizers and molecules of similar structure,
Australian J. Chem., 1968, 21, 873. [all data]
Slifkin and Allison, 1967
Slifkin, M.A.; Allison, A.C.,
Measurement of ionization potentials from contact charge transfer spectra,
Nature, 1967, 215, 949. [all data]
Lang (editor), 1965
Lang (editor), L.,
Absorption Spectra in the Ultraviolet and Visible Region, 1965, 5, 349. [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]
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]
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]
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]
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]
Tretyakov, 2014
Tretyakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [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]
Bogusz, Wijsbeek, et al., 1985
Bogusz, M.; Wijsbeek, J.; Franke, J.P.; de Zeeuw, R.A.; Gierz, J.,
Impact of biological matrix, drug concentration, and method of isolation on detectability and variability of retention index values in gas chromatography,
J. Anal. Toxicol., 1985, 9, 2, 49-54, https://doi.org/10.1093/jat/9.2.49
. [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]
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]
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]
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]
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
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
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