3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine structure
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Common Name | 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine | ||
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| CAS Number | 50-49-7 | Molecular Weight | 280.40700 | |
| Density | 1.041g/cm3 | Boiling Point | 403.1ºC at 760mmHg | |
| Molecular Formula | C19H24N2 | Melting Point | 174°C | |
| MSDS | N/A | Flash Point | 179.7ºC | |
Use of 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amineImipramine is an orally active tertiary amine tricyclic antidepressant. Imipramine is a Fascin1 inhibitor with antitumor activities. Imipramine stimulates U-87MG glioma cells autophagy and induces HL-60 cell apoptosis. Imipramine shows neuroprotective and immunomodulatory effects[1][2][3][4]. |
| Name | imipramine |
|---|---|
| Synonym | More Synonyms |
| Description | Imipramine is an orally active tertiary amine tricyclic antidepressant. Imipramine is a Fascin1 inhibitor with antitumor activities. Imipramine stimulates U-87MG glioma cells autophagy and induces HL-60 cell apoptosis. Imipramine shows neuroprotective and immunomodulatory effects[1][2][3][4]. |
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| Related Catalog | |
| Target |
Fascin1, Autophagy, Apoptosis[1][2][3] |
| In Vitro | Imipramine (0.5-300 μM, 3 days) inhibits HCT-116 cell viability[1]. Imipramine (20 μM) inhibits cell migration (7 h) and invasion (48 h)[1]. Imipramine (50 μM, 0-240 min) inhibites the PI3K/Akt/mTOR signaling pathway in U-87MG glioma cells[2]. Imipramine (60 μM, 24 h) stimulates U-87MG glioma cells autophagy[2]. Imipramine (80 μM, 24 h) induces HL-60 cell apoptosis[3]. Cell Viability Assay[1] Cell Line: DLD-1, HCT-116, and SW-480 Concentration: 0.5-300 μM Incubation Time: 3 days Result: Inhibited cell viability and HCT-116 was more sensitive than DLD-1 and SW-480. Cell Migration Assay [1] Cell Line: DLD-1, HCT-116, and SW-480 Concentration: 20 μM Incubation Time: 7 h Result: Produced a remarkable inhibition of migration in all assayed cell lines. Cell Invasion Assay[1] Cell Line: HCT-116 Concentration: 20 μM Incubation Time: 48 h Result: Inhibited cell invasion through Matrigel. Western Blot Analysis[2] Cell Line: U-87MG Concentration: 50 μM Incubation Time: 0, 15, 30, 60, 120 and 240 min Result: Markedly inhibited the phosphorylation of both Akt (Ser473) and mTOR (Ser2481) in a time-dependent manner. Also dephosphorylated p70 S6K, a downstream target of mTOR. Cell Autophagy Assay[2] Cell Line: U-87MG Concentration: 60 μM Incubation Time: 24 h Result: Stimulated the induction of autophagy through the redistribution of LC3 in U-87MG glioma cells. Apoptosis Analysis[3] Cell Line: HL-60 Concentration: 80 μM Incubation Time: 24 h Result: Induced cell apoptosis. |
| In Vivo | Imipramine (20 mg/kg, i.p. or 15 mg/kg, p.o.; daily for 24 days) attenuates neuroinflammatory signaling and reverses stress-induced social avoidance in mice[4]. Animal Model: Male C57BL/6 mice (6–8 weeks old) subjected to RSD (repeated social defeat) and HCC (home cage control)[4] Dosage: 20 mg/kg or 15 mg/kg Administration: Intraperitoneal injection or oral administration, daily for 24 days Result: Reversed RSD-induced social avoidance behavior, significantly increasing the interaction time, significantly decreased stress-induced mRNA levels for IL-6 in brain microglia. |
| References |
| Density | 1.041g/cm3 |
|---|---|
| Boiling Point | 403.1ºC at 760mmHg |
| Melting Point | 174°C |
| Molecular Formula | C19H24N2 |
| Molecular Weight | 280.40700 |
| Flash Point | 179.7ºC |
| Exact Mass | 280.19400 |
| PSA | 6.48000 |
| LogP | 3.94000 |
| Index of Refraction | 1.574 |
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
MUTATION DATA
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| HS Code | 2933990090 |
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~%
3-(5,6-dihydrob... CAS#:50-49-7 |
| Literature: LUPIN LIMITED Patent: WO2009/47796 A1, 2009 ; Location in patent: Page/Page column 5 ; |
|
~96%
3-(5,6-dihydrob... CAS#:50-49-7 |
| Literature: Gowda, Narendra B.; Rao, Gopal Krishna; Ramakrishna, Ramesha A. Tetrahedron Letters, 2010 , vol. 51, # 43 p. 5690 - 5693 |
|
~81%
3-(5,6-dihydrob... CAS#:50-49-7 |
| Literature: Ram, Siya; Ehrenkaufer, Richard E. Tetrahedron Letters, 1985 , vol. 26, # 44 p. 5367 - 5370 |
|
~81%
3-(5,6-dihydrob... CAS#:50-49-7 |
| Literature: Li, Yuehui; Sorribes, Ivan; Yan, Tao; Junge, Kathrin; Beller, Matthias Angewandte Chemie - International Edition, 2013 , vol. 52, # 46 p. 12156 - 12160 Angew. Chem., 2013 , vol. 125, # 46 p. 12378 - 12382,5 |
|
~%
3-(5,6-dihydrob... CAS#:50-49-7 |
| Literature: Ram, Siya; Ehrenkaufer, Richard E. Tetrahedron Letters, 1985 , vol. 26, # 44 p. 5367 - 5370 |
|
~%
3-(5,6-dihydrob... CAS#:50-49-7 |
| Literature: Schindler; Haeflinger Helvetica Chimica Acta, 1954 , vol. 37, p. 472,481 |
|
~%
3-(5,6-dihydrob... CAS#:50-49-7 |
| Literature: Ram, Siya; Spicer, Leonard D. Synthetic Communications, 1989 , vol. 19, # 20 p. 3561 - 3572 |
|
~%
3-(5,6-dihydrob... CAS#:50-49-7 |
| Literature: Ram, Siya; Ehrenkaufer, Richard E. Tetrahedron Letters, 1985 , vol. 26, # 44 p. 5367 - 5370 |
| Precursor 8 | |
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| DownStream 5 | |
| HS Code | 2933990090 |
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| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
| Berkomine |
| Dimipressin |
| EINECS 200-042-1 |
| Antideprin |
| Nelipramin |
| [14C]-Imipramine |
| Intalpram |
| [3H]-Imipramine |
| Tofranil |
| 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine |
| Melipramine |
| Imidobenzyle |
| 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine |
| Melipramin |