1. Neuronal Signaling Autophagy Apoptosis
  2. Serotonin Transporter Autophagy Apoptosis
  3. Imipramine

Imipramine is an orally active tertiary amine tricyclic antidepressant. Imipramine is a Fascin1 inhibitor with antitumor activities. Imipramine also inhibits serotonin transporter with an IC50 value of 32 nM. Imipramine stimulates U-87MG glioma cells autophagy and induces HL-60 cell apoptosis. Imipramine shows neuroprotective and immunomodulatory effects.

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Imipramine Chemical Structure

Imipramine Chemical Structure

CAS No. : 50-49-7

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Based on 5 publication(s) in Google Scholar

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Description

Imipramine is an orally active tertiary amine tricyclic antidepressant. Imipramine is a Fascin1 inhibitor with antitumor activities. Imipramine also inhibits serotonin transporter with an IC50 value of 32 nM. Imipramine stimulates U-87MG glioma cells autophagy and induces HL-60 cell apoptosis. Imipramine shows neuroprotective and immunomodulatory effects[1][2][3][4][5].

IC50 & Target

Fascin1, Serotonin Transporter, Autophagy, Apoptosis[1][2][3][5]
IC50: 32 nM (human placental serotonin transporter)[5]

Cellular Effect
Cell Line Type Value Description References
CHO IC50
5.1 nM
Compound: Imipramine
Inhibition of human SERT expressed in CHO cell membranes assessed as reduction in [3H]serotonin uptake preincubated for 10 mins followed by [3H]serotonin addition measured after 20 mins by liquid scintillation counting method
Inhibition of human SERT expressed in CHO cell membranes assessed as reduction in [3H]serotonin uptake preincubated for 10 mins followed by [3H]serotonin addition measured after 20 mins by liquid scintillation counting method
[PMID: 27865645]
CHO IC50
8.8 x 10-10 M
Compound: Imipramine
Displacement of [3H]imipramine from human recombinant 5HT transporter expressed in CHO cells measured after 60 mins by scintillation counting method
Displacement of [3H]imipramine from human recombinant 5HT transporter expressed in CHO cells measured after 60 mins by scintillation counting method
[PMID: 27876250]
DG-75 IC50
> 50 μM
Compound: Imipramine
Reduction in cell viability of human DG75 cells after 24 hrs by Alamar blue viability assay
Reduction in cell viability of human DG75 cells after 24 hrs by Alamar blue viability assay
[PMID: 23385211]
HEK293 IC50
17.1 μM
Compound: Imipramine
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells by confocal microscopy
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells by confocal microscopy
[PMID: 18788725]
HEK293 IC50
2.6 nM
Compound: 1
Inhibition of human SERT W103A mutant expressed in HEK293 MSR cells assessed as [3H]-5-HT uptake preincubated for 30 mins followed addition of [3H]-5HT and compound for 10 mins by micro-scintillation counter
Inhibition of human SERT W103A mutant expressed in HEK293 MSR cells assessed as [3H]-5-HT uptake preincubated for 30 mins followed addition of [3H]-5HT and compound for 10 mins by micro-scintillation counter
[PMID: 27160055]
HEK293 IC50
7.95 μM
Compound: Imipramine
Inhibition of human OCT1 expressed in HEK293 cells assessed as decrease in uptake of ASP+ after 2 mins by fluorescence assay
Inhibition of human OCT1 expressed in HEK293 cells assessed as decrease in uptake of ASP+ after 2 mins by fluorescence assay
[PMID: 28230985]
HeLa IC50
40.74 μM
Compound: Imipramine
Reduction in cell viability of human HeLa cells after 24 hrs by Alamar blue viability assay
Reduction in cell viability of human HeLa cells after 24 hrs by Alamar blue viability assay
[PMID: 23385211]
Ventricular myocyte IC50
4.05 μM
Compound: Imipramine
Inhibition of L-type calcium channel measured using whole-cell patch clamp in rat ventricular myocytes
Inhibition of L-type calcium channel measured using whole-cell patch clamp in rat ventricular myocytes
[PMID: 22761000]
Ventricular myocyte IC50
8.3 μM
Compound: Imipramine
Inhibition of L-type calcium channel measured using whole-cell patch clamp in rat ventricular myocytes
Inhibition of L-type calcium channel measured using whole-cell patch clamp in rat ventricular myocytes
[PMID: 22761000]
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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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.
Clinical Trial
Molecular Weight

280.41

Formula

C19H24N2

CAS No.
Appearance

Liquid (Density: 1.041±0.06 g/cm3)

Color

Colorless to light yellow

SMILES

CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Pure form -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : 250 mg/mL (891.55 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.5662 mL 17.8310 mL 35.6621 mL
5 mM 0.7132 mL 3.5662 mL 7.1324 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Purity & Documentation
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 3.5662 mL 17.8310 mL 35.6621 mL 89.1552 mL
5 mM 0.7132 mL 3.5662 mL 7.1324 mL 17.8310 mL
10 mM 0.3566 mL 1.7831 mL 3.5662 mL 8.9155 mL
15 mM 0.2377 mL 1.1887 mL 2.3775 mL 5.9437 mL
20 mM 0.1783 mL 0.8916 mL 1.7831 mL 4.4578 mL
25 mM 0.1426 mL 0.7132 mL 1.4265 mL 3.5662 mL
30 mM 0.1189 mL 0.5944 mL 1.1887 mL 2.9718 mL
40 mM 0.0892 mL 0.4458 mL 0.8916 mL 2.2289 mL
50 mM 0.0713 mL 0.3566 mL 0.7132 mL 1.7831 mL
60 mM 0.0594 mL 0.2972 mL 0.5944 mL 1.4859 mL
80 mM 0.0446 mL 0.2229 mL 0.4458 mL 1.1144 mL
100 mM 0.0357 mL 0.1783 mL 0.3566 mL 0.8916 mL
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