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  3. Isoquinoline

Isoquinoline is an analog of pyridine. Isoquinoline-based alkaloids, such as p-tolyl bisisoquinoline, phthaloyl isoquinoline, and naphthyl isoquinoline, exhibit anticancer activity. Berberine, an isoquinoline alkaloid, exerts anti-inflammatory effects in diabetic mice by downregulating the gene expression ratios of pro-/anti-inflammatory and Th1/Th2 cytokines. Additionally, some isoquinoline-based compounds also possess antidepressant, antibacterial, antimalarial, and anti-HIV activities.

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Isoquinoline Chemical Structure

Isoquinoline Chemical Structure

CAS No. : 119-65-3

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Based on 2 publication(s) in Google Scholar

Other Forms of Isoquinoline:

Top Publications Citing Use of Products

2 Publications Citing Use of MCE Isoquinoline

  • Biological Activity

  • Purity & Documentation

  • References

  • Customer Review

Description

Isoquinoline is an analog of pyridine. Isoquinoline-based alkaloids, such as p-tolyl bisisoquinoline, phthaloyl isoquinoline, and naphthyl isoquinoline, exhibit anticancer activity. Berberine, an isoquinoline alkaloid, exerts anti-inflammatory effects in diabetic mice by downregulating the gene expression ratios of pro-/anti-inflammatory and Th1/Th2 cytokines. Additionally, some isoquinoline-based compounds also possess antidepressant, antibacterial, antimalarial, and anti-HIV activities[1][2][3][4][5][6].

In Vitro

Isoquinoline alkaloids exhibit inhibitory activity against Plasmodium falciparum (drug-resistant mutant strain K1). Among them, dehydrodiscretine and berberine have IC50 values of less than 1 μM, while sallocrytopine, columbamine, dehydroocoteine, jatrorrhizine, norcorydine, thalifendine, and ushinsuninehad have IC50 values ranging from 1 to 10 μM[5].
Berberine (A kind of Isoquinoline) (20-80 μM, 14 days) exerts neuroprotective effects against brain ischemia by modulating apoptotic protein changes and reducing microglial activation[6].

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

Western Blot Analysis[6]

Cell Line: Hippocampal neurons (rat)
Concentration: 20-80 μM
Incubation Time: 14 days
Result: Led that the Bax/Bcl-2 ratio was altered, reduced expression of apoptotic marker Caspase-3.
In Vivo

The isoquinoline compound, 7-fluoro-1,3-diphenylisoquinoline-1-amine (FDPI) (0.1 and 1 mg/kg, i.g., once daily for 35 days) abolishes chronic unpredictable mild stress-induced depressive-like behavior in adult Swiss mice[3].
The isoquinoline alkaloid berberine (50-500 mg/kg, i.g., once daily for 14 weeks) exerts a protective effect on spontaneous inflammation in the spleen, liver, and kidney of mice (non-obese diabetic (NOD) mice that spontaneously develop type 1) diabetes by downregulating the gene expression ratios of pro-/anti-inflammatory and Th1/Th2 cytokines[4].

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

Animal Model: Chronic unpredictable mild stress (CUMS)-induced depressive-like male adult Swiss mice model (25–35 g)
Dosage: 0.1 and 1 mg/kg
Administration: Intragastric administration (i.g), once daily for 35 days
Result: Effectively abolished depressive-like behavior in CUMS-exposed mice, improving self-care and motivation in the splash test and reducing immobility time in the TST and modified FST.
Did not affect spontaneous locomotion, ruling out psychostimulant interference.
Prevented the CUMS-induced increase in NF-κB and pro-inflammatory cytokines (TNF-α, INF-γ, IL-1, IL-6) in the prefrontal cortex and serum, while restoring IL-10 levels.
FDPI prevented the CUMS-induced elevation of corticosterone and ACTH, counteracting the increase in adrenal weight, suggesting regulation of HPA axis hyperactivity.
Prevented the CUMS-induced increase in 5-HT uptake in synaptosomes, indicating modulation of serotonergic neurotransmission.
Counteracted the CUMS-induced increase in pro-BDNF and decrease in TrkB in the prefrontal cortex, suggesting a role in neuroplasticity restoration.
Exerted antidepressant-like effects at lower doses than paroxetine, but its superiority over paroxetine could not be confirmed due to different administration routes (intragastric vs. intraperitoneal).
Demonstrated potential as a multi-target antidepressant, with effects mediated by anti-inflammatory actions, HPA axis modulation, serotonin system regulation, and neurotrophic signaling pathways. Further studies on chronic administration and side effects are needed.
Molecular Weight

129.16

Formula

C9H7N

CAS No.
Appearance

<26°C Solid,>28°C Liquid

Color

Colorless to yellow

SMILES

C12=C(C=NC=C2)C=CC=C1

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 : 100 mg/mL (774.22 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 7.7422 mL 38.7111 mL 77.4221 mL
5 mM 1.5484 mL 7.7422 mL 15.4844 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.

  • Molarity Calculator

  • Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 2.5 mg/mL (19.36 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 2.5 mg/mL (19.36 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation

Purity: 99.66%

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 7.7422 mL 38.7111 mL 77.4222 mL 193.5554 mL
5 mM 1.5484 mL 7.7422 mL 15.4844 mL 38.7111 mL
10 mM 0.7742 mL 3.8711 mL 7.7422 mL 19.3555 mL
15 mM 0.5161 mL 2.5807 mL 5.1615 mL 12.9037 mL
20 mM 0.3871 mL 1.9356 mL 3.8711 mL 9.6778 mL
25 mM 0.3097 mL 1.5484 mL 3.0969 mL 7.7422 mL
30 mM 0.2581 mL 1.2904 mL 2.5807 mL 6.4518 mL
40 mM 0.1936 mL 0.9678 mL 1.9356 mL 4.8389 mL
50 mM 0.1548 mL 0.7742 mL 1.5484 mL 3.8711 mL
60 mM 0.1290 mL 0.6452 mL 1.2904 mL 3.2259 mL
80 mM 0.0968 mL 0.4839 mL 0.9678 mL 2.4194 mL
100 mM 0.0774 mL 0.3871 mL 0.7742 mL 1.9356 mL
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Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Isoquinoline
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