Harmane
Based on 2 publication(s) in Google Scholar
Harmane is a benzodiazepine receptor inhibitor (IC50=7 μM), with IC50 values for mACh, Opioid Receptor, MAO-A/B, and α2-adrenergic receptor of 24 μM, 2.8 μM, 0.5 μM, 5 μM, and 18 μM, respectively. Harmane inhibits the I1 imidazoline receptor (IC50 = 30 nM) to reduce blood pressure and has antidepressant, anti-anxiety, anticonvulsant, and analgesic effects. Harmane inhibits dopamine biosynthesis by decreasing tyrosine hydroxylase (TH) activity and enhancing L-DOPA-induced cytotoxicity in PC12 cells. Additionally, Harmane can increase the mutagenic effect induced by 2-acetylaminofluorene (AAF).
Para uso exclusivo en investigación. No vendemos a pacientes.
- Pureza: 99.91%
- No. CAS: 486-84-0
- Fòrmula: C12H10N2
- Peso molecular:182.23
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Almacenamiento:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Solvente y solubilidad
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Publications Citing Use of MedChemExpress (MCE) Harmane
MoreVer todos los productos específicos de isoformas Adrenergic Receptor
MoreVer todos los productos específicos de isoformas Opioid Receptor
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Actividad biológica
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I1-Imidazoline receptor 30 nM (IC50) |
hMAO-A 0.5 μM (IC50) |
MAO-B 5 μM (IC50) |
α2-adrenergic receptor 18 μM (IC50) |
nAChR 24 μM (IC50) |
benzodiazepine receptor 7 nM (IC50) |
Opioid receptor 2.8 μM (IC50) |
Loperamide 163 μM (IC50) |
Serotonin 101 μM (IC50) |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| 1A9 | ED50 |
6.1 μg/mL
Compound: 2
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In vitro cytotoxic activity was determined against ovarian cancer (1A9) cell line
In vitro cytotoxic activity was determined against ovarian cancer (1A9) cell line
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[PMID: 10612592] |
| A549 | ED50 |
9.3 μg/mL
Compound: 2
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In vitro cytotoxic activity was determined against lung carcinoma (A549) cell line
In vitro cytotoxic activity was determined against lung carcinoma (A549) cell line
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[PMID: 10612592] |
| A549 | IC50 |
>100 μM
Compound: 5
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Antiproliferative activity against human A549 cells after 24 hrs by MTT assay
Antiproliferative activity against human A549 cells after 24 hrs by MTT assay
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10.1039/C5MD00581G |
| Bel-7402 | IC50 |
151 μM
Compound: 5
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Cytotoxicity against human Bel7402 cells by MTT assay
Cytotoxicity against human Bel7402 cells by MTT assay
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[PMID: 18952426] |
| BGC-823 | IC50 |
215 μM
Compound: 5
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Cytotoxicity against human BGC823 cells by MTT assay
Cytotoxicity against human BGC823 cells by MTT assay
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[PMID: 18952426] |
| CAKI-1 | ED50 |
8 μg/mL
Compound: 2
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In vitro cytotoxic activity was determined against renal cancer (CAKI-1) cell line
In vitro cytotoxic activity was determined against renal cancer (CAKI-1) cell line
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[PMID: 10612592] |
| H9 | EC50 |
10.7 μM
Compound: 5
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Antiviral activity against HIV1 in human H9 cells assessed as inhibition of viral replication
Antiviral activity against HIV1 in human H9 cells assessed as inhibition of viral replication
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[PMID: 11473435] |
| H9 | IC50 |
111.5 μM
Compound: 5
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Cytotoxicity against human H9 cells
Cytotoxicity against human H9 cells
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[PMID: 11473435] |
| HEL | ED50 |
9.8 μg/mL
Compound: 2
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In vitro cytotoxic activity was determined against embryonic lung fibroblast (HEL) cell line
In vitro cytotoxic activity was determined against embryonic lung fibroblast (HEL) cell line
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[PMID: 10612592] |
| HeLa | IC50 |
>100 μM
Compound: 5
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Antiproliferative activity against human HeLa cells after 24 hrs by MTT assay
Antiproliferative activity against human HeLa cells after 24 hrs by MTT assay
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10.1039/C5MD00581G |
| HeLa | IC50 |
186 μM
Compound: 5
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Cytotoxicity against human HeLa cells by MTT assay
Cytotoxicity against human HeLa cells by MTT assay
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[PMID: 18952426] |
| HepG2 | IC50 |
115 μM
Compound: 5
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Cytotoxicity against human HepG2 cells by MTT assay
Cytotoxicity against human HepG2 cells by MTT assay
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[PMID: 18952426] |
| HL-60 | IC50 |
>10 μM
Compound: 18
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Antiproliferative activity against human HL60 cells by tryphan blue assay
Antiproliferative activity against human HL60 cells by tryphan blue assay
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[PMID: 28128938] |
| HL-60 | IC50 |
>100 μM
Compound: 5
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Antiproliferative activity against human HL60 cells after 24 hrs by MTT assay
Antiproliferative activity against human HL60 cells after 24 hrs by MTT assay
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10.1039/C5MD00581G |
| KB | ED50 |
15 μg/mL
Compound: 2
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In vitro cytotoxic activity was determined against drug resistant tumor cell line KB-CPT (pleotrophic mechanism including level of topoisomerase I)
In vitro cytotoxic activity was determined against drug resistant tumor cell line KB-CPT (pleotrophic mechanism including level of topoisomerase I)
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[PMID: 10612592] |
| KB | ED50 |
16.5 μg/mL
Compound: 2
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In vitro cytotoxic activity was determined against drug resistant tumor cell line KB-7d (pleotrophic resistance including MRP multidrug resistant protein)
In vitro cytotoxic activity was determined against drug resistant tumor cell line KB-7d (pleotrophic resistance including MRP multidrug resistant protein)
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[PMID: 10612592] |
| KB | ED50 |
17.5 μg/mL
Compound: 2
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In vitro cytotoxic activity was determined against drug resistant tumor cell line KB-VIN (expressing P-glycoprotein)
In vitro cytotoxic activity was determined against drug resistant tumor cell line KB-VIN (expressing P-glycoprotein)
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[PMID: 10612592] |
| KB | ED50 |
8.9 μg/mL
Compound: 2
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In vitro cytotoxic activity was determined against epidermoid carcinoma of the nasopharynx (KB) cell line
In vitro cytotoxic activity was determined against epidermoid carcinoma of the nasopharynx (KB) cell line
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[PMID: 10612592] |
| MCF7 | ED50 |
19 μg/mL
Compound: 2
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In vitro cytotoxic activity against MCF-7 (human breast cancer) cell line.
In vitro cytotoxic activity against MCF-7 (human breast cancer) cell line.
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[PMID: 10612592] |
| MCF7 | IC50 |
>100 μM
Compound: 5
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Antiproliferative activity against human MCF7 cells after 24 hrs by MTT assay
Antiproliferative activity against human MCF7 cells after 24 hrs by MTT assay
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10.1039/C5MD00581G |
| P388 | IC50 |
>12500 ng/mL
Compound: Table S4, R1C1
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Cytotoxicity against mouse P388 cells
Cytotoxicity against mouse P388 cells
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[PMID: 19220033] |
| P388 | IC50 |
25000 ng/mL
Compound: 3
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Cytotoxicity against mouse P388 cells
Cytotoxicity against mouse P388 cells
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[PMID: 1791472] |
| PC-3 | IC50 |
>10 μM
Compound: 18
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Antiproliferative activity against human PC3 cells by MTT assay
Antiproliferative activity against human PC3 cells by MTT assay
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[PMID: 28128938] |
| Platelet | IC50 |
>130 μM
Compound: Harmane
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Antiplatelet aggregation activity against collagen-induced platelet
Antiplatelet aggregation activity against collagen-induced platelet
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[PMID: 20329729] |
| Platelet | IC50 |
130 μM
Compound: Harmane
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Antiplatelet activity in rabbit platelets assessed as inhibition of collagen-induced platelet aggregation
Antiplatelet activity in rabbit platelets assessed as inhibition of collagen-induced platelet aggregation
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[PMID: 21983333] |
| SGC-7901 | IC50 |
>10 μM
Compound: 18
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Antiproliferative activity against human SGC7901 cells by MTT assay
Antiproliferative activity against human SGC7901 cells by MTT assay
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[PMID: 28128938] |
| SGC-7901 | IC50 |
>100 μM
Compound: 5
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Antiproliferative activity against human SGC7901 cells after 24 hrs by MTT assay
Antiproliferative activity against human SGC7901 cells after 24 hrs by MTT assay
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10.1039/C5MD00581G |
| SK-MEL-2 | ED50 |
>20 μg/mL
Compound: 2
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In vitro cytotoxic activity was determined against melanoma cancer (SK-MEL-2) cell line
In vitro cytotoxic activity was determined against melanoma cancer (SK-MEL-2) cell line
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[PMID: 10612592] |
| THP-1 | IC50 |
121 μM
Compound: 34
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Cytotoxicity in human THP1 cells
Cytotoxicity in human THP1 cells
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[PMID: 19781948] |
| U-87MG ATCC | ED50 |
19 μg/mL
Compound: 2
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In vitro cytotoxic activity against U-87-MG (glioblastoma) cell line.
In vitro cytotoxic activity against U-87-MG (glioblastoma) cell line.
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[PMID: 10612592] |
Harmane also inhibits haloperidol and serotonin, with IC50 values of 163 μM and 101 μM, respectively[1].
The IC50 of Harmane for benzodiazepine receptor flunitrazepam is 7 μM, the IC50 for the opioid receptor is 2.8 μM, and in the presence of 50 mM sodium ions, the IC50 for the opioid receptor is 42 μM, and the IC50 for spiropyrinol and serotonin is 163, 101 μM[1].
The IC50 of Harmane for I1 imidazoline receptor is 30 nM), and the IC50 for α2-adrenergic receptor is 18 μM[2].
Harmane (1 μM) increases the mutagenicity of AAF to Salmonella typhimurium TA98 by three times in the presence of an S-9 mixture (containing 4 μM NADH and NADPH per ml but no NADP); in the absence of S-9, it increases the mutagenicity of N-acetyloxy AAF by 2.5 times[4].
Harmane (5-25 μM, 0-72 h) reduced the dopamine content in PC12 cells (IC50 is 21.2 μM) in a concentration-dependent manner and could reduce the dopamine content induces by L-DOPA[6].
Harmane (20 μM, 0-72 h) inhibits the activity of tyrosine hydroxylase (TH) in PC12 cells at 24 h and restores it to normal levels at 72 h; it inhibits the expression of TH mRNA at 6 h and restores it at 48 h[6].
Harmane (20μM, 30min) reduces the intracellular cyclic AMP level and intracellular calcium ion concentration in PC12 cells[6].
Harmane (80-150μM, 24-48h) exhibits cytotoxicity and induces cell death[6].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:PC12
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Concentration:80-150 μM; 20, 100, 150 μM
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Incubation Time:24, 48 h
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Result:Showed cytotoxicity, and cell apoptosis was observed after 48 h of treatment with 150 μM. Concentrations higher than 150 μM could induce apoptotic cell death.
Had stronger cell viability than L-DOPA alone.
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Cell Line:PC12
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Concentration:10-30 μM
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Incubation Time:0-72 h
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Result:Inhibited the increase in dopamine content induced by L-DOPA.
Reduced dopamine content, tyrosine hydroxylase activity and mRNA at 6 h, which was maintained for 48 h and gradually recovered at 72 h.
Harman (0.01-1 nM, injected into rostralventrolateral medulla, single dose) caused a decrease in blood pressure in rats[2].
Harman (2.5-10 mg/kg, i.p., single dose) had anxiolytic and antidepressant effects in rats[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Female Wistar rats[1]
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Dosage:0, 3.125, 6.25 mg/kg, single dose; 0, 1.56, 3.125, 6 25, 12.5 mg/kg, single dose; 0, 1.56, 3.125, 6.25 mg/kg, single dose
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Administration:Intravenous injection (i.v.)
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Result:Delayed apamorphine-induced licking.
Increased body temperature in rats, reaching the highest value in 25 minutes. 3.125 mg/kg or above caused hypothermia in a dose-dependent manner. Body temperature returned to the control level 100 minutes after injection of 3.125 or 6.25 mg/kg.
Prolonged the reaction time to nociception. At 3.125 mg/kg, a delay in reaction could be detected in 20 minutes.
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Animal Model:β-carbon alkali-induced hypotension in rats[2]
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Dosage:0.01-1 nM
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Administration:Injection into RVLM (rostralventrolateral medulla)
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Result:Caused a dose-dependent decrease in mean arterial pressure (MAP) without significant changes in heart rate (HR). Phaloxan could reverse the decrease in MAP.
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Animal Model:Male adult Sprague-Dawley rats[5]
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Dosage:2.5, 5.0, 10 mg/kg
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Administration:Intraperitoneal injection (i.p.)
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Result:Reduced the immobility time in the swimming test and increased the time in the open arms in the maze test dose-dependently.
Chemical Information
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No. CAS 486-84-0
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Appearance Solid
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Peso molecular 182.23
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Fòrmula C12H10N2
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Color White to yellow
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SMILES
CC1=NC=CC2=C1NC3=C2C=CC=C3
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Structure Classification
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Initial Source
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Publications (2)
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Journal Impact Factor
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Most Recent
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mSystems
2026 Jun 9:e0170425. PMID: 42262096 -
Front Mol Neurosci
Harmane Potentiates Nicotine Reinforcement Through MAO-A Inhibition at the Dose Related to Cigarette Smoking. [Abstract]2022 Jun 27;15:925272. PMID: 35832393
Solvente y solubilidad
DMSO : 100 mg/mL (548.77 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
H2O : < 0.1 mg/mL (insoluble)
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.
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.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (13.72 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.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (13.72 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.
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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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
-
+%Tween-80 + +
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%Saline +
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).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
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.
Pureza y Documentación
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Ficha de datos (291 KB)
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SDS (396 KB)
- English - EN (396 KB)
- Français - FR (396 KB)
- Deutsch - DE (396 KB)
- Norwegian - NO (396 KB)
- Español - ES (396 KB)
- Swedish - SV (396 KB)
- Italian - IT (396 KB)
- Korean - KR (396 KB)
- Portuguese - PT (396 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. W E Müller, et al. On the neuropharmacology of harmane and other beta-carbolines. Pharmacol Biochem Behav. 1981 May;14(5):693-9. [Content Brief]
[2]. Musgrave IF, et, al. Harmane produces hypotension following microinjection into the RVLM: possible role of I(1)-imidazoline receptors. Br J Pharmacol. 2000 Mar;129(6):1057-9. [Content Brief]
[3]. Glover V, et, al. β-Carbolines as selective monoamine oxidase inhibitors:In vivo implications [Content Brief]
[4]. Umezawa K, et, al. Comutagenic effect of norharman and harman with 2-acetylaminofluorene derivatives. Proc Natl Acad Sci U S A. 1978 Feb;75(2):928-30. [Content Brief]
[5]. E D Louis, et al. Harmane induces anxiolysis and antidepressant-like effects in rats. Ann N Y Acad Sci. 2005 Aug 9;65(3):391-6. [Content Brief]
[6]. Yoo Jung Yang, et al. Effects of harman and norharman on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells. Eur J Pharmacol. 2008 Jun 10;587(1-3):57-64. [Content Brief]
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 | 5.4877 mL | 27.4385 mL | 54.8769 mL | 137.1923 mL |
| 5 mM | 1.0975 mL | 5.4877 mL | 10.9754 mL | 27.4385 mL | |
| 10 mM | 0.5488 mL | 2.7438 mL | 5.4877 mL | 13.7192 mL | |
| 15 mM | 0.3658 mL | 1.8292 mL | 3.6585 mL | 9.1462 mL | |
| 20 mM | 0.2744 mL | 1.3719 mL | 2.7438 mL | 6.8596 mL | |
| 25 mM | 0.2195 mL | 1.0975 mL | 2.1951 mL | 5.4877 mL | |
| 30 mM | 0.1829 mL | 0.9146 mL | 1.8292 mL | 4.5731 mL | |
| 40 mM | 0.1372 mL | 0.6860 mL | 1.3719 mL | 3.4298 mL | |
| 50 mM | 0.1098 mL | 0.5488 mL | 1.0975 mL | 2.7438 mL | |
| 60 mM | 0.0915 mL | 0.4573 mL | 0.9146 mL | 2.2865 mL | |
| 80 mM | 0.0686 mL | 0.3430 mL | 0.6860 mL | 1.7149 mL | |
| 100 mM | 0.0549 mL | 0.2744 mL | 0.5488 mL | 1.3719 mL |
Harmane Related Classifications
HY-101392 Related Classifications
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