Cat. No.: HY-101392

Harmane

2 Cited Publications

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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).

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Pureté: 99.91%
CAS No.: 486-84-0
Formule: C₁₂H₁₀N₂
Masse moléculaire:182.23

Stockage:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

Harmane Chemical Structure

CAS No.: 486-84-0

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Activité biologique
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Publications (2)
Solvant et solubilité
- In Vitro
- In Vivo
Pureté et documentation
Références
Help & FAQs
Classifications
Bioz

Activité biologique

Description

IC₅₀ & Target^[2]^[3]

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)

Voir tous les produits spécifiques à Isoform Monoamine Oxidase :

MAO-A
MAO-B

Voir tous les produits spécifiques à Isoform Adrenergic Receptor :

Voir tous les produits spécifiques à Isoform Opioid Receptor :

Cellular Effect

Cell Line	Type	Value	Description	References
1A9	ED₅₀	6.1 μg/mL Compound: 2	In vitro cytotoxic activity was determined against ovarian cancer (1A9) cell line In vitro cytotoxic activity was determined against ovarian cancer (1A9) cell line	[PMID: 10612592]
A549	ED₅₀	9.3 μg/mL Compound: 2	In vitro cytotoxic activity was determined against lung carcinoma (A549) cell line In vitro cytotoxic activity was determined against lung carcinoma (A549) cell line	[PMID: 10612592]
A549	IC₅₀	>100 μM Compound: 5	Antiproliferative activity against human A549 cells after 24 hrs by MTT assay Antiproliferative activity against human A549 cells after 24 hrs by MTT assay	10.1039/C5MD00581G
Bel-7402	IC₅₀	151 μM Compound: 5	Cytotoxicity against human Bel7402 cells by MTT assay Cytotoxicity against human Bel7402 cells by MTT assay	[PMID: 18952426]
BGC-823	IC₅₀	215 μM Compound: 5	Cytotoxicity against human BGC823 cells by MTT assay Cytotoxicity against human BGC823 cells by MTT assay	[PMID: 18952426]
CAKI-1	ED₅₀	8 μg/mL Compound: 2	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	[PMID: 10612592]
H9	EC₅₀	10.7 μM Compound: 5	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	[PMID: 11473435]
H9	IC₅₀	111.5 μM Compound: 5	Cytotoxicity against human H9 cells Cytotoxicity against human H9 cells	[PMID: 11473435]
HEL	ED₅₀	9.8 μg/mL Compound: 2	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	[PMID: 10612592]
HeLa	IC₅₀	>100 μM Compound: 5	Antiproliferative activity against human HeLa cells after 24 hrs by MTT assay Antiproliferative activity against human HeLa cells after 24 hrs by MTT assay	10.1039/C5MD00581G
HeLa	IC₅₀	186 μM Compound: 5	Cytotoxicity against human HeLa cells by MTT assay Cytotoxicity against human HeLa cells by MTT assay	[PMID: 18952426]
HepG2	IC₅₀	115 μM Compound: 5	Cytotoxicity against human HepG2 cells by MTT assay Cytotoxicity against human HepG2 cells by MTT assay	[PMID: 18952426]
HL-60	IC₅₀	>10 μM Compound: 18	Antiproliferative activity against human HL60 cells by tryphan blue assay Antiproliferative activity against human HL60 cells by tryphan blue assay	[PMID: 28128938]
HL-60	IC₅₀	>100 μM Compound: 5	Antiproliferative activity against human HL60 cells after 24 hrs by MTT assay Antiproliferative activity against human HL60 cells after 24 hrs by MTT assay	10.1039/C5MD00581G
KB	ED₅₀	15 μg/mL Compound: 2	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)	[PMID: 10612592]
KB	ED₅₀	16.5 μg/mL Compound: 2	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)	[PMID: 10612592]
KB	ED₅₀	17.5 μg/mL Compound: 2	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)	[PMID: 10612592]
KB	ED₅₀	8.9 μg/mL Compound: 2	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	[PMID: 10612592]
MCF7	ED₅₀	19 μg/mL Compound: 2	In vitro cytotoxic activity against MCF-7 (human breast cancer) cell line. In vitro cytotoxic activity against MCF-7 (human breast cancer) cell line.	[PMID: 10612592]
MCF7	IC₅₀	>100 μM Compound: 5	Antiproliferative activity against human MCF7 cells after 24 hrs by MTT assay Antiproliferative activity against human MCF7 cells after 24 hrs by MTT assay	10.1039/C5MD00581G
P388	IC₅₀	>12500 ng/mL Compound: Table S4, R1C1	Cytotoxicity against mouse P388 cells Cytotoxicity against mouse P388 cells	[PMID: 19220033]
P388	IC₅₀	25000 ng/mL Compound: 3	Cytotoxicity against mouse P388 cells Cytotoxicity against mouse P388 cells	[PMID: 1791472]
PC-3	IC₅₀	>10 μM Compound: 18	Antiproliferative activity against human PC3 cells by MTT assay Antiproliferative activity against human PC3 cells by MTT assay	[PMID: 28128938]
Platelet	IC₅₀	>130 μM Compound: Harmane	Antiplatelet aggregation activity against collagen-induced platelet Antiplatelet aggregation activity against collagen-induced platelet	[PMID: 20329729]
Platelet	IC₅₀	130 μM Compound: Harmane	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	[PMID: 21983333]
SGC-7901	IC₅₀	>10 μM Compound: 18	Antiproliferative activity against human SGC7901 cells by MTT assay Antiproliferative activity against human SGC7901 cells by MTT assay	[PMID: 28128938]
SGC-7901	IC₅₀	>100 μM Compound: 5	Antiproliferative activity against human SGC7901 cells after 24 hrs by MTT assay Antiproliferative activity against human SGC7901 cells after 24 hrs by MTT assay	10.1039/C5MD00581G
SK-MEL-2	ED₅₀	>20 μg/mL Compound: 2	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	[PMID: 10612592]
THP-1	IC₅₀	121 μM Compound: 34	Cytotoxicity in human THP1 cells Cytotoxicity in human THP1 cells	[PMID: 19781948]
U-87MG ATCC	ED₅₀	19 μg/mL Compound: 2	In vitro cytotoxic activity against U-87-MG (glioblastoma) cell line. In vitro cytotoxic activity against U-87-MG (glioblastoma) cell line.	[PMID: 10612592]

In Vitro

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.

Cell Cytotoxicity Assay^[6]

Cell Line:

PC12
Concentration:

80-150 μM; 20, 100, 150 μM
Incubation Time:

24, 48 h
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.

Real Time qPCR^[6]

Cell Line:

PC12
Concentration:

10-30 μM
Incubation Time:

0-72 h
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.

In Vivo

Harman (0-12.5mg/kg, i.v., single dose) has an ED₅₀ of 3.6 mg/kg for convulsant activity in rats. Its anticonvulsant effect lasts for a short time and delays the reaction time to pain^[1].
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.

Animal Model:

Female Wistar rats^[1]
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
Administration:

Intravenous injection (i.v.)
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.

Animal Model:

β-carbon alkali-induced hypotension in rats^[2]
Dosage:

0.01-1 nM
Administration:

Injection into RVLM (rostralventrolateral medulla)
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.

Animal Model:

Male adult Sprague-Dawley rats^[5]
Dosage:

2.5, 5.0, 10 mg/kg
Administration:

Intraperitoneal injection (i.p.)
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

CAS No. 486-84-0
Appearance Solid
Masse moléculaire 182.23
Formule C₁₂H₁₀N₂
Color White to yellow
SMILES

CC1=NC=CC2=C1NC3=C2C=CC=C3
Structure Classification
- Alkaloids
- Pyridine Alkaloids
- Alkaloids
- Indole Alkaloids
Initial Source
- Plants
- other families
Livraison

Room temperature in continental US; may vary elsewhere.

Stockage

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

mSystems

Harmane induces apoptosis through RRM2B and suppresses colorectal cancer progression. [Abstract]

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

Solvant et solubilité

In Vitro:

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)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

5.4877 mL

27.4385 mL

54.8769 mL

5 mM

1.0975 mL

5.4877 mL

10.9754 mL

10 mM

0.5488 mL

2.7438 mL

5.4877 mL

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.

Calculateur de molarité

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

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Calculateur de dilution

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

Concentration _(start) Concentration _(start)

Volume _(start) Volume _(start)

Concentration _(final) Concentration _(final)

Volume _(final) Volume _(final)

In Vivo:

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

Stock Solution Working Solution

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 (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.

Protocol 2

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.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.5 mg/mL (13.72 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

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.

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.
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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

Pureté et documentation

Select Batch:

Pureté: 99.98%

Assay: 99.98%

ee.: 99.98%

Fiche technique (291 KB)
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COA (2659 KB)
Elemental Analysis Report (2659 KB)
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OR (2659 KB)
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Other Report (2659 KB)
Instruction de manipulation (2659 KB)

Références

[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]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

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

2 Cited Publications

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Harmane

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Publications Citing Use of MedChemExpress (MCE) Harmane

Voir tous les produits spécifiques à Isoform Monoamine Oxidase

Voir tous les produits spécifiques à Isoform Adrenergic Receptor

Voir tous les produits spécifiques à Isoform Opioid Receptor

Activité biologique

Chemical Information

Publications (2)

Solvant et solubilité

Pureté et documentation

Références

Help & FAQs

Complete Stock Solution Preparation Table

Harmane Related Classifications

HY-101392 Related Classifications