Cat. No.: HY-W008566

Norharmane

(Synonyms: Norharman; β-Carboline)

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Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC₅₀ values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings.

For research use only. We do not sell to patients.

Purity: 99.93%
CAS No.: 244-63-3
Formula: C₁₁H₈N₂
Molecular Weight:168.20

Storage:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year

Norharmane Chemical Structure

CAS No.: 244-63-3

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Sample (0.1mg)

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(In Japan)

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Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Solvent & Solubility
- In Vitro
- In Vivo
Purity & Documentation
References
Help & FAQs
Bioz

Biological Activity

Description

IC₅₀ & Target^[1]

MAO-B

4.7 μM (IC₅₀)

Microbial Metabolite

MAO-A

6.5 μM (IC₅₀)

All Monoamine Oxidase Isoforms :

MAO-A
MAO-B

All Endogenous Metabolite Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	>100 μM Compound: 4	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
H9	EC₅₀	44.1 μM Compound: 7	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	141.7 μM Compound: 7	Cytotoxicity against human H9 cells Cytotoxicity against human H9 cells	[PMID: 11473435]
HeLa	IC₅₀	>100 μM Compound: 4	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	15 μM Compound: 2	Inhibitory activity against IkappaB kinase(IKK) isolated from HeLa cells activated with recombinant MEEK1 in an ELISA phosphorylation assay. Inhibitory activity against IkappaB kinase(IKK) isolated from HeLa cells activated with recombinant MEEK1 in an ELISA phosphorylation assay.	[PMID: 12824047]
HeLa S3	IC₅₀	>100 μM Compound: norharman	Antitumor activity against human HeLaS3 cells after 24 to 72 hrs by MTT assay Antitumor activity against human HeLaS3 cells after 24 to 72 hrs by MTT assay	[PMID: 21194810]
HL-60	IC₅₀	>100 μM Compound: 4	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
MCF7	IC₅₀	>100 μM Compound: 4	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	25000 ng/mL Compound: 10	Cytotoxicity against mouse P388 cells Cytotoxicity against mouse P388 cells	[PMID: 1791472]
Platelet	IC₅₀	>130 μM Compound: Norharmane	Antiplatelet aggregation activity against collagen-induced platelet Antiplatelet aggregation activity against collagen-induced platelet	[PMID: 20329729]
Platelet	IC₅₀	130 μM Compound: Norharmane	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	>100 μM Compound: 4	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

In Vitro

Norharmane attenuates quinolinic acid formation by interferon-gamma-stimulated monocytes THP-1 cells and attenuates L-kynurenine formation, with IC₅₀ values of 51 μM and 43 μM, respectively^[4].
? Norharmane has the potential for use as an antibiotic adjuvant to enhance the efficacy of conventional antibiotics to reduce pathogenic bacterial infections^[6].

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

In Vivo

Norharmane (0-10 mg/kg, IP, once) shows an anxiety- and antidepressant-like behavior, and decreased locomotor activity^[3].

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

Animal Model:

Male NMRI mice (22-25 g)^[3]
Dosage:

0, 2.5, 5 and 10 mg/kg
Administration:

IP, once
Result:

Elicited an anxiety- and antidepressant-like behavior, and decreased locomotor activity.

Chemical Information

CAS No. 244-63-3
Appearance Solid
Molecular Weight 168.20
Formula C₁₁H₈N₂
Color Off-white to yellow
SMILES

N1C2=C(C=CC=C2)C2=C1C=NC=C2
Synonyms

Norharman; β-Carboline
Structure Classification
- Alkaloids
- Pyridine Alkaloids
- Alkaloids
- Indole Alkaloids
Initial Source
- Microorganisms
- Endogenous metabolite
Cyanobacteria
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	2 years
	-20°C	1 year

Solvent & Solubility

In Vitro:

DMSO : 11 mg/mL (65.40 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

5.9453 mL

29.7265 mL

59.4530 mL

5 mM

1.1891 mL

5.9453 mL

11.8906 mL

10 mM

0.5945 mL

2.9727 mL

5.9453 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, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Molarity Calculator

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

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Dilution Calculator

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: ≥ 1.1 mg/mL (6.54 mM); Clear solution

This protocol yields a clear solution of ≥ 1.1 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (11.0 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.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

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:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
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

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (280 KB)
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Portuguese - PT (393 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Herraiz T, et al. Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. Life Sci. 2006 Jan 18;78(8):795-802. [Content Brief]

[2]. López-González D, et al. A natural indole alkaloid, norharmane, affects PIN expression patterns and compromises root growth in Arabidopsis thaliana. Plant Physiol Biochem. 2020 Jun;151:378-390. [Content Brief]

[3]. Ebrahimi-Ghiri M, et al. Anxiolytic and antidepressant effects of ACPA and harmaline co-treatment. Behav Brain Res. 2019 May 17;364:296-302. [Content Brief]

[4]. Saito K, Chen CY, Masana M, Crowley JS, Markey SP, Heyes MP. 4-Chloro-3-hydroxyanthranilate, 6-chlorotryptophan and norharmane attenuate quinolinic acid formation by interferon-gamma-stimulated monocytes (THP-1 cells). Biochem J. 1993 Apr 1;291 ( Pt 1)(Pt 1):11-4. [Content Brief]

[5]. Paul BK, et al. Binding of norharmane with RNA reveals two thermodynamically different binding modes with opposing heat capacity changes. J Colloid Interface Sci. 2019 Mar 7;538:587-596. [Content Brief]

[6]. Luo HZ, et al. Inhibitory effect of norharmane on Serratia marcescens NJ01 quorum sensing-mediated virulence factors and biofilm formation. Biofouling. 2021 Feb;37(2):145-160. [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, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	5.9453 mL	29.7265 mL	59.4530 mL	148.6326 mL
	5 mM	1.1891 mL	5.9453 mL	11.8906 mL	29.7265 mL
	10 mM	0.5945 mL	2.9727 mL	5.9453 mL	14.8633 mL
	15 mM	0.3964 mL	1.9818 mL	3.9635 mL	9.9088 mL
	20 mM	0.2973 mL	1.4863 mL	2.9727 mL	7.4316 mL
	25 mM	0.2378 mL	1.1891 mL	2.3781 mL	5.9453 mL
	30 mM	0.1982 mL	0.9909 mL	1.9818 mL	4.9544 mL
	40 mM	0.1486 mL	0.7432 mL	1.4863 mL	3.7158 mL
	50 mM	0.1189 mL	0.5945 mL	1.1891 mL	2.9727 mL
	60 mM	0.0991 mL	0.4954 mL	0.9909 mL	2.4772 mL

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Norharmane

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All Monoamine Oxidase Isoforms

All Endogenous Metabolite Isoforms

Biological Activity

Chemical Information

Solvent & Solubility

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

Norharmane Related Classifications

Cat. No.: HY-W008566