Norharmane

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[1][2][3][4][5][6].

Product Specifications

CAS Number

[244-63-3]

Product Name Alternative

Norharman; β-Carboline

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Endogenous Metabolite; Monoamine Oxidase

Type

Natural Products

Related Pathways

Metabolic Enzyme/Protease; Neuronal Signaling

Applications

Neuroscience-Neuromodulation

Field of Research

Cancer; Infection; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/norharmane.html

Concentration

10mM

Purity

99.93

Solubility

DMSO : 11 mg/mL (ultrasonic) |H2O : < 0.1 mg/mL

Smiles

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

Molecular Formula

C11H8N2

Molecular Weight

168.20

Precautions

H302, H315, H319, H335

References & Citations

[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.|[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.|[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. |[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. |[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. |[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.