[CAS NO. 244-63-3] Norharmane
PRODUCTS SPECIFICATIONS [244-63-3]
DESCRIPTION [244-63-3]
Overview
| MDL | MFCD00004956 |
|---|---|
| Molecular Weight | 168.20 |
| Molecular Formula | C11H8N2 |
| SMILES | N1C2=C(C=CC=C2)C2=C1C=NC=C2 |
Summary
Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC 50 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] .
IC50 & Target
|
MAO-B 4.7 μM (IC 50 ) |
MAO-A 6.5 μM (IC 50 ) |
Human Endogenous Metabolite
|
In Vitro
Norharmane attenuates quinolinic acid formation by interferon-gamma-stimulated monocytes THP-1 cells and attenuates L-kynurenine formation, with IC
50
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]
.
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] .
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. |
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
| Powder | -20°C | 3 years |
|---|---|---|
| 4°C | 2 years | |
| In solvent | -80°C | 6 months |
| -20°C | 1 month |
Solvent & Solubility
DMSO : 11 mg/mL ( 65.40 mM ; Need ultrasonic)
H 2 O : < 0.1 mg/mL (insoluble)
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 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 |
-
1.
-
2.
Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)
Solubility: 1.1 mg/mL (6.54 mM); Suspended solution; Need ultrasonic
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.
- [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
- [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.
Synonyms