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N6252

Norharmane

Name: Norharmane
Brand: SIGMA

≥98% (TLC), crystalline, monoamine oxidase inhibitor

Synonym(s):

β-Carboline, 9H-Pyrido[3,4-b]indole

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₈N₂

CAS Number:

244-63-3

Molecular Weight:

168.19

NACRES:

NA.77

PubChem Substance ID:

24897776

UNSPSC Code:

12352200

EC Number:

205-959-0

MDL number:

MFCD00004956

Form:

crystalline

Quality level:

200

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Product Name

Norharmane, crystalline

form

crystalline

Quality Level

200

color

light yellow

storage temp.

2-8°C

SMILES string

c1ccc2c(c1)[nH]c3cnccc23

InChI

1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H

InChI key

AIFRHYZBTHREPW-UHFFFAOYSA-N

Gene Information

human ... IKBKB(3551)
rat ... Gabra2(29706)

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

General description

Norharmane is an alkaloid widely present in living organisms and can also be chemically synthesized. It is a β-carboline derivative composed of indole and pyridine.

Application

Norharmane has been used:

as a β-carboline to study its effect on nigrostriatal dopamine (DA) neurons
as an internal standard in gas chromatography-mass spectrometry (GC-MS) analyses using Conidiobulus coronatus filtrates
as a β-carboline-3-carboxylic acid N-methylamide (CMA) analog to study its binding ability with Mcm2-7 (minichromosome maintenance)

Biochem/physiol Actions

Inhibitor of indoleamine 2,3-dioxygenase (IDO).

Norharmane and its derivative exhibit anti-cancer properties. It acts as a monoamine oxidase (MAO) inhibitor and might benefit Parkinson′s disease (PD). High levels of β-carboline in plasma are found in PD.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors.

Eduard Dolušić et al.

Bioorganic & medicinal chemistry, 19(4), 1550-1561 (2011-01-29)

Indoleamine 2,3-dioxygenase (IDO) is a heme dioxygenase which has been shown to be involved in the pathological immune escape of diseases such as cancer. The synthesis and structure-activity relationships (SAR) of a novel series of IDO inhibitors based on the

Deep-sea microbes as tools to refine the rules of innate immune pattern recognition.

Anna E Gauthier et al.

Science immunology, 6(57) (2021-03-14)

The assumption of near-universal bacterial detection by pattern recognition receptors is a foundation of immunology. The limits of this pattern recognition concept, however, remain undefined. As a test of this hypothesis, we determined whether mammalian cells can recognize bacteria that

3-benzylamino-β-carboline derivatives induce apoptosis through G2/M arrest in human carcinoma cells HeLa S-3.

Reiko Ikeda et al.

European journal of medicinal chemistry, 46(2), 636-646 (2011-01-05)

β-carboline derivatives are known as the lead compounds for anti-tumor agents. To examine an optimal structure for anti-tumor activity, we synthesized a variety of β-carboline derivatives, possessing a variety of substituents on the nitrogen atom of the amino group of

Quantitative structure-activity relationship studies of a series of non-benzodiazepine structural ligands binding to benzodiazepine receptor.

Binbin Xia et al.

European journal of medicinal chemistry, 43(7), 1489-1498 (2007-10-30)

Heuristic method (HM) and radial basis function neural network (RBFNN) methods were proposed to generate QSAR models for a set of non-benzodiazepine ligands at the benzodiazepine receptor (BzR). Descriptors calculated from the molecular structures alone were used to represent the

Hollow fibre-supported liquid membrane extraction and LC-MS/MS detection for the analysis of heterocyclic amines in urine samples.

Rosa Busquets et al.

Molecular nutrition & food research, 53(12), 1496-1504 (2009-10-08)

Heterocyclic amines (HCAs) are potent mutagens/carcinogens to which humans are frequently exposed through the consumption of cooked meat and fish food. The effect of normal intake of HCAs and their role in the aetiology of human cancer is unknown. To

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Global Trade Item Number

SKU	GTIN
N6252-100MG	04061834117469
N6252-500MG	04061832557564
N6252-1G	04061826203415

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