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Merck

N6252

Norharmane

≥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:
Molecular Weight:
168.19
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
205-959-0
MDL number:
Form:
crystalline
Quality level:
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Product Name

Norharmane, crystalline

form

crystalline

Quality Level

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)

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.


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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Related Content

Glycobiology and Glycoproteomics Brochure


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
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
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