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N6252

Sigma-Aldrich

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:
244-63-3
Molecular Weight:
168.19
EC Number:
205-959-0
MDL number:
MFCD00004956
UNSPSC Code:
12352200
PubChem Substance ID:
24897776
NACRES:
NA.77

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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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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

N6252-100MG:
N6252-1G:
N6252-500MG:
N6252-BULK:
N6252-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL5811
BCCK7864
BCCH1190
BCCJ0997
BCCH0395

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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
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
Olga I Tarzi et al.
Journal of mass spectrometry : JMS, 44(2), 260-277 (2008-11-18)
The thermal stability of several commonly used crystalline matrix-assisted ultraviolet laser desorption/ionization mass spectrometry (UV-MALDI-MS) matrices, 2,5-dihydroxybenzoic acid (gentisic acid; GA), 2,4,6-trihydroxyacetophenone (THA), alpha-cyano-4-hydroxycinnamic acid (CHC), 3,5-dimethoxy-4-hydroxycinnamic acid (sinapinic acid; SA), 9H-pirido[3,4-b]indole (nor-harmane; nor-Ho), 1-methyl-9H-pirido[3,4-b]indole (harmane; Ho), perchlorate of nor-harmanonium
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