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
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Product Name
Norharmane, crystalline
form
crystalline
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
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 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
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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
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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