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Norharmane (Standard)

CAT: 0804-HY-W008566R-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-W008566R-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Norharmane (Standard) is the analytical standard of Norharmane. This product is intended for research and analytical applications. Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 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].
CAS Number
244-63-3
Product Name Alternative
Norharman (Standard) ; β-Carboline (Standard)
UNSPSC
12352005
Target
Endogenous Metabolite; Monoamine Oxidase; Reference Standards
Type
Reference Standards
Related Pathways
Metabolic Enzyme/Protease; Neuronal Signaling; Others
Field of Research
Cancer; Infection; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/norharmane-standard.html
Smiles
N1C2=C(C=CC=C2)C2=C1C=NC=C2
Molecular Formula
C11H8N2
Molecular Weight
168.20
References & Citations
[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 1) :11-4. |[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.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Beta-Carboline

Beta-carboline is the parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring. It has a role as a marine metabolite and a fungal metabolite. It is a mancude organic heterotricyclic parent and a member of beta-carbolines.

CAS Number244-63-3
PubChem CID64961
IUPAC Name9H-pyrido[3,4-b]indole
Molecular FormulaC11H8N2
Molecular Weight168.19
XLogP3.2
Topological Polar Surface Area28.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Heavy Atom Count13
Formal Charge0
Complexity193
SMILES
C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
InChI
InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
InChIKey
AIFRHYZBTHREPW-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Beta-Carboline
CAS: 244-63-3
CID: 64961
Formula: C11H8N2
MW: 168.19
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight168.19
XLogP33.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass168.068748264
Monoisotopic Mass168.068748264
Topological Polar Surface Area28.7 Ų
Heavy Atom Count13
Formal Charge0
Complexity193
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
319605Norharmane
sc-253201Norharmane hydrochloride
sc-219408Norharmane-d7
N4000-20Norharmane (9H-Pyrido[3,4-b]indole, ß-Carboline)
MBS6085647-01Norharmane (9H-Pyrido[3,4-b]indole, beta-Carboline)
sc-472338Nin-Formyl-L-1,2,3,4-tetrahydro-norharmane-3-carboxylic acid hydrochloride
abx098968-01Standard

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