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Details

Stereochemistry ACHIRAL
Molecular Formula C11H8N2
Molecular Weight 168.1946
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORHARMAN

SMILES

N1C2=CC=CC=C2C3=C1C=NC=C3

InChI

InChIKey=AIFRHYZBTHREPW-UHFFFAOYSA-N
InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H

HIDE SMILES / InChI

Description

Norharman or beta-carboline (9H-pyrido[3,4-b]indole) is a neuroactive alkaloid first isolated from Peganum harmala L. It is implicated in a number of human diseases including Parkinson's disease, tremor, addiction and cancer. Norharman formed endogenously but external sources have been identified (among others fried meat and fish, meat extracts, alcoholic drinks, coffee brews, tobacco smoke). It inhibits monoamine oxidase and indoleamine 2,3-dioxygenase. In addition norharman binds with high affinity to imidazoline I2B receptors. Plasma norharman levels are elevated in chronic alcoholics and Parkinson's disease patients.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.12 mM [Ki]
0.13 mM [Ki]
1.2 µM [Ki]
1.12 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Diagnostic
Unknown
Diagnostic
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Pharmacokinetics of oral norharman in healthy subjects: 7, 65 and 110 microg/kg. Rats: 0.2-20 mg/kg, i.p. Mice: 2.5-10 mg/kg, i.p.
Route of Administration: Other
In Vitro Use Guide
Norharman showed cytotoxicity towards both the HeLa cervical-cancer cell line and the BGC-823 stomach-cancer cell line, with an IC(50) of 5 microg/ml.