Norharman

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 Search

SMILES

N1C2=C(C=CC=C2)C3=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

Molecular Formula	C11H8N2
Molecular Weight	168.1946
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.sciencedirect.com/science/article/pii/B9780124095175000826 | https://www.ncbi.nlm.nih.gov/pubmed/15036003 | https://www.ncbi.nlm.nih.gov/pubmed/15582589 | https://www.ncbi.nlm.nih.gov/pubmed/2789076 | https://www.ncbi.nlm.nih.gov/pubmed/16061219 | https://www.ncbi.nlm.nih.gov/pubmed/1877743 | https://www.ncbi.nlm.nih.gov/pubmed/8750109

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 Target	Pharmacology	Potency
Indoleamine 2,3-dioxygenase 20 Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6431906 \| https://www.ncbi.nlm.nih.gov/pubmed/2789076	Inhibitor 8504	0.12 mM [Ki]
alpha-glucosidase activity 3 Target ID: GO:0090599 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25502825	Inhibitor 8504	0.13 mM [Ki]
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16139309 \| https://www.ncbi.nlm.nih.gov/pubmed/16061219 \| https://www.ncbi.nlm.nih.gov/pubmed/15582589	Inhibitor 8504	1.2 µM [Ki]
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15582589 \| https://www.ncbi.nlm.nih.gov/pubmed/16139309	Inhibitor 8504	1.12 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16183262	Primary	Preclinical	Unknown Approved Use Unknown
Toxoplasmosis 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23663567	Primary	Basic research	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16579793	Primary	Basic research	Unknown Approved Use Unknown
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8750109	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Alcoholism 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8651457 https://www.ncbi.nlm.nih.gov/pubmed/1877743	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Carcinogenicity of aminophenylnorharman, a possible novel endogenous mutagen, formed from norharman and aniline, in F344 rats.	2004-10	15142889
Antibiotic-mediated release of tumour necrosis factor alpha and norharman in patients with hospital-acquired pneumonia and septic encephalopathy.	2004-08	15112034
Cytotoxic alkaloids from the marine sponge Thorectandra sp.	2004-06	15143832
Photophysics of norharmane in micellar environments: a fluorometric study.	2004-05-01	15110944
Dopamine transporter-mediated cytotoxicity of beta-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake.	2004-05	15086525
Pi-delocalized beta-carbolinium cations as potential antimalarials.	2004-04-05	15026051
High-performance liquid chromatographic analysis of beta-carbolines in human scalp hair.	2004-03-26	15058601
Mutagens formed from beta-carbolines with aromatic amines.	2004-03-25	15036005
Exposure to beta-carbolines norharman and harman.	2004-03-25	15036003
Occurrence of heterocyclic amines in several home-cooked meat dishes of the Spanish diet.	2004-03-25	15035999
Regulation and biochemistry of mouse molybdo-flavoenzymes. The DBA/2 mouse is selectively deficient in the expression of aldehyde oxidase homologues 1 and 2 and represents a unique source for the purification and characterization of aldehyde oxidase.	2004-03-05	14665639
The effects of imidazoline agents on the aggregation of human platelets.	2004-02	15005880
Long-term retention of neurotoxic beta-carbolines in brain neuromelanin.	2004-02	14767717
Effects of the beta-carbolines, harmane and pinoline, on insulin secretion from isolated human islets of Langerhans.	2003-12-15	14660022
Effect of harmane on mononeuropathic pain in rats.	2003-12	15028585
Comparative effects of efaroxan and beta-carbolines on the secretory activity of rodent and human beta cells.	2003-12	15028583
Craving for cigarettes among low and high dependent smokers: impact of norharman.	2003-12	14690883
Potent genotoxicity of aminophenylnorharman, formed from non-mutagenic norharman and aniline, in the liver of gpt delta transgenic mouse.	2003-12	12970073
Possibility of the involvement of 9H-pyrido[3,4-b]indole (norharman) in carcinogenesis via inhibition of cytochrome P450-related activities and intercalation to DNA.	2003-11-10	14568301
Influence of antioxidants in virgin olive oil on the formation of heterocyclic amines in fried beefburgers.	2003-11	12963012
Identification of tryptophan and beta-carboline as paralysins in larvae of the yellow mealworm, Tenebrio molitor.	2003-10-10	14511649
Cytotoxic and antimalarial beta-carboline alkaloids from the roots of Eurycoma longifolia.	2003-10	14575431
Tetrahydroisoquinoline and beta-carboline alkaloids from Haloxylon articulatum (Cav.) Bunge (Chenopodiaceae).	2003-08-27	12939030
Detection and characterization of cyclodextrin complexes with beta-carboline derivatives by spectroscopic techniques.	2003-08-08	12899986
Novel IKK inhibitors: beta-carbolines.	2003-07-21	12824047
Photophysical properties of methyl beta-carboline-3-carboxylate mediated by hydrogen-bonded complexes--a comparative study in different solvents.	2003-07-01	12914912
Spectrofluorimetric determination of manzamine A in spiked human urine and plasma.	2003-06	12856999
New manzamine alkaloids with activity against infectious and tropical parasitic diseases from an Indonesian sponge.	2003-06	12828469
Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase.	2003-06	12777961
Design, synthesis, and biological evaluation of non-peptidic ligands at the Xenopus laevis skin-melanocortin receptor.	2003-05	12767598
Chemical constituents of Taraxacum formosanum.	2003-05	12736465
Design, synthesis and biological activity of beta-carboline-based type-5 phosphodiesterase inhibitors.	2003-04-17	12668004
Contribution of individual cytochrome P450 isozymes to the O-demethylation of the psychotropic beta-carboline alkaloids harmaline and harmine.	2003-04	12649384
Shishijimicins A-C, novel enediyne antitumor antibiotics from the ascidian Didemnum proliferum(1).	2003-02-26	12590521
Isolation and identification of two [(3)H]norharman- ([(3)H]beta-carboline)-binding proteins from rat liver.	2003-01-25	12504194
[Serum norharman and harman analysis using high pressure liquid chromatography/mass spectrometry and value of beta-carbolines as blood alcohol markers].	2003-01-21	12532677
Beta-carboline alkaloids from a New Zealand marine bryozoan, Cribricellina cribraria.	2003-01	12674137
Mechanism-based pharmacokinetic/pharmacodynamic modeling of the electroencephalogram effects of GABAA receptor modulators: in vitro-in vivo correlations.	2003-01	12490579
The role of GABA in the pathophysiology and treatment of anxiety disorders.	2003	15131523
Synthesis of beta- and gamma-carbolines by the palladium-catalyzed iminoannulation of alkynes.	2002-12-27	12492334
Elevation of blood beta-carboline alkaloids in essential tremor.	2002-12-24	12499487
Rhythmicity without synchrony in the electrically uncoupled inferior olive.	2002-12-15	12486184
Effects of ayahuasca on sensory and sensorimotor gating in humans as measured by P50 suppression and prepulse inhibition of the startle reflex, respectively.	2002-12	12474114
Determination of N,N-dimethyltryptamine and beta-carboline alkaloids in human plasma following oral administration of Ayahuasca.	2002-11-05	12361741
Structure of DNA adduct formed with aminophenylnorharman, being responsible for the comutagenic action of norharman with aniline.	2002-10	12387627
In vitro and in vivo formation of aminophenylnorharman from norharman and aniline.	2002-09-30	12351144
Contribution of the alpha1-GABA(A) receptor subtype to the pharmacological actions of benzodiazepine site inverse agonists.	2002-09	12367613
High-performance liquid chromatographic, capillary electrophoretic and capillary electrophoretic-electrospray ionisation mass spectrometric analysis of selected alkaloid groups.	2002-08-16	12219932
Tetrahydro-beta-carboline alkaloids that occur in foods and biological systems act as radical scavengers and antioxidants in the ABTS assay.	2002-08	12420751
Identification and occurrence of the bioactive beta-carbolines norharman and harman in coffee brews.	2002-08	12227938

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:55:23 GMT 2025` Edited by `admin` on `Mon Mar 31 19:55:23 GMT 2025`
Record UNII	94HMA1I78O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-84417

Preferred Name

English

Norharman

Common Name

English

CARBAZOLINE

Common Name

English

2,9-DIAZAFLUORENE

Systematic Name

English

.BETA.-CARBOLINE

Systematic Name

English

Code System Code Type Description

MESH

C010262