Showing Compound Card for Norharman (CDB005368)

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Record Information
Version1.0
Created at2020-04-27 16:13:39 UTC
Updated at2021-01-04 20:37:40 UTC
CannabisDB IDCDB005368
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNorharman
Descriptionbeta-Carboline, also known as norharman or 9H-beta-carboline, belongs to the class of organic compounds known as beta carbolines. beta-Carbolines are compounds containing a 9H-pyrido[3,4-beta]indole moiety or more generally, a pyridine indole ring fused to an indole skeleton. beta-Carboline (9H-pyridoindole) is an organic amine that is the prototype of beta-carbolines. beta-Carboline is a strong basic compound that has low solubility in water. beta-Carboline has been detected in chicories. beta-Carboline alkaloids are widely distributed in plants and animals and many are inverse agonists of the gamma-amino-butyric acid (GABA)-A receptor complex (PMID: 17334612 ). Other biological activities demonstrated by these compounds include intercalation of DNA (PMID: 20541950); inhibition of cyclin-dependent kinase (CDK), topoisomerase, and monoamine oxidase; and interaction with 5-hydroxy serotonin receptors. These compounds have also exhibited sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic, and antimicrobial activities (PMID: 17305548 ). beta-Carboline is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,9-DiazafluoreneChEBI
2-AzacarbazoleChEBI
9H-beta-CarbolineChEBI
9H-Pyrido(3,4-b)indoleChEBI
9H-Pyrido[3,4-b]indoleChEBI
CarbazolineChEBI
NorharmanChEBI
NorharmaneChEBI
9H-b-CarbolineGenerator
9H-Β-carbolineGenerator
b-CarbolineGenerator
Β-carbolineGenerator
Norharman hydrochlorideMeSH, HMDB
NorhormaneMeSH, HMDB
beta-CarbolineHMDB
Chemical FormulaC11H8N2
Average Molecular Weight168.19
Monoisotopic Molecular Weight168.0687
IUPAC Name9H-pyrido[3,4-b]indole
Traditional Nameβ-carboline
CAS Registry Number244-63-3
SMILES
N1C2=CC=CC=C2C2=CC=NC=C12
InChI Identifier
InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
InChI KeyAIFRHYZBTHREPW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyridoindoles
Direct ParentBeta carbolines
Alternative Parents
Substituents
  • Beta-carboline
  • Indole
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point199 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP3.17BIAGI,GL ET AL. (1989)
Predicted Properties
PropertyValueSource
logP2.56ALOGPS
logP1.87ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)13.22ChemAxon
pKa (Strongest Basic)5.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.32 m³·mol⁻¹ChemAxon
Polarizability18.07 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSNorharman, non-derivatized, GC-MS Spectrumsplash10-014i-5900000000-3480c725264b958ffc7fSpectrum
GC-MSNorharman, non-derivatized, GC-MS Spectrumsplash10-014i-5900000000-3480c725264b958ffc7fSpectrum
Predicted GC-MSNorharman, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014l-0900000000-fcdb4b3e6837a47248e2Spectrum
Predicted GC-MSNorharman, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-5f1c82b770634430089f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-2900000000-ec1e052158bb7ac51fa52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 11V, negativesplash10-014i-0900000000-8356e3b21f024042498f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 15V, negativesplash10-014i-0900000000-309bca0da39eb9bfe16c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 21V, negativesplash10-014i-0900000000-5a054045fb18991566ad2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-014i-0900000000-6ae41f21021169fba1582020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, negativesplash10-014l-0900000000-18f3f6cb6eddcab3e38c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, negativesplash10-03di-9000000000-eebba0b8b6a195a9bcf62020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 6V, negativesplash10-014i-0900000000-bb0bad9db10636d0020a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-014i-0900000000-81c9902ae9712620ee7b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-014i-0900000000-2ff64ee76e6f4e6e7b472020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-014i-0900000000-eb22bb403f17b41824ee2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-014i-0900000000-710549ac9a89ddcb850f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-014l-0900000000-0560d33cc2baa85680682020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-014i-1900000000-e89060680f0fbbb90fc12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-7bfe2973a911f7d048822021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-c64bc52da34801ce4cf52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-730c48ee2c09863f6c4d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-c27561fcfb62e1fb8dc02021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-eb27fd1af093e93739872016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-675b8bf1bb9442b351a32016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-6b01d3bcbbc7303b646b2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-a18ea037f074412ab5bf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-d9a1aef47a4155b550a72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0900000000-82fd47fe0f1bc435ec2c2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012897
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007945
KNApSAcK IDC00026537
Chemspider ID58486
KEGG Compound IDC20157
BioCyc IDCPD-15304
BiGG IDNot Available
Wikipedia LinkBeta-Carboline
METLIN IDNot Available
PubChem Compound64961
PDB IDNRH
ChEBI ID109895
References
General References
  1. Venault P, Chapouthier G: From the behavioral pharmacology of beta-carbolines to seizures, anxiety, and memory. ScientificWorldJournal. 2007 Feb 19;7:204-23. doi: 10.1100/tsw.2007.48. [PubMed:17334612 ]
  2. Cao R, Peng W, Wang Z, Xu A: beta-Carboline alkaloids: biochemical and pharmacological functions. Curr Med Chem. 2007;14(4):479-500. doi: 10.2174/092986707779940998. [PubMed:17305548 ]