Showing Compound Card for 4,4'-Bipyridine (CDB006028)

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Record Information
Version1.0
Created at2020-04-27 17:22:08 UTC
Updated at2021-01-06 19:07:01 UTC
CannabisDB IDCDB006028
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4,4'-Bipyridine
Description4,4'-Bipyridine, also known as 4,4'-bpy, belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other. 4,4'-Bipyridine can also mediate electronic effects between two paramagnetic metal centers. 4,4'-Bipyridine was first obtained in 1868 by the Scottish chemist Thomas Anderson (1819- 1874) via heating pyridine with sodium metal. However, Anderson's empirical formula for 4,4'-bipyridine was incorrect. 4,4'-Bipyridine is a very strong basic compound (based on its pKa). This species is electroactive, and its toxicity arises from the ability of this dication to interrupt biological electron transfer. Because of its structure, 4,4'-bipyridine can bridge between metal centres to give coordination polymers. The correct empirical formula, and the correct molecular structure, for 4,4'-bipyridine was provided in 1882 by the Austrian chemist Hugo Weidel and his student M. Russo. 4,4'-Bipyridine (abbreviated to 4,4'-bipy or 4,4'-bpy) is a bipyridine which is mainly used as a precursor to N,N-dimethyl-4,4'-bipyridinium [(C5H4NCH3)2]2+, known as paraquat. 4,4'-Bipyridine is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4,4'-BipyridylChEBI
4,4'-BpyChEBI
4,4'-DipyridineChEBI
4,4'-DipyridylChEBI
4,4-BipyridinChEBI
4-(4-Pyridyl)pyridineChEBI
gamma,Gamma'-bipyridylChEBI
gamma,Gamma'-dipyridylChEBI
g,Gamma'-bipyridylGenerator
Γ,gamma'-bipyridylGenerator
g,Gamma'-dipyridylGenerator
Γ,gamma'-dipyridylGenerator
4,4'-Bipyridyl dihydrochlorideMeSH
4,4'-BipyridineMeSH
Chemical FormulaC10H8N2
Average Molecular Weight156.19
Monoisotopic Molecular Weight156.0687
IUPAC Name4,4'-bipyridine
Traditional Namebipyridine
CAS Registry Number37275-48-2
SMILES
C1=CC(=CC=N1)C1=CC=NC=C1
InChI Identifier
InChI=1S/C10H8N2/c1-5-11-6-2-9(1)10-3-7-12-8-4-10/h1-8H
InChI KeyMWVTWFVJZLCBMC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassBipyridines and oligopyridines
Direct ParentBipyridines and oligopyridines
Alternative Parents
Substituents
  • Bipyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.4ALOGPS
logP1.19ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)5.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.88 m³·mol⁻¹ChemAxon
Polarizability16.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4,4'-Bipyridine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-0900000000-5caca1ffa80c12310859Spectrum
Predicted GC-MS4,4'-Bipyridine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0a4i-0900000000-1fdd2e8c2a55cd5608f02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0a4i-0900000000-d4cb2ea0f8feb982cb592021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4i-0900000000-b05fd28a3939c8a883162021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-0900000000-1ec8d8c6a9a93a738be62021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-fe1b528093d0f8f6d6cf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-8a4970391596c2a20c772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-1900000000-76118f16c813075084e62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-111bb826f54113e95f732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-111bb826f54113e95f732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-1900000000-3397286823fd3cfc60f72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-8a6bf55263d2e8824c172021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-dcc9884cf771b62d90f62021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsr-1900000000-df3cc3292d4648d42b142021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-55ef27dd0ecfd19d88642021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-55ef27dd0ecfd19d88642021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-0900000000-375f472bad19f7f5bc642021-10-12View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0246599
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21105699
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4,4%27-Bipyridine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID30985
References
General ReferencesNot Available