Showing Compound Card for Dimethylbenzimidazole (CDB005719)

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Record Information
Version1.0
Created at2020-04-27 16:48:52 UTC
Updated at2021-01-06 19:06:57 UTC
CannabisDB IDCDB005719
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDimethylbenzimidazole
DescriptionDimethylbenzimidazole or 5,6-Dimethylbenzimidazole, also known as dimedazol, belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds). Dimethylbenzimidazole is a very strong basic compound (based on its pKa). Dimethylbenzimidazole exists in all living organisms, ranging from bacteria to humans. 5,6-Dimethylbenzimidazole is a natural benzimidazole derivative. It is a component of vitamin B12 where is serves as a ligand for the cobalt atom (PMID: 13796809 ). 5,6-Dimethylbenzimidazole is biosynthesized from flavin mononucleotide by the enzyme 5,6-dimethylbenzimidazole synthase. 5,6-Dimethylbenzimidazole is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DimedazolChEBI
DimedazoleChEBI
DimesolChEBI
DimezolChEBI
5,6-DimethylbenzimidazoleKegg
5,6-Dimethyl-1H-benzimidazoleHMDB
DimezolDimedazolHMDB
5,6-Dimethylbenzimidazole hydrochlorideMeSH, HMDB
Chemical FormulaC9H10N2
Average Molecular Weight146.19
Monoisotopic Molecular Weight146.0844
IUPAC Name5,6-dimethyl-1H-1,3-benzodiazole
Traditional Name5,6-dimethylbenzimidazole
CAS Registry Number582-60-5
SMILES
CC1=CC2=C(C=C1C)N=CN2
InChI Identifier
InChI=1S/C9H10N2/c1-6-3-8-9(4-7(6)2)11-5-10-8/h3-5H,1-2H3,(H,10,11)
InChI KeyLJUQGASMPRMWIW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • Benzenoid
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point205.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP1.854Not Available
Predicted Properties
PropertyValueSource
logP1.88ALOGPS
logP2.29ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.73ChemAxon
pKa (Strongest Basic)6.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.05 m³·mol⁻¹ChemAxon
Polarizability16.47 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSDimethylbenzimidazole, non-derivatized, GC-MS Spectrumsplash10-000t-2900000000-cf01975179c82b56a747Spectrum
GC-MSDimethylbenzimidazole, 1 TMS, GC-MS Spectrumsplash10-0gb9-5790000000-e422b94d0cbe1bd0345eSpectrum
GC-MSDimethylbenzimidazole, non-derivatized, GC-MS Spectrumsplash10-000t-2900000000-cf01975179c82b56a747Spectrum
GC-MSDimethylbenzimidazole, non-derivatized, GC-MS Spectrumsplash10-0gb9-5790000000-e422b94d0cbe1bd0345eSpectrum
GC-MSDimethylbenzimidazole, non-derivatized, GC-MS Spectrumsplash10-000t-1900000000-1cc9a65e6235151e4820Spectrum
GC-MSDimethylbenzimidazole, non-derivatized, GC-MS Spectrumsplash10-0gb9-2590000000-7f1dc8fd34bdb99d58f6Spectrum
Predicted GC-MSDimethylbenzimidazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-0900000000-94a00940d804552f77d0Spectrum
Predicted GC-MSDimethylbenzimidazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDimethylbenzimidazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-d879a610883483e633262017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-1900000000-7810390c926bc0a2238a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000t-3900000000-0e438f149c15e3ba22382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000t-1900000000-286b3359932c2c63dc232017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-4900000000-4e9fbfe2a1943cc865e52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0002-0900000000-4a48df4993767b5c4eff2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0002-0900000000-93fb22bfd73cbaaecda92020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-5f138fc55912e09c04f82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000t-0900000000-0ac7250afc1fd38defe32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-941f6c90a92fad755dd02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-4900000000-9778293bbdebe312995b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0002-0900000000-0581e550bdf15c825ed12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-4900000000-f22be5bed413f1b519e82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-677d27a4db0421a0c22d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-3c2aee6880c85391a7392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-86d65abcc3c20eeaa9b72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-25408408c64689b319ee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-1900000000-4cefb2993f948a46e8e82021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-92df1f58e19215585f6a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-a09abdb85c0cd07661652015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-2900000000-7ad608a4dad05614e9952015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-2f5826366923dad353412015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-685b19fc37ae77b7006b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-3900000000-1e116130bd866fe7fc712015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-8ffc0ea3ec7f7e0434b82021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003701
DrugBank IDDB02591
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023216
KNApSAcK IDNot Available
Chemspider ID655
KEGG Compound IDC03114
BioCyc IDDIMETHYLBENZIMIDAZOLE
BiGG IDNot Available
Wikipedia LinkDimethylbenzimidazole
METLIN IDNot Available
PubChem Compound675
PDB IDNot Available
ChEBI ID15890
References
General References
  1. BARKER HA, SMYTH RD, WEISSBACH H, TOOHEY JI, LADD JN, VOLCANI BE: Isolation and properties of crystalline cobamide coenzymes containing benzimidazole or 5, 6-dimethylbenzimidazole. J Biol Chem. 1960 Feb;235:480-8. [PubMed:13796809 ]