Showing Compound Card for 2-Methyl-1H-imidazole (CDB000511)

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Record Information
Version1.0
Created at2020-03-19 00:40:59 UTC
Updated at2020-12-07 19:07:29 UTC
CannabisDB IDCDB000511
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Methyl-1H-imidazole
Description2-Methylimidazole, belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-membered ring, that includes two nitrogen atoms at positions 1 and 3, and three carbon atoms. 2-MethylImidazole has the chemical formula CH3C3H2N2H and is a methylated derivative of Imidazole on which a methyl group has been added at position C-2. It is a white or colorless solid that is highly soluble in polar organic solvents and water. It is a precursor to a range of drugs and is a ligand in coordination chemistry. 2-Methylimidazole is prepared by condensation of glyoxal, ammonia, and acetaldehyde, through the Radziszewski reaction. 2-Methylimidazole is a sterically hindered imidazole that is used to simulate the coordination of histidine to heme complexes. It can be deprotonated to make imidazolate-based coordination polymers. 2-Methylimidazole is a precursor to several members of the nitroimidazole antibiotics that are used to combat anaerobic bacterial and parasitic infections. 2-methylimidazole has been found in the volatile fraction of Cannabis sativa (PMID: 26657499 ) and is likely a component of marijuana smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Methylimidazole hydrochlorideHMDB
2-Methylimidazole, silver (1+) saltHMDB
ZN(2-Methylimidazole)2HMDB
Chemical FormulaC4H6N2
Average Molecular Weight82.1
Monoisotopic Molecular Weight82.0531
IUPAC Name2-methyl-1H-imidazole
Traditional Name1H-imidazole, 2-methyl-
CAS Registry Number693-98-1
SMILES
CC1=NC=CN1
InChI Identifier
InChI=1S/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6)
InChI KeyLXBGSDVWAMZHDD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazoles
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Imidazole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.36ALOGPS
logP-0.022ChemAxon
logS0.86ALOGPS
pKa (Strongest Acidic)13.92ChemAxon
pKa (Strongest Basic)7.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity23.45 m³·mol⁻¹ChemAxon
Polarizability8.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Methyl-1H-imidazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Methyl-1H-imidazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 5V, positivesplash10-001i-9000000000-e4f7fea4cd54cb30a9eb2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 150V, Positivesplash10-001i-9000000000-e4f7fea4cd54cb30a9eb2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-4e3785e565516e68dc352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-a6a0a295e7fc4c2f101d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9000000000-216aecf6a69f53d16f7b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-c42fcd9a6442fc5da0cb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-f37830ccb1cef86f29422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c1c8bc19b2db2bff6d252016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-0c4ca615527c02a811972021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0api-9000000000-59d4b654c5e576d17af92021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-9fefb19eb2dbfb5b97422021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-5fba3d16c726bdbb206a2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-e522e427b7835934ef5f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9000000000-9822d44a57700c61f65c2021-10-12View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0245233
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID12225
KEGG Compound IDC19261
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Methylimidazole
METLIN IDNot Available
PubChem Compound12749
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]