Showing Compound Card for 4-Methylquinoline (CDB005523)

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Record Information
Version1.0
Created at2020-04-27 16:29:05 UTC
Updated at2021-01-04 20:37:45 UTC
CannabisDB IDCDB005523
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4-Methylquinoline
Description4-Methylquinoline, also known as Lepidine or cincholepidine, belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyridine ring to form benzo[b]azabenzene. 4-Methylquinoline is a methylated derivative of quinoline in which a methyl group substituted at position 4. It exists as a clear, colorless oil that is only slightly soluble in water. 4-Methylquinoline has a sweet, floral, oily and slightly burnt odor and a sweet, floral, slightly burnt taste. It is used in the cosmetic industry as a perfuming agent. It is found naturally in peppermint oil and garden cress seeds. 4-Methylquinoline (4-MeQ) has been shown have extraordinarily high mutagenicity when compared to quinoline and isomeric methylquinolines (PMID: 8860954 ). 4-Methylquinoline is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-LepidineChEBI
CincholepidineChEBI
gamma-MethylquinolineChEBI
LepidinChEBI
LepidineChEBI
p-MethylquinolineChEBI
g-MethylquinolineGenerator
Γ-methylquinolineGenerator
4-MethylquinolineMeSH
4-Methylquinoline hydrochlorideMeSH
Chemical FormulaC10H9N
Average Molecular Weight143.19
Monoisotopic Molecular Weight143.0735
IUPAC Name4-methylquinoline
Traditional Name4-methylquinoline
CAS Registry Number491-35-0
SMILES
CC1=CC=NC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H9N/c1-8-6-7-11-10-5-3-2-4-9(8)10/h2-7H,1H3
InChI KeyMUDSDYNRBDKLGK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassNot Available
Direct ParentQuinolines and derivatives
Alternative Parents
Substituents
  • Quinoline
  • Methylpyridine
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP2.56ALOGPS
logP2.64ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)5.29ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.02 m³·mol⁻¹ChemAxon
Polarizability15.98 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-05f8ece4108ecaa562aa2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-ea8d1811c2ffad6425e92016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2900000000-981227725a6bc0280e282016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-139cd709f40dd772ac8e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-0c5d8f1296487aef29c82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1900000000-ad799820dca91cc932ce2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-15135
BiGG IDNot Available
Wikipedia LinkLepidine
METLIN IDNot Available
PubChem Compound10285
PDB IDNot Available
ChEBI ID48983
References
General References
  1. Saeki K, Takahashi K, Kawazoe Y: Potent mutagenic potential of 4-methylquinoline: metabolic and mechanistic considerations. Biol Pharm Bull. 1996 Apr;19(4):541-6. doi: 10.1248/bpb.19.541. [PubMed:8860954 ]