Showing Compound Card for 2-Methylnaphthalene (CDB000510)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:40:56 UTC
Updated at2020-12-07 19:07:28 UTC
CannabisDB IDCDB000510
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Methylnaphthalene
Description2-Methylnaphthalene belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 2-methylnaphthalene is a potentially toxic compound. 2-Methylnaphthalene is also considered a Plycyclic Aromatic Hydrocarbon (PAH). NASA announced on February 22, 2014 a greatly upgraded database for detecting and monitoring PAHs in the universe, including 2-methylnaphthalene. According to NASA scientists, over 20% of the carbon in the universe may be associated with PAHs, possible starting materials for the formation of life. PAHs seem to have been formed shortly after the Big Bang, are abundant in the universe, and are associated with new stars and exoplanets. In the human body, many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. Exposure to large amounts of 2-methylnapthalene may also cause nausea, vomiting, diarrhea, blood in the urine, and a yellow color to the skin. 2-Methylnaphthalene has been found in the volatile fraction of Cannabis sativa (PMID: 26657499 ) and is a component of marijuana smoke ( Ref:DOI ). It is volatilized during the combustion of cannabis.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
beta-MethylnaphthaleneChEBI
b-MethylnaphthaleneGenerator
Β-methylnaphthaleneGenerator
2-Methylnaphthalene, ion(1+)MeSH
2-Methylnaphthalene, ion(1-)MeSH
2-Methylnaphthalene, lithium salt, ion(1-)MeSH
2-Methylnaphthalene, methyl-13C-labeledMeSH
2-Methylnaphthalene, naphthalene-1-(13)C-labeledMeSH
Chemical FormulaC11H10
Average Molecular Weight142.2
Monoisotopic Molecular Weight142.0783
IUPAC Name2-methylnaphthalene
Traditional Name2-methylnaphthalene
CAS Registry Number7419-61-6
SMILES
CC1=CC2=CC=CC=C2C=C1
InChI Identifier
InChI=1S/C11H10/c1-9-6-7-10-4-2-3-5-11(10)8-9/h2-8H,1H3
InChI KeyQIMMUPPBPVKWKM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.83ALOGPS
logP3.48ChemAxon
logS-3.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.55 m³·mol⁻¹ChemAxon
Polarizability16.78 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-2900000000-9ac29319d37f96c9e8712014-09-20View Spectrum
GC-MS2-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-9800000000-1ae0df46161af462c53dSpectrum
GC-MS2-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-2900000000-e3d5d8950004ca237838Spectrum
GC-MS2-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-fc999862e44e7aea8048Spectrum
Predicted GC-MS2-Methylnaphthalene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-0900000000-f176e8ebeee029c8ad89Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-8f9f0039a7c67ac751502016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-58f20b5190f45805880e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-2900000000-b954930335ee0c854ed72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-682acebb92e0b06e8e282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-682acebb92e0b06e8e282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-0bcf13e1acfdfe6564362016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Glycine N-methyltransferaseGNMT6p12Q14749 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Aryl hydrocarbon receptorAHR7p15P35869 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Aryl hydrocarbon receptorAHR7p15P35869 details
Concentrations Data
Not Available
HMDB IDHMDB0062000
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007631
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14098
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Methylnaphthalene
METLIN IDNot Available
PubChem Compound7055
PDB IDNot Available
ChEBI ID50720
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 ]

Enzymes

Enzyme Details
1. Glycine N-methyltransferase
General function:
Involved in folic acid binding
Specific function:
Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine.
Gene Name:
GNMT
Uniprot ID:
Q14749
Molecular weight:
32742.0