Showing Compound Card for 1-Methylnaphthalene (CDB005827)

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Record Information
Version1.0
Created at2020-04-27 17:00:31 UTC
Updated at2021-01-04 18:49:23 UTC
CannabisDB IDCDB005827
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1-Methylnaphthalene
Description1-Methylnaphthalene also known as α-methylnaphthalene is a methylated derivative of naphthalene. It belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. There are two known isomers of methylnaphthalene including 1-Methylnaphthalene and 2-Methylnaphthalene. 1-Methylnaphthalene exists as a clear, colorless liquid that is insoluble in water. 1-Methylnaphthalene has a camphorous chemical, of medicinal aroma and green, must taste. 1-Methylnaphthalene is found naturally in a number of foods and beverages including apples, grapes, capsicum peppers, black walnuts, milk products, strawberries, peas, asian pears and corn which makes 1-methylnaphthalene a potential biomarker for the consumption of these foods. Methylnaphthalenes are also found in cannabis smoke. 1-Methylnaphthalene is formed during the combustion of cannabis ( Ref:DOI ). 1-Methylnaphthalene is a potentially toxic compound. It is one of over 100 known polycyclic aromatic hydrocarbons (PAH). The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. 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 phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. These enzymes metabolize PAH's into their toxic intermediates. 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. PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. 
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-MethylnaphthaleneChEBI
a-MethylnaphthaleneGenerator
Α-methylnaphthaleneGenerator
1-Methyl naphthaleneHMDB
1-Methyl-naphthaleneHMDB
alpha-Methyl naphthalenesHMDB
alpha-Methyl-naphthaleneHMDB
FEMA 3193HMDB
Methyl naphthaleneHMDB
Methyl-1-naphthaleneHMDB
Methyl-naphthaleneHMDB
Naphthalene, methyl-, homopolymerHMDB
PolymethylnaphthaleneHMDB
Chemical FormulaC11H10
Average Molecular Weight142.2
Monoisotopic Molecular Weight142.0783
IUPAC Name1-methylnaphthalene
Traditional Name1-methylnaphthalene
CAS Registry Number90-12-0
SMILES
CC1=CC=CC2=CC=CC=C12
InChI Identifier
InChI=1S/C11H10/c1-9-5-4-7-10-6-2-3-8-11(9)10/h2-8H,1H3
InChI KeyQPUYECUOLPXSFR-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
Disposition

Route of exposure:

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Role

Indirect biological role:

Environmental role:

Industrial application:

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Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-22 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.026 mg/mL at 25 °CNot Available
logP3.87Not Available
Predicted Properties
PropertyValueSource
logP3.84ALOGPS
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
Polarizability16.61 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)splash10-0006-2900000000-53cda581a6605326e48c2014-09-20View Spectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-5900000000-1053593aad42a77aa98bSpectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-2900000000-56264ce7fb87f61d59e3Spectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-3900000000-466eebbbc710f9d74e3bSpectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-3900000000-5b7a1e8903022a3f5a57Spectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-e017871c9adc6ee00fb9Spectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-e2ebef06c838787a1720Spectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-5900000000-1053593aad42a77aa98bSpectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-2900000000-56264ce7fb87f61d59e3Spectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-3900000000-466eebbbc710f9d74e3bSpectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-3900000000-5b7a1e8903022a3f5a57Spectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-e017871c9adc6ee00fb9Spectrum
GC-MS1-Methylnaphthalene, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-e2ebef06c838787a1720Spectrum
Predicted GC-MS1-Methylnaphthalene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-0900000000-0da70ea2233c3affb638Spectrum
Predicted GC-MS1-Methylnaphthalene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-9a9a9f94bee2dbaba3c02015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5692907557a9baf3d2572015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-3900000000-7eef39e40fe85545ba502015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-4b4ea885969f2a72f1b72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-4b4ea885969f2a72f1b72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-e204af06be24fa547ed92015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-c989a442d4404542ed612021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2900000000-4c5f4b7cbec6cfd38b142021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9800000000-c7005946673c7bd7a9262021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-84dab5fd9e005e323db02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-84dab5fd9e005e323db02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1900000000-3a4e7194998e40dc39cf2021-09-25View 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
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0032860
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010838
KNApSAcK IDC00050647
Chemspider ID6736
KEGG Compound IDC14082
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1-Methylnaphthalene
METLIN IDNot Available
PubChem Compound7002
PDB IDNot Available
ChEBI ID50717
References
General ReferencesNot Available