Showing Compound Card for 4-Methylphenethylamine (CDB000539)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:42:36 UTC
Updated at2020-11-18 16:35:15 UTC
CannabisDB IDCDB000539
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4-Methylphenethylamine
Description4-Methylphenethylamine also known as para-methylphenethylamine, with the chemical formula of C9H13N, belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. 4-Methylphenethylamine is a very strong basic compound (based on its pKa). As its monomethylated isomers, α-methylphenethylamine, β-methylphenethylamine, and N-methylphenethylamine, 4-methylphenethylamine is an agonist of the trace amine associated receptor 1 (TAAR1) in humans (PMID: 17038507 ). Furthermore, there is also evidence showing that 4-methylphenethylamine might inhibit the cytochrome P450 CYP1A2 and CYP2A6 enzymes, in humans. 4-Methylphenetylamine has been detected as a volatile component in Marijuana samples obtained in police seizures (PMID:26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC9H13N
Average Molecular Weight135.21
Monoisotopic Molecular Weight135.1048
IUPAC Name2-(4-methylphenyl)ethan-1-amine
Traditional Namebenzeneethanamine, 4-methyl-
CAS Registry Number3261-62-9
SMILES
CC1=CC=C(CCN)C=C1
InChI Identifier
InChI=1S/C9H13N/c1-8-2-4-9(5-3-8)6-7-10/h2-5H,6-7,10H2,1H3
InChI KeyVKJXAQYPOTYDLO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • 2-arylethylamine
  • Aralkylamine
  • Toluene
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.67ALOGPS
logP1.9ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)9.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.33 m³·mol⁻¹ChemAxon
Polarizability16.54 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-MS4-Methylphenethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytochrome P450 1A2CYP1A215q24.1P05177 details
Cytochrome P450 2A6CYP2A619q13.2P11509 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Trace amine-associated receptor 1TAAR16q23.2Q96RJ0 details
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 ID69207
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Methylphenethylamine
METLIN IDNot Available
PubChem Compound76751
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL: Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1. J Pharmacol Exp Ther. 2007 Jan;320(1):475-85. doi: 10.1124/jpet.106.112532. Epub 2006 Oct 12. [PubMed:17038507 ]
  2. 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 ]