Back to Compounds

Showing Compound N-Methylphenethylamine (FDB010581)

Record Information
Version1.0
Creation date2010-04-08 22:09:12 UTC
Update date2025-11-18 23:20:39 UTC
Primary IDFDB010581
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Methylphenethylamine
DescriptionN-methylphenethylamine, also known as N-methylphenethylamine hydrochloride or N-methylphenethylamine, conjugate acid, is a member of the class of 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. N-methylphenethylamine is slightly soluble (in water) and a very strong basic compound (based on its pKa). N-methylphenethylamine can be found in a number of food items such as apple, white cabbage, carrot, and cabbage, which makes N-methylphenethylamine a potential biomarker for the consumption of these food products. N-Methylphenethylamine (NMPEA) is a naturally occurring trace amine neuromodulator in humans that is derived from the trace amine, phenethylamine (PEA). It has been detected in human urine (<1 μg over 24 hours) and is produced by phenylethanolamine N-methyltransferase with phenethylamine as a substrate. PEA and NMPEA are both alkaloids that are found in a number of different plant species as well. Some Acacia species, such as A. rigidula, contain remarkably high levels of NMPEA (~2300–5300 ppm). NMPEA is also present at low concentrations (< 10 ppm) in a wide range of foodstuffs .
CAS Number589-08-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
N-Methyl-2-phenylethanamineMeSH
N-Methyl-beta-phenethylamineMeSH
N-Methylphenethylamine hydrochlorideMeSH
N-Methylphenethylamine sodiumMeSH
N-Methylphenethylamine, conjugate acidMeSH
N-MethylphenylethylamineMeSH
Methyl-phenethyl-amineChEMBL
N-MethylphenethylamineChEMBL
α-phenyl-β-methylaminoethanebiospider
1-Phenyl-2-methylamino-aethanbiospider
1-Phenyl-2-methylaminoethanebiospider
Alpha-phenyl-beta-methylaminoethanebiospider
Benzeneethanamine, n-methyl-biospider
Benzeneethanamine, N-methyl- (9CI)biospider
N-(phenylethyl)methylaminebiospider
N-methyl-β-phenethylaminebiospider
N-methyl-β-phenylaethylaminbiospider
N-methyl-β-phenylethylaminebiospider
N-Methyl-2-phenylethylaminebiospider
N-methyl-beta-phenylaethylaminbiospider
N-methyl-beta-phenylethylaminebiospider
N-Methyl-N-(2-phenylethyl)aminebiospider
N-methyl-phenethylaminebiospider
N-methylbenzeneethanaminebiospider
N-methylphenylethylaminebiospider
Phenethylamine, n-methyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility3.28 g/LALOGPS
logP1.75ALOGPS
logP1.82ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)10.13ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.06 m³·mol⁻¹ChemAxon
Polarizability16.42 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H13N
IUPAC namemethyl(2-phenylethyl)amine
InChI IdentifierInChI=1S/C9H13N/c1-10-8-7-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3
InChI KeySASNBVQSOZSTPD-UHFFFAOYSA-N
Isomeric SMILESCNCCC1=CC=CC=C1
Average Molecular Weight135.2062
Monoisotopic Molecular Weight135.104799421
Classification
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
  • Aralkylamine
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 79.95%; H 9.69%; N 10.36%DFC
Melting PointNot Available
Boiling PointBoiling Pt : 206 oCDFC
Experimental Water SolubilityNot Available
Experimental logP1.91SANGSTER (1993)
Experimental pKa10.1
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-effe7d16c0450ba4163e2015-03-01View Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-0b3ccf61e92660764a182016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2900000000-4c8e988c763e254477c82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054o-9400000000-61da4530d8c715638da82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-fbefa09553f0098f544d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-9c40140f6a6b0204b0352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pel-9600000000-57fd80b7875aa52825482016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-d2bab66b3b200a21bc5b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-5900000000-fcaa09a2074577b5ba372021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9100000000-d0002fa14bfea646bfa22021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-4cd0d6803306f5174da52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-3bf81a9d64ea97cad8fa2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9000000000-5dde657a4ee84cbb2a232021-10-21View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
ChemSpider ID11019
ChEMBL IDCHEMBL45763
KEGG Compound IDNot Available
Pubchem Compound ID11503
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDFFC18-E:FFC19-F
EAFUS IDNot Available
Dr. Duke IDN-METHYL-PHENETHYLAMINE| N-METHYL-BETA-PHENETHYLAMINE
BIGG IDNot Available
KNApSAcK IDC00042776
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDN-Methylphenethylamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).