Livestock Metabolome Database: Showing metabocard for Phenylethylamine (LMDB00573)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:52:50 UTC

Update Date

2016-09-23 18:45:38 UTC

Lmdb

LMDB00573

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phenylethylamine

Description

Phenethylamine (PEA) is an aromatic amine, which is a colorless liquid at room temperature. It is soluble in water, ethanol, and ether. Similar to other low-molecular-weight amines, it has a fishy odor. Upon exposure to air, it forms a solid carbonate salt with carbon dioxide. Phenethylamine is strongly basic and forms a stable crystalline hydrochloride salt with a melting point of 217 oC. Phenethylamine is also a skin irritant and possible sensitizer. Phenethylamine also has a constitutional isomer (+)-phenylethylamine (1-phenylethylamine), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. In the animal brain, 2-phenethylamine is believed to function as a neuromodulator or neurotransmitter (a trace amine). Phenethylamine can be biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. It is also found in many foods such as chocolate, especially after microbial fermentation. However trace amounts from food are quickly metabolized by the enzyme MAO-B (into phenylacetic acid), preventing significant concentrations from reaching the brain. Phenylethylamine is a precursor to the neurotransmitter phenylethanolamine. High levels of PEA have been found in the urine of schizophrenics but it is not significantly elevated in the serum or CSF of schizophrenics (PMID: 7906896 , PMID: 7360842 ). Urinary levels of PEA are significantly lower in children with attention deficit hyperactivity disorder (ADHD) (PMID: 12205654 ). It has been found that PEA is the primary compound found in carnivore (especially cat) urine that leads to rodent (mouse and rat) avoidance. In other words, phenylethylamine is useful for scaring off rodent pests. Quantitative HPLC analysis across 38 mammalian species has shown that PEA production in urine is especially enhanced in carnivores, with some producing >3,000-fold more than herbivores (PMID: 21690383 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Benzeneethanamine	ChEBI
beta-Aminoethylbenzene	ChEBI
beta-Phenethylamine	ChEBI
beta-Phenylethylamine	ChEBI
Phenethylamine	ChEBI
2-Phenylethylamine	Kegg
b-Aminoethylbenzene	Generator
Β-aminoethylbenzene	Generator
b-Phenethylamine	Generator
Β-phenethylamine	Generator
b-Phenylethylamine	Generator
Β-phenylethylamine	Generator
(2-Aminoethyl)benzene	HMDB
(2-Aminoethyl)polystyrene	HMDB
1-amino-2-Phenylethane	HMDB
1-Phenethylamine	HMDB
1-Phenyl-2-amino-athan	HMDB
1-Phenyl-2-aminoethane	HMDB
1TNJ	HMDB
1Utm	HMDB
1Uto	HMDB
2-amino-1-Phenylethane	HMDB
2-amino-Fenylethan	HMDB
2-Fenylethylamin	HMDB
2-Phenethylamine	HMDB, MeSH
2-Phenyl-ethanamine	HMDB
2-Phenylethanamine	HMDB
2-Phenylethanamine (acd/name 4.0)	HMDB
2-Phenylethylamine (acd/name 4.0)	HMDB
b-Phenylaethylamin	HMDB
Benzeneethanamine hydrochloride	HMDB
beta Phenethylamine	HMDB
beta-Phenylaethylamin	HMDB
Omega-phenylethylamine	HMDB
PEA	HMDB
Phenethylamine hydrochloride	HMDB, MeSH
Polystyrene a-NH2	HMDB
Phenethylamine hydrobromide	MeSH, HMDB
Phenethylamine tosylate	MeSH, HMDB
Phenethylamine conjugate acid	MeSH, HMDB
Phenethylamine sulfate	MeSH, HMDB
Phenethylamine, monolithium salt	MeSH, HMDB
2-Phenylethylammonium chloride	MeSH, HMDB
Phenethylamine sulfate (2:1)	MeSH, HMDB
Phenethylamine, 15N-labeled CPD	MeSH, HMDB
Phenethylamine mesylate	MeSH, HMDB
Phenethylamine perchlorate	MeSH, HMDB
Phenethylamine, beta-(14)C-labeled CPD	MeSH, HMDB
Diphenethylamine sulfate	MeSH, HMDB

Chemical Formula

C₈H₁₁N

Average Molecular Weight

121.1796

Monoisotopic Molecular Weight

121.089149357

IUPAC Name

2-phenylethan-1-amine

Traditional Name

2-phenylethylamine

CAS Registry Number

64-04-0

SMILES

NCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2

InChI Key

BHHGXPLMPWCGHP-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Phenethylamine
2-arylethylamine
Aralkylamine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alkaloid (CHEBI:18397 )
aralkylamine (CHEBI:18397 )
phenylethylamine (CHEBI:18397 )
Biogenic amines (C05332 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.41	ALOGPS
logP	1.39	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	9.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	39.29 m³·mol⁻¹	ChemAxon
Polarizability	14.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0udi-3900000000-c931498c67dbf88820ee	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00dr-5900000000-d15a3c803d2534e366d8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-7713ab7346491f1f5f42	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-94774bbd6283b4a26a51	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0abc-5900000000-724c680a9564ac27f7ee	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-5ba434a8565ec0014b6b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-053r-9000000000-f312ab6fe99f8eca86e7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-3900000000-c931498c67dbf88820ee	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00dr-5900000000-d15a3c803d2534e366d8	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-4900000000-4c37abb4c50d5582d87c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9100000000-3e2562db471b8bb298d2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-95c5a1366bba1014e2aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ab9-0900000000-5ad03d29c0ff6167539c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0900000000-1b25fe0d03af3ce715ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-056r-7900000000-a6478bab1f5bd04c7329	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9100000000-abdacae4bceb2048614f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-d61f8f9b0d593297d010	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ab9-0900000000-e3d2be06e661bac2f739	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0900000000-fc4c40ae6333ed1f04f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-056r-7900000000-f25cc18055d08500ec9d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9100000000-0e8ece94eaa349e6fd21	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0uk9-2900000000-272fff4a446fcf053de8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-e833e9ebdd0584ee9cff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-f51c34f8fd6e67925a52	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-162188a06251a43ccc54	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-162188a06251a43ccc54	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-2a12817c62551d9dee50	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-ac8b555024a8bbc5e78b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-926231c14695be35af04	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-c5e8005c53eaf96bc957	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-6f9e6a6eb6c2ac8f4531	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-1900000000-aeb026a07351a147ae19	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-3900000000-a6c6357f047322c4efe1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a6r-6900000000-0a32d01e2dda19a78c83	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-056r-9600000000-be832e76b1211d35978c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-004i-9400000000-ab97002137a57a7802bc	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-bf5d1e8f4a14683bd0aa	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Ruminal Fluid	Detected and Quantified	20.2 +/- 6.0 uM	Not Available	Bovine	Saleem F, Bouatra...	details

External Links

DrugBank ID

DB04325

HMDB ID

HMDB0012275

FooDB ID

FDB010580

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001426

BiGG ID

Not Available

BioCyc ID

PHENYLETHYLAMINE

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

O'Reilly RL, Davis BA: Phenylethylamine and schizophrenia. Prog Neuropsychopharmacol Biol Psychiatry. 1994 Jan;18(1):63-75. [7906896 ]
Potkin SG, Wyatt RJ, Karoum F: Phenylethylamine (PEA) and phenylacetic acid (PAA) in the urine of chronic schizophrenic patients and controls. Psychopharmacol Bull. 1980 Jan;16(1):52-4. [7360842 ]
Kusaga A, Yamashita Y, Koeda T, Hiratani M, Kaneko M, Yamada S, Matsuishi T: Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. Ann Neurol. 2002 Sep;52(3):372-4. [12205654 ]
Ferrero DM, Lemon JK, Fluegge D, Pashkovski SL, Korzan WJ, Datta SR, Spehr M, Fendt M, Liberles SD: Detection and avoidance of a carnivore odor by prey. Proc Natl Acad Sci U S A. 2011 Jul 5;108(27):11235-40. doi: 10.1073/pnas.1103317108. Epub 2011 Jun 20. [21690383 ]

Showing metabocard for Phenylethylamine (LMDB00573)

Structure for LMDB00573 (Phenylethylamine)