Showing Compound 2-Phenylethylamine (FDB010580)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:12 UTC

Update date

2020-09-17 15:30:49 UTC

Primary ID

FDB010580

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Phenylethylamine

Description

Phenylethylamine (PEA) is an aromatic amine which has a constitutional isomer (+)-phenylethylamine (1-phenylethylamine), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. It is a strongly basic, colorless liquid at room temperature which 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. Phenylethylamines can be biosynthesized in mammals from the amino acid phenylalanine by enzymatic decarboxylation. Phenylethylamine is produced after microbial fermentation and is a metabolite of Bacillus, Enterococcus, Pseudomanas and Lactobacillus (PMID: 22953951; PMID: 17307265; PMID: 16630269) and has anti-microbial properties against pathogenic strains of E. coli. It is found in many foods such as chocolate. However, trace amounts from food are quickly metabolized by the enzyme monoamine oxidase (MAO-B) into phenylacetic acid, preventing significant concentrations from reaching the brain. In the human brain, phenylethylamine is a central nervous system stimulant that binds to the human trace amine-associated receptor 1 (hTAAR1) as an agonist (PMID 27424325). It 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). Phenylethylamine is also a skin irritant and possible sensitizer. PEA is the primary compound found in carnivore urine (especially cat) that repels mice and rats. Quantitative HPLC analysis across 38 mammalian species has shown that PEA production in urine is especially high in carnivores, with some producing >3,000-fold more than herbivores (PMID: 21690383).

CAS Number

64-04-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	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
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
Polystyrene a-NH2	HMDB
Phenethylamine hydrobromide	HMDB
Phenethylamine tosylate	HMDB
Phenethylamine conjugate acid	HMDB
Phenethylamine sulfate	HMDB
Phenethylamine, monolithium salt	HMDB
2-Phenylethylammonium chloride	HMDB
Phenethylamine sulfate (2:1)	HMDB
Phenethylamine, 15N-labeled CPD	HMDB
Phenethylamine mesylate	HMDB
Phenethylamine perchlorate	HMDB
Phenethylamine, beta-(14)C-labeled CPD	HMDB
Diphenethylamine sulfate	HMDB
.omega.-phenylethylamine	biospider
β	biospider
β-aminoethylbenzene	biospider
β-phenethylamine	biospider
β-phenylaethylamin	biospider
β-phenylaethylamin (german)	biospider
β-phenylethylamine	biospider
«omega»-phenylethylamine	biospider
1-Phenyl-2-amino-athan (GERMAN)	biospider
1-Phenyl-2-aminoethane hydrochloride	biospider
1tnj	biospider
1utm	biospider
1uto	biospider
2-phenyl-Ethanamine	biospider
2-Phenylethylamine hydrochloride	biospider
3-Methylbutanoic acid	biospider
B-phenethylamine	biospider
B-phenylaethylamin	biospider
B-phenylaethylamin (german)	biospider
B-phenylethylamine	biospider
Benzeneethanamine, 9CI	db_source
Benzeneethanamine, hydrochloride	biospider
Beta phenethylamine	biospider
Beta-aminoethylbenzene	biospider
Beta-phenethylamine	biospider
Beta-phenylaethylamin	biospider
Beta-phenylethylamine	biospider
Ethanamine, 2-phenyl-	biospider
Ethylamine, 2-phenyl-	biospider
FEMA 3220	db_source
Phenethylamine, β	biospider
Phenethylamine, 8CI	db_source
Phenethylamine, beta	biospider
Phenethylamine, hydrochloride	biospider
Phenethylammonium chloride	biospider
Phenylethylamine	biospider
Polystyrene A-NH2	biospider
Polystyrene A-NH2;	biospider
β-aminoethylbenzene	Generator
β-phenethylamine	Generator
β-phenylethylamine	Generator

Predicted Properties

Property	Value	Source
Water Solubility	2.19 g/L	ALOGPS
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

Chemical Formula

C8H11N

IUPAC name

2-phenylethan-1-amine

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

Isomeric SMILES

NCCC1=CC=CC=C1

Average Molecular Weight

121.1796

Monoisotopic Molecular Weight

121.089149357

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.

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

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Animal

Microbe:

Lactobacillus:

Bacillus:

Bacillus subtilis

Enterococcus:

Enterococcus faecium

Plant:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 79.29%; H 9.15%; N 11.56%	DFC
Melting Point	-60 oC
Boiling Point	Bp7 70-71°	DFC
Experimental Water Solubility	Not Available
Experimental logP	1.41	HANSCH,C ET AL. (1995)
Experimental pKa	9.83
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d244 0.96	DFC
Refractive Index	n25D 1.5290	DFC

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0udi-3900000000-c931498c67dbf88820ee	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00dr-5900000000-d15a3c803d2534e366d8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-7713ab7346491f1f5f42	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-94774bbd6283b4a26a51	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0abc-5900000000-724c680a9564ac27f7ee	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-5ba434a8565ec0014b6b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-053r-9000000000-f312ab6fe99f8eca86e7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-3900000000-c931498c67dbf88820ee	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00dr-5900000000-d15a3c803d2534e366d8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-4900000000-4c37abb4c50d5582d87c	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9100000000-3e2562db471b8bb298d2	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-95c5a1366bba1014e2aa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ab9-0900000000-5ad03d29c0ff6167539c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0900000000-1b25fe0d03af3ce715ba	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-056r-7900000000-a6478bab1f5bd04c7329	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9100000000-abdacae4bceb2048614f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-d61f8f9b0d593297d010	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ab9-0900000000-e3d2be06e661bac2f739	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0900000000-fc4c40ae6333ed1f04f6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-056r-7900000000-f25cc18055d08500ec9d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9100000000-0e8ece94eaa349e6fd21	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0uk9-2900000000-272fff4a446fcf053de8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-e833e9ebdd0584ee9cff	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-f51c34f8fd6e67925a52	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-162188a06251a43ccc54	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-162188a06251a43ccc54	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-2a12817c62551d9dee50	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-ac8b555024a8bbc5e78b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-926231c14695be35af04	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-c5e8005c53eaf96bc957	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0900000000-10a3aff16ce06e5488bb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-c8186da6e772bfd9759c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9500000000-2745e56fb8603507394b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-b746d7d1eb593614d234	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1900000000-f4ada8157d6dde803051	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ufu-9500000000-54d2d2a1b68d878200b8	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-bf5d1e8f4a14683bd0aa	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18397

Phenol-Explorer ID

Not Available

DrugBank ID

DB04325

HMDB ID

HMDB12275

CRC / DFC (Dictionary of Food Compounds) ID

FFC18-E:FFC18-E

EAFUS ID

2958

Dr. Duke ID

2-PHENYLETHYL-AMINE|BETA-PHENYLETHYLAMINE|PHENETHYLAMINE|PHENYLETHYLAMINE

BIGG ID

Not Available

KNApSAcK ID

C00001426

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1035561

SuperScent ID

Not Available

Wikipedia ID

2-Phenylethylamine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
central nervous system stimulant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
irritant			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Aromatic-L-amino-acid decarboxylase	DDC	P20711
Serotonin N-acetyltransferase	AANAT	Q16613

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
ammoniacal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fishy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.