Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:12 UTC |
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Update date | 2024-11-29 22:25:29 UTC |
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Primary ID | FDB010580 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 2-Phenylethylamine |
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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). |
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CAS Number | 64-04-0 |
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Structure | |
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Synonyms | Synonym | Source |
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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 | .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-Amino-2-phenylethane | biospider | 1-Phenyl-2-amino-athan (GERMAN) | biospider | 1-Phenyl-2-aminoethane hydrochloride | biospider | 1tnj | biospider | 1utm | biospider | 1uto | biospider | 2-Amino-1-phenylethane | biospider | 2-Amino-fenylethan | 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 |
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Predicted Properties | |
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Chemical Formula | C8H11N |
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IUPAC name | 2-phenylethan-1-amine |
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InChI Identifier | InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2 |
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InChI Key | BHHGXPLMPWCGHP-UHFFFAOYSA-N |
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Isomeric SMILES | NCCC1=CC=CC=C1 |
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Average Molecular Weight | 121.1796 |
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Monoisotopic Molecular Weight | 121.089149357 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Phenethylamines |
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Direct Parent | Phenethylamines |
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Alternative Parents | |
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Substituents | - Phenethylamine
- 2-arylethylamine
- Aralkylamine
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organonitrogen compound
- Primary aliphatic amine
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Role | Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 79.29%; H 9.15%; N 11.56% | DFC |
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Melting Point | -60 oC | |
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Boiling Point | Bp7 70-71° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | 1.41 | HANSCH,C ET AL. (1995) |
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Experimental pKa | 9.83 | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | d244 0.96 | DFC |
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Refractive Index | n25D 1.5290 | DFC |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-001i-9000000000-bf5d1e8f4a14683bd0aa | 2015-03-01 | View Spectrum | GC-MS | 2-Phenylethylamine, 1 TMS, GC-MS Spectrum | splash10-0udi-3900000000-c931498c67dbf88820ee | Spectrum | GC-MS | 2-Phenylethylamine, 2 TMS, GC-MS Spectrum | splash10-00dr-5900000000-d15a3c803d2534e366d8 | Spectrum | GC-MS | 2-Phenylethylamine, non-derivatized, GC-MS Spectrum | splash10-001i-9000000000-7713ab7346491f1f5f42 | Spectrum | GC-MS | 2-Phenylethylamine, non-derivatized, GC-MS Spectrum | splash10-001i-9000000000-94774bbd6283b4a26a51 | Spectrum | GC-MS | 2-Phenylethylamine, non-derivatized, GC-MS Spectrum | splash10-0abc-5900000000-724c680a9564ac27f7ee | Spectrum | GC-MS | 2-Phenylethylamine, non-derivatized, GC-MS Spectrum | splash10-001i-9000000000-5ba434a8565ec0014b6b | Spectrum | GC-MS | 2-Phenylethylamine, non-derivatized, GC-MS Spectrum | splash10-053r-9000000000-f312ab6fe99f8eca86e7 | Spectrum | GC-MS | 2-Phenylethylamine, non-derivatized, GC-MS Spectrum | splash10-0udi-3900000000-c931498c67dbf88820ee | Spectrum | GC-MS | 2-Phenylethylamine, non-derivatized, GC-MS Spectrum | splash10-00dr-5900000000-d15a3c803d2534e366d8 | Spectrum | GC-MS | 2-Phenylethylamine, non-derivatized, GC-MS Spectrum | splash10-00dr-4900000000-4c37abb4c50d5582d87c | Spectrum | Predicted GC-MS | 2-Phenylethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001l-9100000000-3e2562db471b8bb298d2 | Spectrum | Predicted GC-MS | 2-Phenylethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-0900000000-95c5a1366bba1014e2aa | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0ab9-0900000000-5ad03d29c0ff6167539c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0a4i-0900000000-1b25fe0d03af3ce715ba | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-056r-7900000000-a6478bab1f5bd04c7329 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9100000000-abdacae4bceb2048614f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9000000000-d61f8f9b0d593297d010 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0ab9-0900000000-e3d2be06e661bac2f739 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0a4i-0900000000-fc4c40ae6333ed1f04f6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-056r-7900000000-f25cc18055d08500ec9d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9100000000-0e8ece94eaa349e6fd21 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0uk9-2900000000-272fff4a446fcf053de8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-0900000000-e833e9ebdd0584ee9cff | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-0900000000-f51c34f8fd6e67925a52 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-0900000000-162188a06251a43ccc54 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-0900000000-162188a06251a43ccc54 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-0900000000-2a12817c62551d9dee50 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-0900000000-ac8b555024a8bbc5e78b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-0900000000-926231c14695be35af04 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-0900000000-c5e8005c53eaf96bc957 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-0900000000-6f9e6a6eb6c2ac8f4531 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-1900000000-aeb026a07351a147ae19 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-3900000000-a6c6357f047322c4efe1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a6r-6900000000-0a32d01e2dda19a78c83 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-056r-9600000000-be832e76b1211d35978c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-004i-9400000000-ab97002137a57a7802bc | 2017-09-14 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum |
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External Links |
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ChemSpider ID | 13856352 |
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ChEMBL ID | CHEMBL610 |
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KEGG Compound ID | C05332 |
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Pubchem Compound ID | 1001 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18397 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB04325 |
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HMDB ID | HMDB12275 |
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CRC / DFC (Dictionary of Food Compounds) ID | FFC18-E:FFC18-E |
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EAFUS ID | 2958 |
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Dr. Duke ID | 2-PHENYLETHYL-AMINE|BETA-PHENYLETHYLAMINE|PHENETHYLAMINE|PHENYLETHYLAMINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001426 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1035561 |
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SuperScent ID | Not Available |
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Wikipedia ID | 2-Phenylethylamine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Anti depressant | 52217 | An agent that regulates mood, reducing symptoms of depression and anxiety by altering neurotransmitter levels in the brain, commonly used in managing depression, anxiety disorders, and other mood disorders. | DUKE | Central nervous system stimulant | 35470 | An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood. | DUKE | Insectifuge | 24852 | A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission. | DUKE | Irritant | | An agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Aromatic-L-amino-acid decarboxylase | DDC | P20711 | Serotonin N-acetyltransferase | AANAT | Q16613 |
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Pathways | Name | SMPDB Link | KEGG Link |
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Metabolism and Physiological Effects of Phenylacetic Acid | SMP0123256 | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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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.
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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.
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