General Information of MET (ID: META00873)
Name Phenylethylamine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2-Aminoethyl)benzene; (2-Aminoethyl)polystyrene; 1-Amino-2-phenylethane; 1-Phenethylamine; 1-Phenyl-2-amino-athan; 1-Phenyl-2-aminoethane; 1TNJ; 1Utm; 1Uto; 2-Amino-1-phenylethane; 2-Amino-fenylethan; 2-Fenylethylamin; 2-Phenethylamine; 2-Phenyl-ethanamine; 2-Phenylethanamine; 2-Phenylethanamine (acd/name 4.0); 2-Phenylethylamine; 2-Phenylethylamine (acd/name 4.0); 2-Phenylethylammonium chloride; Benzeneethanamine; Benzeneethanamine hydrochloride; Diphenethylamine sulfate; Omega-phenylethylamine; PEA; Phenethylamine; Phenethylamine conjugate acid; Phenethylamine hydrobromide; Phenethylamine hydrochloride; Phenethylamine mesylate; Phenethylamine perchlorate; Phenethylamine sulfate; Phenethylamine sulfate (2:1); Phenethylamine tosylate; Phenethylamine, 15N-labeled CPD; Phenethylamine, beta-(14)C-labeled CPD; Phenethylamine, monolithium salt; Polystyrene a-NH2; b-Phenylaethylamin; beta Phenethylamine; beta-Aminoethylbenzene; beta-Phenethylamine; beta-Phenylaethylamin; beta-Phenylethylamine
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food additives;TCM Ingredients;Microbial
Structure Type   Phenethylamines  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Benzene and substituted derivatives
Phenethylamines
PubChem CID
1001
HMDB ID
HMDB0012275
Formula
C8H11N
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C05332
DrugBank ID
DB04325
ChEBI ID
18397
FooDB ID
FDB010580
ChemSpider ID
13856352
Physicochemical Properties Molecular Weight 121.18 Topological Polar Surface Area 26
XlogP 1.4 Complexity 65
Heavy Atom Count 9 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Function
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 human 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. Urinary levels of PEA are significantly lower in children with attention deficit hyperactivity disorder (ADHD). 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. Phenethylamine has been found to be a metabolite of Bacillus, Enterococcus and Lactobacillus.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      GPCR rhodopsin (GPCR-1)
            Trace amine receptor 1 (TAAR1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Phenylethylamine addition (0.33 hours)
                      Induced Change TAAR1 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that phenylethylamine addition causes the increase of TAAR1 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            R2R3-MYB (AN2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Overexpression of AN2
                      Induced Change Phenylethylamine concentration: decrease (FC = 0.47)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the decrease of phenylethylamine levels compared with control group.
References
1 Trace amines: identification of a family of mammalian G protein-coupled receptors. Proc Natl Acad Sci U S A. 2001 Jul 31;98(16):8966-71.
2 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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