Showing metabocard for Phenylethylamine (MMDBc0000263)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:48:00 UTC
Update Date2024-04-30 19:31:43 UTC
Metabolite IDMMDBc0000263
Metabolite Identification
Common NamePhenylethylamine
DescriptionPhenethylamine (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 (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 ). Phenethylamine has been found to be a metabolite of Bacillus, Enterococcus and Lactobacillus (PMID: 22953951 ; PMID: 17307265 ; PMID: 16630269 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000564af37c3028>


  Mrv1652303202018592D          

  9  9  0  0  0  0            999 V2000
   13.9049  -11.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0800  -11.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -11.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6675  -11.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9049  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6675  -13.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8426  -13.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0800  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4302  -14.1382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  8  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000564af37c3028>

HMDB0012275
     RDKit          3D
Phenylethylamine
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.0884    0.5367    1.4140 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075   -0.1311    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -1.1147   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129   -0.4661   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101    0.0401   -1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8455    0.6516   -1.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863    0.7394   -0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    0.2484    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8868   -0.3557    0.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025   -0.0420    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674    1.5034    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746   -0.6397    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.6504   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -1.5595   -1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -1.9178    0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212   -0.0293   -2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420    1.0529   -2.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688    1.2201   -0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    0.3389    1.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -0.7262    1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
M  END
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3D SDF for #<Metabolite:0x0000564af37c3028>


  Mrv1652303202018592D          

  9  9  0  0  0  0            999 V2000
   13.9049  -11.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0800  -11.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -11.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6675  -11.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9049  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6675  -13.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8426  -13.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0800  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4302  -14.1382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  8  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000263

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C8H11N

> <MOLECULAR_WEIGHT>
121.1796

> <EXACT_MASS>
121.089149357

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.346174019011707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-phenylethan-1-amine

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.3876754570000003

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.791742642861854

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
39.28639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-phenylethylamine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x0000564af37c3028>

HMDB0012275
     RDKit          3D
Phenylethylamine
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.0884    0.5367    1.4140 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075   -0.1311    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -1.1147   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129   -0.4661   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101    0.0401   -1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8455    0.6516   -1.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863    0.7394   -0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    0.2484    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8868   -0.3557    0.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025   -0.0420    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674    1.5034    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746   -0.6397    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.6504   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -1.5595   -1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -1.9178    0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212   -0.0293   -2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420    1.0529   -2.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688    1.2201   -0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    0.3389    1.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -0.7262    1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
M  END
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PDB for #<Metabolite:0x0000564af37c3028>

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      25.956 -21.057   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.416 -21.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.726 -22.391   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.646 -22.391   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.956 -23.725   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.646 -25.059   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.106 -25.059   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.416 -23.725   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      21.336 -26.391   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    4    5    6                                                  
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for #<Metabolite:0x0000564af37c3028>

COMPND    HMDB0012275
HETATM    1  N1  UNL     1       2.088   0.537   1.414  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.307  -0.131   0.167  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.200  -1.115  -0.155  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.113  -0.466  -0.252  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.610   0.040  -1.428  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.845   0.652  -1.525  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.586   0.739  -0.364  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.136   0.248   0.843  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.887  -0.356   0.878  1.00  0.00           C  
HETATM   10  H1  UNL     1       1.702  -0.042   2.164  1.00  0.00           H  
HETATM   11  H2  UNL     1       1.767   1.503   1.354  1.00  0.00           H  
HETATM   12  H3  UNL     1       3.275  -0.640   0.200  1.00  0.00           H  
HETATM   13  H4  UNL     1       2.380   0.650  -0.623  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.425  -1.559  -1.156  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.199  -1.918   0.596  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.021  -0.029  -2.352  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.242   1.053  -2.451  1.00  0.00           H  
HETATM   18  H9  UNL     1      -3.569   1.220  -0.417  1.00  0.00           H  
HETATM   19  H10 UNL     1      -2.756   0.339   1.739  1.00  0.00           H  
HETATM   20  H11 UNL     1      -0.577  -0.726   1.852  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5    5    9
CONECT    5    6   16
CONECT    6    7    7   17
CONECT    7    8   18
CONECT    8    9    9   19
CONECT    9   20
END
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SMILES for #<Metabolite:0x0000564af37c3028>

NCCC1=CC=CC=C1
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INCHI for #<Metabolite:0x0000564af37c3028>

InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
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Synonyms
ValueSource
BenzeneethanamineChEBI
beta-AminoethylbenzeneChEBI
beta-PhenethylamineChEBI
beta-PhenylethylamineChEBI
PhenethylamineChEBI
2-PhenylethylamineKegg
b-AminoethylbenzeneGenerator
Β-aminoethylbenzeneGenerator
b-PhenethylamineGenerator
Β-phenethylamineGenerator
b-PhenylethylamineGenerator
Β-phenylethylamineGenerator
(2-Aminoethyl)benzeneHMDB
(2-Aminoethyl)polystyreneHMDB
1-amino-2-PhenylethaneHMDB
1-PhenethylamineHMDB
1-Phenyl-2-amino-athanHMDB
1-Phenyl-2-aminoethaneHMDB
1TNJHMDB
1UtmHMDB
1UtoHMDB
2-amino-1-PhenylethaneHMDB
2-amino-FenylethanHMDB
2-FenylethylaminHMDB
2-PhenethylamineHMDB, MeSH
2-Phenyl-ethanamineHMDB
2-PhenylethanamineHMDB
2-Phenylethanamine (acd/name 4.0)HMDB
2-Phenylethylamine (acd/name 4.0)HMDB
b-PhenylaethylaminHMDB
Benzeneethanamine hydrochlorideHMDB
beta PhenethylamineHMDB
beta-PhenylaethylaminHMDB
Omega-phenylethylamineHMDB
PEAHMDB
Phenethylamine hydrochlorideHMDB, MeSH
Polystyrene a-NH2HMDB
Phenethylamine hydrobromideMeSH, HMDB
Phenethylamine tosylateMeSH, HMDB
Phenethylamine conjugate acidMeSH, HMDB
Phenethylamine sulfateMeSH, HMDB
Phenethylamine, monolithium saltMeSH, HMDB
2-Phenylethylammonium chlorideMeSH, HMDB
Phenethylamine sulfate (2:1)MeSH, HMDB
Phenethylamine, 15N-labeled CPDMeSH, HMDB
Phenethylamine mesylateMeSH, HMDB
Phenethylamine perchlorateMeSH, HMDB
Phenethylamine, beta-(14)C-labeled CPDMeSH, HMDB
Diphenethylamine sulfateMeSH, HMDB
Molecular FormulaC8H11N
Average Mass121.1796
Monoisotopic Mass121.089149357
IUPAC Name2-phenylethan-1-amine
Traditional Name2-phenylethylamine
CAS Registry Number64-04-0
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 KeyBHHGXPLMPWCGHP-UHFFFAOYSA-N