Human Metabolome Database: Showing metabocard for 1-Phenylethylamine (HMDB0002017)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

enzymes (5) Show 5 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:32 UTC

Update Date

2020-02-26 21:23:43 UTC

HMDB ID

HMDB0002017

Secondary Accession Numbers

HMDB0002654
HMDB0005942
HMDB0006062
HMDB02017
HMDB02654
HMDB05942
HMDB06062

Metabolite Identification

Common Name

1-Phenylethylamine

Description

1-Phenylethylamine, also known as a-aminoethylbenzene or a-methylbenzylamine, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. 1-Phenylethylamine is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Amino-1-phenylethane	ChEBI
1-Phenethylamine	ChEBI
alpha-Aminoethylbenzene	ChEBI
alpha-Methylbenzenemethanamine	ChEBI
alpha-Methylbenzylamine	ChEBI
alpha-Phenylethylamine	ChEBI
a-Aminoethylbenzene	Generator
Α-aminoethylbenzene	Generator
a-Methylbenzenemethanamine	Generator
Α-methylbenzenemethanamine	Generator
a-Methylbenzylamine	Generator
Α-methylbenzylamine	Generator
a-Phenylethylamine	Generator
Α-phenylethylamine	Generator
(1-Aminoethyl)benzene	HMDB
1-Fenylethylamin	HMDB
1-Phenyl-1-ethanamine	HMDB
1-Phenylethanamine	HMDB
a-Phenethylamine	HMDB
alpha-Phenethylamine	HMDB
Sumine 2079	HMDB
1-Phenethylamine, (R)-isomer	HMDB
1-Phenethylamine hydrochloride	HMDB
1-Phenethylamine hydrochloride, (+-)-isomer	HMDB
1-Phenethylamine, (+-)-isomer	HMDB
1-Phenethylamine, (S)-isomer	HMDB

Chemical Formula

C₈H₁₁N

Average Molecular Weight

121.1796

Monoisotopic Molecular Weight

121.089149357

IUPAC Name

1-phenylethan-1-amine

Traditional Name

(+/-)-α-methylbenzylamine

CAS Registry Number

98-84-0

SMILES

CC(N)C1=CC=CC=C1

InChI Identifier

InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3

InChI Key

RQEUFEKYXDPUSK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Benzenoid
Monocyclic benzene moiety
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary aliphatic amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylethylamine (CHEBI:670 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	42 mg/L at 20 °C	Not Available
LogP	1.49	MEYLAN,WM & HOWARD,PH (1995)

Predicted Properties

Property	Value	Source
Water Solubility	3.7 g/L	ALOGPS
logP	1.36	ALOGPS
logP	1.52	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	9.73	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	1	ChemAxon
Refractivity	38.95 m³·mol⁻¹	ChemAxon
Polarizability	14.19 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0900000000-135bdaa3f3418b359765	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0900000000-2a4fe768d40a2f4f0d72	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-9700000000-2e29a83dd23d9c59dd09	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0a4i-1900000000-f1e9aac2f4bed1fdabac	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0900000000-c24ecc231eb7dac647e5	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-18cd62e45ebef721cf15	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-135bdaa3f3418b359765	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-2a4fe768d40a2f4f0d72	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9800000000-034169b06cf971ea0de8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-2900000000-3c3e1297242c1758bc62	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-8c3a3f7f817d09e21f60	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0fb9-9000000000-b504746c5cd545cd988e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0a6r-9700000000-fc38e120d18302f980be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positive	splash10-0a4i-1900000000-4fdd915024cb2a9a7b77	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0900000000-c9d262cb8c31aebbb587	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-1900000000-8d9a32725dd560f52860	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9700000000-bcd17c3f76f1c2307615	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-6f5156a9d2c3dbf44ab9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1900000000-6932727e42783d167646	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-9700000000-9cf44cfe1d047fdb41b1	Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.014 +/- 0.0065 uM	Adult (>18 years old)	Both	Normal	11197147	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.14 +/- 0.027 uM	Adult (>18 years old)	Both	Normal	6527139	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.0070 +/- 0.002 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0071 +/- 0.0045 uM	Adult (>18 years old)	Both	Parkinson's disease	11197147	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Parkinson's disease
Miura Y: Plasma beta-phenylethylamine in Parkinson's disease. Kurume Med J. 2000;47(4):267-72. [PubMed:11197147 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

168600 (Parkinson's disease)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022799

KNApSAcK ID

Not Available

Chemspider ID

7130

KEGG Compound ID

C02455

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

670

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Lee, C. C.; Spinks, J. W. T. Rearrangement in the reaction between 2-phenylethylamine-1-C14 and nitrous acid. Canadian Journal of Chemistry (1953), 31 761-7.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Miura Y: Plasma beta-phenylethylamine in Parkinson's disease. Kurume Med J. 2000;47(4):267-72. [PubMed:11197147 ]
Samonina-Kosicka J, Kanska M: Mechanistic studies of reactions catalysed by diamine oxidase using isotope effects. Isotopes Environ Health Stud. 2013;49(3):357-64. doi: 10.1080/10256016.2013.825612. [PubMed:24117430 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Enzyme Details

3. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Enzyme Details

4. Membrane primary amine oxidase

General function:: Involved in copper ion binding
Specific function:: Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:: AOC3
Uniprot ID:: Q16853
Molecular weight:: 84621.27

Enzyme Details

5. Retina-specific copper amine oxidase

General function:: Involved in copper ion binding
Specific function:: Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:: AOC2
Uniprot ID:: O75106
Molecular weight:: 80515.11

Showing metabocard for 1-Phenylethylamine (HMDB0002017)

Structure for HMDB0002017 (1-Phenylethylamine)

Enzymes