Milk Composition Database: Showing metabocard for 2-Hydroxyphenethylamine (BMDB0001065)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:40:38 UTC

Update Date

2020-05-11 20:55:23 UTC

MCDB ID

BMDB0001065

Secondary Accession Numbers

BMDB01065

Metabolite Identification

Common Name

2-Hydroxyphenethylamine

Description

2-Hydroxyphenethylamine, also known as beta-phenylethanolamine or 2-amino-1-phenylethanol, 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. 2-Hydroxyphenethylamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 2-Hydroxyphenethylamine exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-1-phenylethanol	ChEBI
2-Hydroxy-2-phenylethylamine	ChEBI
2-Phenyl-2-hydroxyethylamine	ChEBI
alpha-(Aminomethyl)benzyl alcohol	ChEBI
beta-Hydroxy-beta-phenylethylamine	ChEBI
beta-Hydroxyphenethylamine	ChEBI
beta-Phenethanolamine	ChEBI
beta-Phenylethanolamine	ChEBI
Bisnorephedrine	ChEBI
Phenethanolamine	ChEBI
a-(Aminomethyl)benzyl alcohol	Generator
Α-(aminomethyl)benzyl alcohol	Generator
b-Hydroxy-b-phenylethylamine	Generator
Β-hydroxy-β-phenylethylamine	Generator
b-Hydroxyphenethylamine	Generator
Β-hydroxyphenethylamine	Generator
b-Phenethanolamine	Generator
Β-phenethanolamine	Generator
b-Phenylethanolamine	Generator
Β-phenylethanolamine	Generator
2-amino-1-Phenyl-1-ethanol	HMDB
2-amino-1-Phenylethanol-1	HMDB
beta-Hydroxy-beta-phenyl-ethylamine	HMDB
beta-Hydroxy-phenethylamine	HMDB
beta-Hydroxyphenylethylamine	HMDB
DL-beta-Phenyl-beta-hydroxyethylamine	HMDB
Hydroxyethylamine	HMDB
Phenylethanolamine	HMDB
beta Phenylethanolamine	MeSH, HMDB
2 Hydroxyphenethylamine	MeSH, HMDB
2 Phenylethanolamine	MeSH, HMDB
2-Phenylethanolamine	MeSH, HMDB
beta Hydroxyphenethylamine	MeSH, HMDB
2-Hydroxyphenethylamine	ChEBI

Chemical Formula

C₈H₁₁NO

Average Molecular Weight

137.179

Monoisotopic Molecular Weight

137.084063979

IUPAC Name

2-amino-1-phenylethan-1-ol

Traditional Name

β phenylethanolamine

CAS Registry Number

7568-93-6

SMILES

NCC(O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2

InChI Key

ULSIYEODSMZIPX-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
Secondary alcohol
1,2-aminoalcohol
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic alcohol
Primary amine
Organooxygen compound
Primary aliphatic amine
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylethanolamines (CHEBI:16343 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	56.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	45.8 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.31	ALOGPS
logP	0.47	ChemAxon
logS	-0.81	ALOGPS
pKa (Strongest Acidic)	14.13	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.49 m³·mol⁻¹	ChemAxon
Polarizability	15.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9300000000-3c170028e90978bc78a4	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00gi-7900000000-4e2e2029648810b69611	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-f2517cf936d9f21d158a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-51bc9ce0c5b6d016f940	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-ed3ceb3389fd7dae6eab	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0000900000-548706c8c2ce9f09a548	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-0900000000-c3f1f0f273348db1d32d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0udi-6900000000-bdb37afcb3284184bb38	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0fk9-2900000000-3bcb695c5b0cc370aa24	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-0900000000-86abd5e86e5c59cb0a09	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-9c580bd32266d4f02916	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-3900000000-3768160518b34fa45421	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-e243bccdf642ef6d157c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-3900000000-e0a333a28c523433bf7f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-ae56725698697f1c1902	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-bd82f79b668f12d41456	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-f801fd7106bd297ab8be	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05n0-2900000000-f0de7984aa0ca45bf458	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9300000000-2d60aec56b29f9023bce	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014r-3900000000-461ccf661690efd8885e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-016u-8900000000-c402bd52eafa7e43b742	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-9300000000-967a3865b7420c183235	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0900000000-7cef59c17238b64bcf36	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-0900000000-2c5c6655275c45187596	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9700000000-1cbd1ee009138bc1c30a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-2900000000-a937d4b5d96c3f30b42d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9400000000-8d40a0ed200312a3740e	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 28306241	details

External Links

HMDB ID

HMDB0001065

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022404

KNApSAcK ID

Not Available

Chemspider ID

975

KEGG Compound ID

C02735

BioCyc ID

PHENYLETHANOLAMINE

BiGG ID

Not Available

Wikipedia Link

Phenylethanolamine

METLIN ID

PubChem Compound

1000

PDB ID

Not Available

ChEBI ID

16343

References

Synthesis Reference

Ye, Qizhuang. Syntheses of conformationally defined analogs of tyramine and phenylethanolamine and their biological evaluations at central dopamine receptors and the active site of phenylethanolamine N-methyltransferase. (1988), 152 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]

Showing metabocard for 2-Hydroxyphenethylamine (BMDB0001065)

Structure for BMDB0001065 (2-Hydroxyphenethylamine)