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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:25 UTC

HMDB ID

HMDB0001065

Secondary Accession Numbers

HMDB01065

Metabolite Identification

Common Name

2-Hydroxyphenethylamine

Description

2-Hydroxyphenethylamine, also known as beta-phenethanolamine 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. It is the simplest member of the class of phenylethanolamines that is 2-aminoethanol bearing a phenyl substituent at the 1-position. 2-Hydroxyphenethylamine exists in all living organisms, ranging from bacteria to humans. 2-Hydroxyphenethylamine ia an amine found in the brain. It may be modulator of sympathetic functions. Its derivatives are adrenergic agonists and antagonists.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 3137238)

Organ

Testicle (HMDB: HMDB0001065)
Testicle (HMDB: HMDB0001065)

Source

Endogenous

Endogenous (HMDB: HMDB0001065)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	21.4 g/L	ALOGPS
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.359	31661259
DarkChem	[M+H]+	128.359	31661259
DarkChem	[M-H]-	124.827	31661259
DarkChem	[M-H]-	124.827	31661259
AllCCS	[M+H]+	130.707	32859911
AllCCS	[M-H]-	129.225	32859911
DeepCCS	[M+H]+	128.439	30932474
DeepCCS	[M-H]-	124.797	30932474
DeepCCS	[M-2H]-	162.217	30932474
DeepCCS	[M+Na]+	137.389	30932474
AllCCS	[M+H]+	130.7	32859911
AllCCS	[M+H-H2O]+	126.1	32859911
AllCCS	[M+NH4]+	135.0	32859911
AllCCS	[M+Na]+	136.3	32859911
AllCCS	[M-H]-	129.2	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	132.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.87 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0999 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.96 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	197.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	593.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	310.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	95.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	68.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	248.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	280.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	643.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	644.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	98.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	728.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	184.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	232.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	498.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	405.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	119.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyphenethylamine	NCC(O)C1=CC=CC=C1	1929.1	Standard polar	33892256
2-Hydroxyphenethylamine	NCC(O)C1=CC=CC=C1	1263.8	Standard non polar	33892256
2-Hydroxyphenethylamine	NCC(O)C1=CC=CC=C1	1326.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyphenethylamine,1TMS,isomer #1	C[Si](C)(C)OC(CN)C1=CC=CC=C1	1359.7	Semi standard non polar	33892256
2-Hydroxyphenethylamine,1TMS,isomer #2	C[Si](C)(C)NCC(O)C1=CC=CC=C1	1462.7	Semi standard non polar	33892256
2-Hydroxyphenethylamine,2TMS,isomer #1	C[Si](C)(C)NCC(O[Si](C)(C)C)C1=CC=CC=C1	1422.2	Semi standard non polar	33892256
2-Hydroxyphenethylamine,2TMS,isomer #1	C[Si](C)(C)NCC(O[Si](C)(C)C)C1=CC=CC=C1	1517.6	Standard non polar	33892256
2-Hydroxyphenethylamine,2TMS,isomer #1	C[Si](C)(C)NCC(O[Si](C)(C)C)C1=CC=CC=C1	1711.9	Standard polar	33892256
2-Hydroxyphenethylamine,2TMS,isomer #2	C[Si](C)(C)N(CC(O)C1=CC=CC=C1)[Si](C)(C)C	1602.5	Semi standard non polar	33892256
2-Hydroxyphenethylamine,2TMS,isomer #2	C[Si](C)(C)N(CC(O)C1=CC=CC=C1)[Si](C)(C)C	1697.2	Standard non polar	33892256
2-Hydroxyphenethylamine,2TMS,isomer #2	C[Si](C)(C)N(CC(O)C1=CC=CC=C1)[Si](C)(C)C	1875.8	Standard polar	33892256
2-Hydroxyphenethylamine,3TMS,isomer #1	C[Si](C)(C)OC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	1667.9	Semi standard non polar	33892256
2-Hydroxyphenethylamine,3TMS,isomer #1	C[Si](C)(C)OC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	1679.7	Standard non polar	33892256
2-Hydroxyphenethylamine,3TMS,isomer #1	C[Si](C)(C)OC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	1725.2	Standard polar	33892256
2-Hydroxyphenethylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN)C1=CC=CC=C1	1596.8	Semi standard non polar	33892256
2-Hydroxyphenethylamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC(O)C1=CC=CC=C1	1690.3	Semi standard non polar	33892256
2-Hydroxyphenethylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	1872.9	Semi standard non polar	33892256
2-Hydroxyphenethylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	1924.6	Standard non polar	33892256
2-Hydroxyphenethylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2007.0	Standard polar	33892256
2-Hydroxyphenethylamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2021.2	Semi standard non polar	33892256
2-Hydroxyphenethylamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2082.9	Standard non polar	33892256
2-Hydroxyphenethylamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2092.5	Standard polar	33892256
2-Hydroxyphenethylamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2288.2	Semi standard non polar	33892256
2-Hydroxyphenethylamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2249.0	Standard non polar	33892256
2-Hydroxyphenethylamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2093.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyphenethylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9300000000-3c170028e90978bc78a4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyphenethylamine GC-MS (1 TMS) - 70eV, Positive	splash10-00gi-7900000000-4e2e2029648810b69611	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyphenethylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014i-0000900000-548706c8c2ce9f09a548	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00di-0900000000-c3f1f0f273348db1d32d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0udi-6900000000-bdb37afcb3284184bb38	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 35V, Positive-QTOF	splash10-0fk9-2900000000-3bcb695c5b0cc370aa24	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 35V, Positive-QTOF	splash10-00di-0900000000-86abd5e86e5c59cb0a09	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 10V, Positive-QTOF	splash10-00di-0900000000-9c580bd32266d4f02916	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 20V, Positive-QTOF	splash10-0udi-3900000000-3768160518b34fa45421	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 40V, Positive-QTOF	splash10-004i-9000000000-e243bccdf642ef6d157c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 20V, Positive-QTOF	splash10-0udi-3900000000-e0a333a28c523433bf7f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 10V, Positive-QTOF	splash10-00di-0900000000-ae56725698697f1c1902	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 40V, Positive-QTOF	splash10-004i-9000000000-bd82f79b668f12d41456	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 10V, Negative-QTOF	splash10-004i-9000000000-f2517cf936d9f21d158a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 20V, Negative-QTOF	splash10-004i-9200000000-51bc9ce0c5b6d016f940	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 40V, Negative-QTOF	splash10-000i-9000000000-ed3ceb3389fd7dae6eab	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 10V, Positive-QTOF	splash10-00dr-0900000000-7cef59c17238b64bcf36	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 20V, Positive-QTOF	splash10-0uk9-0900000000-2c5c6655275c45187596	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 40V, Positive-QTOF	splash10-0udi-9700000000-1cbd1ee009138bc1c30a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 10V, Negative-QTOF	splash10-000i-0900000000-f801fd7106bd297ab8be	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 20V, Negative-QTOF	splash10-05n0-2900000000-f0de7984aa0ca45bf458	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 40V, Negative-QTOF	splash10-004i-9300000000-2d60aec56b29f9023bce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 10V, Positive-QTOF	splash10-00di-2900000000-a937d4b5d96c3f30b42d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 20V, Positive-QTOF	splash10-0006-9400000000-8d40a0ed200312a3740e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 40V, Positive-QTOF	splash10-004i-9100000000-d9f9fa7efd82edc1a2d7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 10V, Negative-QTOF	splash10-014r-3900000000-461ccf661690efd8885e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyphenethylamine 20V, Negative-QTOF	splash10-016u-8900000000-c402bd52eafa7e43b742	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00033 +/- 0.00023 uM	Adult (>18 years old)	Both	Normal	3137238	details
Blood	Detected and Quantified	0.0052 +/- 0.0016 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00052 +/- 0.00052 uM	Adult (>18 years old)	Both	Cirrhosis	3137238	details

Associated Disorders and Diseases

Disease References

Cirrhosis
Yonekura T, Kamata S, Wasa M, Okada A, Yamatodani A, Watanabe T, Wada H: Simultaneous determination of plasma phenethylamine, phenylethanolamine, tyramine and octopamine by high-performance liquid chromatography using derivatization with fluorescamine. J Chromatogr. 1988 Jun 3;427(2):320-5. [PubMed:3137238 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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

Buller KM, Hamlin AS, Osborne PB: Dissection of peripheral and central endogenous opioid modulation of systemic interleukin-1beta responses using c-fos expression in the rat brain. Neuropharmacology. 2005 Aug;49(2):230-42. [PubMed:15993445 ]
Davidoff MS, Ungefroren H, Middendorff R, Koeva Y, Bakalska M, Atanassova N, Holstein AF, Jezek D, Pusch W, Muller D: Catecholamine-synthesizing enzymes in the adult and prenatal human testis. Histochem Cell Biol. 2005 Sep;124(3-4):313-23. Epub 2005 Oct 28. [PubMed:16052322 ]
Evinger MJ, Mathew E, Cikos S, Powers JF, Lee YS, Sheikh S, Ross RA, Tischler AS: Nicotine stimulates expression of the PNMT gene through a novel promoter sequence. J Mol Neurosci. 2005;26(1):39-55. [PubMed:15968085 ]
Gee CL, Nourse A, Hsin AY, Wu Q, Tyndall JD, Grunewald GL, McLeish MJ, Martin JL: Disulfide-linked dimers of human adrenaline synthesizing enzyme PNMT are catalytically active. Biochim Biophys Acta. 2005 Jun 15;1750(1):82-92. Epub 2005 Apr 2. [PubMed:15893506 ]

Enzymes

Enzyme Details

1. Phenylethanolamine N-methyltransferase

General function:: Involved in methyltransferase activity
Specific function:: Converts noradrenaline to adrenaline.
Gene Name:: PNMT
Uniprot ID:: P11086
Molecular weight:: 30854.745

Reactions

S-Adenosylmethionine + 2-Hydroxyphenethylamine → S-Adenosylhomocysteine + N-Methylphenylethanolamine	details

Showing metabocard for 2-Hydroxyphenethylamine (HMDB0001065)

MOL for HMDB0001065 (2-Hydroxyphenethylamine)

3D MOL for HMDB0001065 (2-Hydroxyphenethylamine)

3D SDF for HMDB0001065 (2-Hydroxyphenethylamine)

3D-SDF for HMDB0001065 (2-Hydroxyphenethylamine)

PDB for HMDB0001065 (2-Hydroxyphenethylamine)

3D PDB for HMDB0001065 (2-Hydroxyphenethylamine)

SMILES for HMDB0001065 (2-Hydroxyphenethylamine)

INCHI for HMDB0001065 (2-Hydroxyphenethylamine)

Structure for HMDB0001065 (2-Hydroxyphenethylamine)

3D Structure for HMDB0001065 (2-Hydroxyphenethylamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions