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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-30 15:51:23 UTC

Update Date

2023-02-21 17:17:57 UTC

HMDB ID

HMDB0013231

Secondary Accession Numbers

HMDB13231

Metabolite Identification

Common Name

Ethylamine

Description

Ethylamine, also known as 1-aminoethane or ethanamine, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Ethylamine exists in all living organisms, ranging from bacteria to humans. Ethylamine is an ammonia and fishy tasting compound. Ethylamine can be found found in a few different foods, such as barley, apples, and corns and in a lower concentration in white cabbages, wild carrots, and cabbages. Ethylamine has also been detected, but not quantified, in several different foods, such as black elderberries, common grapes, french plantains, soy beans, and spinachs. Ethylamine is a uremic toxin. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. Ethylamine is component of normal human urine it has been suggested that this short aliphatic chain may play a significant role in the central nervous system disturbances observe during hepatic and renal disease especially when the blood brain barrier is compromised.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Aminoethane	ChEBI
Aminoethane	ChEBI
ETHANAMINE	ChEBI
Aethylamine	HMDB
Ethyl amine	HMDB
Ethylamine solution	HMDB
Etilamina	HMDB
Etyloamina	HMDB
Monoethylamine	HMDB
Ethylamine hydrochloride	MeSH
Ethylamine hydrobromide	MeSH
Ethylamine, 14C-labeled	MeSH

Chemical Formula

C₂H₇N

Average Molecular Weight

45.0837

Monoisotopic Molecular Weight

45.057849229

IUPAC Name

ethanamine

Traditional Name

ethylamine

CAS Registry Number

75-04-7

SMILES

CCN

InChI Identifier

InChI=1S/C2H7N/c1-2-3/h2-3H2,1H3

InChI Key

QUSNBJAOOMFDIB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Monoalkylamines

Alternative Parents

Substituents

Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary aliphatic amine (CHEBI:15862 )
a small molecule (ETHANAMINE )

Ontology

Physiological effect

Health effect

Renal system and urinary system

Renal disorder

Kidney disease (HMDB: HMDB0013231)
Uremia (HMDB: HMDB0013231)
Chronic kidney disease (HMDB: HMDB0013231)

Observation

Nervous system disorder

Coma (HMDB: HMDB0013231)

Central nervous system disorder

Psychiatric disorder

Psychosis (HMDB: HMDB0013231)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (HMDB: HMDB0013231)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 22626821)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)
Feces (PMID: 24029555)

Cellular substructure

Cytoplasm (HMDB: HMDB0013231)
Extracellular (HMDB: HMDB0013231)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0013231)

Enteral

Ingestion (HMDB: HMDB0013231)

Source

Endogenous

Endogenous (HMDB: HMDB0013231)

Plant

Exogenous

Food

Food (HMDB: HMDB0013231)

Apple (FooDB: FOOD00105)

Tropical fruit

French plantain (FooDB: FOOD00436)

Berry

Common grape (FooDB: FOOD00204)
Black elderberry (FooDB: FOOD00166)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Corn (FooDB: FOOD00205)

Soy

Soy bean (FooDB: FOOD00085)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Leaf vegetable

Spinach (FooDB: FOOD00178)

Cabbage

White cabbage (FooDB: FOOD00887)
Cabbage (FooDB: FOOD00851)

Process

Not Available

Role

Environmental role

Air pollutant (HMDB: HMDB0013231)

Industrial application

Food and nutrition

Food and nutrition (HMDB: HMDB0013231)

Pharmaceutical industry

Biomarker

Uremia (MarkerDB: MDB00029874)

Biological role

Human metabolite (HMDB: HMDB0013231)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-81.2 °C	Not Available
Boiling Point	16.00 to 17.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.13	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	367 g/L	ALOGPS
logP	-0.2	ALOGPS
logP	-0.27	ChemAxon
logS	0.9	ALOGPS
pKa (Strongest Basic)	10.23	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	0	ChemAxon
Refractivity	14.67 m³·mol⁻¹	ChemAxon
Polarizability	5.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	117.91	30932474
DeepCCS	[M-H]-	116.014	30932474
DeepCCS	[M-2H]-	151.638	30932474
DeepCCS	[M+Na]+	126.065	30932474

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.	0.86 minutes	32390414
Predicted by Siyang on May 30, 2022	7.7069 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.31 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	303.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	464.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	324.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	101.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	241.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	88.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	250.6 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	243.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	663.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	524.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	48.5 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	560.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	204.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	281.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	604.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	462.3 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	251.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethylamine	CCN	704.9	Standard polar	33892256
Ethylamine	CCN	374.0	Standard non polar	33892256
Ethylamine	CCN	408.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethylamine,1TMS,isomer #1	CCN[Si](C)(C)C	685.5	Semi standard non polar	33892256
Ethylamine,1TMS,isomer #1	CCN[Si](C)(C)C	725.9	Standard non polar	33892256
Ethylamine,1TMS,isomer #1	CCN[Si](C)(C)C	776.4	Standard polar	33892256
Ethylamine,2TMS,isomer #1	CCN([Si](C)(C)C)[Si](C)(C)C	964.0	Semi standard non polar	33892256
Ethylamine,2TMS,isomer #1	CCN([Si](C)(C)C)[Si](C)(C)C	970.6	Standard non polar	33892256
Ethylamine,2TMS,isomer #1	CCN([Si](C)(C)C)[Si](C)(C)C	910.8	Standard polar	33892256
Ethylamine,1TBDMS,isomer #1	CCN[Si](C)(C)C(C)(C)C	946.7	Semi standard non polar	33892256
Ethylamine,1TBDMS,isomer #1	CCN[Si](C)(C)C(C)(C)C	914.8	Standard non polar	33892256
Ethylamine,1TBDMS,isomer #1	CCN[Si](C)(C)C(C)(C)C	973.7	Standard polar	33892256
Ethylamine,2TBDMS,isomer #1	CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1353.7	Semi standard non polar	33892256
Ethylamine,2TBDMS,isomer #1	CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1367.9	Standard non polar	33892256
Ethylamine,2TBDMS,isomer #1	CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1183.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9000000000-6aa6ace25db55efb49cc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-e422139902e26a3df1fe	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethylamine LC-ESI-QQ , positive-QTOF	splash10-0002-9000000000-033f05ec7cce649f8009	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethylamine LC-ESI-QQ , positive-QTOF	splash10-0002-9000000000-2639db170e818688d7ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethylamine LC-ESI-QQ , positive-QTOF	splash10-03di-9200000000-0a455838aa5b351373a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethylamine LC-ESI-QQ , positive-QTOF	splash10-03fr-9100000000-bee30c9a05e01b4aad87	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethylamine LC-ESI-QQ , positive-QTOF	splash10-02di-9100000000-bd259a9e5886b3b57cab	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 10V, Positive-QTOF	splash10-0002-9000000000-274e873dba0d4ad103b7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 20V, Positive-QTOF	splash10-0002-9000000000-6e85adff9c6b1415c0c5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 40V, Positive-QTOF	splash10-004i-9000000000-a836286cd9de57a2ad46	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 10V, Negative-QTOF	splash10-0006-9000000000-6ace2b096232f6eaf08e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 20V, Negative-QTOF	splash10-0006-9000000000-98a7d493e57f6a7cec1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 40V, Negative-QTOF	splash10-0006-9000000000-52fc39e2fe2d45ff7588	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 10V, Positive-QTOF	splash10-0002-9000000000-e97e92727205304cdb09	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 20V, Positive-QTOF	splash10-0002-9000000000-e97e92727205304cdb09	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 40V, Positive-QTOF	splash10-0006-9000000000-ffdcb547a0eba6bb26fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 10V, Negative-QTOF	splash10-0006-9000000000-46fb6b0f3d2dcd71d159	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 20V, Negative-QTOF	splash10-0006-9000000000-46fb6b0f3d2dcd71d159	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylamine 40V, Negative-QTOF	splash10-0006-9000000000-46fb6b0f3d2dcd71d159	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected and Quantified	0.57 +/- 0.13 uM	Adult (>18 years old)	Both	Normal	22626821	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Urine	Detected but not Quantified	Not Quantified	Not Available	Not Available	Normal	19309105	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.53 +/- 0.23 uM	Adult (>18 years old)	Both	uremia	22626821	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Uremia
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Ethylamine

METLIN ID

Not Available

PubChem Compound

6341

PDB ID

NEH

ChEBI ID

15862

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029874

Good Scents ID

rw1245941

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Mitchell SC, Zhang AQ, Smith RL: Ethylamine in human urine. Clin Chim Acta. 2000 Dec;302(1-2):69-78. [PubMed:11074065 ]
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]

Showing metabocard for Ethylamine (HMDB0013231)

MOL for HMDB0013231 (Ethylamine)

3D MOL for HMDB0013231 (Ethylamine)

3D SDF for HMDB0013231 (Ethylamine)

3D-SDF for HMDB0013231 (Ethylamine)

PDB for HMDB0013231 (Ethylamine)

3D PDB for HMDB0013231 (Ethylamine)

SMILES for HMDB0013231 (Ethylamine)

INCHI for HMDB0013231 (Ethylamine)

Structure for HMDB0013231 (Ethylamine)

3D Structure for HMDB0013231 (Ethylamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra