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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:35 UTC

HMDB ID

HMDB0000164

Secondary Accession Numbers

HMDB0002983
HMDB00164
HMDB0060291
HMDB02983
HMDB60291

Metabolite Identification

Common Name

Methylamine

Description

Methylamine occurs endogenously from amine catabolism and its tissue levels increase in some pathological conditions, including diabetes. Interestingly, methylamine and ammonia levels are reciprocally controlled by a semicarbazide-sensitive amine oxidase activity that deaminates methylamine to formaldehyde with the production of ammonia and hydrogen peroxide. Methylamine also targets the voltage-operated neuronal potassium channels, probably inducing release of neurotransmitter(s). Semicarbazide-sensitive amine oxidase (SSAO) catalyzes the deamination of primary amines. Such deamination has been shown capable of regulating glucose transport in adipose cells. It has been independently discovered that the primary structure of vascular adhesion protein-1 (VAP-1) is identical to SSAO. Increased serum SSAO activities have been found in patients with diabetic mellitus, vascular disorders, and Alzheimer's disease. The SSAO-catalyzed deamination of endogenous substrates like methylamine led to production of toxic formaldehyde. Chronic elevated methylamine increases the excretion of malondialdehyde and microalbuminuria. Amine oxidase substrates such as methylamine have been shown to stimulate glucose uptake by increasing the recruitment of the glucose transporter GLUT4 from vesicles within the cell to the cell surface. Inhibition of this effect by the presence of semicarbazide and catalase led to the suggestion that the process is mediated by the hydrogen peroxide produced in the oxidation of these amines (PMID: 16049393 , 12686132 , 17406961 ). Methylamine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Aminomethane	ChEBI
CH3-NH2	ChEBI
MeNH2	ChEBI
Methanamine	ChEBI
MMA	ChEBI
Monomethylamine	ChEBI
Anhydrous methylamine	HMDB
Carbinamine	HMDB
Imizin	HMDB
Mercurialin	HMDB
Methyl group	HMDB
Methyl OF gamma-N-methylasparagine	HMDB
Methylamine anhydrous	HMDB
Methylamine aqueous solution	HMDB
Methylamine solution	HMDB
Methylamine solutions	HMDB
Methylaminen	HMDB
Metilamine	HMDB
Metyloamina	HMDB
N-Methylamine	HMDB
NMA	HMDB
NME	HMDB
Methylamine ion (1-)	HMDB
Methylamine nitrate	HMDB
Methylamine perchlorate	HMDB
Methylamine sulfate (1:1)	HMDB
Methylamine sulfate (2:1)	HMDB
Methylamine, 13C-labeled	HMDB
Methylamine, 14C-labeled	HMDB
Methylamine, 15N-labeled	HMDB
Methylamine hydrobromide	HMDB
Methylamine hydrochloride, 14C-labeled	HMDB
Methylamine, cesium salt	HMDB
Methylamine, monopotassium salt	HMDB
Methylammonium	HMDB
Methylammonium ion	HMDB
Methylamine hydroiodide	HMDB
Methylamine, monosodium salt	HMDB
Methylamine bisulfite	HMDB
Methylamine hydride	HMDB
Methylamine hydrochloride	HMDB
Methylamine hydrofluoride	HMDB
Methylamine hydrogen cyanide	HMDB
Monomethylammonium ion	HMDB

Chemical Formula

CH₅N

Average Molecular Weight

31.0571

Monoisotopic Molecular Weight

31.042199165

IUPAC Name

methanamine

Traditional Name

methylamine

CAS Registry Number

74-89-5

SMILES

InChI Identifier

InChI=1S/CH5N/c1-2/h2H2,1H3

InChI Key

BAVYZALUXZFZLV-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

one-carbon compound (CHEBI:16830 )
primary aliphatic amine (CHEBI:16830 )
methylamines (CHEBI:16830 )
a small molecule (METHYLAMINE )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Coma (HMDB: HMDB0000164)
Convulsion (HMDB: HMDB0000164)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (HMDB: HMDB0000164)

Bleeding (HMDB: HMDB0000164)
Weight loss (HMDB: HMDB0000164)

Digestive system disorder

Gastrointestinal disorder

Vomiting (HMDB: HMDB0000164)
Nausea (HMDB: HMDB0000164)

Renal system and urinary system

Renal disorder

Chronic kidney disease (HMDB: HMDB0000164)
Uremia (HMDB: HMDB0000164)
Kidney disease (HMDB: HMDB0000164)

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000164)
Extracellular (HMDB: HMDB0000164)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000164)
Saliva (HMDB: HMDB0000164)

Dermal (HMDB: HMDB0000164)

Enteral

Ingestion (HMDB: HMDB0000164)

Source

Endogenous

Endogenous (HMDB: HMDB0000164)

Plant

Exogenous

Food

Food (HMDB: HMDB0000164)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Fruit

Pome

Apple (FooDB: FOOD00105)

Tropical fruit

French plantain (FooDB: FOOD00436)

Berry

Common grape (FooDB: FOOD00204)

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)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Tea

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Hawkinsinuria (PathBank: SMP0000190)
Alkaptonuria (PathBank: SMP0000169)
Tyrosinemia Type I (PathBank: SMP0000218)
Tyrosinemia, Transient, of the Newborn (PathBank: SMP0000494)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0000498)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0000533)

Metabolic pathway

Tyrosine Metabolism (PathBank: SMP0000006)
Tyrosine Metabolism (HMDB: HMDB0000164)

Drug action pathway

Disulfiram Action Pathway (PathBank: SMP0000429)
Citalopram Action Pathway (HMDB: HMDB0000164)

Role

Biological role

Irritant (HMDB: HMDB0000164)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000164)

Biomarker

Uremia (MarkerDB: MDB00000080)

Environmental role

Air pollutant (HMDB: HMDB0000164)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-93.4 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1080 mg/mL at 25 °C	Not Available
LogP	-0.57	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	367 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.63	ChemAxon
logS	1.07	ALOGPS
pKa (Strongest Basic)	10.08	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	9.92 m³·mol⁻¹	ChemAxon
Polarizability	3.86 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]+	113.095	30932474
DeepCCS	[M-H]-	111.199	30932474
DeepCCS	[M-2H]-	146.383	30932474
DeepCCS	[M+Na]+	120.617	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methylamine	CN	1027.7	Standard polar	33892256
Methylamine	CN	322.7	Standard non polar	33892256
Methylamine	CN	392.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methylamine,1TMS,isomer #1	CN[Si](C)(C)C	623.3	Semi standard non polar	33892256
Methylamine,1TMS,isomer #1	CN[Si](C)(C)C	658.5	Standard non polar	33892256
Methylamine,1TMS,isomer #1	CN[Si](C)(C)C	715.5	Standard polar	33892256
Methylamine,2TMS,isomer #1	CN([Si](C)(C)C)[Si](C)(C)C	866.2	Semi standard non polar	33892256
Methylamine,2TMS,isomer #1	CN([Si](C)(C)C)[Si](C)(C)C	851.8	Standard non polar	33892256
Methylamine,2TMS,isomer #1	CN([Si](C)(C)C)[Si](C)(C)C	822.0	Standard polar	33892256
Methylamine,1TBDMS,isomer #1	CN[Si](C)(C)C(C)(C)C	865.9	Semi standard non polar	33892256
Methylamine,1TBDMS,isomer #1	CN[Si](C)(C)C(C)(C)C	834.7	Standard non polar	33892256
Methylamine,1TBDMS,isomer #1	CN[Si](C)(C)C(C)(C)C	896.0	Standard polar	33892256
Methylamine,2TBDMS,isomer #1	CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1258.3	Semi standard non polar	33892256
Methylamine,2TBDMS,isomer #1	CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1258.0	Standard non polar	33892256
Methylamine,2TBDMS,isomer #1	CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1106.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-50fb665f1ba89a03baf9	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-43b9d7b881c659f2ceb1	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 - Methylamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-9000000000-93f5049fa2e67d0da26d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9000000000-53c64a174764bada8913	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-9000000000-1c10568342e547416eaf	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 10V, Positive-QTOF	splash10-001i-9000000000-2910620cfb01718df17f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 20V, Positive-QTOF	splash10-001i-9000000000-2910620cfb01718df17f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 40V, Positive-QTOF	splash10-001i-9000000000-2910620cfb01718df17f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 10V, Negative-QTOF	splash10-001i-9000000000-f140127f4f4b677d2975	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 20V, Negative-QTOF	splash10-001i-9000000000-f140127f4f4b677d2975	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 40V, Negative-QTOF	splash10-001i-9000000000-f140127f4f4b677d2975	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 10V, Negative-QTOF	splash10-001i-9000000000-986b844d44ea8cab8877	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 20V, Negative-QTOF	splash10-001i-9000000000-986b844d44ea8cab8877	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 40V, Negative-QTOF	splash10-001i-9000000000-986b844d44ea8cab8877	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 10V, Positive-QTOF	splash10-001i-9000000000-d90d418cf76ae365e6c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 20V, Positive-QTOF	splash10-001i-9000000000-d90d418cf76ae365e6c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylamine 40V, Positive-QTOF	splash10-001i-9000000000-d90d418cf76ae365e6c5	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
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 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 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

Cytoplasm

Biospecimen Locations

Blood
Feces
Saliva
Sweat
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Alkaptonuria		Not Available
Hawkinsinuria		Not Available
Tyrosinemia Type I		Not Available
Tyrosinemia, transient, of the newborn		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.0 (0.37-4.0) uM	Adult (>18 years old)	Both	Normal	15380725	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25670064	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	27622378	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17269711	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17269711	details
Feces	Detected and Quantified	258 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Feces	Detected and Quantified	196 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Feces	Detected and Quantified	178 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Saliva	Detected and Quantified	25.55 +/- 13.26 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	158 (0.00-316) uM	Adult (>18 years old)	Both	Normal	12097436	details
Sweat	Detected and Quantified	< 10 uM	Adult (60 years old)	Male	Normal	22194922	details
Sweat	Detected and Quantified	< 10 uM	Adult (40 years old)	Male	Normal	22194922	details
Urine	Detected and Quantified	5.906 +/- 3.776 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	1.46 +/- 0.13 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	16260971	details
Urine	Detected and Quantified	13.6 +/- 3.1 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	16260971	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	4.0 (1.5-11.9) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	10.5 (9.8-12.5) 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	18.68 +/- 3.22 uM	Adult (>18 years old)	Both	uremia	22626821	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn disease	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	asymptomatic diverticulosis	27622378	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	symptomatic uncomplicated diverticular disease	27622378	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn's disease	17269711	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	17269711	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn’s Disease	17269711	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17269711	details
Urine	Detected and Quantified	8.09 +/- 6.297 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	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 ]
Crohn's disease
Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ] Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Ulcerative colitis
Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ] Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Diverticular disease
Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

266600 (Crohn's disease)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB01828

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003958

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16830

Food Biomarker Ontology

Not Available

VMH ID

MMA

MarkerDB ID

MDB00000080

Good Scents ID

Not Available

References

Synthesis Reference

Denham, William S.; Knapp, Lionel F. The preparation of methylamine from ammonium methyl sulfate. Journal of the Chemical Society, Transactions (1920), 117 236-47.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
Wolfe CL, Warrington JA, Davis S, Green S, Norcum MT: Isolation and characterization of human nuclear and cytosolic multisynthetase complexes and the intracellular distribution of p43/EMAPII. Protein Sci. 2003 Oct;12(10):2282-90. [PubMed:14500886 ]
Wolkers WF, Looper SA, Fontanilla RA, Tsvetkova NM, Tablin F, Crowe JH: Temperature dependence of fluid phase endocytosis coincides with membrane properties of pig platelets. Biochim Biophys Acta. 2003 Jun 10;1612(2):154-63. [PubMed:12787933 ]
Stanic P, Tandara M, Sonicki Z, Simunic V, Radakovic B, Suchanek E: Comparison of protective media and freezing techniques for cryopreservation of human semen. Eur J Obstet Gynecol Reprod Biol. 2000 Jul;91(1):65-70. [PubMed:10817881 ]
Zeisel SH, Gettner S, Youssef M: Formation of aliphatic amine precursors of N-nitrosodimethylamine after oral administration of choline and choline analogues in the rat. Food Chem Toxicol. 1989 Jan;27(1):31-4. [PubMed:2703191 ]
O'Sullivan J, Unzeta M, Healy J, O'Sullivan MI, Davey G, Tipton KF: Semicarbazide-sensitive amine oxidases: enzymes with quite a lot to do. Neurotoxicology. 2004 Jan;25(1-2):303-15. [PubMed:14697905 ]
Sawetawan C, Bruns ES, Prins GS: Improvement of post-thaw sperm motility in poor quality human semen. Fertil Steril. 1993 Oct;60(4):706-10. [PubMed:8405530 ]
Gunnarsson M, Sundstrom P, Stigbrand T, Jensen PE: Native and transformed alpha2-macroglobulin in plasma from patients with multiple sclerosis. Acta Neurol Scand. 2003 Jul;108(1):16-21. [PubMed:12807388 ]
Kokubo T, Kushitani H, Sakka S, Kitsugi T, Yamamuro T: Solutions able to reproduce in vivo surface-structure changes in bioactive glass-ceramic A-W. J Biomed Mater Res. 1990 Jun;24(6):721-34. [PubMed:2361964 ]
Mashige F, Imai K, Osuga T: A simple and sensitive assay of total serum bile acids. Clin Chim Acta. 1976 Jul 1;70(1):79-86. [PubMed:947625 ]
Wosikowski K, Biedermann E, Rattel B, Breiter N, Jank P, Loser R, Jansen G, Peters GJ: In vitro and in vivo antitumor activity of methotrexate conjugated to human serum albumin in human cancer cells. Clin Cancer Res. 2003 May;9(5):1917-26. [PubMed:12738750 ]
Tencer J, Thysell H, Andersson K, Grubb A: Long-term stability of albumin, protein HC, immunoglobulin G, kappa- and lambda-chain-immunoreactivity, orosomucoid and alpha 1-antitrypsin in urine stored at -20 degrees C. Scand J Urol Nephrol. 1997 Feb;31(1):67-71. [PubMed:9060087 ]
Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
Pirisino R, Ghelardini C, De Siena G, Malmberg P, Galeotti N, Cioni L, Banchelli G, Raimondi L: Methylamine: a new endogenous modulator of neuron firing? Med Sci Monit. 2005 Aug;11(8):RA257-61. Epub 2005 Jul 25. [PubMed:16049393 ]
Yu PH, Wright S, Fan EH, Lun ZR, Gubisne-Harberle D: Physiological and pathological implications of semicarbazide-sensitive amine oxidase. Biochim Biophys Acta. 2003 Apr 11;1647(1-2):193-9. [PubMed:12686132 ]
McDonald A, Tipton K, O'Sullivan J, Olivieri A, Davey G, Coonan AM, Fu W: Modelling the roles of MAO and SSAO in glucose transport. J Neural Transm (Vienna). 2007;114(6):783-6. Epub 2007 Apr 5. [PubMed:17406961 ]
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 ]

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

Reactions

Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxide	details
Metanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylamine	details
N-Desmethylcitalopram + Oxygen + Water → Citalopram aldehyde + Methylamine + Hydrogen peroxide	details

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

Reactions

Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxide	details
Metanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylamine	details
N-Desmethylcitalopram + Oxygen + Water → Citalopram aldehyde + Methylamine + Hydrogen peroxide	details

Enzyme Details

3. 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

Reactions

Methylamine + Oxygen + Water → Formaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

4. 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

Reactions

Methylamine + Oxygen + Water → Formaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

5. Glycine dehydrogenase [decarboxylating], mitochondrial

General function:: Involved in lyase activity
Specific function:: The glycine cleavage system catalyzes the degradation of glycine. The P protein binds the alpha-amino group of glycine through its pyridoxal phosphate cofactor; CO(2) is released and the remaining methylamine moiety is then transferred to the lipoamide cofactor of the H protein.
Gene Name:: GLDC
Uniprot ID:: P23378
Molecular weight:: 112728.805

Showing metabocard for Methylamine (HMDB0000164)

MOL for HMDB0000164 (Methylamine)

3D MOL for HMDB0000164 (Methylamine)

3D SDF for HMDB0000164 (Methylamine)

3D-SDF for HMDB0000164 (Methylamine)

PDB for HMDB0000164 (Methylamine)

3D PDB for HMDB0000164 (Methylamine)

SMILES for HMDB0000164 (Methylamine)

INCHI for HMDB0000164 (Methylamine)

Structure for HMDB0000164 (Methylamine)

3D Structure for HMDB0000164 (Methylamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

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