Livestock Metabolome Database: Showing metabocard for Methylamine (LMDB00073)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:41:47 UTC

Update Date

2016-07-20 20:20:03 UTC

Lmdb

LMDB00073

Secondary Accession Numbers

None

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 H (2) O (2) produced in the oxidation of these amines. (PMID: 16049393 , 12686132 , 17406961 ).

Structure

MOL SDF PDB SMILES InChI

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

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-50fb665f1ba89a03baf9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-9000000000-93f5049fa2e67d0da26d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-53c64a174764bada8913	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-1c10568342e547416eaf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-2910620cfb01718df17f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-2910620cfb01718df17f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-2910620cfb01718df17f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-f140127f4f4b677d2975	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-f140127f4f4b677d2975	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-f140127f4f4b677d2975	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-986b844d44ea8cab8877	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-986b844d44ea8cab8877	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-986b844d44ea8cab8877	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-d90d418cf76ae365e6c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-d90d418cf76ae365e6c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-d90d418cf76ae365e6c5	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-43b9d7b881c659f2ceb1	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Ruminal Fluid
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	22370585	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	22370585	details
Ruminal Fluid	Detected and Quantified	34.3 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	136 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	202 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	608 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	28.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	89.9 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	108.4 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	703.3 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	213 +/- 32 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	445 +/- 44 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	489 +/- 63 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	14.75 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	23.86 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	17.53 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	108 +/- 104 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	49 +/- 12 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	49 +/- 12 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	703 +/- 119 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	85 +/- 72 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	90 +/- 33 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	2,240 +/- 150 uM	Not Available	Caprine	22706048	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	24617926	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details

External Links

DrugBank ID

DB01828

HMDB ID

HMDB0000164

FooDB ID

FDB003958

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

1800349

BioCyc ID

METHYLAMINE

METLIN ID

3767

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB00164

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [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. [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. [17406961 ]

Showing metabocard for Methylamine (LMDB00073)

Structure for LMDB00073 (Methylamine)