MiMeDB: Showing metabocard for Methylamine (MMDBc0000052)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:28:38 UTC

Update Date

2024-10-07 02:50:19 UTC

Metabolite ID

MMDBc0000052

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

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

Molecular Formula

CH₅N

Average Mass

31.0571

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-50fb665f1ba89a03baf9	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-9000000000-93f5049fa2e67d0da26d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-53c64a174764bada8913	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-1c10568342e547416eaf	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-2910620cfb01718df17f	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-2910620cfb01718df17f	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-2910620cfb01718df17f	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-f140127f4f4b677d2975	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-f140127f4f4b677d2975	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-f140127f4f4b677d2975	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-986b844d44ea8cab8877	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-986b844d44ea8cab8877	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-986b844d44ea8cab8877	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-d90d418cf76ae365e6c5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-d90d418cf76ae365e6c5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-d90d418cf76ae365e6c5	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-43b9d7b881c659f2ceb1	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Saliva
Sweat
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191832	Amine oxidase [flavin-containing] B	Unknown	P27338	Homo sapiens
MMDBp0191840	Amine oxidase [flavin-containing] A	Unknown	P21397	Homo sapiens
MMDBp0192060	Membrane primary amine oxidase	Unknown	Q16853	Homo sapiens
MMDBp0192061	Retina-specific copper amine oxidase	Unknown	O75106	Homo sapiens
MMDBp0192415	Glycine dehydrogenase [decarboxylating], mitochondrial	Enzyme	P23378	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000087	Epinephrine	3,4-Dihydroxymandelaldehyde	monoamine oxidase A	VMH	15035803 8920635 9653080
MMDBr0001620	Methylamine	Formaldehyde	Not Available	VMH	11136547 14715500 9131641
MMDBr0010409	Metanephrine	3-Methoxy-4-hydroxyphenylglycolaldehyde	monoamine oxidase A	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Uremia	Increased	Association	Human Blood	HMDB	22626821
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Thermodesulfobacteria	1		Microbial culture
Bacteria	Proteobacteria	28	Human ; Human feces; Human sputum; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria	Firmicutes	6	Human feces; Human stool; Human ; Goat feces; Sheep feces	Microbial culture
Archaea	Euryarchaeota	2		Microbial culture
Bacteria	Actinobacteria	7	Human feces; Human	Microbial culture; Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	3		Microbial culture

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	29291809
Food			FooDB	3271892
Plant	Seed	Glycine max	FooDB	DUKE
Plant	Leaves		FooDB	DUKE
Plant	Leaves		FooDB	DUKE
Plant	Root	Daucus carota ssp. sativus	FooDB	DUKE
Plant	Leaves		FooDB	DUKE
Plant	Leaves	Spinacia oleracea	FooDB	DUKE
Plant	Fruit juice	Vitis vinifera	FooDB	DUKE
Plant	Leaves	Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	DUKE
Plant	Leaves	Brassica oleracea var. capitata	FooDB	DUKE
Plant	Stem	Apium graveolens	FooDB	DUKE
Plant	Fruit	Malus pumila	FooDB	DUKE
Plant	Leaves	Camellia sinensis	FooDB	DUKE
Plant	Root	Daucus carota	FooDB	DUKE
Plant	Fruit	Musa x paradisiaca	FooDB	DUKE
Plant	Pericarp	Malus pumila	FooDB	DUKE

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	18.68	3.22			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Feces	Detected and Quantified	178				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	196				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	258				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Sweat	Detected and Quantified	< 10				uM	Adult (60 years old)	Male	Normal	HMDB	22194922
Human Sweat	Detected and Quantified	< 10				uM	Adult (40 years old)	Male	Normal	HMDB	22194922
Human Blood	Detected and Quantified	1.0		0.37	4.0	uM	Adult (>18 years old)	Both	Normal	HMDB	15380725
Human Urine	Detected and Quantified	1.46	0.13			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	16260971
Human Urine	Detected and Quantified	13.6	3.1			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	16260971
Human Saliva	Detected and Quantified	158		0.00	316	uM	Adult (>18 years old)	Both	Normal	HMDB	12097436
Human Urine	Detected and Quantified	4.0		1.5	11.9	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	8.09	6.297			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.906	3.776			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	10.5		9.8	12.5	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	25.55	13.26			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17269711
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25670064
Human Feces	Detected but not Quantified						Not Specified	Both	Normal	HMDB	25486321
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17269711
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	27622378
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	28842642

External Links

HMDB ID

HMDB0000164

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1110/ps.03147903. [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. doi: 10.1016/s0005-2736(03)00114-7. [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. doi: 10.1016/s0301-2115(99)00255-9. [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. doi: 10.1016/0278-6915(89)90089-6. [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. doi: 10.1016/S0161-813X(03)00117-7. [PubMed:14697905 ]
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. doi: 10.1177/154405910208100613. [PubMed:12097436 ]
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. doi: 10.1016/s0015-0282(16)56227-x. [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. doi: 10.1034/j.1600-0404.2003.00079.x. [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. doi: 10.1002/jbm.820240607. [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. doi: 10.1016/0009-8981(76)90007-3. [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 ]
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. doi: 10.1021/ac00101a004. [PubMed:7762816 ]
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. doi: 10.3109/00365599709070305. [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. doi: 10.1016/s1570-9639(03)00101-8. [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. doi: 10.1007/s00702-007-0688-6. 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 ]

Showing metabocard for Methylamine (MMDBc0000052)

MOL for #<Metabolite:0x00007fdb0fb548b0>

3D MOL for #<Metabolite:0x00007fdb0fb548b0>

3D SDF for #<Metabolite:0x00007fdb0fb548b0>

3D-SDF for #<Metabolite:0x00007fdb0fb548b0>

PDB for #<Metabolite:0x00007fdb0fb548b0>

3D PDB for #<Metabolite:0x00007fdb0fb548b0>

SMILES for #<Metabolite:0x00007fdb0fb548b0>

INCHI for #<Metabolite:0x00007fdb0fb548b0>

Structure for #<Metabolite:0x00007fdb0fb548b0>

3D Structure for #<Metabolite:0x00007fdb0fb548b0>