Cannabis Compound Database: Showing Compound Card for Methylamine (CDB006145)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (5)transporters (1) Show 8 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:21:38 UTC

Updated at

2020-12-07 19:06:55 UTC

CannabisDB ID

CDB006145

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Methylamine

Description

Methylamine, also known as aminomethane or methanamine, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing a primary aliphatic amine group. Methylamine is a strong basic compound (based on its pKa). It has a strong odor similar to fish. Industrially, methylamine is used as a building block for the synthesis of many other commercially available compounds. Methylamine exists in all living organisms, ranging from bacteria to humans. Methylamine is found in relatively high concentrations in a number of plant foods such as wild carrots, carrots, and tea and in a lower concentration in cabbages, corns, and barley. Methylamine has also been detected, but not quantified in, several other plant foods, such as soybeans, wild celeries, french plantains, and common grapes. It has also been detected in cow‚Äôs milk. This could make methylamine a potential biomarker for the consumption of these foods. Methylamine occurs endogenously from amine catabolism and its tissue levels increase in some pathological conditions, including diabetes. In the human body 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 ( PMID: 18845121 ). Methylamine also targets the voltage-operated neuronal potassium channels, probably inducing release of neurotransmitter(s) ( PMID: 16049393 ). Semicarbazide-sensitive amine oxidase (SSAO) catalyzes the deamination of primary amines. This kind of deamination has been shown capable of regulating glucose transport in adipose cells. Increased serum SSAO activities have been found in patients with diabetic mellitus, vascular disorders, and Alzheimer's disease (PMID: 18691041 ). The SSAO-catalyzed deamination of endogenous substrates like methylamine is known to lead to the 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. Methylamine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).

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

31.06

Monoisotopic Molecular Weight

31.0422

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

Dermal

Enteral:

Ingestion

Biofluid and excreta:

Subcellular:

Cytoplasm

Role

Indirect biological role:

Uremic toxin

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Environmental role:

Air pollutant

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-93.4 °C	Not Available
Boiling Point	−6.0 °C	Wikipedia
Water Solubility	1080 mg/mL at 25 °C	Not Available
logP	-0.57	HANSCH,C ET AL. (1995)

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	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-43b9d7b881c659f2ceb1	2014-09-20	View Spectrum
Predicted GC-MS	Methylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9000000000-50fb665f1ba89a03baf9	Spectrum
Predicted GC-MS	Methylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-9000000000-93f5049fa2e67d0da26d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-53c64a174764bada8913	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-1c10568342e547416eaf	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-2910620cfb01718df17f	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-2910620cfb01718df17f	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-2910620cfb01718df17f	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-f140127f4f4b677d2975	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-f140127f4f4b677d2975	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-f140127f4f4b677d2975	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-986b844d44ea8cab8877	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-986b844d44ea8cab8877	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-986b844d44ea8cab8877	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-d90d418cf76ae365e6c5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-d90d418cf76ae365e6c5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-d90d418cf76ae365e6c5	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Spectrum

Pathways

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

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Amine oxidase [flavin-containing] B	MAOB	Xp11.23	P27338	details
Amine oxidase [flavin-containing] A	MAOA	Xp11.3	P21397	details
Membrane primary amine oxidase	AOC3	17q21	Q16853	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details
Glycine dehydrogenase [decarboxylating], mitochondrial	GLDC	9p22	P23378	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Solute carrier family 2, facilitated glucose transporter member 4	SLC2A4	17p13	P14672	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Membrane primary amine oxidase	AOC3	17q21	Q16853	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000164

DrugBank ID

DB01828

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

General References

Xiao S, Yu PH: A fluorometric high-performance liquid chromatography procedure for simultaneous determination of methylamine and aminoacetone in blood and tissues. Anal Biochem. 2009 Jan 1;384(1):20-6. doi: 10.1016/j.ab.2008.09.029. Epub 2008 Sep 25. [PubMed:18845121 ]
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 ]
Dunkel P, Gelain A, Barlocco D, Haider N, Gyires K, Sperlagh B, Magyar K, Maccioni E, Fadda A, Matyus P: Semicarbazide-sensitive amine oxidase/vascular adhesion protein 1: recent developments concerning substrates and inhibitors of a promising therapeutic target. Curr Med Chem. 2008;15(18):1827-39. doi: 10.2174/092986708785133022. [PubMed:18691041 ]
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

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

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

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

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

Transporters

Enzyme Details

1. Solute carrier family 2, facilitated glucose transporter member 4

General function:: Not Available
Specific function:: Insulin-regulated facilitative glucose transporter.
Gene Name:: SLC2A4
Uniprot ID:: P14672
Molecular weight:: 54786.79

Showing Compound Card for Methylamine (CDB006145)

Structure for CDB006145 (Methylamine)

Enzymes

Transporters