Basic Info

Common NameTrimethylamine(F05247)
2D Structure
Description

Trimethylamine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Trimethylamine, also known as NMe3, N(CH3)3, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia like odor in higher concentrations. Trimethylamine has a boiling point of 2.9 degree centigrade and is a gas at room temperature. Trimethylamine usually comes in pressurized gas cylinders or as a 40% solution in water. Trimethylamine is a nitrogenous base and its positively charged cation is called trimethylammonium cation. A common salt of trimethylamine is trimethylammonium chloride, a hygroscopic colorless solid. Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the fishy odor often associated with fouling fish, bacterial vagina infections, and bad breath. It is also associated with taking large doses of choline. Trimethylaminuria is a genetic disorder in which the body is unable to metabolize trimethylamine from food sources. Patients develop a characteristic fish odour of their sweat, urine, and breath after the consumption of choline-rich foods. Trimethylaminuria is an autosomal recessive disorder involving a trimethylamine oxidase deficiency. Trimethylaminuria has also been observed in a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell.

FRCD IDF05247
CAS Number75-50-3
PubChem CID1146
FormulaC3H9N
IUPAC Name

N,N-dimethylmethanamine

InChI Key

GETQZCLCWQTVFV-UHFFFAOYSA-N

InChI

InChI=1S/C3H9N/c1-4(2)3/h1-3H3

Canonical SMILES

CN(C)C

Isomeric SMILES

CN(C)C

WikipediaTrimethylamine
Synonyms
        
            trimethylamine
        
            N,N-dimethylmethanamine
        
            75-50-3
        
            Methanamine, N,N-dimethyl-
        
            Dimethylmethaneamine
        
            N-Trimethylamine
        
            Trimethylamine solution
        
            (CH3)3N
        
            TRIMETHYL AMINE
        
            Trimethylamin
        
Classifies
                

                  
                    Predicted: Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassAmines
Intermediate Tree NodesTertiary amines
Direct ParentTrialkylamines
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsTertiary aliphatic amine - Organopnictogen compound - Hydrocarbon derivative - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.

Properties

Property NameProperty Value
Molecular Weight59.112
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Complexity8
Monoisotopic Mass59.073
Exact Mass59.073
XLogP0.3
Formal Charge0
Heavy Atom Count4
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9596
Human Intestinal AbsorptionHIA+0.9601
Caco-2 PermeabilityCaco2+0.6932
P-glycoprotein SubstrateNon-substrate0.8240
P-glycoprotein InhibitorNon-inhibitor0.9670
Non-inhibitor0.9824
Renal Organic Cation TransporterNon-inhibitor0.8590
Distribution
Subcellular localizationLysosome0.7284
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8198
CYP450 2D6 SubstrateNon-substrate0.8046
CYP450 3A4 SubstrateNon-substrate0.6002
CYP450 1A2 InhibitorNon-inhibitor0.8897
CYP450 2C9 InhibitorNon-inhibitor0.9536
CYP450 2D6 InhibitorNon-inhibitor0.9610
CYP450 2C19 InhibitorNon-inhibitor0.9508
CYP450 3A4 InhibitorNon-inhibitor0.9587
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9184
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9316
Non-inhibitor0.9001
AMES ToxicityNon AMES toxic0.9133
CarcinogensCarcinogens 0.7793
Fish ToxicityLow FHMT0.7221
Tetrahymena Pyriformis ToxicityLow TPT0.9920
Honey Bee ToxicityHigh HBT0.6993
BiodegradationNot ready biodegradable0.7047
Acute Oral ToxicityII0.7608
Carcinogenicity (Three-class)Non-required0.5899

Model Value Unit
Absorption
Aqueous solubility0.4577LogS
Caco-2 Permeability1.5693LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0604LD50, mol/kg
Fish Toxicity2.4815pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.4386pIGC50, ug/L

References

TitleJournalDatePubmed ID
Gut Microbiota and Cardiovascular Uremic Toxicities.Toxins (Basel)2018 Jul 1129997362
A triangle study of human, instrument and bioelectronic nose for non-destructive sensing of seafood freshness.Sci Rep2018 Jan 1129323222
Moderate Renal Impairment and Toxic Metabolites Produced by the Intestinal Microbiome: Dietary Implications.J Ren Nutr2018 Aug 930100156
Relationship between serum trimethylamine N-oxide and exposure to dioxin-like pollutants.Environ Res2018 Apr29353125
An in vitro evaluation of the effects of a Yucca schidigera extract and chestnut tannins on composition and metabolic profiles of canine and feline faecal microbiota.Arch Anim Nutr2017 Oct28758797
Nutrients Turned into Toxins: Microbiota Modulation of Nutrient Properties in Chronic Kidney Disease.Nutrients2017 May 1228498348
Nopal feeding reduces adiposity, intestinal inflammation and shifts the cecalmicrobiota and metabolism in high-fat fed rats.PLoS One2017 Feb 1428196086
Antibacterial activities and preservative effect of chitosan oligosaccharideMaillard reaction products on Penaeus vannamei.Int J Biol Macromol2017 Dec28732733
Comparing the effects of different dietary organic acids on the growth,intestinal short-chain fatty acids, and liver histopathology of red hybridtilapia (Oreochromis sp.) and potential use of these as preservatives.Fish Physiol Biochem2017 Aug28349418
(1)H-NMR based metabolomics study for the detection of the human urine metabolic profile effects of Origanum dictamnus tea ingestion.Food Funct2016 Sep 1427602787
Human risk of diseases associated with red meat intake: Analysis of current theories and proposed role for metabolic incorporation of a non-human sialic acid.Mol Aspects Med2016 Oct27421909
National Safety Associates nutritional supplementation trial of fruit and vegetable extracts and vascular function (NNTV): study protocol for a randomised controlled trial.Trials2016 Feb 426846357
Inhibition of biofilm development and spoilage potential of Shewanella baltica byquorum sensing signal in cell-free supernatant from Pseudomonas fluorescens.Int J Food Microbiol2016 Aug 227149651
Development of an SPME-GC-MS method for the specific quantification ofdimethylamine and trimethylamine: use of a new ratio for the freshness monitoringof cod fillets.J Sci Food Agric2016 Aug26676937
Trimethylamine N-Oxide From Gut Microbiota in Chronic Kidney Disease Patients: Focus on Diet.J Ren Nutr2015 Nov26235933
Metabolic profiles in the response to supplementation with composite antimicrobial peptides in piglets challenged with deoxynivalenol.J Anim Sci2015 Mar26020888
Inhibition of quorum sensing, biofilm, and spoilage potential in Shewanellabaltica by green tea polyphenols.J Microbiol2015 Dec26626353
Dietary Modulation of Gut Microbiota Contributes to Alleviation of Both Genetic and Simple Obesity in Children.EBioMedicine2015 Aug26425705
Hepatotoxic constituents and toxicological mechanism of Xanthium strumarium L. fruits.J Ethnopharmacol2014 Mar 1424447814
SYNbiotics Easing Renal failure by improving Gut microbiologY (SYNERGY): a protocol of placebo-controlled randomised cross-over trial.BMC Nephrol2014 Jul 424996842

Targets

General Function:
Vitamin d binding
Specific Function:
May have weak glycosidase activity towards glucuronylated steroids. However, it lacks essential active site Glu residues at positions 239 and 872, suggesting it may be inactive as a glycosidase in vivo. May be involved in the regulation of calcium and phosphorus homeostasis by inhibiting the synthesis of active vitamin D (By similarity). Essential factor for the specific interaction between FGF23 and FGFR1 (By similarity).The Klotho peptide generated by cleavage of the membrane-bound isoform may be an anti-aging circulating hormone which would extend life span by inhibiting insulin/IGF1 signaling.
Gene Name:
KL
Uniprot ID:
Q9UEF7
Molecular Weight:
116179.815 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
General Function:
Superoxide-generating nadph oxidase activity
Specific Function:
Constitutive NADPH oxidase which generates superoxide intracellularly upon formation of a complex with CYBA/p22phox. Regulates signaling cascades probably through phosphatases inhibition. May function as an oxygen sensor regulating the KCNK3/TASK-1 potassium channel and HIF1A activity. May regulate insulin signaling cascade. May play a role in apoptosis, bone resorption and lipolysaccharide-mediated activation of NFKB. May produce superoxide in the nucleus and play a role in regulating gene expression upon cell stimulation. Isoform 3 is not functional. Isoform 5 and isoform 6 display reduced activity.Isoform 4: Involved in redox signaling in vascular cells. Constitutively and NADPH-dependently generates reactive oxygen species (ROS). Modulates the nuclear activation of ERK1/2 and the ELK1 transcription factor, and is capable of inducing nuclear DNA damage. Displays an increased activity relative to isoform 1.
Gene Name:
NOX4
Uniprot ID:
Q9NPH5
Molecular Weight:
66930.995 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]