Trimethylamine
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Basic Info
Common Name | Trimethylamine(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. |
FRCD ID | F05247 |
CAS Number | 75-50-3 |
PubChem CID | 1146 |
Formula | C3H9N |
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 |
Wikipedia | Trimethylamine |
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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic nitrogen compounds |
Class | Organonitrogen compounds |
Subclass | Amines |
Intermediate Tree Nodes | Tertiary amines |
Direct Parent | Trialkylamines |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | Tertiary aliphatic amine - Organopnictogen compound - Hydrocarbon derivative - Aliphatic acyclic compound |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 59.112 |
Hydrogen Bond Donor Count | 0 |
Hydrogen Bond Acceptor Count | 1 |
Rotatable Bond Count | 0 |
Complexity | 8 |
Monoisotopic Mass | 59.073 |
Exact Mass | 59.073 |
XLogP | 0.3 |
Formal Charge | 0 |
Heavy Atom Count | 4 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9596 |
Human Intestinal Absorption | HIA+ | 0.9601 |
Caco-2 Permeability | Caco2+ | 0.6932 |
P-glycoprotein Substrate | Non-substrate | 0.8240 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9670 |
Non-inhibitor | 0.9824 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8590 |
Distribution | ||
Subcellular localization | Lysosome | 0.7284 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8198 |
CYP450 2D6 Substrate | Non-substrate | 0.8046 |
CYP450 3A4 Substrate | Non-substrate | 0.6002 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8897 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9536 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9610 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9508 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9587 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9184 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9316 |
Non-inhibitor | 0.9001 | |
AMES Toxicity | Non AMES toxic | 0.9133 |
Carcinogens | Carcinogens | 0.7793 |
Fish Toxicity | Low FHMT | 0.7221 |
Tetrahymena Pyriformis Toxicity | Low TPT | 0.9920 |
Honey Bee Toxicity | High HBT | 0.6993 |
Biodegradation | Not ready biodegradable | 0.7047 |
Acute Oral Toxicity | II | 0.7608 |
Carcinogenicity (Three-class) | Non-required | 0.5899 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | 0.4577 | LogS |
Caco-2 Permeability | 1.5693 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.0604 | LD50, mol/kg |
Fish Toxicity | 2.4815 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -1.4386 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Gut Microbiota and Cardiovascular Uremic Toxicities. | Toxins (Basel) | 2018 Jul 11 | 29997362 |
A triangle study of human, instrument and bioelectronic nose for non-destructive sensing of seafood freshness. | Sci Rep | 2018 Jan 11 | 29323222 |
Moderate Renal Impairment and Toxic Metabolites Produced by the Intestinal Microbiome: Dietary Implications. | J Ren Nutr | 2018 Aug 9 | 30100156 |
Relationship between serum trimethylamine N-oxide and exposure to dioxin-like pollutants. | Environ Res | 2018 Apr | 29353125 |
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 Nutr | 2017 Oct | 28758797 |
Nutrients Turned into Toxins: Microbiota Modulation of Nutrient Properties in Chronic Kidney Disease. | Nutrients | 2017 May 12 | 28498348 |
Nopal feeding reduces adiposity, intestinal inflammation and shifts the cecalmicrobiota and metabolism in high-fat fed rats. | PLoS One | 2017 Feb 14 | 28196086 |
Antibacterial activities and preservative effect of chitosan oligosaccharideMaillard reaction products on Penaeus vannamei. | Int J Biol Macromol | 2017 Dec | 28732733 |
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 Biochem | 2017 Aug | 28349418 |
(1)H-NMR based metabolomics study for the detection of the human urine metabolic profile effects of Origanum dictamnus tea ingestion. | Food Funct | 2016 Sep 14 | 27602787 |
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 Med | 2016 Oct | 27421909 |
National Safety Associates nutritional supplementation trial of fruit and vegetable extracts and vascular function (NNTV): study protocol for a randomised controlled trial. | Trials | 2016 Feb 4 | 26846357 |
Inhibition of biofilm development and spoilage potential of Shewanella baltica byquorum sensing signal in cell-free supernatant from Pseudomonas fluorescens. | Int J Food Microbiol | 2016 Aug 2 | 27149651 |
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 Agric | 2016 Aug | 26676937 |
Trimethylamine N-Oxide From Gut Microbiota in Chronic Kidney Disease Patients: Focus on Diet. | J Ren Nutr | 2015 Nov | 26235933 |
Metabolic profiles in the response to supplementation with composite antimicrobial peptides in piglets challenged with deoxynivalenol. | J Anim Sci | 2015 Mar | 26020888 |
Inhibition of quorum sensing, biofilm, and spoilage potential in Shewanellabaltica by green tea polyphenols. | J Microbiol | 2015 Dec | 26626353 |
Dietary Modulation of Gut Microbiota Contributes to Alleviation of Both Genetic and Simple Obesity in Children. | EBioMedicine | 2015 Aug | 26425705 |
Hepatotoxic constituents and toxicological mechanism of Xanthium strumarium L. fruits. | J Ethnopharmacol | 2014 Mar 14 | 24447814 |
SYNbiotics Easing Renal failure by improving Gut microbiologY (SYNERGY): a protocol of placebo-controlled randomised cross-over trial. | BMC Nephrol | 2014 Jul 4 | 24996842 |
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
- 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
- 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
- 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 ]