Name | trimethylamine N-oxide |
Synonyms | TMAO Triox trimethyloxamine Trimethylamine oxide trimethylamine N-oxide TRIMETHYLAMINE N-OXIDE n,n-dimethyl-methanaminn-oxide TRIMETHYLAMINE OXIDE HYDROCHLORIDE TRIMETHYLAMINE N-OXIDE HYDROCHLORIDE |
CAS | 1184-78-7 |
EINECS | 214-675-6 |
InChI | InChI=1/C10H11Cl2NO3/c1-5-7(11)4-6(10(14)15)8(12)9(5)13(2,3)16/h4H,1-3H3,(H,14,15) |
Molecular Formula | C3H9NO |
Molar Mass | 75.11 |
Density | 0.9301 (rough estimate) |
Melting Point | 220-222 °C (lit.) |
Boling Point | 133.8°C (rough estimate) |
JECFA Number | 1614 |
Water Solubility | 793g/L at 24.5℃ |
Solubility | Chloroform, DMSO, Methanol (Slightly) |
Vapor Presure | 23.5Pa at 20℃ |
Appearance | White powder or solid |
Color | Pale Yellow |
Merck | 14,9711 |
pKa | 4.65(at 25℃) |
Storage Condition | Hygroscopic, Room Temperature, under inert atmosphere |
Stability | Hygroscopic |
Refractive Index | 1.4698 (estimate) |
MDL | MFCD00002048 |
In vitro study | The size and migration of fibroblasts are increased after Trimethylamine N-oxide (TMAO) treatment compared with non-treated fibroblasts in vitro. Trimethylamine N-oxide increases TGF-β receptor I expression, which promotes the phosphorylation of Smad2 and up-regulates the expression of α-SMA and collagen I. The ubiquitination of TGF-βRI is decreased in neonatal mouse fibroblasts after Trimethylamine N-oxide treatment. Trimethylamine N-oxide also inhibits the expression of smurf2. Trimethylamine N-oxide is frequently found in the tissues of a variety of marine organisms that protects against the adverse effects of temperature, salinity, high urea and hydrostatic pressure. |
In vivo study | Trimethylamine N-oxide (TMAO) contributes to cardiovascular diseases by promoting inflammatory responses. C57BL/6 mice are fed a normal diet, high-choline diet and/or 3-dimethyl-1-butanol (DMB) diet. The levels of Trimethylamine N-oxide and choline are increased in choline-fed mice. Left ventricular hypertrophy, pulmonary congestion, and diastolic dysfunction are markedly exacerbated in heart failure with preserved ejection fraction (HFpEF) mice fed high-choline diets compared with mice fed the control diet. Myocardial fibrosis and inflammation were markedly increased in HFpEF mice fed high-choline diets compared with animals fed the control diet. |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
WGK Germany | 3 |
Reference Show more | 1. [IF=5.25] Yixiao Luo et al."Exogenous microbiota-derived metabolite trimethylamine N-oxide treatment alters social behaviors: Involvement of hippocampal metabolic adaptation."Neuropharmacology. 2021 Jun;191:108563 2. [IF=4.411] Mingshuai He et al."Determination of Trimethylamine N-oxide and Betaine in Serum and Food by Targeted Metabonomics."Molecules. 2021 Jan;26(5):1334 3. [IF=2.419] Shanshan Gao et al."Development and validation of a sensitive and reliable targeted metabolomics method for the quantification of cardiovascular disease-related biomarkers in plasma by using UPLC-MS/MS."Rapid Communications In Mass Spectrometry. 2022 Mar |