TRIMETHYLAMINE OXIDE HYDROCHLORIDE
trimethylamine N-oxide
CAS: 1184-78-7
Molecular Formula: C3H9NO
TRIMETHYLAMINE OXIDE HYDROCHLORIDE - Names and Identifiers
| 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) |
TRIMETHYLAMINE OXIDE HYDROCHLORIDE - Physico-chemical Properties
| 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. |
TRIMETHYLAMINE OXIDE HYDROCHLORIDE - Risk and Safety
| 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 |
TRIMETHYLAMINE OXIDE HYDROCHLORIDE - Reference
| 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 |
TRIMETHYLAMINE OXIDE HYDROCHLORIDE - Reference Information
| FEMA | 4245 | TRIMETHYLAMINE OXIDE |
| LogP | -2.79 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| biological activity | Trimethylamine N-oxide is an intestinal microbial-dependent metabolite of dietary choline and other trimethylamine-containing nutrients. Trimethylamine N-oxide induce inflammation by activating ROS/NLRP3 inflammatory body. Trimethylamine N-oxide also accelerates fibroblast differentiation and induces cardiac fibrosis by activating TGF-β/smad2 signaling pathway. |
| target | ROS/NLRP3 inflammasome TGF-β/smad2 |
| production method | 100ml of trimethylamine aqueous solution is mixed with 600ml of hydrogen peroxide solution. after being left at room temperature for 24 hours, if there is still the smell of amine, 100~200ml of hydrogen peroxide solution is added. when all amines are oxidized, they evaporate to dryness under reduced pressure. The residue was recrystallized with an ethanol-ether mixture. Trimethylamine dihydrate was obtained as a long needle crystal with 95% yield. In the oil bath, the pressure is reduced to 1.33 ~ 1.6kpa and heated to 120 ℃, and the temperature is slowly increased to 150 ℃. When the water is removed, the temperature is increased to 180 ℃ ~ 200 ℃, and the pure anhydrous trimethylamine oxide is sublimated on the cooler neck of the bottle. Another dehydration method: 45.0g of trimethylamine dihydrate is dissolved in 300ml of hot DMF and placed in a round bottom flask for distillation. First heat at normal pressure to evaporate the solvent until the boiling point reaches 152~153 ℃. Then decompress with a water pump to remove the remaining solvent. At the end of distillation, the temperature of the oil bath was slowly raised to 120 ℃. The remaining anhydrous trimethylamine oxide weighs 30g. |
Last Update：2024-04-09 02:00:06
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TRIMETHYLAMINE OXIDE HYDROCHLORIDE
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PHENYLGLYOXAL MONOHYDRATE
Soap
FMOC-D-3-(3-苯并噻吩基)丙氨酸
2-(3-(三氟甲基)苯基)环丙胺盐酸盐
LITHIUM TRI-TERT-BUTOXYALUMINUM HYDRIDE
苯甲酮二甲基乙缩醛
2-氨基-2-环丁基乙腈
2-腈基苯硼酸新戊二醇酯频呢醇酯
5-氟喹啉-8-胺
PHENYLGLYOXAL MONOHYDRATE
Soap