HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylamine oxide
TMAO · Trimetlylamine Oxide · N,N-dimethylmethanamine oxide · trimethyloxamine · Trimethylamine N-Oxide Anhydrous · Triox · TMANO Anhydrous · TRIMETHYLAMINOXIDE
Identifiers & Physical Properties
| CAS No. | 1184-78-7 |
|---|---|
| Molecular formula | C3H9NO |
| Average molar mass | 75.11 g/mol |
| Monoisotopic mass | 75.06841391 g/mol |
| SMILES | C[N+](C)(C)[O-] |
| InChIKey | UYPYRKYUKCHHIB-UHFFFAOYSA-N |
| PubChem CID | 1145 |
| ChEBI | CHEBI:15724 |
| EC No. | 214-675-6 |
| DTXSID | DTXSID8049678 |
Chemical & Physical Properties
| XLogP | -0.3 |
|---|---|
| Topological polar surface area | 18.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 5 |
| Formal charge | 0 |
| Complexity | 28.4 |
| Chemical classes | Nitrogen Compounds -> Amine Oxides |
| Drugs | Pharmaceuticals -> Metabolite of Levocarnitine |
| SpringerMaterials Properties | Schoenflies notation |
| LogP (partition coefficient) | -2.570 |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Flavoring agents | EU Flavoring substances |
| Solubility | 454 mg/mLSoluble in waterSoluble (in ethanol)Chloroform, DMSO, Methanol (Slightly)793g/L at 24.5℃ |
| Melting point | 95 - 99 °C220-222 °C (lit.) |
| Physical Description | LiquidColorless solidHighly hygroscopic[Merck Index]Colourless to yellow solidOdourless |
| Boiling point | 133.8°C (rough estimate) |
| Density | 0.9301 (rough estimate) |
| Vapor pressure | 23.5Pa at 20℃ |
| Refractive index | 1.4698 (estimate) |
| FEMA | 4245 | TRIMETHYLAMINE OXIDE |
| FLAVIS Number | 11.025 | Trimethylamine oxide |
| Storage conditions | Hygroscopic, Room Temperature, under inert atmosphere |
| pKa (acidity coefficient) | 4.65(at 25℃) |
| Physical state | Solid |
| Color | Pale Yellow |
| Odor | odorless |
| Merck | 14,9711 |
| JECFA Number | 1614 |
| Stability | Hygroscopic |
| InChI | 1S/C3H9NO/c1-4(2,3)5/h1-3H3 |
| InChIKey | UYPYRKYUKCHHIB-UHFFFAOYSA-N |
| SMILES | C[N+](C)(C)[O-] |
| LogP (partition coefficient) | -2.79 |
| Substances Added to Food (formerly EAFUS) | TRIMETHYLAMINE OXIDE |
| EWG's Food Scores | 1 |
| FDA UNII | FLD0K1SJ1A |
| EPA Substance Registry System | Methanamine, N,N-dimethyl-, N-oxide (1184-78-7) |
| UNSPSC Code | 12352116 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302+H332 |
| GHS precautionary statements | P261-P264-P270-P271-P301+P312-P304+P340+P312 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-37/39 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 2904.20.5000 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Acute Tox. 4 InhalationAcute Tox. 4 Oral |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | DangerH302 (71.8%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 188 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302+H332 (31.5%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oralacute toxicity, inhalation] |
|---|---|
| Regulatory information | Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Methanamine, N,N-dimethyl-, N-oxide is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanamine, N,N-dimethyl-, N-oxide are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 03-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/25104Methanamine, N,N-dimethyl-, N-oxide: Does not have an individual approval but may be used under an appropriate group standardAmines, C12-16-alkyldimethyl, N-oxides: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Hazards summary | The dihydrate is CAS# 62637-93-8May cause skin, eye, and respiratory tract irritation[Merck Index] Safe when used as a flavoring agent in food[JECFA] A skin and strong eye irritant[Sigma-Aldrich MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (57.6%)Acute Tox. 4 (71.8%) |
| Minimum Risk Level | >75 uM in blood |
| Treatment | Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. Treatments for atherosclerosis may include lifestyle changes (exercise, eating fruits and vegetables), medicines (statins), and medical procedures or surgery (angioplasty). |
| Health effects | High endogenous levels of TMAO in the blood (>100 uM) can lead to uremia which can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Chronically high levels of TMAO in the blood can also lead to the development of atherosclerosis and atherosclerotic plaques. |
| Exposure routes | Endogenous, Ingestion |
| Toxicity summary | Uremic toxins such as TMAO are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (5). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (6). TMAO appears to contribute to the development of atherosclerosis in part by promoting cholesterol accumulation within macrophages, perhaps by inducing scavenger receptors such as CD36 and SRA1, both of which are involved in the uptake of modified lipoproteins (A15344). |
| Signs and Symptoms | As a uremic toxin, TMAO can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. Symptoms of atherosclerosis include angina, chest pain, breathlessness, nausea, dizziness, leg pains, weakness or numbness in the legs, erectile dysfunction, hairloss on legs or feet and leg sores that never heal. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Toxicity Data | >100 uM in blood is usually indicative of uremia |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 2904.20.5000 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-37/39 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302+H332 |
| REACH registrations | Active |
| Hazard class | Acute Tox. 4 InhalationAcute Tox. 4 Oral |
| GHS precautionary statements | P261-P264-P270-P271-P301+P312-P304+P340+P312 |
Applications & Uses
Description
Trimethylamine N-oxide (TMAO) is a metabolite of choline, phosphatidylcholine, and L-carnitine . It is formed by gut microbiota-mediated metabolism of choline, phosphatidylcholine, and L-carnitine to TMA followed by oxidation of TMA by flavin-containing monooxygenase 3 (FMO3) in the liver. Dietary administration of TMAO (0.12% w/w) increases renal tubulointerstitial fibrosis, collagen deposition, and Smad3 phosphorylation in mice and increases aortic lesion area in atherosclerosis-prone ApoE-/- mice. Plasma levels of TMAO are elevated in patients with chronic kidney disease and decreased in patients with active, compared with inactive, ulcerative colitis. Elevated plasma levels of TMAO are associated with increased risk of cardiovascular disease.
Uses
TrimethylamineN-oxide can be used:As a demetallationand decarbonylationreagent for organometallic compounds.To prepare azomethine ylide by reaction with lithium di-isopropylamide. This, in turn, may be reacted with simple alkenes to obtain corresponding pyrrolidines.To mediate the conversion of thiols to disulfides.
General Description
TrimethylamineN-oxide is an organic compound that belongs to the class of amine oxides. It is generally found in the tissues of marine organisms, wherein it helps protect them from harsh conditions like salinity, hydrostatic pressure, temperature, and high urea.