Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C3H9N |
| Molecular Weight | 59.1103 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C
InChI
InChIKey=GETQZCLCWQTVFV-UHFFFAOYSA-N
InChI=1S/C3H9N/c1-4(2)3/h1-3H3
| Molecular Formula | C3H9N |
| Molecular Weight | 59.1103 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Trimethylamine (or TMA) a tertiary amine, is synthesized by the action of microbial enzymes in humans. The decrease of TMA metabolism and excessive TMA excretion cause the disease trimethylaminuria and some other diseases associated with the abnormal level of TMA, e.g., obesity, diabetes, cardiovascular diseases. It was shown, that TMS is a full agonist of human trace amine-associated receptor 5, TAAR5. In addition, TMA is a precursor of N-oxide form, an emergent biomarker of human health that can lead to renal diseases, neurological disorders, and cancer.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Prolonged epileptiform bursting induced by 0-Mg(2+) in rat hippocampal slices depends on gap junctional coupling. | 2001 |
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| Characterization of sodiated glycerol phosphatidylcholine phospholipids by mass spectrometry. | 2001 |
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| Effect of acute exposure to ammonia on glutamate transport in glial cells isolated from the salamander retina. | 2001 Aug |
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| Formation of aerosol particles from reactions of secondary and tertiary alkylamines: characterization by aerosol time-of-flight mass spectrometry. | 2001 Aug 1 |
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| Exploring the recognized bio-mimicry materials for gas sensing. | 2001 Dec |
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| Cloning, sequencing, tissue distribution, and heterologous expression of rat flavin-containing monooxygenase 3. | 2001 Jul 1 |
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| Detection of the mutated K-Ras biomarker in colorectal carcinoma. | 2001 Jun |
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| Characterization of Methanococcus voltaei strain P2F9701a: a new methanogen isolated from estuarine environment. | 2001 Jun |
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| Altering intracellular pH disrupts development and cellular organization in preimplantation hamster embryos. | 2001 Jun |
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| The relationship between the interfacial properties of surfactants and their toxicity to aquatic organisms. | 2001 Mar 1 |
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| Significance of volatile compounds produced by spoilage bacteria in vacuum-packed cold-smoked salmon (Salmo salar) analyzed by GC-MS and multivariate regression. | 2001 May |
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| Enhanced temporal stability of cholinergic hippocampal gamma oscillations following respiratory alkalosis in vitro. | 2001 May |
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| A marriage of bacteriology with cell biology results in twin arginines. | 2001 May |
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| Olfactory response to mushroom composting emissions as a function of chemical concentration. | 2001 May-Jun |
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| Methanosarcina lacustris sp. nov., a new psychrotolerant methanogenic archaeon from anoxic lake sediments. | 2001 Nov |
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| A novel denitrifying bacterial isolate that degrades trimethylamine both aerobically and anaerobically via two different pathways. | 2001 Oct |
|
| Preferential binding of polyethylene glycol-coated liposomes containing a novel cationic lipid, TRX-20, to human subendthelial cells via chondroitin sulfate. | 2001 Sep |
|
| Methanofollis aquaemaris sp. nov., a methanogen isolated from an aquaculture fish pond. | 2001 Sep |
|
| Axonal gap junctions between principal neurons: a novel source of network oscillations, and perhaps epileptogenesis. | 2002 |
|
| Sensory, chemical and bacteriological changes during storage of iced squid (Todaropsis eblanae). | 2002 |
|
| Stationary phase effects on the dynamic affinity of low-molecular-mass displacers. | 2002 Apr 19 |
|
| SecA specificity for different signal peptides. | 2002 Apr 30 |
|
| Validation of methyl malondialdehyde as internal standard for malondialdehyde detection by capillary electrophoresis. | 2002 Aug 1 |
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| Chitosan as an edible invisible film for quality preservation of herring and atlantic cod. | 2002 Aug 28 |
|
| Monomeric sarcosine oxidase: evidence for an ionizable group in the E.S complex. | 2002 Aug 6 |
|
| Deodorizing effects of tea catechins on amines and ammonia. | 2002 Feb |
|
| Trimethylamine oxide accumulation in marine animals: relationship to acylglycerol storage. | 2002 Feb |
|
| High-performance liquid chromatographic determination of alpha-amino acids in pharmaceutical dosage forms using aqueous mobile phase containing copper (II) ions. | 2002 Jan-Feb |
|
| Methanobrevibacter acididurans sp. nov., a novel methanogen from a sour anaerobic digester. | 2002 Jul |
|
| Quantitation of trimethyl amine by headspace gas chromatography-mass spectrometry using a base-modified column. | 2002 Jul |
|
| Amino acid decarboxylase activity and other chemical characteristics as related to freshness loss in iced cod (Gadus morhua). | 2002 Jul |
|
| A new conceptual framework for enzyme catalysis. Hydrogen tunnelling coupled to enzyme dynamics in flavoprotein and quinoprotein enzymes. | 2002 Jul |
|
| Volatile N-nitrosamine inhibition after intake Korean green tea and Maesil (Prunus mume SIEB. et ZACC.) extracts with an amine-rich diet in subjects ingesting nitrate. | 2002 Jul |
|
| Computational studies of aliphatic amine basicity. | 2002 Jul 26 |
|
| Measurement of microbial activity in soil by colorimetric observation of in situ dye reduction: an approach to detection of extraterrestrial life. | 2002 Jul 31 |
|
| 1H and (13)C NMR spectroscopic analysis of human saliva. | 2002 Jun |
|
| Oxidative pyrolysis of organic ion exchange resins in the presence of metal oxide catalysts. | 2002 Jun 10 |
|
| Elevated levels of trimethylamine oxide in deep-sea fish: evidence for synthesis and intertissue physiological importance. | 2002 Jun 15 |
|
| Gas-phase analysis of trimethylamine, propionic and butyric acids, and sulfur compounds using solid-phase microextraction. | 2002 Mar 1 |
|
| Low-abundance plasma and urinary [(15)N]urea enrichments analyzed by gas chromatography/combustion/isotope ratio mass spectrometry. | 2002 May |
|
| Human flavin-containing monooxygenase (form 3): polymorphisms and variations in chemical metabolism. | 2002 May |
|
| Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of amphoteric glycolipid analogues from the porcine nematode, Ascaris suum. | 2002 May |
|
| The effect of intensity and duration on the light-induced sodium and potassium currents in the Hermissenda type B photoreceptor. | 2002 May 15 |
|
| Reactions of AlH(3) x NMe(3) with nitriles: structural characterization and substitution reactions of hexameric aluminum imides. | 2002 May 6 |
|
| CaiT of Escherichia coli, a new transporter catalyzing L-carnitine/gamma -butyrobetaine exchange. | 2002 Oct 18 |
|
| Characterization and multiple molecular forms of TorD from Shewanella massilia, the putative chaperone of the molybdoenzyme TorA. | 2002 Sep |
|
| Human trace amine-associated receptor TAAR5 can be activated by trimethylamine. | 2013 |
|
| The complex metabolism of trimethylamine in humans: endogenous and exogenous sources. | 2016 Apr 29 |
|
| Soluble Dietary Fiber Reduces Trimethylamine Metabolism via Gut Microbiota and Co-Regulates Host AMPK Pathways. | 2017 Dec |
|
| Screening gut microbial trimethylamine production by fast and cost-effective capillary electrophoresis. | 2019 May |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:47:01 GMT 2025
by
admin
on
Mon Mar 31 18:47:01 GMT 2025
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| Record UNII |
LHH7G8O305
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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LOINC |
3056-9
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JECFA EVALUATION |
TRIMETHYLAMINE
Created by
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EPA PESTICIDE CODE |
221801
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LOINC |
17748-5
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1146
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LHH7G8O305
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1599
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58389
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C023336
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808
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1999994
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DTXSID2026238
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18139
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m11150
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PRIMARY | Merck Index | ||
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200-875-0
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75-50-3
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Trimethylamine
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Amine from Acorus calamus rhizome.
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (TLC)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
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