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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
Structure of Trimethylamine

SMILES

CN(C)C

InChI

InChIKey=GETQZCLCWQTVFV-UHFFFAOYSA-N
InChI=1S/C3H9N/c1-4(2)3/h1-3H3

HIDE SMILES / InChI

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O14804
Gene ID: 9038.0
Gene Symbol: TAAR5
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Prolonged epileptiform bursting induced by 0-Mg(2+) in rat hippocampal slices depends on gap junctional coupling.
2001
Characterization of sodiated glycerol phosphatidylcholine phospholipids by mass spectrometry.
2001
Effect of acute exposure to ammonia on glutamate transport in glial cells isolated from the salamander retina.
2001 Aug
Formation of aerosol particles from reactions of secondary and tertiary alkylamines: characterization by aerosol time-of-flight mass spectrometry.
2001 Aug 1
Exploring the recognized bio-mimicry materials for gas sensing.
2001 Dec
Cloning, sequencing, tissue distribution, and heterologous expression of rat flavin-containing monooxygenase 3.
2001 Jul 1
Detection of the mutated K-Ras biomarker in colorectal carcinoma.
2001 Jun
Characterization of Methanococcus voltaei strain P2F9701a: a new methanogen isolated from estuarine environment.
2001 Jun
Altering intracellular pH disrupts development and cellular organization in preimplantation hamster embryos.
2001 Jun
The relationship between the interfacial properties of surfactants and their toxicity to aquatic organisms.
2001 Mar 1
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
Enhanced temporal stability of cholinergic hippocampal gamma oscillations following respiratory alkalosis in vitro.
2001 May
A marriage of bacteriology with cell biology results in twin arginines.
2001 May
Olfactory response to mushroom composting emissions as a function of chemical concentration.
2001 May-Jun
Methanosarcina lacustris sp. nov., a new psychrotolerant methanogenic archaeon from anoxic lake sediments.
2001 Nov
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
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 Mon Mar 31 18:47:01 GMT 2025
Edited
by admin
on Mon Mar 31 18:47:01 GMT 2025
Record UNII
LHH7G8O305
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIMETHYLAMINUM
HPUS  
Preferred Name English
Trimethylamine
FCC   FHFI   HSDB   MI  
Systematic Name English
ACETYLCHOLINE CHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
TRIMETHYLAMINE [FCC]
Common Name English
METHANAMINE, N,N-DIMETHYL-
Systematic Name English
FEMA NO. 3241
Code English
TRIMETHYLAMINE [FHFI]
Common Name English
MELDONIUM DIHYDRATE IMPURITY A [EP IMPURITY]
Common Name English
TRIMETHYLAMINE [HSDB]
Common Name English
TRIMETHYLAMINE [MI]
Common Name English
TRIMETHYLAMINUM [HPUS]
Common Name English
N,N-DIMETHYLMETHANAMINE
Systematic Name English
Classification Tree Code System Code
LOINC 3056-9
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
JECFA EVALUATION TRIMETHYLAMINE
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
EPA PESTICIDE CODE 221801
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
LOINC 17748-5
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
Code System Code Type Description
PUBCHEM
1146
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
FDA UNII
LHH7G8O305
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
JECFA MONOGRAPH
1599
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
CHEBI
58389
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
MESH
C023336
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
HSDB
808
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
RXCUI
1999994
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
EPA CompTox
DTXSID2026238
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
CHEBI
18139
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
MERCK INDEX
m11150
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
200-875-0
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
CAS
75-50-3
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
WIKIPEDIA
Trimethylamine
Created by admin on Mon Mar 31 18:47:01 GMT 2025 , Edited by admin on Mon Mar 31 18:47:01 GMT 2025
PRIMARY
Related Record Type Details
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PARENT -> IMPURITY
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