U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C3H9N.ClH
Molecular Weight 95.571
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIMETHYLAMINE HYDROCHLORIDE

SMILES

Cl.CN(C)C

InChI

InChIKey=SZYJELPVAFJOGJ-UHFFFAOYSA-N
InChI=1S/C3H9N.ClH/c1-4(2)3;/h1-3H3;1H

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

Molecular Formula ClH
Molecular Weight 36.461
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
Screening gut microbial trimethylamine production by fast and cost-effective capillary electrophoresis.
2019-05
Soluble Dietary Fiber Reduces Trimethylamine Metabolism via Gut Microbiota and Co-Regulates Host AMPK Pathways.
2017-12
The complex metabolism of trimethylamine in humans: endogenous and exogenous sources.
2016-04-29
Human trace amine-associated receptor TAAR5 can be activated by trimethylamine.
2013
CaiT of Escherichia coli, a new transporter catalyzing L-carnitine/gamma -butyrobetaine exchange.
2002-10-18
Characterization and multiple molecular forms of TorD from Shewanella massilia, the putative chaperone of the molybdoenzyme TorA.
2002-09
Chitosan as an edible invisible film for quality preservation of herring and atlantic cod.
2002-08-28
Monomeric sarcosine oxidase: evidence for an ionizable group in the E.S complex.
2002-08-06
Validation of methyl malondialdehyde as internal standard for malondialdehyde detection by capillary electrophoresis.
2002-08-01
Measurement of microbial activity in soil by colorimetric observation of in situ dye reduction: an approach to detection of extraterrestrial life.
2002-07-31
Computational studies of aliphatic amine basicity.
2002-07-26
Methanobrevibacter acididurans sp. nov., a novel methanogen from a sour anaerobic digester.
2002-07
Quantitation of trimethyl amine by headspace gas chromatography-mass spectrometry using a base-modified column.
2002-07
Amino acid decarboxylase activity and other chemical characteristics as related to freshness loss in iced cod (Gadus morhua).
2002-07
A new conceptual framework for enzyme catalysis. Hydrogen tunnelling coupled to enzyme dynamics in flavoprotein and quinoprotein enzymes.
2002-07
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.
2002-07
High-performance liquid chromatographic determination of alpha-amino acids in pharmaceutical dosage forms using aqueous mobile phase containing copper (II) ions.
2002-06-18
Elevated levels of trimethylamine oxide in deep-sea fish: evidence for synthesis and intertissue physiological importance.
2002-06-15
Oxidative pyrolysis of organic ion exchange resins in the presence of metal oxide catalysts.
2002-06-10
1H and (13)C NMR spectroscopic analysis of human saliva.
2002-06
The effect of intensity and duration on the light-induced sodium and potassium currents in the Hermissenda type B photoreceptor.
2002-05-15
Reactions of AlH(3) x NMe(3) with nitriles: structural characterization and substitution reactions of hexameric aluminum imides.
2002-05-06
Low-abundance plasma and urinary [(15)N]urea enrichments analyzed by gas chromatography/combustion/isotope ratio mass spectrometry.
2002-05
Human flavin-containing monooxygenase (form 3): polymorphisms and variations in chemical metabolism.
2002-05
Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of amphoteric glycolipid analogues from the porcine nematode, Ascaris suum.
2002-05
SecA specificity for different signal peptides.
2002-04-30
Stationary phase effects on the dynamic affinity of low-molecular-mass displacers.
2002-04-19
Proton transfer reactions on semiconductor surfaces.
2002-04-17
Modeling of the biotransformation of crotonobetaine into L-(-)-carnitine by Escherichia coli strains.
2002-03-30
Sensory, chemical and bacteriological changes in vacuum-packed pressurised squid mantle (Todaropsis eblanae) stored at 4 degrees C.
2002-03-25
Essential cytoplasmic domains in the Escherichia coli TatC protein.
2002-03-22
Electron transfer and conformational change in complexes of trimethylamine dehydrogenase and electron transferring flavoprotein.
2002-03-08
Gas-phase analysis of trimethylamine, propionic and butyric acids, and sulfur compounds using solid-phase microextraction.
2002-03-01
Analysis of spontaneous mRNA cytokine production in peripheral blood.
2002-03-01
Monovalent cation permeability and Ca(2+) block of the store-operated Ca(2+) current I(CRAC )in rat basophilic leukemia cells.
2002-03
Deodorizing effects of tea catechins on amines and ammonia.
2002-02
Trimethylamine oxide accumulation in marine animals: relationship to acylglycerol storage.
2002-02
Cloning, sequencing, and tissue-dependent expression of flavin-containing monooxygenase (FMO) 1 and FMO3 in the dog.
2002-02
Combined ab initio/empirical approach for optimization of Lennard-Jones parameters for polar-neutral compounds.
2002-01-30
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
A genetic screen for suppressors of Escherichia coli Tat signal peptide mutations establishes a critical role for the second arginine within the twin-arginine motif.
2001-12
Population distribution of human flavin-containing monooxygenase form 3: gene polymorphisms.
2001-12
Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes.
2001-12
Methanosarcina lacustris sp. nov., a new psychrotolerant methanogenic archaeon from anoxic lake sediments.
2001-11
Quantitative assessment of primary skin irritants in vitro in a cytotoxicity model: comparison with in vivo human irritation tests.
2001-11
Synthetic studies on glycosphingolipids from Protostomia phyla: synthesis of amphoteric glycolipid analogues containing a phosphocholine residue from the earthworm Pheretima hilgendorfi.
2001-11
Pharmacokinetics of trimethylamine in rats, including the effects of a synthetic diet.
2001-10
Sequencing, expression, and characterization of cDNA expressed flavin-containing monooxygenase 2 from mouse.
2001
Freud's struggle with misogyny: homosexuality and guilt in the dream of Irma's injection.
2001
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:47:48 GMT 2025
Edited
by admin
on Mon Mar 31 17:47:48 GMT 2025
Record UNII
UW38SRM77K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HEGZADESIL
Preferred Name English
TRIMETHYLAMINE HYDROCHLORIDE
MI  
Systematic Name English
TRIMETHYLAMINE MONOHYDROCHLORIDE
Systematic Name English
TRIMETHYLAMINE HYDROCHLORIDE [MI]
Common Name English
NSC-91484
Code English
TRIMETHYLAMINE, HYDROCHLORIDE
Systematic Name English
METHANAMINE, N,N-DIMETHYL-, HYDROCHLORIDE
Systematic Name English
TRIMETHYLAMINE HYDROCHLORIC ACID
Systematic Name English
TRIMETHYLAMMONIUM CHLORIDE [HSDB]
Common Name English
METHANAMINE, N,N-DIMETHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
UW38SRM77K
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID5027229
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
NSC
91484
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
RXCUI
1999993
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
ECHA (EC/EINECS)
209-810-0
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
DAILYMED
UW38SRM77K
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
MERCK INDEX
m11150
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY Merck Index
CHEBI
64700
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
HSDB
5710
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
PUBCHEM
11649
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
CAS
593-81-7
Created by admin on Mon Mar 31 17:47:48 GMT 2025 , Edited by admin on Mon Mar 31 17:47:48 GMT 2025
PRIMARY
Related Record Type Details
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