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

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
Characterization of sodiated glycerol phosphatidylcholine phospholipids by mass spectrometry.
2001
Research of quality indices for cold-smoked salmon using a stepwise multiple regression of microbiological counts and physico-chemical parameters.
2001 Apr
Syntheses of the first amine-dicarboxyboranes and their bis(methylester) and bis(N-ethylamide) derivatives.
2001 Apr 9
Effect of acute exposure to ammonia on glutamate transport in glial cells isolated from the salamander retina.
2001 Aug
Coupled electron/proton transfer in complex flavoproteins: solvent kinetic isotope effect studies of electron transfer in xanthine oxidase and trimethylamine dehydrogenase.
2001 Aug 17
Exploring the recognized bio-mimicry materials for gas sensing.
2001 Dec
Freud's struggle with misogyny: homosexuality and guilt in the dream of Irma's injection.
2001 Fall
Capillary zone electrophoretic chiral discrimination using a cationic cyclodextrin derivative: determination of velocity and association constants of each enantiomer of the amino acid derivative with 6-trimethylammonio-deoxy-beta-cyclodextrin.
2001 Feb
Synthesis and chain length-anti-HIV activity relationship of fully N- and O-sulfated homooligomers of tyrosine.
2001 Feb
The effects of intracellular pH changes on resting cytosolic calcium in voltage-clamped snail neurones.
2001 Feb 1
Export of active green fluorescent protein to the periplasm by the twin-arginine translocase (Tat) pathway in Escherichia coli.
2001 Jan
Formation of biogenic amines in bulk-stored chilled hake (Merluccius merluccius L.) packed under atmospheres.
2001 Jul
Reversible carnitine palmitoyltransferase inhibitors with broad chemical diversity as potential antidiabetic agents.
2001 Jul 19
The palmitoyl groups of lung surfactant protein C reduce unfolding into a fibrillogenic intermediate.
2001 Jul 20
Inactivation of C30A trimethylamine dehydrogenase by N-cyclopropyl-alpha-methylbenzylamine, 1-phenylcyclopropylamine, and phenylhydrazine.
2001 Jul 24
Deuterium isotope effects during carbon-hydrogen bond cleavage by trimethylamine dehydrogenase. Implications for mechanism and vibrationally assisted hydrogen tunneling in wild-type and mutant enzymes.
2001 Jul 6
pH regulation and buffering power in gastric smooth muscle.
2001 Jun
Investigation of Escherichia coli dimethyl sulfoxide reductase assembly and processing in strains defective for the sec-independent protein translocation system membrane targeting and translocation.
2001 Jun 8
alpha Arg-237 in Methylophilus methylotrophus (sp. W3A1) electron-transferring flavoprotein affords approximately 200-millivolt stabilization of the FAD anionic semiquinone and a kinetic block on full reduction to the dihydroquinone.
2001 Jun 8
Novel aluminum hydride derivatives from the reaction of H(3)Al.NMe(3) with the cyclosilazanes.
2001 Mar 12
Growth and metabolic activity of Shewanella putrefaciens maintained under different CO2 and O2 concentrations.
2001 Mar 20
On-line sample concentration in micellar electrokinetic chromatography using cationic surfactants.
2001 May 4
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
Involvement of coenzyme A esters and two new enzymes, an enoyl-CoA hydratase and a CoA-transferase, in the hydration of crotonobetaine to L-carnitine by Escherichia coli.
2001 Sep 18
The amber codon in the gene encoding the monomethylamine methyltransferase isolated from Methanosarcina barkeri is translated as a sense codon.
2001 Sep 7
Protein dynamics enhance electronic coupling in electron transfer complexes.
2001 Sep 7
Axonal gap junctions between principal neurons: a novel source of network oscillations, and perhaps epileptogenesis.
2002
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
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
1H and (13)C NMR spectroscopic analysis of human saliva.
2002 Jun
Analysis of spontaneous mRNA cytokine production in peripheral blood.
2002 Mar 1
Essential cytoplasmic domains in the Escherichia coli TatC protein.
2002 Mar 22
Electron transfer and conformational change in complexes of trimethylamine dehydrogenase and electron transferring flavoprotein.
2002 Mar 8
Human flavin-containing monooxygenase (form 3): polymorphisms and variations in chemical metabolism.
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
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 Thu Jul 06 00:47:53 UTC 2023
Edited
by admin
on Thu Jul 06 00:47:53 UTC 2023
Record UNII
LHH7G8O305
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIMETHYLAMINE
FCC   FHFI   HSDB   MI  
Systematic Name English
ACETYLCHOLINE CHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
TRIMETHYLAMINE [FCC]
Common Name English
TRIMETHYLAMINUM
HPUS  
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 Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
JECFA EVALUATION TRIMETHYLAMINE
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
EPA PESTICIDE CODE 221801
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
LOINC 17748-5
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
Code System Code Type Description
PUBCHEM
1146
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
FDA UNII
LHH7G8O305
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
CHEBI
58389
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
MESH
C023336
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
HSDB
808
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
RXCUI
1999994
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID2026238
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
CHEBI
18139
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
MERCK INDEX
M11150
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
200-875-0
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
CAS
75-50-3
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
WIKIPEDIA
Trimethylamine
Created by admin on Thu Jul 06 00:47:53 UTC 2023 , Edited by admin on Thu Jul 06 00:47:53 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Amine from Acorus calamus rhizome.
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY