TRIMETHYLAMINE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27126549 | https://www.ncbi.nlm.nih.gov/pubmed/27573063

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

Primary Target	Pharmacology	Condition	Potency
Trace amine-associated receptor 5 4 Target ID: O14804 Gene ID: 9038.0 Gene Symbol: TAAR5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23393561	Agonist 2662

PubMed

Title	Date	PubMed
Characterization of sodiated glycerol phosphatidylcholine phospholipids by mass spectrometry.	2001	11344540
Research of quality indices for cold-smoked salmon using a stepwise multiple regression of microbiological counts and physico-chemical parameters.	2001 Apr	11309070
Syntheses of the first amine-dicarboxyboranes and their bis(methylester) and bis(N-ethylamide) derivatives.	2001 Apr 9	11312731
Effect of acute exposure to ammonia on glutamate transport in glial cells isolated from the salamander retina.	2001 Aug	11495954
Coupled electron/proton transfer in complex flavoproteins: solvent kinetic isotope effect studies of electron transfer in xanthine oxidase and trimethylamine dehydrogenase.	2001 Aug 17	11395485
Exploring the recognized bio-mimicry materials for gas sensing.	2001 Dec	11679274
Freud's struggle with misogyny: homosexuality and guilt in the dream of Irma's injection.	2001 Fall	11809024
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	11258758
Synthesis and chain length-anti-HIV activity relationship of fully N- and O-sulfated homooligomers of tyrosine.	2001 Feb	11249140
The effects of intracellular pH changes on resting cytosolic calcium in voltage-clamped snail neurones.	2001 Feb 1	11158272
Export of active green fluorescent protein to the periplasm by the twin-arginine translocase (Tat) pathway in Escherichia coli.	2001 Jan	11123687
Formation of biogenic amines in bulk-stored chilled hake (Merluccius merluccius L.) packed under atmospheres.	2001 Jul	11456190
Reversible carnitine palmitoyltransferase inhibitors with broad chemical diversity as potential antidiabetic agents.	2001 Jul 19	11448219
The palmitoyl groups of lung surfactant protein C reduce unfolding into a fibrillogenic intermediate.	2001 Jul 20	11453699
Inactivation of C30A trimethylamine dehydrogenase by N-cyclopropyl-alpha-methylbenzylamine, 1-phenylcyclopropylamine, and phenylhydrazine.	2001 Jul 24	11456490
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	11304539
pH regulation and buffering power in gastric smooth muscle.	2001 Jun	11484779
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	11389150
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	11285259
Novel aluminum hydride derivatives from the reaction of H(3)Al.NMe(3) with the cyclosilazanes.	2001 Mar 12	11300835
Growth and metabolic activity of Shewanella putrefaciens maintained under different CO2 and O2 concentrations.	2001 Mar 20	11294349
On-line sample concentration in micellar electrokinetic chromatography using cationic surfactants.	2001 May 4	11382284
Olfactory response to mushroom composting emissions as a function of chemical concentration.	2001 May-Jun	11401265
Methanosarcina lacustris sp. nov., a new psychrotolerant methanogenic archaeon from anoxic lake sediments.	2001 Nov	11822671
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	11551212
The amber codon in the gene encoding the monomethylamine methyltransferase isolated from Methanosarcina barkeri is translated as a sense codon.	2001 Sep 7	11435424
Protein dynamics enhance electronic coupling in electron transfer complexes.	2001 Sep 7	11429403
Axonal gap junctions between principal neurons: a novel source of network oscillations, and perhaps epileptogenesis.	2002	12013024
Trimethylamine oxide accumulation in marine animals: relationship to acylglycerol storage.	2002 Feb	11854367
High-performance liquid chromatographic determination of alpha-amino acids in pharmaceutical dosage forms using aqueous mobile phase containing copper (II) ions.	2002 Jan-Feb	12064059
Amino acid decarboxylase activity and other chemical characteristics as related to freshness loss in iced cod (Gadus morhua).	2002 Jul	12117250
A new conceptual framework for enzyme catalysis. Hydrogen tunnelling coupled to enzyme dynamics in flavoprotein and quinoprotein enzymes.	2002 Jul	12084049
1H and (13)C NMR spectroscopic analysis of human saliva.	2002 Jun	12097436
Analysis of spontaneous mRNA cytokine production in peripheral blood.	2002 Mar 1	11861077
Essential cytoplasmic domains in the Escherichia coli TatC protein.	2002 Mar 22	11781311
Electron transfer and conformational change in complexes of trimethylamine dehydrogenase and electron transferring flavoprotein.	2002 Mar 8	11756429
Human flavin-containing monooxygenase (form 3): polymorphisms and variations in chemical metabolism.	2002 May	12052141
The effect of intensity and duration on the light-induced sodium and potassium currents in the Hermissenda type B photoreceptor.	2002 May 15	12019339
Human trace amine-associated receptor TAAR5 can be activated by trimethylamine.	2013	23393561
The complex metabolism of trimethylamine in humans: endogenous and exogenous sources.	2016 Apr 29	27126549
Soluble Dietary Fiber Reduces Trimethylamine Metabolism via Gut Microbiota and Co-Regulates Host AMPK Pathways.	2017 Dec	28884952
Screening gut microbial trimethylamine production by fast and cost-effective capillary electrophoresis.	2019 May	30859269

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

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Name

Type

Language

TRIMETHYLAMINE

Systematic Name

English

ACETYLCHOLINE CHLORIDE IMPURITY C [EP IMPURITY]

Common Name

English

TRIMETHYLAMINE [FCC]

Common Name

English

TRIMETHYLAMINUM

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