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 2678

PubMed

Title	Date	PubMed
Prolonged epileptiform bursting induced by 0-Mg(2+) in rat hippocampal slices depends on gap junctional coupling.	2001	11516825
Characterization of sodiated glycerol phosphatidylcholine phospholipids by mass spectrometry.	2001	11344540
Identification of a twin-arginine leader-binding protein.	2001 Apr	11309116
Syntheses of the first amine-dicarboxyboranes and their bis(methylester) and bis(N-ethylamide) derivatives.	2001 Apr 9	11312731
Early detection and population monitoring of Ceratitis capitata (Diptera: Tephritidae) in a mixed-fruit orchard in northern Greece.	2001 Aug	11561860
Influence of acetate and CO2 on the TMAO-reduction reaction by Shewanella baltica.	2001 Aug 15	11545211
Population distribution of human flavin-containing monooxygenase form 3: gene polymorphisms.	2001 Dec	11717182
Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes.	2001 Dec	11714893
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
In vivo variability of TMA oxidation is partially mediated by polymorphisms of the FMO3 gene.	2001 Jul	11461189
Formation of biogenic amines in bulk-stored chilled hake (Merluccius merluccius L.) packed under atmospheres.	2001 Jul	11456190
Inactivation of C30A trimethylamine dehydrogenase by N-cyclopropyl-alpha-methylbenzylamine, 1-phenylcyclopropylamine, and phenylhydrazine.	2001 Jul 24	11456490
pH regulation and buffering power in gastric smooth muscle.	2001 Jun	11484779
Characterization of Methanococcus voltaei strain P2F9701a: a new methanogen isolated from estuarine environment.	2001 Jun	11381337
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
A novel deletion in the flavin-containing monooxygenase gene (FMO3) in a Greek patient with trimethylaminuria.	2001 Mar	11266081
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	11368607
Olfactory response to mushroom composting emissions as a function of chemical concentration.	2001 May-Jun	11401265
Quantitative assessment of primary skin irritants in vitro in a cytotoxicity model: comparison with in vivo human irritation tests.	2001 Nov	11736893
Synthetic studies on glycosphingolipids from Protostomia phyla: synthesis of amphoteric glycolipid analogues containing a phosphocholine residue from the earthworm Pheretima hilgendorfi.	2001 Nov	11724239
Optimizing the Michaelis complex of trimethylamine dehydrogenase: identification of interactions that perturb the ionization of substrate and facilitate catalysis with trimethylamine base.	2001 Nov 16	11553643
Chlorination of guanosine and other nucleosides by hypochlorous acid and myeloperoxidase of activated human neutrophils. Catalysis by nicotine and trimethylamine.	2001 Nov 2	11533049
Silicon surfaces as electron acceptors: dative bonding of amines with Si(001) and Si(111) surfaces.	2001 Nov 7	11686703
alpha,beta-poly(asparthylhydrazide)-glycidyltrimethylammonium chloride copolymers (PAHy-GTA): novel polymers with potential for DNA delivery.	2001 Nov 9	11689267
Human neutrophil membrane fluidity after exposure to structurally different lipid emulsions.	2001 Nov-Dec	11688941
Pharmacokinetics of trimethylamine in rats, including the effects of a synthetic diet.	2001 Oct	11695853
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
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
Proton transfer reactions on semiconductor surfaces.	2002 Apr 17	11942841
Stationary phase effects on the dynamic affinity of low-molecular-mass displacers.	2002 Apr 19	12058897
Validation of methyl malondialdehyde as internal standard for malondialdehyde detection by capillary electrophoresis.	2002 Aug 1	12137784
Chitosan as an edible invisible film for quality preservation of herring and atlantic cod.	2002 Aug 28	12188625
Deodorizing effects of tea catechins on amines and ammonia.	2002 Feb	11999411
Cloning, sequencing, and tissue-dependent expression of flavin-containing monooxygenase (FMO) 1 and FMO3 in the dog.	2002 Feb	11792679
Combined ab initio/empirical approach for optimization of Lennard-Jones parameters for polar-neutral compounds.	2002 Jan 30	11924734
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
Quantitation of trimethyl amine by headspace gas chromatography-mass spectrometry using a base-modified column.	2002 Jul	12137206
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	12065217
Computational studies of aliphatic amine basicity.	2002 Jul 26	12126393
1H and (13)C NMR spectroscopic analysis of human saliva.	2002 Jun	12097436
Oxidative pyrolysis of organic ion exchange resins in the presence of metal oxide catalysts.	2002 Jun 10	12031614
Gas-phase analysis of trimethylamine, propionic and butyric acids, and sulfur compounds using solid-phase microextraction.	2002 Mar 1	11924963
Sensory, chemical and bacteriological changes in vacuum-packed pressurised squid mantle (Todaropsis eblanae) stored at 4 degrees C.	2002 Mar 25	11929163
Electron transfer and conformational change in complexes of trimethylamine dehydrogenase and electron transferring flavoprotein.	2002 Mar 8	11756429
The effect of intensity and duration on the light-induced sodium and potassium currents in the Hermissenda type B photoreceptor.	2002 May 15	12019339
Reactions of AlH(3) x NMe(3) with nitriles: structural characterization and substitution reactions of hexameric aluminum imides.	2002 May 6	11978101
CaiT of Escherichia coli, a new transporter catalyzing L-carnitine/gamma -butyrobetaine exchange.	2002 Oct 18	12163501
Characterization and multiple molecular forms of TorD from Shewanella massilia, the putative chaperone of the molybdoenzyme TorA.	2002 Sep	12192070

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:28:13 GMT 2023` Edited by `admin` on `Fri Dec 15 17:28:13 GMT 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