Trimethylamine

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Trimethylamine[1]
Skeletal formula of trimethylamine with all implicit hydrogens shown
Ball and stick model of trimethylamine
Spacefill model of trimethylamine
Identifiers
75-50-3 YesY
3DMet B00133
956566
ChEBI CHEBI:18139 YesY
ChEMBL ChEMBL439723 YesY
ChemSpider 1114 YesY
EC Number 200-875-0
Jmol 3D model Interactive image
KEGG C00565 N
PubChem 1146
RTECS number PA0350000
UNII LHH7G8O305 YesY
UN number 1083
Properties
C3H9N
Molar mass 59.11 g·mol−1
Appearance Colorless gas
Odor Fishy, ammoniacal
Density 670 kg m−3 (at 0 °C)
627.0 kg m−3 (at 25 °C)
Melting point −117.20 °C; −178.96 °F; 155.95 K
Boiling point 3 to 7 °C; 37 to 44 °F; 276 to 280 K
Miscible
log P 0.119
Vapor pressure 188.7 kPa (at 20 °C) [2]
95 μmol Pa−1 kg−1
Basicity (pKb) 4.19
Thermochemistry
−24.5 to −23.0 kJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H220, H315, H318, H332, H335
P210, P261, P280, P305+351+338
Extremely Flammable F+ Harmful Xn
R-phrases R12, R20, R37/38, R41
S-phrases (S2), S16, S26, S29
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −7 °C (19 °F; 266 K)
190 °C (374 °F; 463 K)
Explosive limits 2–11.6%
Lethal dose or concentration (LD, LC):
500 mg kg−1 (oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
none[3]
REL (Recommended)
TWA 10 ppm (24 mg/m3) ST 15 ppm (36 mg/m3)[3]
IDLH (Immediate danger)
N.D.[3]
Related compounds
Related amines
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. This colorless, hygroscopic, and flammable tertiary amine has a strong "fishy" odor in low concentrations and an ammonia-like odor at higher concentrations. It is a gas at room temperature but is usually sold in pressurized gas cylinders or as a 40% solution in water. TMA is a nitrogenous base and can be readily protonated to give trimethylammonium cation. Trimethylammonium chloride is a hygroscopic colorless solid prepared from hydrochloric acid. Trimethylamine is a good nucleophile, and this reaction is the basis of most of its applications.

Trimethylamine is a product of decomposition of plants and animals. In humans, it is synthesized exclusively by gut microbiota from dietary nutrients such as choline and carnitine.[4][5] High levels of trimethylamine are associated with the development of fish odor syndrome and atherosclerosis, which arise from the foul, fishy odor of trimethylamine and the proatherogenic property of its metabolite, trimethylamine N-oxide, respectively.[4][5] TMA is the substance mainly responsible for the odor often associated with rotting fish, some infections, bad breath and can be a cause of vaginal odor due to bacterial vaginosis. It is also associated with taking large doses of choline and carnitine.

In 2013, trimethylamine was identified as a potent full agonist of human TAAR5,[6][7][8] a trace amine-associated receptor that is expressed in the olfactory epithelium and functions as an olfactory receptor for tertiary amines.[8][9] One or more additional odorant receptors appear to be involved in trimethylamine olfaction in humans as well.[9]

Production[edit]

Trimethylamine is prepared by the reaction of ammonia and methanol employing a catalyst:[10]

3 CH3OH + NH3 → (CH3)3N + 3 H2O

This reaction coproduces the other methylamines, dimethylamine (CH3)2NH and methylamine CH3NH2.

Trimethylamine has also been prepared via a reaction of ammonium chloride and paraformaldehyde,[11] according to the following equation:

9 (CH2=O)n + 2n NH4Cl → 2n (CH3)3N•HCl + 3n H2O + 3n CO2

Applications[edit]

Trimethylamine is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators or herbicides, strongly basic anion exchange resins, dye leveling agents and a number of basic dyes.[10][12] Gas sensors to test for fish freshness detect trimethylamine.

Trimethylaminuria[edit]

Main article: Trimethylaminuria

Trimethylaminuria is a genetic disorder in which the body is unable to metabolize trimethylamine from food sources. Patients develop a characteristic fish odour of their sweat, urine, and breath after the consumption of choline-rich foods. Trimethylaminuria is an autosomal recessive disorder involving a trimethylamine oxidase deficiency. A condition similar to trimethylaminuria has also been observed in a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell, especially after eating food containing a high proportion of rapeseed.[citation needed]

See also[edit]

References[edit]

  1. ^ Merck Index, 11th Edition, 9625.
  2. ^ The Vapor Pressure of Trimethylamine from 0 to 40° (http://pubs.acs.org/doi/abs/10.1021/ja01221a508)
  3. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0636". National Institute for Occupational Safety and Health (NIOSH). 
  4. ^ a b Falony G, Vieira-Silva S, Raes J (2015). "Microbiology Meets Big Data: The Case of Gut Microbiota-Derived Trimethylamine". Annu. Rev. Microbiol. 69: 305–321. doi:10.1146/annurev-micro-091014-104422. PMID 26274026. we review literature on trimethylamine (TMA), a microbiota-generated metabolite linked to atherosclerosis development. 
  5. ^ a b Gaci N, Borrel G, Tottey W, O'Toole PW, Brugère JF (November 2014). "Archaea and the human gut: new beginning of an old story". World J. Gastroenterol. 20 (43): 16062–16078. doi:10.3748/wjg.v20.i43.16062. PMC 4239492. PMID 25473158. Trimethylamine is exclusively a microbiota-derived product of nutrients (lecithin, choline, TMAO, L-carnitine) from normal diet, from which seems originate two diseases, trimethylaminuria (or Fish-Odor Syndrome) and cardiovascular disease through the proatherogenic property of its oxidized liver-derived form. 
  6. ^ Wallrabenstein I, Kuklan J, Weber L, Zborala S, Werner M, Altmüller J, Becker C, Schmidt A, Hatt H, Hummel T, Gisselmann G (2013). "Human trace amine-associated receptor TAAR5 can be activated by trimethylamine". PLoS ONE 8 (2): e54950. doi:10.1371/journal.pone.0054950. PMC 3564852. PMID 23393561. 
  7. ^ Zhang J, Pacifico R, Cawley D, Feinstein P, Bozza T (February 2013). "Ultrasensitive detection of amines by a trace amine-associated receptor". J. Neurosci. 33 (7): 3228–39. doi:10.1523/JNEUROSCI.4299-12.2013. PMC 3711460. PMID 23407976. We show that [human TAAR5] responds to the tertiary amine N,N-dimethylethylamine and to a lesser extent to trimethylamine, a structurally related agonist for mouse and rat TAAR5 (Liberles and Buck, 2006; Staubert et al., 2010; Ferrero et al., 2012). 
  8. ^ a b Zhang LS, Davies SS (April 2016). "Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions". Genome Med 8 (1): 46. doi:10.1186/s13073-016-0296-x. PMC 4840492. PMID 27102537. 
    Table 2: Microbial metabolites: their synthesis, mechanisms of action, and effects on health and disease
    Figure 1: Molecular mechanisms of action of indole and its metabolites on host physiology and disease
  9. ^ a b Liberles SD (October 2015). "Trace amine-associated receptors: ligands, neural circuits, and behaviors". Curr. Opin. Neurobiol. 34: 1–7. doi:10.1016/j.conb.2015.01.001. PMID 25616211. 
  10. ^ a b A. B. van Gysel, W. Musin "Methylamines" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. doi:10.1002/14356007.a16_535
  11. ^ Roger Adams, B. K. Brown. "Trimethylamine". Org. Synth. ; Coll. Vol. 1, p. 75 
  12. ^ Ashford's Dictionary of Industrial Chemicals (3rd ed.). 2011. p. 9362. ISBN 978-0-9522674-3-0. 

External links[edit]