Trimethylamine

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Trimethyl amine
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Trimethylamine[1]
Skeletal formula of trimethylamine with all implicit hydrogens shown
Ball and stick model of trimethylamine
Ball and stick model of trimethylamine
Spacefill model of trimethylamine
Spacefill model of trimethylamine
Names
Preferred IUPAC name
N,N-Dimethylmethanamine
Other names
(Trimethyl)amine (The name trimethylamine is deprecated.)[2]
Identifiers
3D model (
JSmol
)
3DMet
956566
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.000.796 Edit this at Wikidata
EC Number
  • 200-875-0
KEGG
RTECS number
  • PA0350000
UNII
UN number 1083
  • InChI=1S/C3H9N/c1-4(2)3/h1-3H3 checkY
    Key: GETQZCLCWQTVFV-UHFFFAOYSA-N checkY
  • CN(C)C
Properties
C3H9N
Molar mass 59.112 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)[3]
95 μmol Pa−1 kg−1
Basicity (pKb) 4.19
0.612 D
Thermochemistry
Std enthalpy of
formation
(ΔfH⦵298)
 −24.5 to −23.0 kJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
Danger
H220, H315, H318, H332, H335
P210, P261, P280, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
4
0
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)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[4]
REL (Recommended)
 TWA 10 ppm (24 mg/m3) ST 15 ppm (36 mg/m3)[4]
IDLH
(Immediate danger)
 N.D.[4]
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 checkY☒N ?)

Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It is a trimethylated derivative of ammonia. TMA is widely used in industry.[5][6] At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes on contact.[7] At lower concentrations, it has a "fishy" odor, the odor associated with rotting fish.

Physical and chemical properties

TMA is a colorless,

water. It is also sold in pressurized gas cylinders
.

TMA

Lewis acids.[8]

Production

Industry and laboratory

Trimethylamine is prepared by the reaction of ammonia and methanol employing a catalyst:[5]

3 CH3OH + NH3 → (CH3)3N + 3 H2O

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

Trimethylammonium chloride has been prepared by a reaction of ammonium chloride and paraformaldehyde:[9]

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

Biosynthesis

Trimethylamine is produced by several routes in nature. Well studied are the degradation of choline and carnitine.[10]

Applications

Trimethylamine is used in the synthesis of

anion exchange resins, dye leveling agents and a number of basic dyes.[5][6]
Gas sensors to test for fish freshness detect trimethylamine.

Toxicity

In humans, ingestion of certain plant and animal (e.g., red meat, egg yolk) food containing

atherogenic substance which may accelerate atherosclerosis in those eating foods with a high content of TMA precursors.[12] TMA also causes the odor of some human infections, bad breath, and bacterial vaginosis
.

Trimethylamine is a

tertiary amines.[15][16] One or more additional odorant receptors appear to be involved in trimethylamine olfaction in humans as well.[16]

Acute and chronic toxic effects of TMA were suggested in medical literature as early as the 19th century. TMA causes eye and skin irritation, and it is suggested to be a

uremic toxin.[17] In patients, trimethylamine caused stomach ache, vomiting, diarrhoea, lacrimation, greying of the skin and agitation.[18] Apart from that, reproductive/developmental toxicity has been reported.[7] Some experimental studies suggested that TMA may be involved in etiology of cardiovascular diseases.[19][20]

Guidelines with exposure limit for workers are available e.g. the Recommendation from the

Scientific Committee on Occupational Exposure Limits by the European Union Commission.[21]

Trimethylaminuria

Main article: Trimethylaminuria

Trimethylaminuria is an

breath after the consumption of choline-rich foods. 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.[22][23]

In the history of psychoanalysis

The first dream of his own which Sigmund Freud tried to analyse in detail, when he was developing his theories about the interpretation of dreams, involved a patient of Freud's who had to have an injection of trimethylamine, and the chemical formula of the substance, written in bold letters on the bottle, jumping out at Freud.[24]

See also

References

  1. ^ Merck Index, 11th Edition, 9625.
  2. ISBN 978-0-85404-182-4
    .
  3. doi:10.1021/ja01221a508
    .
  4. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0636". National Institute for Occupational Safety and Health (NIOSH).
  5. ^
    ISBN 978-3527306732
    .
  6. ^
    ISBN 978-0-9522674-3-0
    .
  7. ^
    ISBN 978-3527600410
  8. doi:10.1021/ed054p612
    .
  9. doi:10.15227/orgsyn.001.0079
    .
  10. PMID 23151509
    .
  11. ^
    PMID 26274026
    . we review literature on trimethylamine (TMA), a microbiota-generated metabolite linked to atherosclerosis development.
  12. ^
    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.
  13. PMID 23393561
    .
  14. 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)
  15. ^
    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
  16. ^
    PMID 25616211
    .
  17. PMID 7023344
    .
  18. S2CID 221459303
    .
  19. PMID 31504256
    .
  20. PMID 31454905
    .
  21. OCLC 1032584642
    .
  22. doi:10.1002/jsfa.2740300809
    .
  23. doi:10.17221/330-CJAS
    . Retrieved 19 December 2016.
  24. ^ Sigmund Freud, Standard Ed., 4:116-119.

External links

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