*** Welcome to piglix ***

Trimethylamine

Trimethylamine
Skeletal formula of trimethylamine with all implicit hydrogens shown
Ball and stick model of trimethylamine
Spacefill model of trimethylamine
Names
Preferred IUPAC name
N,N-Dimethylmethanamine
Other names
(Trimethyl)amine
(The name trimethylamine is deprecated.)
Identifiers
3D model (Jmol)
3DMet B00133
956566
ChEBI
ChemSpider
ECHA InfoCard 100.000.796
EC Number 200-875-0
KEGG
PubChem CID
RTECS number PA0350000
UNII
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)
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):
LD50 (median dose)
 500 mg kg−1(oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
 none
REL (Recommended)
 TWA 10 ppm (24 mg/m3) ST 15 ppm (36 mg/m3)
IDLH (Immediate danger)
 N.D.
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  (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. High levels of trimethylamine are associated with the development of fish odor syndrome, which arise from the foul, fishy odor of trimethylamine. 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.


...
Wikipedia

...