Chemical compound responsible for rotten fish odor
Trimethylamine[1]
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.)[2]
Identifiers
CAS Number
75-50-3Y
3D model (JSmol)
Interactive image
3DMet
B00133
Beilstein Reference
956566
ChEBI
CHEBI:18139Y
ChEMBL
ChEMBL439723Y
ChemSpider
1114Y
ECHA InfoCard
100.000.796
EC Number
200-875-0
KEGG
C00565N
PubChem CID
1146
RTECS number
PA0350000
UNII
LHH7G8O305Y
UN number
1083
CompTox Dashboard (EPA)
DTXSID2026238
InChI
InChI=1S/C3H9N/c1-4(2)3/h1-3H3Y
Key: GETQZCLCWQTVFV-UHFFFAOYSA-NY
SMILES
CN(C)C
Properties
Chemical formula
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
Solubility in water
Miscible
log P
0.119
Vapor pressure
188.7 kPa (at 20 °C)[3]
Henry's law constant (kH)
95 μmol Pa−1 kg−1
Basicity (pKb)
4.19
Dipole moment
0.612 D
Thermochemistry
Std enthalpy of formation (ΔfH⦵298)
−24.5 to −23.0 kJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word
Danger
Hazard statements
H220, H315, H318, H332, H335
Precautionary statements
P210, P261, P280, P305+P351+P338
NFPA 704 (fire diamond)
2
4
0
Flash point
−7 °C (19 °F; 266 K)
Autoignition temperature
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)
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
Dimethylamine
N-Nitrosodimethylamine
Diethylamine
Triethylamine
Diisopropylamine
Dimethylaminopropylamine
Diethylenetriamine
N,N-Diisopropylethylamine
Triisopropylamine
Tris(2-aminoethyl)amine
Mechlorethamine
HN1 (nitrogen mustard)
HN3 (nitrogen mustard)
Related compounds
Unsymmetrical dimethylhydrazine
Biguanide
Dithiobiuret
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound
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.
^Merck Index, 11th Edition, 9625.
^IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-62.2.2.1". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.
^Swift, Elijah; Hochanadel, Helen Phillips (May 1945). "The Vapor Pressure of Trimethylamine from 0 to 40°". Journal of the American Chemical Society. 67 (5): 880–881. doi:10.1021/ja01221a508.
^ abcNIOSH Pocket Guide to Chemical Hazards. "#0636". National Institute for Occupational Safety and Health (NIOSH).
^Cite error: The named reference Ullmann was invoked but never defined (see the help page).
^Ashford, Robert D. (2011). Ashford's Dictionary of Industrial Chemicals (3rd ed.). Wavelength. p. 9362. ISBN 978-0-9522674-3-0.
^"Trimethylamine [MAK Value Documentation, 1983]", The MAK-Collection for Occupational Health and Safety, Wiley-VCH Verlag GmbH & Co. KGaA, 27 October 2014, pp. 1–9, doi:10.1002/3527600418.mb7550e0914, ISBN 978-3527600410
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. At higher...
convert the fishy-smelling chemical trimethylamine (TMA) from precursor compounds in food digestion into trimethylamine oxide (TMAO), through a process called...
at depth, it has 3 kinds of hemoglobin and a high concentration of trimethylamine N-oxide in its tissues to increase buoyancy. This causes the meat to...
urea and trimethylamine oxide (nitrogenous waste products) in their tissues as osmoprotectants and to increase their buoyancy. Trimethylamine oxide also...
methanol in the presence of an aluminosilicate catalyst. Dimethylamine and trimethylamine are co-produced; the reaction kinetics and reactant ratios determine...
attraction to trimethylamine in mice and aversion to trimethylamine in rats). In humans, hTAAR5 presumably mediates aversion to trimethylamine, which is known...
In enzymology, a trimethylamine dehydrogenase (EC 1.5.8.2) is an enzyme that catalyzes the chemical reaction trimethylamine + H2O + electron-transferring...
acid). Choline bitartrate can be produced by the chemical reaction of trimethylamine with ethylene oxide and water, followed by reaction with tartaric acid...
often encountered as a colorless viscous hydrated syrup that smells of trimethylamine (TMA). Aqueous solutions of choline are stable, but the compound slowly...
is an enzyme that catalyzes the chemical reaction acetyl phosphate + trimethylamine + thioredoxin disulfide ⇌ {\displaystyle \rightleftharpoons } N,N,N-trimethylglycine...
top of the shark, allowing poisonous internal fluids, like urea and trimethylamine oxide, to be pressed and drained out of the body. The meat is then cured...
also associated with liver failure, and it has been suggested that trimethylamine is also a contributor to the odor of fetor hepaticus. Fetor Van den...
hydrogen chloride, and trimethylamine, or from the pre-formed salt: Choline chloride can also be made by treating trimethylamine with 2-chloroethanol....
alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines...
propanoic, 2-methylpropanoic, butanoic, and 3-methylbutanoic acids; and trimethylamine, and 2-piperidone. They often use these techniques to escape when ensnared...
ammonium CH3-NH+ 2-CH3 is 10.73, a value above methylamine (10.64) and trimethylamine (9.79). Dimethylamine reacts with acids to form salts, such as dimethylamine...
by the reaction of acetylene with trimethylamine. Neurine is unstable and decomposes readily to form trimethylamine. Gardner, C.; Kerrigan, V.; Rose,...
environments because of the high concentration of urea (up to 2.5%) and trimethylamine N-oxide (TMAO), allowing them to be in osmotic balance with the seawater...
attraction to trimethylamine in mice and aversion to trimethylamine in rats. In humans, hTAAR5 presumably mediates aversion to trimethylamine, which is known...
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