Trimethylamine (ECMDB00906) (M2MDB000200)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:02:02 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 15:15:20 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Trimethylamine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Trimethylamine, also known as NMe3, N(CH3)3, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia-like odor in higher concentrations. Trimethylamine has a boiling point of 2.9 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C3H9N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 59.1103 Monoisotopic: 59.073499293 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | GETQZCLCWQTVFV-UHFFFAOYSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C3H9N/c1-4(2)3/h1-3H3 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 75-50-3 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | trimethylamine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | trimethylamine | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CN(C)C | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic nitrogen compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organonitrogen compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Amines | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Trialkylamines | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Liquid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | -117.1 °C | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Hydrogen ion + Menaquinol 8 + Trimethylamine N-Oxide > Water + Menaquinone 8 + Trimethylamine 2-Demethylmenaquinol 8 + Hydrogen ion + Trimethylamine N-Oxide > 2-Demethylmenaquinone 8 + Water + Trimethylamine a menaquinol + Hydrogen ion + Trimethylamine N-Oxide > a menaquinone + Water + Trimethylamine Trimethylamine N-Oxide + NADH + Hydrogen ion > Trimethylamine + NAD + Water Trimethylamine + 2 (ferricytochrome c)-subunit + Water > Trimethylamine N-Oxide +2 (ferrocytochrome c)-subunit +2 Hydrogen ion Trimethylamine N-Oxide + 3 Hydrogen ion + Menaquinol 8 + 2 Electron > Trimethylamine + Water +2 Hydrogen ion + menaquinone-8 Trimethylamine N-Oxide + NADH + 2 Hydrogen ion > Trimethylamine + NAD + Water | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Hirohata, Saneo; Tanba, Kiyonobu; Inoue, Kenichi. Preparation of trimethylamine by zeolite-catalyzed reaction of methanol and ammonia. Jpn. Kokai Tokkyo Koho (2006), 5pp. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in electron carrier activity
- Specific function:
- Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
- Gene Name:
- ynfG
- Uniprot ID:
- P0AAJ1
- Molecular weight:
- 22752
- General function:
- Involved in dimethyl sulfoxide reductase activity
- Specific function:
- Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. Allows E.coli to grow anaerobically on Me(2)SO as respiratory oxidant
- Gene Name:
- dmsA
- Uniprot ID:
- P18775
- Molecular weight:
- 90398
Reactions
Dimethylsulfide + menaquinone + H(2)O = dimethylsulfoxide + menaquinol. |
- General function:
- Involved in electron carrier activity
- Specific function:
- Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
- Gene Name:
- dmsB
- Uniprot ID:
- P18776
- Molecular weight:
- 22869
- General function:
- Involved in dimethyl sulfoxide reductase activity
- Specific function:
- Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
- Gene Name:
- ynfE
- Uniprot ID:
- P77374
- Molecular weight:
- 89779
- General function:
- Involved in dimethyl sulfoxide reductase activity
- Specific function:
- Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
- Gene Name:
- ynfF
- Uniprot ID:
- P77783
- Molecular weight:
- 89986
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Reduces trimethylamine-N-oxide (TMAO) into trimethylamine; an anaerobic reaction coupled to energy-yielding reactions. Can also reduce other N- and S-oxide compounds such as 4-methylmorpholine-N-oxide and biotin sulfoxide (BSO), but with a lower catalytic efficiency
- Gene Name:
- torZ
- Uniprot ID:
- P46923
- Molecular weight:
- 88964
Reactions
Trimethylamine + 2 (ferricytochrome c)-subunit + H(2)O = trimethylamine N-oxide + 2 (ferrocytochrome c)-subunit + 2 H(+). |
- General function:
- Involved in iron ion binding
- Specific function:
- Part of the anaerobic respiratory chain of trimethylamine-N-oxide reductase torZ. Required for electron transfer to the torZ terminal enzyme
- Gene Name:
- torY
- Uniprot ID:
- P52005
- Molecular weight:
- 40286
- General function:
- Involved in anaerobic electron transport chain
- Specific function:
- Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. DmsC anchors the dmsAB dimer to the membrane and stabilizes it
- Gene Name:
- dmsC
- Uniprot ID:
- P18777
- Molecular weight:
- 30826
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Reduces trimethylamine-N-oxide (TMAO) into trimethylamine; an anaerobic reaction coupled to energy-yielding reactions
- Gene Name:
- torA
- Uniprot ID:
- P33225
- Molecular weight:
- 94455
Reactions
Trimethylamine + 2 (ferricytochrome c)-subunit + H(2)O = trimethylamine N-oxide + 2 (ferrocytochrome c)-subunit + 2 H(+). |
- General function:
- Involved in iron ion binding
- Specific function:
- Part of the anaerobic respiratory chain of trimethylamine-N-oxide reductase torA. Acts by transferring electrons from the membranous menaquinones to torA. This transfer probably involves an electron transfer pathway from menaquinones to the N-terminal domain of torC, then from the N-terminus to the C-terminus, and finally to torA. TorC apocytochrome negatively autoregulates the torCAD operon probably by inhibiting the torS kinase activity
- Gene Name:
- torC
- Uniprot ID:
- P33226
- Molecular weight:
- 43606
- General function:
- Involved in anaerobic electron transport chain
- Specific function:
- Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. The C subunit anchors the other two subunits to the membrane and stabilize the catalytic subunits
- Gene Name:
- ynfH
- Uniprot ID:
- P76173
- Molecular weight:
- 30523
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368