Page last updated: 2024-12-05

n,n,n',n'-tetramethylethylenediamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

N,N,N',N'-Tetramethylethylenediamine (TMEDA) is a colorless, hygroscopic liquid with a strong amine odor. It is a bidentate ligand that is commonly used in organic synthesis. TMEDA is synthesized by the reaction of ethylenediamine with formaldehyde and dimethylamine. It is a powerful base and a good nucleophile, and it is used in a variety of reactions, including the alkylation of Grignard reagents, the formation of amides, and the polymerization of alkenes. TMEDA is also used as a catalyst in many organic reactions. It is a versatile reagent that can be used to promote a variety of chemical transformations. TMEDA is a very common ligand in organometallic chemistry, where it is often used to stabilize transition metal complexes. It is also used as a catalyst in a variety of organic reactions. TMEDA is important because it is a very versatile reagent that can be used in a variety of chemical reactions. It is also a relatively safe and easy-to-handle reagent, making it a popular choice for chemists. TMEDA is studied because of its importance in organic synthesis and organometallic chemistry. Its ability to stabilize transition metal complexes and promote a variety of chemical transformations makes it a valuable reagent for research and development.'

N,N,N',N'-tetramethylethylenediamine: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N,N,N',N'-tetramethylethylenediamine : An ethylenediamine derivative in which each nitrogen carries two methyl substituents. It is widely employed both as a ligand for metal ions and as a catalyst in organic polymerisation. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID8037
CHEMBL ID3181913
CHEBI ID32850
SCHEMBL ID15334
MeSH IDM0047562

Synonyms (137)

Synonym
HMS1787N22
[2-(dimethylamino)ethyl]dimethylamine
tmeda
CHEBI:32850 ,
temed
110-18-9
tetramethyldiaminoethane
tmen
ethylenediamine, n,n,n',n'-tetramethyl-
n,n,n',n'-tetramethyl-1,2-ethanediamine
inchi=1/c6h16n2/c1-7(2)5-6-8(3)4/h5-6h2,1-4h
n,n,n',n'-tetramethylethane-1,2-diamine
1,2-ethanediamine, n,n,n',n'-tetramethyl-
n,n,n',n'-tetramethylethylenediamine
tetramethyl ethylene diamine
n,n,n',n'-tetramethyl-1,2-diaminoethane
dimethyl(2-(dimethylamino)ethyl)amine
1,2-bis-(dimethylamino)ethane
einecs 203-744-6
tetrameen
n,n,n',n'-tetramethylethanediamine
hsdb 5396
un2372
propamine d
ccris 4870
1,2-bis(dimethylamino)ethane
ai3-26631
n,n,n',n'-tetramethylethylenediamine, reagentplus(r), 99%
n,n,n',n'-tetramethylethylenediamine, bioreagent, for molecular biology, >=99% (gc)
n,n,n',n'-tetramethylethylenediamine, bioreagent, suitable for electrophoresis, ~99%
n,n,n',n'-tetramethylethylenediamine, >=99.5%, purified by redistillation
T2515
n,n,n',n'-tetramethyl-ethylenediamine
T0147
AKOS000119849
A802159
NCGC00248573-01
tetramethylethylenediamine
1,2-ethanediamine, n1,n1,n2,n2-tetramethyl-
unii-k90jub7941
1,2-di-(dimethylamino)ethane
k90jub7941 ,
1,2-di-(dimethylamino)ethane [un2372] [flammable liquid]
NCGC00257795-01
cas-110-18-9
tox21_200241
dtxsid5026122 ,
dtxcid206122
BBL011565
STL146736
n,n,n,n-tetramethylethylenediamine
tetramethylethylenediamine, n,n,n',n'-
temed [mi]
n,n,n',n'-tetramethyl-1,2-ethanediamine [hsdb]
BP-30082
SCHEMBL15334
dimethyl[2-(dimethylamino)ethyl]amine
(ch3)2nch2ch2n(ch3)2
un 2372
n,n,n1,n1-tetramethylethylenediamine
n,n,n',n'-tetramethylethenediamine
1,2-diaminoethane, n,n,n',n'-tetramethyl-
n,n,n',n'-tetramethyl-ethylendiamin
1,2-bis(dimethyl-amino)ethane
n,n,n',n',-tetramethylethylenediamine
n,n,n',n'-tetramethyletane-1,2-diamine
n,n,n',n'-tetra methyl ethylene diamine
n,n,n',n'-tetra methyl ethylenediamine
n,n,n',n'-tetramethylethylene diamine
n,n, n',n'-tetramethylethylenediamine
n,n,n',n'-tetramethyl ethylene diamine
n,n,n,n,-tetramethylethylenediamine
tetramethylethyenediamine
n,n,n', n'-tetramethylethylenediamine
n,n,n', n'-tetramethylethylene diamine
n,n,n',n'-tetramethyl-ethylene diamine
tetramethylethylendiamine
n,n,n',n'-tetramethyl ethylenediamine
n, n, n', n'-tetramethylethylene diamine
n,n,n', n'-tetramethyl-ethylenediamine
n,n,n,n-tetramethylethylene diamine
n,n,n',n'-tetramethyl ethylendiamine
n,n,n',n'-tetra-methylethylenediamine
n,n,n',n'-tetramethylethylendiamine
n, n, n', n'-tetra-methylethylenediamine
n,n,n',n'-tetramethyl-ethane-1,2-diamine
n, n, n', n'-tetramethylethylenediamine
n,n'-tetramethylethylenediamine
n,n,n',n' tetramethyl-1,2-ethanediamine
n,n, n', n'-tetramethylethylenediamine
tetramethyl ethylenediamine
n1,n1,n2,n2-tetramethylethane-1,2-diamine
n,n,n',n'- tetramethylethylenediamine
1,2-di(dimethylamino) ethane
tetramethylethlenediamine
n,n,n',n' tetramethylethylenediamine
n,n,n',n'-tetramethylethlenediamine
tetramethyl-ethylenediamine
n,n,n',n'-tetramethyl-ethylendiamine
n,n,n',n'tetramethylethylenediamine
n,n,n',n'-tetramethyletylenediamine
n, n, n',n'-tetramethylethylenediamine
n,n,n',n'-tetramethylethylene-diamine
n,n,n2,n2-tetramethylethane-1,2-diamine
n,n,n',n'-tetramethyl-1,2-ethylenediamine
tetramethylethylene-diamine
n1, n1,n2,n2-tetramethylethane-1,2-diamine
tetramethylethylene diamine
n,n,n,n -tetramethylethylene diamine
CHEMBL3181913
n,n,n',n'-tetramethylethylenediamine, electrophoresis grade
mfcd00008335
n,n,n',n'-tetramethylethylenedamne
J-523208
J-002395
n,n,n',n'-tetramethylethylenediamine, purum, >=98.0% (gc)
F0001-0217
n,n,n',n'-tetramethylethylenediamine, >=99.0%
n,n,n',n'-tetramethylethylenediamine, temed, biochemical grade suitable for electrophoresis
n,n,n',n'-tetramethylethylenediamine, 99%
n,n,n',n'-tetramethylethylenediamine, vetec(tm) reagent grade, >=99%
n,n,n`,n`-tetramethylethylenediamine
n,n,n',n'-tetramethylethylenediamine, redistilled
BCP25463
tetramethylethylenediamine temed td n,n,n
n,n,n
VS-02982
temed ultra-pure grade 100ml
n-n-n-n-tetramethylethylenediamine-temed
n,n,n',n'-tetramethylethylenediamine (temed)
n~1~,n~1~,n~2~,n~2~-tetramethylethane-1,2-diamine
9U3 ,
5-bromo-1h-pyrrolo[2,3-d]pyrimidin-4-ylamine
D97674
EN300-16690
pentafluorophenylglycine
Z56755629

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Of all the bioassays to determine acute toxicity described in the literature, those that employ bacteria as indicator organisms are usually the most rapid and the most economic, although alone they cannot predict the possible toxic effect of any type of substance."( A trial to compare the effects of pH, buffer concentration, and NaCl, on one fluorescent and two bioluminescent bacterial tests for acute toxicity.
Carnero, M; Fernández-Crehuet, J; Gómez-Aracena, J; Mariscal, A, 1997
)
0.3
"Recognition of the occupational hazards from exposure to the propellants hydrazine and monomethylhydrazine (MMH) has led to research into less toxic alternatives."( Genotoxicity assessment of two hypergolic energetic propellant compounds.
Johnson, MS; Mecchi, MS; Reddy, G; Song, J, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
chelatorA ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
catalystA substance that increases the rate of a reaction without modifying the overall standard Gibbs energy change in the reaction.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
ethylenediamine derivativeAny organic amino compound that is a derivative of ethylenediamine.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AR proteinHomo sapiens (human)Potency51.18700.000221.22318,912.5098AID1259243; AID1259381; AID743040; AID743042
progesterone receptorHomo sapiens (human)Potency27.19500.000417.946075.1148AID1346784
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency6.89040.000214.376460.0339AID720692
estrogen nuclear receptor alphaHomo sapiens (human)Potency58.33550.000229.305416,493.5996AID1259244; AID743079
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency6.08820.000323.4451159.6830AID743065
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency48.36030.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency48.36030.001551.739315,848.9004AID1259244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (87)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (6.90)18.7374
1990's16 (18.39)18.2507
2000's22 (25.29)29.6817
2010's38 (43.68)24.3611
2020's5 (5.75)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.06

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index30.06 (24.57)
Research Supply Index4.51 (2.92)
Research Growth Index4.90 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.06)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other89 (98.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]