Tetramethylphenylenediamine (TMPD) is an organic compound with the formula C10H16N2. It is a white solid that is soluble in organic solvents. TMPD is a versatile reagent in organic chemistry and has been studied for its use in various applications, including:
* **Dyeing and Textile Industry**: TMPD serves as a dye intermediate and can be used to create colored materials.
* **Antioxidant**: Due to its electron-donating properties, TMPD exhibits antioxidant activity, protecting against free radical damage.
* **Electrochemistry**: TMPD is a well-known redox active compound and is often used as a standard for electrochemical measurements.
* **Organic Synthesis**: It acts as a reagent in various organic reactions, including oxidation and reduction processes.
* **Photochemistry**: TMPD exhibits interesting photochemical properties, making it suitable for use in photocatalytic reactions.
TMPD can be synthesized through a variety of methods, including the following:
* **Reaction of p-phenylenediamine with methyl iodide**: This reaction involves alkylation of the amino groups of p-phenylenediamine with methyl iodide.
* **Reduction of N,N,N',N'-tetramethyl-p-benzoquinone**: This method involves the reduction of the corresponding quinone derivative.
The study of TMPD is important due to its diverse applications in various scientific fields, including organic chemistry, electrochemistry, and materials science.'
1,4-bis(dimethylamino)benzene: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 7490 |
| CHEMBL ID | 1393325 |
| SCHEMBL ID | 65261 |
| MeSH ID | M0021244 |
| Synonym |
|---|
| M710 , |
| (4-dimethylaminophenyl)-dimethyl-amine |
| p-phenylenediamine, n,n,n',n'-tetramethyl- |
| 1,4-benzenediamine, n,n,n',n'-tetramethyl- |
| n,n,n',n'-tetramethyl-p-phenylenediamine |
| 100-22-1 |
| NCGC00091150-01 |
| p-bis(dimethylamino)benzene |
| ccris 4728 |
| n,n,n',n'-tetramethyl-p-fenylendiamin [czech] |
| 1,4-bis(dimethylamino)benzene |
| tl 85 |
| ai3-51106 |
| einecs 202-831-6 |
| n,n,n,n-tetramethyl-1,4-benzenediamine |
| wurster's reagent |
| benzene, 1,4-bis(dimethylamino)- |
| tetramethyl-p-phenylenediamine |
| wurster's blue |
| n,n,n',n'-tetramethylbenzene-1,4-diamine |
| n,n,n',n'-tetramethyl-p-phenylenediamine, 99%, powder |
| 1-n,1-n,4-n,4-n-tetramethylbenzene-1,4-diamine |
| n,n,n',n'-tetramethyl-1,4-phenylenediamine |
| NCGC00091150-03 |
| NCGC00091150-02 |
| p4p3ac32zb , |
| n,n,n',n'-tetramethyl-p-fenylendiamin |
| unii-p4p3ac32zb |
| 1,4-benzenediamine, n1,n1,n4,n4-tetramethyl- |
| NCGC00258171-01 |
| cas-100-22-1 |
| dtxcid006124 |
| dtxsid5026124 , |
| tox21_200617 |
| benzenediamine, n,n,n',n'-tetramethyl- |
| FT-0629354 |
| AKOS015889542 |
| tetramethyl-1,4-phenylenediamine |
| p-bis(dimethylamine)benzene |
| tetramethyl-p-phenylenediamine, n,n,n',n'- |
| n,n,n',n'-tetramethyl-1,4-benzenediamine |
| tetramethyl-p-phenylenediamine [mi] |
| SCHEMBL65261 |
| n1,n1,n4,n4-tetramethylbenzene-1,4-diamine |
| n,n,n',n'-tetramethyl-benzene-1,4-diamine |
| n,n,n',n,-tetramethyl-p-phenylenediamine |
| tetramethyl-p-phenyldiamine |
| W-200619 |
| CHEMBL1393325 |
| 4-(dimethylamino)-n,n-dimethylaniline |
| mfcd00008309 |
| n,n,n',n'-tetramethyl-p-phenylenediamine, 98% |
| n,n,n,n-tetramethyl-1,4-phenylenediamine |
| Q408762 |
| AMY25074 |
| BS-14141 |
| D81852 |
| SB76556 |
| EN300-1707416 |
| n1,n1,n4,n4-tetramethyl-1,4-benzenediamine |
| SY101111 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " There were also increases in plasma 2HG in CER-treated rats on Days 8 and 11 and in TMPD-treated rats at 24 hr after dosing and increases in plasma hexanoylcarnitine in CER-treated rats on Day 11 and in TMPD-treated rats at 6 and 24 hr after dosing." | ( Plasma 2-hydroxyglutarate and hexanoylcarnitine levels are potential biomarkers for skeletal muscle toxicity in male Fischer 344 rats. Asai, F; Kobayashi, N; Nezu, Y; Obayashi, H; Shirai, M; Yamoto, T, 2017) | 0.46 |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE | Homo sapiens (human) | Potency | 31.6228 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
| Chain A, HADH2 protein | Homo sapiens (human) | Potency | 3.1623 | 0.0251 | 20.2376 | 39.8107 | AID886 |
| Chain B, HADH2 protein | Homo sapiens (human) | Potency | 3.1623 | 0.0251 | 20.2376 | 39.8107 | AID886 |
| Luciferase | Photinus pyralis (common eastern firefly) | Potency | 63.4674 | 0.0072 | 15.7588 | 89.3584 | AID1224835 |
| interleukin 8 | Homo sapiens (human) | Potency | 74.9780 | 0.0473 | 49.4806 | 74.9780 | AID651758 |
| acetylcholinesterase | Homo sapiens (human) | Potency | 50.4340 | 0.0025 | 41.7960 | 15,848.9004 | AID1347395; AID1347397; AID1347398 |
| 15-lipoxygenase, partial | Homo sapiens (human) | Potency | 25.1189 | 0.0126 | 10.6917 | 88.5700 | AID887 |
| pregnane X receptor | Rattus norvegicus (Norway rat) | Potency | 50.1187 | 0.0251 | 27.9203 | 501.1870 | AID651751 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 8.6613 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 38.0014 | 0.0007 | 14.5928 | 83.7951 | AID1259368; AID1259392 |
| AR protein | Homo sapiens (human) | Potency | 43.7443 | 0.0002 | 21.2231 | 8,912.5098 | AID588515; AID743042; AID743054 |
| aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 25.1189 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 5.0119 | 0.0013 | 18.0743 | 39.8107 | AID926; AID938 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 68.7989 | 0.0006 | 57.9133 | 22,387.1992 | AID1259378 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 53.5060 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 15.9798 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553; AID1159555 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 30.9939 | 0.0008 | 17.5051 | 59.3239 | AID1159527; AID1159531 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 36.5651 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 39.8107 | 0.3758 | 27.4851 | 61.6524 | AID588527 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 68.7989 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 33.8091 | 0.0002 | 29.3054 | 16,493.5996 | AID1259244; AID1259248; AID743069; AID743080; AID743091 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 49.1220 | 0.0010 | 19.4141 | 70.9645 | AID743191 |
| aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 53.6492 | 0.0007 | 23.0674 | 1,258.9301 | AID743085; AID743122 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 77.1937 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 46.8096 | 0.0016 | 28.0151 | 77.1139 | AID1259385; AID1259393; AID1259395 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 21.9420 | 0.0578 | 21.1097 | 61.2679 | AID1159528 |
| Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 81.8144 | 0.0391 | 47.5451 | 146.8240 | AID1224845; AID1224896 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 61.3171 | 0.0003 | 23.4451 | 159.6830 | AID743067 |
| histone deacetylase 9 isoform 3 | Homo sapiens (human) | Potency | 53.2965 | 0.0376 | 17.0823 | 61.1927 | AID1259364; AID1259388 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 43.1814 | 0.0006 | 27.2152 | 1,122.0200 | AID651741; AID720636; AID743202; AID743219 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 33.5521 | 0.0079 | 8.2332 | 1,122.0200 | AID2546; AID2551 |
| Voltage-dependent calcium channel gamma-2 subunit | Mus musculus (house mouse) | Potency | 30.7314 | 0.0015 | 57.7890 | 15,848.9004 | AID1259244 |
| Glutamate receptor 2 | Rattus norvegicus (Norway rat) | Potency | 30.7314 | 0.0015 | 51.7393 | 15,848.9004 | AID1259244 |
| Nuclear receptor ROR-gamma | Homo sapiens (human) | Potency | 2.9849 | 0.0266 | 22.4482 | 66.8242 | AID651802 |
| Inositol monophosphatase 1 | Rattus norvegicus (Norway rat) | Potency | 14.1254 | 1.0000 | 10.4756 | 28.1838 | AID1457 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| plasma membrane | Glutamate receptor 2 | Rattus norvegicus (Norway rat) |
| nucleus | Nuclear receptor ROR-gamma | Homo sapiens (human) |
| nucleoplasm | Nuclear receptor ROR-gamma | Homo sapiens (human) |
| nuclear body | Nuclear receptor ROR-gamma | Homo sapiens (human) |
| chromatin | Nuclear receptor ROR-gamma | Homo sapiens (human) |
| nucleus | Nuclear receptor ROR-gamma | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1310985 | Inhibition of ATGL in mouse 3T3L1 cells assessed as inhibition of isoproterenol-stimulated lipolysis by measuring reduction in non-esterified fatty acid release in media at 20 uM preincubated for 4 hrs followed by isoproterenol addition measured after 1 h | 2016 | European journal of medicinal chemistry, Aug-08, Volume: 118 | New Atglistatin closely related analogues: Synthesis and structure-activity relationship towards adipose triglyceride lipase inhibition. |
| AID1310986 | Inhibition of ATGL in mouse 3T3L1 cells assessed as inhibition of isoproterenol-stimulated lipolysis by measuring reduction in glycerol release in media at 20 uM preincubated for 4 hrs followed by isoproterenol addition measured after 1 hr by colorimetric | 2016 | European journal of medicinal chemistry, Aug-08, Volume: 118 | New Atglistatin closely related analogues: Synthesis and structure-activity relationship towards adipose triglyceride lipase inhibition. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 1 (14.29) | 29.6817 |
| 2010's | 5 (71.43) | 24.3611 |
| 2020's | 1 (14.29) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (32.83) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 7 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||