Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H15N.ClH |
| Molecular Weight | 137.651 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)NC(C)C
InChI
InChIKey=URAZVWXGWMBUGJ-UHFFFAOYSA-N
InChI=1S/C6H15N.ClH/c1-5(2)7-6(3)4;/h5-7H,1-4H3;1H
| Molecular Formula | C6H15N |
| Molecular Weight | 101.19 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: http://www.tceq.com/assets/public/implementation/tox/dsd/proposed/dec15/diisopropylamine.pdfCurator's Comment: description was created based on several sources, including
http://nj.gov/health/eoh/rtkweb/documents/fs/0728.pdf
http://www.infopest.com.au/labels/msds/41000/41592msd.pdf
http://www.ceva.com.au/content/download/56970/1086588/version/2/file/NV%20DADA%20250%20INJECTION_Mar2016.pdf
https://racehorsemeds.com/product/dada-250-injection-50ml/
https://books.google.ru/books?id=5GpcTQD_L2oC&pg=PA343&lpg=PA343&dq=DIISOPROPYLAMINE+liverall&source=bl&ots=epgtbErf2A&sig=Xmv-eD6Uc4ick5tCfNDsR_7t-Cw&hl=ru&sa=X&ved=0ahUKEwj5_f6a7PDPAhWDQZoKHRcUBUgQ6AEILDAC#v=onepage&q=DIISOPROPYLAMINE%20liverall&f=false
Sources: http://www.tceq.com/assets/public/implementation/tox/dsd/proposed/dec15/diisopropylamine.pdf
Curator's Comment: description was created based on several sources, including
http://nj.gov/health/eoh/rtkweb/documents/fs/0728.pdf
http://www.infopest.com.au/labels/msds/41000/41592msd.pdf
http://www.ceva.com.au/content/download/56970/1086588/version/2/file/NV%20DADA%20250%20INJECTION_Mar2016.pdf
https://racehorsemeds.com/product/dada-250-injection-50ml/
https://books.google.ru/books?id=5GpcTQD_L2oC&pg=PA343&lpg=PA343&dq=DIISOPROPYLAMINE+liverall&source=bl&ots=epgtbErf2A&sig=Xmv-eD6Uc4ick5tCfNDsR_7t-Cw&hl=ru&sa=X&ved=0ahUKEwj5_f6a7PDPAhWDQZoKHRcUBUgQ6AEILDAC#v=onepage&q=DIISOPROPYLAMINE%20liverall&f=false
Diisopropylamine (DIPA) is a secondary amine, which is used as a chemical intermediate, and catalyst for the synthesis of pesticides and pharmaceuticals. DIPA is primarily used as a precursor for the herbicides dilate and triallate, as well as certain sulfenamides used in the vulcanization of rubber. It is used for adjusting pH in cosmetic formulations, in colognes, and toilet cleaners. It is associated with tobacco either as a natural component of tobacco, pyrolysis product (in tobacco smoke), or additive for one or more types of tobacco products. When given intravenously to hypertensive patients, DIPA is known as an antihypertensive agent. DIPA exerts its action by lowering arterial blood pressure, reduction of stroke volume and cardiac output. DIPA reduced blood glucose concentrations in fasted mice and in fasted, glucose-loaded, or streptozotocin-diabetic rats. DADA (diisopropylamine dichloroacetate) was identified as an active domain of pangamic acid. DADA is a vasodilator of peripheral and cerebral arterioles. DADA also considered to aid in the detoxification of chemical and metallic metabolites, possibly by the formation of chelate-like compounds whose excretion by the kidneys is facilitated and increased. DADA increases oxygen utilization and cortical glucose uptake.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14840945
Curator's Comment: DADA (diisopropylamine dichloroacetate) was identified as an active domain of pangamic acid, which Krebs had detected as one of the water-soluble components extracted from the apricot nucleus.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4141 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24865588 |
50.9 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Rivaol Approved UseUnknown |
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| Primary | Rivaol Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis and cytotoxic activity of alpha-santonin derivatives. | 2009-09 |
|
| Synthesis of dihydrothiophenes or spirocyclic compounds by domino reactions of 1,3-thiazolidinedione. | 2009-05-01 |
|
| Synthesis of 2-alkyl-substituted chromone derivatives using microwave irradiation. | 2009-04-03 |
|
| Lithium diisopropylamide-mediated ortholithiations: lithium chloride catalysis. | 2009-03-06 |
|
| Structural and magnetic insights into the trinuclear ferrocenophane and unexpected hydrido inverse crown products of alkali-metal-mediated manganation(II) of ferrocene. | 2009 |
|
| Autocatalysis in lithium diisopropylamide-mediated ortholithiations. | 2008-12-31 |
|
| Synthesis of a 7-azaindole by chichibabin cyclization: reversible base-mediated dimerization of 3-picolines. | 2008-12-19 |
|
| Zinc-mediated allylation and alkylation of aminals in the presence of TMSCl and diisopropylamine. | 2008-11-21 |
|
| Reluctance of 4-chloro-5-metalla-1,3,2-diazaborolines to undergo metal halide beta-elimination: an opportunity for C-functionalization of 1,3,2-diazaborolines. | 2008-11-03 |
|
| Synthesis and antimicrobial activities of silver(I) 3-(substituted phenyl)sulfanylpropenoates. | 2008-11 |
|
| Anionic Snieckus-Fries rearrangement: solvent effects and role of mixed aggregates. | 2008-10-15 |
|
| Sulfimidation of thioether groups--a versatile method for modifying and linking thia/oxa crowns. | 2008-10-07 |
|
| Dichloroacetate (DCA) as a potential metabolic-targeting therapy for cancer. | 2008-10-07 |
|
| The mechanism of the phosphoramidite synthesis of polynucleotides. | 2008-09-21 |
|
| Crystallographic analysis of human serum albumin complexed with 4Z,15E-bilirubin-IXalpha. | 2008-08-29 |
|
| Second-generation difluorinated cyclooctynes for copper-free click chemistry. | 2008-08-27 |
|
| Total synthesis of (+/-)-actinophyllic acid. | 2008-06-18 |
|
| N,N-Di-iso-propylcarbamato complexes of boron. | 2008-06-16 |
|
| Development of a supercritical fluid chromatography high-resolution separation method suitable for pharmaceuticals using cyanopropyl silica. | 2008-03-28 |
|
| Synthesis and characterization of polyacetylene with side-chain thiophene functionality. | 2008-03 |
|
| Structural basis of GC-1 selectivity for thyroid hormone receptor isoforms. | 2008-01-31 |
|
| Transamination chemistry of sodium TMP-zincate: synthesis and crystal structure of a chiral amidozincate. | 2008-01-14 |
|
| Decoupling deprotonation from metalation: Thia-Fries rearrangement. | 2008 |
|
| Syntheses, structures, and sensitized lanthanide luminescence by Pt --> Ln (Ln = Eu, Nd, Yb) energy transfer for heteronuclear PtLn2 and Pt2Ln4 complexes with a terpyridyl-functionalized alkynyl ligand. | 2007-12-10 |
|
| Lithium diisopropylamide-mediated reactions of imines, unsaturated esters, epoxides, and aryl carbamates: influence of hexamethylphosphoramide and ethereal cosolvents on reaction mechanisms. | 2007-11-28 |
|
| Synthesis and biological evaluation of phosphate prodrugs of 4-phospho-D-erythronohydroxamic acid, an inhibitor of 6-phosphogluconate dehydrogenase. | 2007-08 |
|
| Synthesis and antimicrobial activities of silver(I) sulfanylcarboxylates. Structural isomers with identically or unequally coordinated Ag centers in an Ag4S4 ring. | 2007-07-28 |
|
| A new method for the synthesis of organopolyoxometalate hybrid compounds. | 2007-07-09 |
|
| Revalidation and rationale for high pKa values of unconjugated bilirubin. | 2007-05-02 |
|
| An efficient conversion of carboxylic acids to one-carbon degraded aldehydes via 2-hydroperoxy acids. | 2007-05 |
|
| Variations in product in reactions of naphthoquinone with primary amines. | 2007-03-01 |
|
| Diisopropylammonium 2-[(2,4-dinitrophenyl)sulfanylaminocarbonyl]benzoate. | 2007-01 |
|
| Regioselective synthesis of bis(2-halo-3-pyridyl) dichalcogenides (E = S, Se and Te): directed ortho-lithiation of 2-halopyridines. | 2007 |
|
| Lithium diisopropylamide: solution kinetics and implications for organic synthesis. | 2007 |
|
| Mechanistic study on rearrangement cascades starting from annulated 2-aza-hepta-2,4-dienyl-6-ynyl anions: formation of aniline and azepine derivatives. | 2007 |
|
| Lithium diisopropylamide solvated by hexamethylphosphoramide: substrate-dependent mechanisms for dehydrobrominations. | 2006-12-06 |
|
| Potent antagonists of the Kv1.5 potassium channel: synthesis and evaluation of analogous N,N-diisopropyl-2-(pyridine-3-yl)acetamides. | 2006-11-15 |
|
| Lithium diisopropylamide-mediated ortholithiation and anionic fries rearrangement of aryl carbamates: role of aggregates and mixed aggregates. | 2006-10-25 |
|
| Synthesis of an X-ray opaque biodegradable copolyester by chemical modification of poly (epsilon-caprolactone). | 2006-10 |
|
| One-shot double elimination process: a practical and concise protocol for diaryl acetylenes. | 2006-09-18 |
|
| Lithium diisopropylamide-mediated enolization: catalysis by hemilabile ligands. | 2006-08-09 |
|
| Synthesis of 2-chloro-2-imidoylaziridines via aza-Darzens-type reaction of 3,3-dichloro-1-azaallylic anions and N-(arylsulfonyl)imines. | 2006-08-04 |
|
| Lithium carbenoids-ultra-reactive yet selective reagents for methylenation and halomethylenation of sulfones. | 2006-07-21 |
|
| Solid-phase synthesis of m-phenylene ethynylene heterosequence oligomers. | 2006-07-07 |
|
| An experimental and theoretical study of the enantioselective deprotonation of cyclohexene oxide with isopinocampheyl-based chiral lithium amides. | 2006-07 |
|
| Enantioselective modular synthesis of 2,4-disubstituted cyclopentenones by iridium-catalyzed allylic alkylation. | 2006-04-03 |
|
| Microemulsion mediated in situ derivatization-extraction and gas chromatography-mass spectrometric analysis of alkylphosphonic acids. | 2006-03-10 |
|
| Metal enolates of alpha-CF3 ketones: theoretical guideline, direct generation, and synthetic use. | 2006 |
|
| Synthesis of a novel series of 2-methylsulfanyl fatty acids and their toxicity on the human K-562 and U-937 leukemia cell lines. | 2005-10 |
|
| 2- and 8-alkynyl-9-ethyladenines: Synthesis and biological activity at human and rat adenosine receptors. | 2005-06 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15727691
Curator's Comment: The patients were randomly assigned to 2 groups treated with either a high dosage (120 mg/d) or a low dosage (60 mg/d) of diisopropylamine dichloroacetate for 8 weeks.
60 mg/d, 120 mg/d
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10545828
After Normal human keratinocytes (NHEK) were inoculated in a 24-well plate coated with collagen at 1x10^4 cells/ml/well and cultured under 5% CO2 at 37°C until the next day, diisopropylamine dichloroacetate (DADA) was added to each medium without EGF and BPE, followed by culturing for 4 days. The concentration of DADA in the medium was 1, 10, 30 and 100 ug/ml each. Addition of DADA to this basic medium enhanced cell growth, and its peak was shown at 10–30 ug/ml of DADA.
| Substance Class |
Chemical
Created
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