P-Indoleacetic acid

SYNS HETEROAUXIN IA. p-INDOLEACETIC ACID p-INDOLE-3-ACETIC ACID 3-INDOLE-ACETIC ACID INDOLYLACETIC ACID a-INDOL-3-YL-ACETIC ACID P-INDOLYLACETIC ACID ... 

P-INDOLEACETIC ACID see ICNOOO P-INDOLE-3-ACETIC ACID see ICNOOO 1H-INDOLE-3-ACETIC ACID, l-(4-CHLOROBENZOYL)-5-METHOXY-2-iMETHYL-, SODIUM SALT, TRIHYDRATE see IDAIOO INDOLEACETONITRILE see ICWOOO INDOLE-3-ACETONITRILE see ICWOOO lH-INDOLE-3-ACETONITRILE see ICWOOO INDOLE-3-ALANINE see TNXOOO INDOLE, 5-BENZYLOXY-3-ISONIPECOTOYL- see BFC200... 

The plant hormone auxin has been shown to be radiosensitive. The product of the irradiation of auxin (p-indoleacetic acid) is a polymer similar to that obtained in the radiolysis of indole. 

CAS 87-51-4 EINECS/ELINCS 201-748-2 Synonyms Heteroauxin lA lAA 1H-lndole-3-acetic acid lndole-3-acetic acid P-Indoleacetic acid p-lndole-3-acetic acid Indolylacetic acid lndol-3-ylacetic acid lndolyl-3-acetic acid... 

Dimethylaminomethylindole (gramine). Cool 42 5 ml. of aqueous methylamine solution (5 2N ca. 25 per cent, w/v) contained in an 100 ml. flask in an ice bath, add 30 g. of cold acetic acid, followed by 17 -2 g. of cold, 37 per cent, aqueous formaldehyde solution. Pour the solution on to 23 -4 g. of indole use 10 ml. of water to rinse out the flask. Allow the mixture to warm up to room temperature, with occasional shaking as the indole dissolves. Keep the solution at 30-40° overnight and then pour it, with vigorous stirring, into a solution of 40 g. of potassium hydroxide in 300 ml. of water crystals separate. Cool in an ice bath for 2 hours, collect the crystalline solid by suction flltration, wash with three 50 ml. portions of cold water, and dry to constant weight at 50°. The yield of gramine is 34 g. this is quite suitable for conversion into 3-indoleacetic acid. The pure compound may be obtained by recrystaUisation from acetone-hexane m.p. 133-134°. 

Indoleacetic acid In a 1-litre flask, fitted with a reflux condenser, place a solution of 35 2 g. of sodium cyanide in 70 ml. of water, then add 25 g. of gramine and 280 ml. of 95 per cent, ethanol. Reflux the mixture (steam bath) for 80 hours. Dilute the cooled reaction mixture with 35 ml. of water, shake with a little activated charcoal (e.g., Norit), filter and concentrate to about 350 ml. imder reduced pressure (water pump) in order to remove most of the alcohol. Cool to about 5°, filter off the solid and wash it with a little cold water keep the filtrate (A). Recrystallise the solid from alcohol-ether to give 5-0 g. of 3-indoleacetamide, m.p. 150-151°. 

Cool the filtrate (A) to 5-10° and add concentrated hydrochloric acid dropwise and with vigorous stirring (FUME CUPBOARD hydrogen cyanide is evolved) to a pH of 1-2 (about 50 ml.) a crude, slightly pink 3-indoleacetic acid is precipitated. The yield of crude acid, m.p. 159-161°, is 20 g. Recrystallise from ethylene dichloride containing a small amount of ethanol 17 -5 g. of pure 3 indoleacetic acid, m.p. 167-168°, are obtained. 

A solution of 1.330 g sodium hydroxide in 20 ml water is slowly admixed with 2.330 g hydroxylamine hydrochloride while cooling, whereupon 1 g chloride of 1-p-chlorobenzoyl-2-methyl-5-methoxy-3-indoleacetic acid is distempered in this neutral or slightly alkaline solution by vigorously stirring during a few minutes. 

Audus and Quastel (4) have found that the presence of p-aminobenzoic acid exerts an antagonism, though a relatively feeble one, to the root growth inhibitory actions of 2,4-dichlorophenoxyacetic acid, 2-chloro-4-methylphenoxyacetic acid, 2-naphthoxyacetic acid, and 2-indoleacetic acid. For any marked degree of antagonism the concentration ratio of p-aminobenzoic acid to the growth substance must be of the order of 10,000. This relatively feeble action is ii marked contrast to the effect of p-aminobenzoic acid on the... 

A 1M p-methoxy-aniline (p-anisidine), 0.5 M ethyl-gamma-Br-acetoacetate (brominate as described above for 1-methyl-DET synthesis) cool and add 250 ml ether. Filter, evaporate in vacuum and reflux residue fifteen hours with 60 g ZnCI2 in 250 ml ethanol. Evaporate in vacuum, wash precipitate with water and dissolve residue in benzene. Wash with 4N HCI and water and dry, evaporate in vacuum. Reflux prcipitate two hours in ethanol-KOH to get about 70% yield of 5-methoxy-indoleacetic acid (I). 

Concn, of Applied K Gibberellate, P.P.M. Indoleacetic Acid, fig./50 Grams Fresh Weight... 

The principal reason that DMT must be administered parenterally is its rapid and efficient metabolism. It can be oxidized to the N-oxide. It can be cyclized to P-carbolines, both with and without an N-methyl group. It can be N-dealkylated to form NMT and simple tryptamine itself. Best known is its oxidative destruction, by the monoamine oxidase system, to the inactive indoleacetic acid. There is a wild biochemical conversion process known tor tryptophan that involves an enzymatic conversion to kynurenine by the removal of the indole-2-carbon. A similar product, N,N-dimethylkynurenine or DMK, has been seen with DMT, when it was added to whole human blood in vitro. 

Several classes of non-polar binding sites also are present on the Con A molecule. Two of these, a site adjacent to the carbohydrate-specific site that interacts with phenyl P-glycosides of mannose, glucose and iV-acetylglucosamine [84], and 4 low affinity sites (one per subunit) that bind various non-polar molecules such as tryptophan and indoleacetic acid [85], are of special interest. 

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