Indoleacetic acid, 256 extraction

SYNTHESIS (from indoleacetone) To a solution of 1.55 g NaOAc in 5 mL acetic anhydride there was added 2.0 g 3-indoleacetic acid and the mixture was heated at 135-140 °C for 18 h. Removal of all volatiles on the rotary evaporator under vacuum produced a pale yellow residue that was the 1-acetylindole-3-acetone. This was dissolved in MeOH to which 0.93 g MeONa was added, and the solution held a reflux several hours. After removal of the solvent under vacuum, the residue was suspended in H20 and extracted with several portions of Et20. These extracts were pooled, and removal of the solvent under vacuum gave 0.41 g (21%) indole-3-acetone as a white solid, mp 115-117 °C. MS (in m/z) indolemethylene+ 130 (100%) parent ion 173 (16%). IR (in cm-1) 691,753,761,780. 1017, 1110, 1172, and a broad C=0 at 1710. 

On account of the activity of these plant extracts and the isolation from them of iV,iV-dimethyltryptamine, the physiological activity of this base in humans is of interest. When injected intramuscularly, it causes hallucinations and illusions, which are characterized by their rapid appearance and brief duration (80). Apparently, dimethyltrypt-amine is rapidly metabolized and excreted mainly as indoleacetic acid, although the urine is enriched with 5-hydroxyindoleacetic acid whether this is the result of oxidation at the 5-position or stimulation of the metabolism of serotonin in the brain is not yet known (80). 

TrvDtoDhol. Tryptophol [12] is a natural product in plants and microorganisms and is involved in indoleacetic acid metabolism. A major metabolite from Drechslera nodulosum. tryptophol was isolated and identified from extracts of culture filtrates of this fungal pathogen (8S). This report was the first to show that this compound was phytotoxic and caused necrotic lesions on goosegrass (Eleusine indica L.), the weed host of this fungus. Necrotic injury in. goosegrass occurred after application of tryptophol at 6.2 x 10 ... 

Kugimiya, A. Takeuchi, T. Application of indoleacetic acid-imprinted polymer to solid phase extraction. Anal. Chim. Acta 1999, 395, 251-255. 

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