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Metabolism of acetonitrile and propionitrile by Nocardia rhodochrous LL100-21.

Six nitrile compounds and two amide derivatives were degraded by Nocardia rhodochrous LL100-21. Acetonitrile, hydroacrylonitrile, and propionitrile were the best sources of carbon and nitrogen for growth, whereas butenenitrile, succinonitrile, and acetamide supported less growth. Acrylonitrile and acrylamide supported growth but only as a source of nitrogen. Gas chromatography of the culture medium revealed a decrease in acetonitrile with the sequential formation of acetamide and acetic acid. Ammonia was also detected by colorimetric procedures. The enzyme system responsible for the hydrolysis of acetonitrile was shown to be intracellular and inducible. The breakdown of acetonitrile by a crude bacterial extract was a two-step enzymatic hydrolysis with acetamide as the intermediate product and acetic acid and ammonia as the final products. Product formation was stoichiometric with substrate disappearance. When propionitrile was the growth substrate, there was complete conversion of the nitrile to propionic acid and ammonia as the major products. The enzymatic breakdown of the propionitrile, although slower than acetonitrile, yielded the corresponding carboxylic acid and ammonia. Propionamide was produced in very small amounts as an intermediate product.

Acetamides

Use of acetonitrile for the extraction of herbicide residues from soils.

Using a 10% aqueous acetonitrile solution for extraction and an identical solvent clean-up procedure, soil-based residues of the herbicides alachlor, benzoyl-prop-ethyl, flufenprop-isopropyl, flufenprop-methyl, dichlorfop-methyl, nitrofen, and profluralin were recovered reproducibly from three prairie soils fortified at 0.5 and 0.1 ppm levels. The acidic herbicides benazolin, 2,4-D, and 2,4,5-T, together with the acids derived from benzoylprop-ethyl, dichlorfop-methyl, flufenprop-isopropyl, and flufenprop-methyl were reproducibly recovered from the three prairie soils fortified at 0.5 and 0.1 ppm levels using 30% aqueous acetonitrile containing 1% acetic acid after identical clean-up stages. All compounds were analysed by gas chromatographic means utilising an electron-capture detector. The two procedures described were developed for the routine extraction and analysis of neutral and acidic herbicide residues from field soil persistence studies.

Acetonitriles

Electrochemical properties of polycyclic compounds studied by the polarographic method in anhydrous systems. V. Oxidation potentials of carcinogenic hydrocarbons in acetonitrile.

The half-wave oxidation potentials of polycyclic carcinogenic hydrocarbons have been studied at the rotating platinum electrode in anhydrous acetonitrile with sodium perchlorate as the supporting electrolyte. The good agreement was obtained by the comparison of the carcinogenic activity of studied compounds with the values of the oxidation potentials. The values of the oxidation half-wave potentials were correlated also with the reduction potentials measured in acetonitrile and with the root xn of the Hückel secular equation for the highest bonding orbital.

Acetonitriles

The biochemical pathway for the breakdown of methyl cyanide (acetonitrile) in bacteria.

[2-14C]Methyl cyanide (acetonitrile) is metabolized to citrate, succinate, fumarate, malate, glutamate, pyrrolidonecarboxylic acid and aspartate. Non-radioactive acetamide and acetate compete with 14C from methyl cyanide, and [2-14C]acetate and [2-14C]methyl cyanide are metabolized at similar rates, giving identical products. This evidence, combined with the inhibitory effect of fluoroacetate and arsenite on methyl cyanide metabolism, indicates that the pathway is: methyl cyanide leads to acetamide leads to acetate leads to tricarboxylic acid-cycle intermediates. The pathway was investigated in a species of Pseudomonas (group III; N.C.I.B. 10477), but comparison of labelling patterns suggests that it also exists in several higher plants.

Acetamides

Ion binding properties in acetonitrile of cyclopeptides built up from proline and glycine residues.

Ion binding properties of antamanide-like cyclopeptides cyclo-(Pro2-Glyn-Pro2-Gly m) (n,m=1-3) have been studies by CD spectroscopy and by conductivity measurements. Cyclo-(Pro2-Gly-Pro2-Gly) forming complexes of different stoichiometry can be characterized by a strong preference of selectivity for Mg++ and Ca++ ions over alkali ions whereas the other members of the series bind selectively alkali and alkaline earth cations with ion radius of about 1 A. Three main types of CD spectra of cyclic peptides and their complexes can be differentiated. Type I showing two negative Cotton effects at around 220 nm and 200 nm (Ib, Fig. 3), type II showing a positive band around 220 nm and a strong negative one below 190 nm (e.g. Ic in acetonitrile, Fig. 4), and type III showing a strong negative band in the 205 nm region (e.g. mental complexes of Id, Fig. 6).

Acetonitriles

Hydrolysis derivatives of (pyridyl-2)acetonitrile.

The alkaline hydrolysis (KOH/EtOH) of alkyl derivatives of (pyridyl-2)acetonitriles gave the corresponding amides. Lactones: 3-(pyridyl-2')3-alkyl-5-methyl-tetrahydrofuran-2-ones were synthesized as result of the hydrolysis of (pyridyl-2) alkylallylacetamides in presence of 85% H3P04. Soporific and anticonvulsive activity exhibited (pyridyl-2)diallylacetic amide 2 and (pyridyl-2)di-n-propylacetamine 3.

Acetonitriles

The quantitative determination of acrylonitrile, acrolein, acetonitrile and acetone in workplace air.

A simple and sensitive procedure for the routine determination of personnel exposures to organic vapors in the workplace has been developed using porous polymer adsorption/thermal desorption with a subsequent analysis by gas chromatography. Detailed instructions for the packing of the adsorption tube and the operation of the thermal concentrator (flasher) are given. Calibration data obtained with both a static on tube injection procedure and a dynamic method using a permeation device are discussed. More than two years of experience with 6000 samples involving a wide variety of compounds has shown the sensitivity and versatility of the techniques. The additional equipment involved is commercially available costing about $2000.

Acetone

The effect of 2-bromo-alpha-ergocryptine and 2-chloro-alpha-methylergoline-8beta-acetonitrile (lergotrile mesylate) on the prolactin secretion of the ewe.

The effects of two ergot alkaloids, 2-bromo-alpha-ergocryptine methane-sulphonate (CB154, Sandoz) and lergotrile mesylate (LM, E. Lilly & Co.), on the basal secretion of prolactin and on the prolactin response to TRH or the milking stimulus was investigated in the sheep. Both CB154 (c. 0.5 mg/kg) and LM (c. 0.75 mg/kg) markedly reduced basal levels of prolactin and inhibited the TRH-induced prolactin release in ewes in the mid-luteal phase of the oestrous cycle. Both compounds also suppressed basal levels of prolactin in lactating ewes and inhibited the prolactin response to the milking stimulus in lactating ewes.

Acetonitriles

Collagen and mechanical strength in various organs of rats treated with D-penicillamine or amino-acetonitrile.

After oral treatment with D-penicillamine (D-Pc) or with aminoacetonitrile (AAn) for 10 days, mechanical and chemical parameters were studied simultaneously in various organs of Sprague Dawley rats. Tensile strength of skin strips and of tail tendons, breaking strength of femur bones and tensile strength of granuloma tissue (induced by implanted glass rods) were measured and calculated. In the same tissue the soluble collagen fractions and the insoluble collagen were determined. Total collagen and the ratio insoluble vs. soluble collagen were calculated. Tensile strength of skin, tendon and granuloma tissue were greatly reduced by D-Pc treatment but only minimally influenced by AAN treatment. On the other hand only AAN significantly reduced the breaking strength of bone. All these changes were closely correlated with the content of insoluble collagen in the respective tissues. The correlation coefficients to total collagen were similar but lower. The correlation coefficients between strength and the ratio insoluble vs. soluble collagen were generally still lower. Earlier findings in aged and corticoid treated rats, proving that insoluble collagen content determines mechanical strength of connnective and supporting tissue thus could be confirmed.

Acetonitriles

Cardiovascular profile of 5-methyl-2-phenyl-4-imidazole-acetonitrile (MCN-2378), a cerebral vasodilator.

I.v. administration of McN-2378 appeared to preferentially increase cerebral blood flow as opposed to systemic (femoral) blood flow in two strains of monkeys. This cerebral vasodilation was not affected by theta-adrenergic blockade. In the anesthetized dog, the compound transiently lowered systemic arterial pressure with an associated transient decrease in femoral vascular resistance and increased heart rate. Cardiac output in the anesthetized dog was also transiently elevated. Although the compound contains a nitrile group, there is no evidence to suggest that cyanide release is mediating the cerebral vasodilation.

Animals

Determination of chlorinated pesticide residues in foods. I. Rapid screening method for chlorinated pesticides in milk.

A rapid analytical method for determining chlorinated pesticide residues in milk was developed. Thirteen pesticides were almost completely extracted. Ten mL samples of fortified milk were extracted 3 times with 20 mL portions of n-hexane as follows: (A) in the absence of water-soluble solvent; in the presence of (B) 1 mL acetonitrile; (C) 3 mL acetonitrile; (D) 5 mL acetonitrile; (E) 5 mL ethanol; (F) 5 mL acetonitrile and 1 mL ethanol. System F produced the highest pesticide recoveries but the lowest fat extraction, thus eliminating the necessity for liquid-liquid partitioning and minimizing Florisil column cleanup. Pesticide recoveries throughout the procedure were 94--103%. It was noticed, however, that the fat in high fat-containing raw milk is more readily extracted than that in commercial milk.

Animals

Determination of chlorinated pesticide residues in foods. II. Simultaneous analysis of chlorinated pesticide and phthalate ester residues by using AgNO3-coated Florisil column chromatography for cleanup of various samples.

A simplified method suitable for simultaneous analysis of chlorinated pesticide and phthalate ester residues in various foods was developed. Chemical residues were quantitatively extracted from fatty and vegetable samples with acetonitrile as follows: Chemical standard in 0.5 mL ethanol solution was added to 10 g homogenized sample. After 3 hr, pork and beef were extracted 3 times with 20 mL portions of acetonitrile. The acetonitrile layers were diluted with water and extracted with n-hexane. Rice samples were combined with 10 mL water, 5 mL acetonitrile and 1 mL ethanol and extracted 3 times with 20 mL portions of n-hexane. The n-hexane concentrate from each sample was submitted to AgNO3-coated Florisil column chromatography. The AgNO3 coating adequately adsorbed interfering coextractives. Extracts of fish and vegetable samples were separated into 2 fractions by the above column chromatography. Supplemental cleanup procedures were also developed to accurately determine phthalate esters eluted in the second fraction. Satisfactory gas chromatograms were obtained for most samples.

Animals