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At least 19 records
All sourcesNASA NTRSDOE OSTI
NASA NTRS2017

Pathways to Meteoritic Glycine and Methylamine

Glycine and methylamine are meteoritic water-soluble organic compounds that provide insights into the processes that occurred before, during, and after the formation of the Solar System. Both glycine and methylamine and many of their potential synthetic precursors have been studied in astrophysical environments via observations, laboratory experiments, and modeling. Despite these studies, the synthetic mechanisms for their formation leading to their occurrence in meteorites remain poorly understood. Typical 13C-isotopic values ((delta)13C) of meteoritic glycine and methylamine are 13C-enriched relative to their terrestrial counterparts; thus, analyses of their stable carbon isotopic compositions (13C/12C) may be used not only to assess terrestrial contamination in meteorites but also to provide information about their synthetic routes inside the parent body. Here, we examine potential synthetic routes of glycine and methylamine from a common set of precursors present in carbonaceous chondrite meteorites, using data from laboratory analyses of the well-studied CM2 Murchison meteorite. Several synthetic mechanisms for the origins of glycine and methylamine found in carbonaceous chondrites may be possible, and the prevalence of these mechanisms will largely depend on (a) the molecular abundance of the precursor molecules and (b) the levels of processing (aqueous and thermal) that occurred inside the parent body. In this work, we also aim to contextualize the current knowledge about gas-phase reactions and irradiated ice grain chemistry for the synthesis of these species through parent body processes. Our evaluation of various mechanisms for the origins of meteoritic glycine and methylamine from simple species shows what work is still needed to evaluate both the abundances and isotopic compositions of simpler precursor molecules from carbonaceous chondrites as well as the effects of parent body processes on those abundances and isotopic compositions. The analyses presented here combined with the indicated measurements will aid a better interpretation of quantitative analysis of reaction rates, molecular stability, and distribution of organic products from laboratory simulations of interstellar ices, astronomical observations, and theoretical modeling.

interstellar ice↗
NASA NTRS1977

The distribution of methylamine in the Jovian atmosphere

An estimate has been made of the methylamine concentration in the Jupiter atmosphere on the basis of the possible overlap between the regions of hydrocarbon and ammonia photochemistry. It was found that the maximum production rate of 6 x 10 to the 4th/cu cm/Jovian day occurs in the vicinity of 60 km above the ammonia cloud layer. The volumetric mixing ratio is 3 x 10 to the -11th, if the downward transport of methylamine equals the production rate.

Kuhn, W. R.↗
NASA NTRS1983

Formation and photochemistry of methylamine in Jupiter's atmosphere

In the upper troposphere and lower stratosphere of Jupiter, translationally hot H atoms are produced in the photolysis of ammonia, phospine, and acetylene which react with methane to form methyl radicals. The latter combine with NH2 to form methylamine. It is presently shown that the combined production of methylamine and subsequent photolysis to HCN is unlikely to account for the HCN observed near Jupiter's tropopause. The recommendation of NH2 and C2H3 radicals to yield C2H5N, followed by photolysis to HCN, is the preferred path. An upper limit column density on CH3PH2 is estimated to be about 10 to the 13th/sq cm, as compared to 10 to the 15th/sq cm for CH3NH2.

Kaye, J. A.↗
NASA NTRS2001

Cultured rat vascular smooth muscle cells are resistant to methylamine toxicity: no correlation to semicarbazide-sensitive amine oxidase

Methylamine (MA), a component of serum and a metabolite of nicotine and certain insecticides and herbicides, is metabolized by semicarbazide-sensitive amine oxidase (SSAO). MA is toxic to cultured human umbilical vein and calf pulmonary artery endothelial cells. Endothelial cells, which do not exhibit endogenous SSAO activity, are exposed to SSAO circulating in serum. In contrast, vascular smooth muscle cells (VSMC) do exhibit innate SSAO activity both in vivo and in vitro. This property, together with the critical localization of VSMC within the arterial wall, led us to investigate the potential toxicity of MA to VSMC. Cultured rat VSMC were treated with MA (10-5 to 1 M). In some cultures, SSAO was selectively inhibited with semicarbazide or MDL-72145 [(E)-2-(3,4-dimethoxyphenyl)-3-fluoroallylamine]. Cytotoxicity was measured via MTT, vital dye exclusion, and clonogenic assays. MA proved to be toxic to VSMC only at relatively high concentrations (LC(50) of 0.1 M). The inhibition of SSAO with semicarbazide or MDL-72145 did not increase MA toxicity, suggesting that the production of formaldehyde via tissue-bound, SSAO-mediated MA metabolism does not play a role in the minimal toxicity observed in isolated rat VSMC. The omission of fetal calf serum (FCS), which contains high SSAO activity, from media similarly showed little effect on cytotoxicity. We conclude that VSMC--in contrast to previous results in endothelial cells--are relatively resistant to MA toxicity, and SSAO does not play a role in VSMC injury by MA.

Amine Oxidase (Copper-Containing)/metabolism↗
NASA NTRS1973

Rapid gas-phase reactions - The reaction of ammonia and the methylamines with boron trifluoride. III - Pressure dependence of rate constant.

A steady-state flow apparatus, shown earlier to be suitable for the study of rapid gas reactions, has been used to determine the pressure dependence of the relative quasi-bimolecular rate constants for the reactant pairs ammonia (AM)-trimethylamine (TMA) and dimethylamine (DMA)-trimethylamine in reaction with boron trifluoride. The pressure dependence of the former was determined in the range 0.03-75 torr and that of the latter in the range 0.02-720 torr.

Glicker, S.↗
NASA NTRS1984

Process for producing tris s(n-methylamino) methylsilane

A method of producing tris (N-methylamine) methylsilane is described including the steps of forming and cooling a liquid solution of methylamine in an inert solvent and under an inert atmosphere at a temperature of about -30 C and slowly adding a quantity of methyltricholorosilane while maintaining said temperature. The reaction mixture is then heated for about 60 minutes at a temperature of about 40 C, followed by filtering the solid portion from the liquid portion. The liquid is distilled to remove the solvent, resulting in a high yield of tris (N-methylamine) methylsilane.

Clemons, J. M.↗
NASA NTRS2016

Aliphatic Amines in Antarctic CR2, CM2, and CM1/2 Carbonaceous Chondrites

Meteoritic water-soluble organic compounds provide a unique record of the processes that occurred during the formation of the solar system and the chemistry preceding the origins of life on Earth. We have investigated the molecular distribution, compound-specific delta13C isotopic ratios and enantiomeric compositions of aliphatic monoamines present in the hot acid-water extracts of the carbonaceous chondrites LAP 02342 (CR2), GRA 95229 (CR2), LON 94101 (CM2), LEW 90500 (CM2), and ALH 83100 (CM1/2). Analyses of the concentration of monoamines in these meteorites revealed: (a) the CR2 chondrites studied here contain higher concentrations of monoamines relative to the analyzed CM2 chondrites; (b) the concentration of monoamines decreases with increasing carbon number; and (c) isopropylamine is the most abundant monoamine in these CR2 chondrites, while methylamine is the most abundant amine species in these CM2 and CM1/2 chondrites. The delta13C values of monoamines in CR2 chondrite do not correlate with the number of carbon atoms; however, in CM2 and CM1/2 chondrites, the 13C enrichment decreases with increasing monoamine carbon number. The delta13C values of methylamine in CR2 chondrites ranged from −1 to +10per mille, while in CM2 and CM1/2 chondrites the delta13C values of methylamine ranged from +41 to +59per mille. We also observed racemic compositions of sec-butylamine, 3-methyl-2-butylamine, and sec-pentylamine in the studied carbonaceous chondrites. Additionally, we compared the abundance and delta13C isotopic composition of monoamines to those of their structurally related amino acids. We found that monoamines are less abundant than amino acids in CR2 chondrites, with the opposite being true in CM2 and CM1/2 chondrites. We used these collective data to evaluate different primordial synthetic pathways for monoamines in carbonaceous chondrites and to understand the potential common origins these molecules may share with meteoritic amino acids.

Meteoritic water-soluble organic compounds↗
NASA NTRS2010

Cometary Glycine Detected in Stardust-Returned Samples

In January 2006, NASA's Stardust spacecraft returned samples from comet 81P/Wild 2 to Earth. The Stardust cometary collector consisted of aerogel cells lined with aluminum foils designed to capture impacting particles and facilitate removal of the aerogel. Preliminary examinations of these comet-exposed materials revealed a suite of organic compounds, including several amines and amino acids which were later examined in more detail. Methylamine (NH2CH3) and ethylamine (NH2C2H5) were detected in the exposed aerogel at concentrations greatly exceeding those found in control samples, while the amino acid glycine (NH2CH2COOH) was detected in several foil samples as well as in the comet-exposed aerogel. None of these three compounds had been previously detected in comets, although methylamine had been observed in the interstellar medium. Although comparison with control samples suggested that the detected glycine was cometary. the previous work was not able to conclusively identify its origin. Here, we present the results of compound-specific carbon isotopic analysis of glycine in Stardust cometary collector foils. Several foils from the interstellar side of the Stardust collector were also analyzed for amino acid abundance, but concentrations were too low to perform isotopic ana!ysis.

Elsila, Jamie E.↗
NASA NTRS1964

The X-Irradiation of Hydrazine and 1,1- Dimethylhydrazine

Hydrazine and 1,1-dimethylhydrazine were radiolyzed at room temperature by using about 1 gram of liquid or 1/2 to 2 liters of vapor at room-temperature vapor pressure. A tungsten-target X-ray source operating at 300 kilovolts and 6 to 8 milliamperes (0.1 to 1.0 A) was used at intensities of 1 times 10 (sup 2) to 1 times 10 (sup 3) roentgens per minute to give total doses of 4.1 rads to 2.3 times 10 (sup 6) rads. The amounts of decomposition were dependent on total dose and independent of dose rate. In the case of hydrazine vapor, the decomposition was also directly related to surface area. There was a lesser surface effect with liquid hydrazine, but this variable was not studied for 1,1-dimethylhydrazine. The order of decreasing sensitivity to X-radiation is as follows: hydrazine vapor, 1,1-dimethylhydrazine vapor, 1,1-dimethylhydrazine liquid, and hydrazine liquid. The decomposition products of hydrazine were nitrogen, hydrogen, ammonia, and unidentified products. The same products plus methylamine, dimethylamine, and hydrazine were found from the decomposition of 1,1-dimethylhydrazine. In addition, the 1,1-dimethylhydrazine underwent post-irradiation changes. Values for G (number of molecules of sample decomposed per 100 electronvolts of absorbed energy) of the order of 10 (sup 6) suggest that the vapor-phase decompositions are chain reactions.

X-RAY IRRADIATION↗
NASA NTRS1967

Infusible silazane polymer and process for producing same

Coatings of high thermal and chemical stability for application to metal, glass, ceramics, and other surfaces are formed by reacting diphenyldichlorosilane in the presence of triethylamine with a nitrogen base selected from the group consisting of ammonia and methylamine. The pl polymeric, noncrystalline reaction product is heated in a reaction zone open to the atmosphere at a temperature ranging from approximately 250 C to 450 C until the infusible polymer is formed.

Burks, R. E., Jr.↗
NASA NTRS1983

Galactic cosmic rays and N2 dissociation on Titan

The electromagnetic and particle cascade resulting from the absorption of galactic cosmic rays in the atmosphere of Titan is shown to be an important mechanism for driving the photochemistry at pressures of 1 to 50 mbar in the atmosphere. In particular, the cosmic ray cascade dissociates N2, a process necessary for the synthesis of nitrogen organics such as HCN. The important interactions of the cosmic ray cascade with the atmosphere are discussed. The N2 excitation and dissociation rates and the ionization rates of the principal atmospheric consituents are computed for a Titan model atmosphere that is consistent with Voyager 1 observations. It is suggested that HCN may be formed efficiently in the lower atmosphere through the photodissociation of methylamine. It is also argued that models of nitrogen and hydrocarbon photochemistry in the lower atmosphere of Titan should include the absorption of galactic cosmic rays as an important energy source.

Capone, L. A.↗
NASA NTRS1985

Photochemistry and clouds of Jupiter, Saturn and Uranus

Photochemistry of ammonia, methane, phosphine, hydrogen sulfide, methylamine, hydrogen cyanide and carbon monoxide in the atmospheres of Jupiter, Saturn and Uranus is discussed. Condensation of ammonia, ammonium hydrosulfide, water, methane, ethane and acetylene below and near the tropopause of these planets is formulated. Whenever necessary, new calculations are included. Candidates for the upper atmospheric hazes, and the reddish-brown chromosphore in the clouds of Jupiter and Saturn are discussed.

Atreya, S. K.↗
NASA NTRS1986

Regulation of Ca(2+)-dependent protein turnover in skeletal muscle by thyroxine

Dantrolene, an agent that inhibits Ca(2+) mobilization, improved protein balance in skeletal muscle, as thyroid status was increased, by altering rates of protein synthesis and degradation. Thyroxine (T4) caused increases in protein degradation that were blocked by leupeptin, a proteinase inhibitor previously shown to inhibit Ca(2+)-dependent nonlysosomal proteolysis in these muscles. In addition, T4 abolished sensitivity to the lysosomotropic agent methylamine and the autophagy inhibitor 3-methyladenine, suggesting that T4 inhibits autophagic/lysosomal proteolysis.

Zeman, Richard J.↗
NASA NTRS2001

Detecting Pyrolysis Products from Bacteria on Mars

A pyrolysis/sublimation technique was developed to isolate volatile amine compounds from a Mars soil analogue inoculated with approx. 10 billion Escherichia coli cells. In this technique, the inoculated soil is heated to 500 C for several seconds at Martian ambient pressure and the sublimate, collected by a cold finger, then analyzed using high performance liquid chromatography. Methylamine and ethylamine, produced from glycine and alanine decarboxylation, were the most abundant amine compounds detected after pyrolysis of the cells. A heating cycle similar to that utilized in our experiment was also used to release organic compounds from the Martian soil in the 1976 Viking gas chromatography/mass spectrometry (GC/MS) pyrolysis experiment. The Viking GC/MS did not detect any organic compounds of Martian origin above a level of a few parts per billion in the Martian surface soil. Although the Viking GC/MS instruments were not specifically designed to search for the presence of living cells on Mars, our experimental results indicate that at the part per billion level, the degradation products generated from several million bacterial cells per gram of Martian soil would not have been detected.

Glavin, Daniel↗
NASA NTRS1995

Activation of the ATP-ubiquitin-proteasome pathway in skeletal muscle of cachectic rats bearing a hepatoma

Rats implanted with Yoshida ascites hepatoma (YAH) show a rapid and selective loss of muscle protein due mainly to a marked increase (63-95%) in the rate of protein degradation (compared with rates in muscles of pair-fed controls). To define which proteolytic pathways contribute to this increase, epitrochlearis muscles from YAH-bearing and control rats were incubated under conditions that modify different proteolytic systems. Overall proteolysis in either group of rats was not affected by removal of Ca2+ or by blocking the Ca(2+)-dependent proteolytic system. Inhibition of lysosomal function with methylamine reduced proteolysis (-12%) in muscles from YAH-bearing rats, but not in muscles of pair-fed rats. When ATP production was also inhibited, the remaining accelerated proteolysis in muscles of tumor-bearing rats fell to control levels. Muscles of YAH-bearing rats showed increased levels of ubiquitin-conjugated proteins and a 27-kDa proteasome subunit in Western blot analysis. Levels of mRNA encoding components of proteolytic systems were quantitated using Northern hybridization analysis. Although their total RNA content decreased 20-38%, pale muscles of YAH-bearing rats showed increased levels of ubiquitin mRNA (590-880%) and mRNA for multiple subunits of the proteasome (100-215%). Liver, kidney, heart, and brain showed no weight loss and no change in these mRNA species. Muscles of YAH-bearing rats also showed small increases (30-40%) in mRNA for cathepsins B and D, but not for calpain I or heat shock protein 70. Our findings suggest that accelerated muscle proteolysis and muscle wasting in tumor-bearing rats result primarily from activation of the ATP-dependent pathway involving ubiquitin and the proteasome.

NASA Discipline Musculoskeletal↗
NASA NTRS1992

Dietary protein deficiency reduces lysosomal and nonlysosomal ATP-dependent proteolysis in muscle

When rats are fed a protein deficient (PD) diet for 7 days, rates of proteolysis in skeletal muscle decrease by 40-50% (N. E. Tawa, Jr., and A. L. Goldberg. Am. J. Physiol. 263 (Endocrinol. Metab. 26): E317-325, 1992). To identify the underlying biochemical adaptations, we measured different proteolytic processes in incubated muscles. The capacity for intralysosomal proteolysis, as shown by sensitivity to methylamine or lysosomal protease inhibitors, fell 55-75% in muscles from PD rats. Furthermore, extracts of muscles of PD rats showed 30-70% lower activity of many lysosomal proteases, including cathepsins B, H, and C, and carboxypeptidases A and C, as well as other lysosomal hydrolases. The fall in cathepsin B and proteolysis was evident by 3 days on the PD diet, and both returned to control levels 3 days after refeeding of the normal diet. In muscles maintained under optimal conditions, 80-90% of protein breakdown occurs by nonlysosomal pathways. In muscles of PD rats, this ATP-dependent process was also 40-60% slower. Even though overall proteolysis decreased in muscles of PD rats, their capacity for Ca(2+)-dependent proteolysis increased (by 66%), as did the activity of the calpains (+150-250%). Thus the lysosomal and the ATP-dependent processes decrease coordinately and contribute to the fall in muscle proteolysis in PD animals.

Non-NASA Center↗