We also thank Dr. Robert Minard and the Dr. Clifford N. Matthews research group at the University of Chicago for providing the Murchison meteorite and Professor Reid R. Keays from the University of Melbourne for collecting and providing the Murchison soil sample. 54, 123 (2007), V. Bereau, V. Jubera, P. Arnaud, A. Kaiba, P. Guionneau, J. Sutter, Dalton Trans.
Hexamine (Hexamethylenetetramine) - The Chemical Company - Global Vinogradoff, V., Bernard, S., Le Guillou, C. & Remusat, L. Evolution of interstellar organic compounds under asteroidal hydrothermal conditions. 23, 2839 (1991), D.I. ADS The absence of these species on the mass chromatograms for the HMT standard reagent (Supplementary Fig. Chem. Prikl. The pretreatment eliminates HPLC/ESI-Orbitrap-MS potential artefacts including a chromatographic retention shift27,47, ion suppression and ion-enhancement effect48,49. Gang, Chin. Astron. Acta 269, 150166 (2020). Tax calculation will be finalised during checkout. 9, 666 (1998), A.I. Izumi A, Nakao T, Shibayama M. Gelation and cross-link inhomogeneity of phenolic resins studied by small- and wide-angle X-ray scattering and 1H-pulse NMR spectroscopy. Influence of phyllosilicates on the hydrothermal alteration of organic matter in asteroids: experimental perspectives. The mass chromatogram was shown in Supplementary Fig. : H11300 : Sigma-Aldrich : 612-101-00-2 : 100-97- 1.2 Relevant identified uses of the substance or mixture and uses advised against Identified uses : Laboratory chemicals, Synthesis of substances 1.3 Details of the supplier of the safety data sheet Company 81 (1974) 120 788, D.J. Meteor. Urex (methenamine hippurate) is a urinary tract antiseptic drug used to treat and prevent urinary tract infections. The MS/MS experiment was also performed using a hybrid quadrupole-Orbitrap mass spectrometer (Q-Exactive Plus, Thermo Fischer Scientific) with the identical HPLC and ionization conditions used for the full-scan analysis. ADS
An insight into hexamethylenetetramine: a versatile - Home - Springer If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate. The flammable solid heterocyclic organic compound sublimes in a vacuum at about 505 F with some decomposition. Cosmochim. The 10g chip was crushed and homogenized at the NASA Goddard Space Flight Center and a 2g portion of the powder was sent to Tohoku University. Furthermore, the estimated relative abundances of these HMT-derivatives in the organic residues (orders of magnitudes less abundant than HMT)17,19 are in reasonable agreement with those of the meteoritic HMT-derivatives (Supplementary Fig. J. Chem. Yang, Org. Adv. Soc. 354, 11331140 (2004). Here, we report the hexamethylenetetramine (HMT) synthesis and H2 evolution from methanol and ammonia in one pot using a nanophotocatalyst of the conventional semiconductor TiO2 (P25) loaded with Pt (Pt/P25). Hexamethylenetetramine (HMTA or hexa) is by far the most important curing agent for novolac. 113, 87838839 (2013). 531, 116011 (2020).
Methenamine: Uses, Interactions, Mechanism of Action | DrugBank Online 98, 1512 (1967), N. Blazevic, V. Sunjic, I. Crvelin, D. Kolbah, F. Kajfez, J. Heterocycl. PubMed Central Mass chromatograms at the m/z of 141.1135 within a3ppm exact mass window at each monoisotopic mass for a hexamethylenetetramine (HMT) standard reagent, b HMT in Murchison, c Tagish Lake, and d Murray meteorites, measured using the InertSustain PFP column. Soc. analysed the sample. Ingestion of a 1-gram dose of methenamine hippurate produces antibacterial activity in the urine within 1/2 hour. Astrophys. Proc. The authors declare that they have no conflict of interest. Planet. The final fraction was dissolved in ~1mL of ultra-pure H2O and filtered by 0.20m PTFE cartridge filter just before the HRMS. Google Scholar.
Hexamethylenetetramine | Uses, Dosage, Side Effects, FAQ - MedicinesFAQ Baumgarten, J.M. Sternbach, J. Org. HMT and other water-extractable hydrophilic molecules (e.g., sugars) were recovered from ~2g of the Murchison powder and the cation desalting fraction as described in Furukawa et al.5 was used for this study. 69, 1355 (1947), N. Masurier, E. Moreau, C. Lartigue, V. Gaumet, J. Chezal, A. Heitz, J. Teulade, O. Chavignon, J. Org. Ehrenfreund, P. & Charnley, S. B. Organic molecules in the interstellar medium, comets, and meteorites: a voyage from dark clouds to the earth Earth. Astrophys. Shenoy, P.R. 2012;8:843845. (1), Hexamethylenetetramine is primarily eliminated via the kidneys. (S), 2, 154 (1998), M.M. Engl. Baumgarten, J.M. Bachmann, N.C. Deno, J. Eur., BP, 99-100.5% (calc. Syn. However, the argumentthat HMT is the origin of amino acids during workup is weakened by Murray, which has a similar abundance of amino acids to Murchison8, yet the HMT concentration was lower by about an order of magnitude than Murchison. Chem. 10, 4413 (2019). In addition, the likely detection of several HMT-derivatives also bolsters this conclusion; unlike HMT itself, to our best knowledge, these HMT-derivatives are commercially unavailable and their presence in terrestrial environments has not been reported. Trans Faraday Soc. Crosslink distribution of epoxy networks studied by small-angle neutron-scattering.
Syn. Chem. Not. Chem.
One-Pot Synthesis of Hexamethylenetetramine Coupled with H2 Evolution The network structure evolution of a hexamethylenetetramine (HMTA)-cured novolac-type phenolic resin over a curing temperature range of 135155C was investigated using 1H-pulse nuclear magnetic resonance spectroscopy and small-angle and wide-angle X-ray scattering techniques. Natl Acad. Cohen Addad JP (editor). Virin, V.R. Peredelskiy, Zh. Correspondence to 18, 4958 (2004). Since methanol is abundant in interstellar ices3, the HMT formation is likely to take place in the interstellar medium (ISM) and become incorporated into solar system ices similar to other interstellar molecules21,22. 6, 239 (2009), R.M. Kaufman, Org. Uses advised against Food, drug, pesticide or biocidal product use. the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Chem. Article Sci. Kozenko, Zh. Zaytsev, R.J. Anderson, A. Bedernjak, P.W. https://doi.org/10.1007/s13738-013-0260-2, DOI: https://doi.org/10.1007/s13738-013-0260-2. https://doi.org/10.1038/s41467-020-20038-x, DOI: https://doi.org/10.1038/s41467-020-20038-x. Google Scholar. hexamethylenetetramine, 1,3,5,7-tetraazaadamantane; Cohedur H 30; Hexamethylene-tetramine cation Hexamethylene-tetramine dication. Rev. Biomol. Tung, ARKIVOC ii, 182 (2003), E. Reimann, Justus Liebigs Ann. Astrophys. Proc. Article (1) Certain bacteria such as Proteus sp. Hexamethylenetetramine is prepared by combining formaldehyde and ammonia. CAS Izumi A, Nakao T, Shibayama M. Synthesis and properties of a deuterated phenolic resin. Muoz Caro, G. M. & Schutte, W. A. UV-photoprocessing of interstellar ice analogs: new infrared spectroscopic results. Nitrates, hexamethylenetetramine (HMT), and polyphosphates are the chemicals more commonly used against clostridia in cheese technology. It is reasonable that ISM-derived HMT would be highly D-enriched19. Bastide J, Candau SJ. The eluent programme for this HPLC setup is as follows: solvent A (H2O), solvent B (acetonitrile+0.1% formic acid by volume)=90:10 for the initial 5min, followed by a linear gradient of A:B=50:50 at 20min, and it was kept at this ratio for 25min. Sarbaev, V.I. Google Scholar, I.M. (Harcourt College, Philadelphia, 2002), R.I. Fryer, L.H. Paris 253, 2706 (1961), CAS App. & Mazzeo, J. R. A study of ion suppression effects in electrospray ionization from mobile phase additives and solidphase extracts. 2013;9:418897. Asano A. NMR relaxation studies of elastomers. 38, 328334 (2005). Chem. Urex is available in generic form. However, these HMT-derivatives have been identified in organic residues produced by photolysis of interstellar ice analogues followed by warming to room temperatures, which mimics the processes of molecular evolution toward star formation17,19. https://doi.org/10.1111/maps.13451 (2020). Astron. Schreiber, J. Liu, M.W. Soc. ADS Astron. Baxendale, S.V. Rao, Ind. If material is not included in the articles Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. Mass Spectrom. PubMed Iwakami, Y., Takazono, M. & Tsuchiya, T. Thermal decomposition of hexamethylenetetramine. 70, 391 (2005), M. Bakherad, A. Keivanloo, B. Bahramian, M. Hashemi, Tetrahedron Lett. Cody, G. D. et al. Hexamethylenetetramine has been shown to protect human lung cells against SM toxicity and has also been shown to be effective in vivo against phosgene. For prophylactic or suppressive treatment of frequently recurring urinary tract infections when long-term therapy is considered necessary. Kolbasov, Y.A. Shudo Y, Izumi A, Hagita K, Nakao T, Shibayama M. Large-scale molecular dynamics simulation of crosslinked phenolic resins using pseudo-reaction model. After the solid/liquid separation by the centrifugation (10min, 3000rpm), the supernatant liquid phase was recovered; the water-extractable fraction procedures were repeated for three times. Not. Figure2 shows mass chromatograms of the Murchison, Murray, and Tagish Lake meteorites at the mass-to-charge ratio (m/z) of 141.11350.0004, which corresponds to the protonated ion of HMT (i.e., [M+H]+ as [C6H12N4+H]+) formed by electrospray ionization (ESI), analysed by a HPLC equipped with an InertSustain PFP analytical column. Life Sci. Kaur, N., Kishore, D. An insight into hexamethylenetetramine: a versatile reagent in organic synthesis. Macromol Theory Simul. Sabaghiani, M. Bakavoli, M. Ghassemzadehc, K.J. Google Scholar. Kilin, F.V. Trans Faraday Soc. While in Murray, the concentration of HMT (299ppb) is lower than individual amino acid concentrations (512834ppb) in the same meteorite8. Simkus, D. N. et al. 2nd completely rev. ADS Rev. Chem. Experimental evidence for glycolaldehyde and ethylene glycol formation by surface hydrogenation of CO molecules under dense molecular cloud conditions. Its chemical formula is (CH2)6N4. Pepperman, G. Bondreaux, J. Heterocycl. Pascault JP, Sautereau H, Verdu J, Williams RJJ. For sample preparation, D.P.G. Mass peaks attributable to the deuterium (D)-, 13C-, and 15N-substituted isotopologues of HMT were also identified in the mass spectra of the Murchison extract (Supplementary Fig. Hexamethylenetetramine has been used in relatively high doses (2-6 g/day) in the therapy of acute and chronic urinary tract infections. 4e) shows at least three peaks, which might be derived from HMT-CH2OH and its structural isomers methoxy-HMT (HMT-OCH3) and monohydroxy-monomethyl-HMT (HMT-OH(-CH3)) (Fig. J IRAN CHEM SOC 10, 11931228 (2013).
Hexamethylenetetramine ACS reagent, = 99.0 100-97-0 - Sigma-Aldrich All glassware and the quartz wool were cleaned by heating in air at 450C for 3hr. It has a cage-like structure similar to adamantane. ISSN 1349-0540 (online) 1). Naeimi, Chin. Importance of thermal reactivity for hexamethylenetetramine formation from simulated interstellar ices. Still, contrasting experimental results appear in the literature on the microscopic mechanisms leading to high aspect ratio and vertically aligned ZnO NRs. USA 108, 1399513998 (2011). 3). The influence of van der Waals forces and primary bonds on binding energy, strength and orientation, with special reference to some artificial resins. Substance identity. There seems no obvious trend in the concentrations of HMT with glycine, suggesting no obvious correlation in terms of their formation history in each meteorite. Vinogradoff, V. et al. Volatile species in comet 67P/Churyumov-Gerasimenko: investigating the link from the ISM to the terrestrial planets. Though HMT is an infrared active molecule, its detection in the presence of deep NH, CH, and CN bands in ices, as well as the presence of a strong silicate band at 10m, would complicate its definitive identification, so it is also not surprising that it has not yet been observed in interstellar or planetary ices23.
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