9, 531 (1972), C. Dauth, H.G.O. Chem. Chem. Shudo Y, Izumi A, Hagita K, Nakao T, Shibayama M. Large-scale molecular dynamics simulation of crosslinked phenolic resins using pseudo-reaction model. Albers, R. Karmacharya, E. Koh et al., Transpl. & Bada, J. L. Extraterrestrial organic compounds in meteorites. 1990;23:224551. Planet. Antonova, Coord. Earth Planets Space 68, 7 (2016). Botta, O. Chem. Soft Matter. 34, 48 (1972), M. Mihalic, F. Sunjic, P. Mildner, F. Kajfez, Croat. 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. hexamethylenetetramine, 1,3,5,7-tetraazaadamantane; Cohedur H 30; Hexamethylene-tetramine cation Hexamethylene-tetramine dication. 4, 237 (2011), L. Campaigne, J. 547, 276 (1945), P.L. Commun. 45, 19481972 (2010). Rev. Chem. The final fraction was dissolved in ~1mL of ultra-pure H2O and filtered by 0.20m PTFE cartridge filter just before the HRMS. J. Chem. Chemistry Amines Hexamine Hexamine - C6H12N4 What is Hexamine? Unusual nonterrestrial l-proteinogenic amino acid excesses in the Tagish Lake meteorite. Methenamine: Uses, Interactions, Mechanism of Action | DrugBank Online 69, 1053 (2004), B. Liang, M. Dai, J. Chen, Z.J. Network structure evolution of a hexamethylenetetramine-cured phenolic berg, K. I. Photochemistry and astrochemistry: photochemical pathways to interstellar complex organic molecules. volume51,pages 155160 (2019)Cite this article. Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases. Soc. By submitting a comment you agree to abide by our Terms and Community Guidelines. The flow rate was 0.1mLmin1. Rozenberg, G.V. Macromolecules. Strictly Necessary Cookie should be enabled at all times so that we can save your preferences for cookie settings. CAS 2018;27:1700103. Soc. 15,18), it should have more opportunity to be incorporated into inner solar system bodies. Gardziella A, Pilato LA, Knop A. Phenolic resins: Chemistry, applications, standardization, safety and ecology. 106, 69 (1973), S.S. Kumar, F.M.I. 2, 1280 (2011), S.S. Kumar, F.M.I. Mass fragmentation patterns of hexamethylenetetramine (HMT) in a the standard reagent and b the Murchison extract measured by MS/MS experiments (see the Methods section). Internet Explorer). and J.P.D. volume11, Articlenumber:6243 (2020) Duchet J, Pascault JP. Kolbasov, Y.A. ACS Earth Space Chem. Med. 55, 1156 (2008), E.V. Correspondence to 73, 5989 (2008), S.J. Talanta 179, 238245 (2018). Since HMT is susceptible to degradation by 100C water15 and acid hydrolysis methods19 traditionally used in meteoritic soluble organic analyses4; a different method to extract HMT from meteorites was developed. The mass peak assigned to C7H11 (m/z=95.0856) is a background signal on the LC condition. Patil, S.D. Ingestion of a 1-gram dose of methenamine hippurate produces antibacterial activity in the urine within 1/2 hour. Article Hexamethylenetetramine, 99+%, Thermo Scientific Chemicals - Fisher Sci Madawale, S.T. It . J IRAN CHEM SOC 10, 11931228 (2013). Soc. Besides the lack of astronomical detection, there has also been no report on the detection of HMT in any extraterrestrial materials including carbonaceous meteorites, interstellar dust particles, and cometary return samples. Oba, Y. et al. Soc. Pascault JP, Sautereau H, Verdu J, Williams RJJ. Hexamethylenetetramine = Hexamine = Methenamine = HMTA. Hexamine, also known as Hexamethylenetetramine, CAS No. Lett. Y.T., Y.F. 3, 617 (2011), S.O. The LXD was a minor structure having a cross-link fraction of 0.2, which was 56nm in size and comprised a few meshes. Bachmann, N.C. Deno, J. Chem. Jpn. 10, 4413 (2019). Chem. 38, 261 (2004), L.H. Experimental evidence for glycolaldehyde and ethylene glycol formation by surface hydrogenation of CO molecules under dense molecular cloud conditions. Soc. The exterior surfaces of these meteorite samples were independently washed by 0.1M HCl solution (water was qTOF grade, Fujifilm Wako Co. Ltd) with a soak (3min at ambient temperature) and gentle ultra-sonication (0.5min, <38kHz by double glass containers) to peel the meteoritic surface layer, and the supernatant was removed. Adv. & Kobayashi, K. Molecular evolution during hydrothermal reactions from formaldehyde and ammonia simulating aqueous alteration in meteorite parent bodies. Piani, L., Yurimoto, H. & Remusat, L. A dual origin for water in carbonaceous asteroids revealed by CM chondrites. Bastide J, Candau SJ. Polym J. ACS Appl Mater Interfaces. It is reasonable that ISM-derived HMT would be highly D-enriched19. These mass peaks can be assigned to other species or fragments, which are not related to HMT, coexisting in the Murchison extract. Nevertheless, there are still a number of uncertainties on the origin of the difference in HMT abundance between three meteorites analysed in the present study (e.g. 1936;32:1037. These results do not contradict the assumption that Tagish Lake, at least the specimen used in the present study, could have experienced less extensivehydrothermal alteration than Murchison and Murray on their parent bodies. 30, 14811488 (2002). Cookie information is stored in your browser and performs functions such as recognising you when you return to our website and helping our team to understand which sections of the website you find most interesting and useful. Schreiber, J. Liu, M.W. Atsushi Izumi or Mitsuhiro Shibayama. Khim. 2016;103:26176. 2015;59:22633. analysed the sample. Once HMT is incorporated into planetary systems and into a meteorite parent body, it has three likely fates: (1) physicochemical desorption from the surface of asteroids into the gas phase of the solar system, (2) decomposition, and (3) preservation. Chem. ODonnell, A.C. Flick, J. Li, Bioorg. Zaytsev, R.J. Anderson, A. Bedernjak, P.W. CAS The final elution containing HMTs was dried by a vacuum freeze dryer (EYELA Co., Ltd) under ambient temperature. Astrophys. Jpn 70, 520 (1950), B.P. Hazard classification & labelling. Correspondence to Article The m/z=171.1240 trace (Fig. Do epoxy-amine networks become inhomogeneous at the nanometric scale? Geochim. Rev. Synchrotron Radiat News. One-pot synthesis of amino acid precursors with insoluble organic matter in planetesimals with aqueous activity. R. Astron. Urex is available in generic form. 113, 87838839 (2013). Chem. It is also called Methenamine, Hexamethylenetetramine or Urotropin. Yasuhiro Oba. 531, 116011 (2020). The similar consistency was also observed when the sample was analysed under different analytical conditions where Hypercarb or InertSustain Amide was used as a separation column for HPLC analysis (see the Methods section and Supplementary Table1). Hexamethylenetetramine - an overview | ScienceDirect Topics Eddhif, B. et al. 2004;170:1113. This work was supported by the Photon and Quantum Basic Research Coordinated Development Program by MEXT with the grant number 13004017. Izumi A, Shudo Y, Nakao T, Shibayama M. Cross-link inhomogeneity in phenolic resins at the initial stage of curing studied by 1H-pulse NMR spectroscopy and complementary SAXS/WAXS and SANS/WANS with a solvent-swelling technique. Burke, M.J. Kolbezen, R.J. Reynolds, G.A. Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula (CH 2) 6 N 4. The extracted positive ions m/z 141.110.2 were reacted with high-energy (30 in arbitrary unit) collision N2 gas to produce fragmental ions, in which the mass range of m/z 50160 was monitored using an Orbitrap MS with a mass resolution of ~140,000. ACS Earth Space Chem. 18, 3787 (2008), B. Ahmad, M. Rashid, A. Husain, R. Mishra, Ind. Development of liquid chromatography high resolution mass spectrometry strategies for the screening of complex organic matter: application to astrophysical simulated materials. CAS 49, 49 (2011), H.E. Anyone you share the following link with will be able to read this content: Sorry, a shareable link is not currently available for this article. Chem. 77, 375 (1947), W.J. Chem. Google Scholar. Shibayama M. Structure-mechanical property relationship of tough hydrogels. A key molecule to solve the problem, hexamethylenetetramine (HMT) has not been confirmed in extraterrestrial materials despite extensive laboratory experimental evidence that it can be produced in interstellar or cometary environments. Shankaran, S.B. Naeimi, Chin. Also, small levels of fluctuation in the retention time are caused by variations in daily conditions of the liquid chromatograph. For the Tagish Lake and Murray meteorites, we were unable to perform MS/MS measurements due to the low concentration of HMT in the extracts. contracts here. 27, 01 (2009), W. Brown, C. Foote, Organic Chemistry, 3rd edn. Hexamethylenetetramine is a versatile reagent in organic synthesis. Internet Explorer). Sci. SAFETY DATA SHEET Revision Date 05/24/2023 Version 6 - Sigma-Aldrich Takahara A, Takeda T, Kanaya T, Kido N, Sakurai K, Masunaga H, et al. Petrunin, M.T. and D.P.G. We also observed several peaks with the m/z values well consistent with the HMT derivatives methyl-HMT (HMT-CH3), amino-HMT (HMT-NH2), hydroxy-HMT (HMT-OH), and hydroxymethyl-HMT (HMT-CH2OH), (Fig. 1999;71:699712. Planet. 6, 682 (2008), S.R. Pharm. (London), 7, 1067 (1976), P. Sharma, B. Vashistha, R. Tyagi, V. Srivastava, M. Shorey, B. Singh, D. Kishore, Int. HMT abundance when each parent body is formed by accretion). It is also used in the medical profession for the treatment of urinary tract infections. Hexamethylenetetramine is a versatile reagent in organic synthesis. The concentration of HMT in Murchison (84637 ppb) is within the range of individual water-extractable and acid-produced amino acids (2005000ppb)26 and higher than that of sugars (<180ppb) and nucleobases (<~70ppb) in the Murchison meteorite5,6. You are using a browser version with limited support for CSS. Acad, Sci. Soc. Space Res. Chem. 70, 1555 (1948), J. Hartough, Am. Provided by the Springer Nature SharedIt content-sharing initiative. Sci. Meteor. UV-photoprocessing of interstellar ice analogs: detection of hexamethylenetetramine-based species. the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Motsarev, V.J. 3a). Hexamethylenetetramine ReagentPlus , 99 100-97-0 - MilliporeSigma The addition of . Mon. Astrophys. Sakya, C.J. Article Based on the retention time and mass accuracy (within 3ppm of the theoretical m/z), even under the different analytical conditions, the observed peak can be confidently assigned to HMT. Sailer, Prakt. Sci. 3). Uses advised against Food, drug, pesticide or biocidal product use. Gang, Chin. Soc. J Polym Sci, Part B: Polym Phys. Kilin, F.V. Chem. We have confirmed that the loss of HMT is negligible (see the Methods section) and that there is no hydrogen isotopic fractionation of HMT during our analytical procedure (Supplementary Fig. It may cause corrosion of the respiratory tract. Based on laboratory experiments simulating photochemical and thermal reactions of interstellar and cometary ice analogues (at ~10K) initially made of observed molecules, such as water (H2O), ammonia (NH3), and methanol (CH3OH), HMT is in general a significant product (up to 60% by weight) in the total organic products16,17,18,19,20. Bekaert, D. V. et al. Astrophys. Chem. Mol. The collisions of high-energy N2 with the protonated HMT ion (m/z 141.1135) gave two major fragmental ions; C5H10N3+ (m/z 112.0869) and C4H9N2+ (m/z 85.0761), as well as its non-fragmented parent ion (m/z 141.1135, Fig. All glassware and the quartz wool were cleaned by heating in air at 450C for 3hr. Large quantities of hexamine are used in the foundry, tire and rubber, and phenolformaldehyde resins industries and in other diverse applications. Hexamethylenetetramine - ScienceDirect.com The solvent extraction blank analysis with ultra-sonication procedure was performed using 2g of combusted quartz sand45 through the same extraction process to verify the potential impurity in the meteorite extracts. Acta 73, 21502162 (2009). Siele, M. Warman, E.E. 100-97-0, and chemical formula C6H12N4, is an odorless, white crystalline powder or colorless lustrous crystal. Astrophys. Google Scholar, D.J. Wu WL, Shibayama M, Roy S, Kurokawa H, Coyne LD, Nomura S, et al. Hence, the presence of HMT in carbonaceous meteorites promises its pivotal role to carry interstellar prebiotic precursors to the inner solar system, which should contribute to the chemical evolution in the primordial stage on Earth. Med. Icarus 347, 113827 (2020). Reddy, Y.W. Pepperman, S.L. Vinogradoff, V. et al. Organic compounds produced by photolysis of realistic interstellar and cometary ice analogs containing methanol. 1985;26:10537. Samant, Tetrahedron Lett. 70, 391 (2005), M. Bakherad, A. Keivanloo, B. Bahramian, M. Hashemi, Tetrahedron Lett. Vinogradoff, V., Bernard, S., Le Guillou, C. & Remusat, L. Evolution of interstellar organic compounds under asteroidal hydrothermal conditions. Glavin, D. P. et al. We set up an inverse gradient programme to maintain the ionization efficiency during the ESI. 6, 584 (1936), A.R. 1) in the mass chromatograms at the m/z of 155.1291, 156.1244, 157.1084, and 171.1240, respectively, as each protonated ion formula in Murchison (Fig. 413, 209216 (2004). 70, 83 (1998), J. It plays a major role in modern organic synthesis. Sci. 53, 541581 (2015). 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). Am. Google Scholar. The eluent programme for Hypercarb is as follows: at t=0, solvent A (water), solvent B (acetonitrile+0.1% formic acid)=100:0, followed by a linear gradient of A:B=80:20 at t=20min and it was kept at this ratio for 5min. 49, 1160 (2008), A.T. Bottini, V. Dev, J. Org. Murashova, L.I. After the headspace of the tube was purged with dry N2 gas, the other side was also crimped, and the sample tube was heated at 100C for up to 31 days using an autoclave (MMS-50, OM Labotec, Japan). Mechanical properties and inhomogeneous nanostructures of dicyandiamide-cured epoxy resins. New York: Oxford University Press; 2000. This review focuses on hexamine reagent for its significant role in organic synthesis during the past decades and is able to provide a valuable perspective from synthetic point of view. Vinogradoff, V. et al. For sample preparation, D.P.G. Kshirsagar, N.R. 11, 407 (1974), Article Petersen, Org. (lit.) J. Res. Annu Rep NMR Spectrosc. Annu. We thank Prof. Akira Tsuchiyama (Ritsumeikan University) for providing amorphous forsterite powder, Dr. Minako Hashiguchi (Nagoya University) for her technical advice on the sample analysis by the Orbitrap MS. Prof. Akira Kouchi and Prof. Naoki Watanabe (ILTS, Hokkaido University) are acknowledged for the discussion on the formation of HMT in interstellar environments. Learn more about Institutional subscriptions, M. Fatehi, J. Ethnopharmacol. Article Mass Spectrom. Hexamine; Hexaminum. 24, 23172323 (2010). Excretion of the orally administered substance takes place largely in the urine (up to 80 % within 3 hours). Exposure may cause skin rash and kidney irritation. Angyal, R.C. Chem. A key molecule to solve the problems is hexamethylenetetramine (HMT; C6H12N4; monoisotopic mass of 140.1062Da), which is a polyheterocyclic organic molecule (Fig. Bower, J. For example, Supplementary Fig. Supplementary Figs. The recovery of HMT was measured using its standard reagent to be >90%. and JavaScript. Cosmochim. Hexamethylenetetramine: a review Then, the sample followed an organic solvent soak (3min at ambient temperature) by dichloromethane/methanol (50:50, v/v) with gentle ultra-sonication (0.5min, <38kHz by double glass container). Polymer. 98, 1512 (1967), N. Blazevic, V. Sunjic, I. Crvelin, D. Kolbah, F. Kajfez, J. Heterocycl. PubMedGoogle Scholar. Chem. Ehrenfreund, P. et al. Khim. Sabaghiani, M. Bakavoli, M. Ghassemzadehc, K.J. HEXAMETHYLENETETRAMINE | CAMEO Chemicals | NOAA Typically, about 10% of hexa will be added to novolac. Kaur, N., Kishore, D. An insight into hexamethylenetetramine: a versatile reagent in organic synthesis. Natl Acad. Correspondence to This review focuses on hexamine reagent for its significant role in organic synthesis during the past decades and is able to provide a valuable perspective from synthetic point of view. The flammable solid has a cage-like structure similar to adamantine. Vail, J. Heterocycl. Chute, D.C. Astrophys. Natl Acad. Hexamethylenetetramine is a urinary tract antiseptic and antibacterial drug used for the prophylaxis and treatment of frequently recurring urinary tract infections requiring a long-term therapy. 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. (1). Mohamed, Int. Astron. Astrophys. Chem. 25, 223 (1975), S.L. In salt form it is used for the treatment of urinary tract infection (Example: methenamine hippurate which is the hippuric acid salt of methenamine). The mass peak assigned to C7H11 (m/z=95.0856) is a background signal on the LC condition. Berlin: Springer; 1999. de Boer JH. Becker, J. Prakt. Life Sci. Sci. Hexamethylenetetramine, also known as methenamine, is a white crystalline heterocyclic organic compound that is highly solubi.in water and polar organic solvents. USA 108, 1399513998 (2011). For prophylactic or suppressive treatment of frequently recurring urinary tract infections when long-term therapy is considered necessary. 1998;199:130. Am. Ehrenfreund, P. & Charnley, S. B. Organic molecules in the interstellar medium, comets, and meteorites: a voyage from dark clouds to the earth Earth. 1). Furness, J. Chem. Hexamethylenetetramine has been used in relatively high doses (2-6 g/day) in the therapy of acute and chronic urinary tract infections. Prikl. Am. https://doi.org/10.1038/s41428-018-0133-8, DOI: https://doi.org/10.1038/s41428-018-0133-8. 5) indicates that these are likely not formed during workup or clusters or N-functionalizations formed by ESI and so should be indigenous to the meteorite samples. 2014;27:1923. 3, e1602093 (2017). Pharm. Vinogradoff, V. et al. The mass chromatogram was shown in the Supplementary Fig. 143308. 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. Solomon, H.B. Proc. Sci. Chem. Multipurpose soft-material SAXS/WAXS/GISAXS beamline at SPring-8. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. Oba, Y. et al. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edn. Shenoy, P.R. Analytical details have been reported in Oba et al. Engl. 827, L18 (2016). Google Scholar, I.M. Google Scholar. Int. Am. Hexamine, also known as Hexamethylenetetramine, CAS No. 2015;86:172. Google Scholar. Paris 253, 2706 (1961), CAS Bai SJ. Daigle, A.B. Yet, it is still possible that the HMT detected has an interstellar provenance and the ISM D was lost to exchange with comparatively D-poor parent body fluids. Rep. 7, 636 (2017). 30, 524 (1965), K.K.C. 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. Dilley, Org. Iwakami, Y., Takazono, M. & Tsuchiya, T. Thermal decomposition of hexamethylenetetramine. 810 show mass chromatograms of each meteorite extract at the m/z values corresponding to imidazole (C3H4N2; monoisotopic mass of 68.0374Da) and its alkyl-substituted homologues (up to seven carbon chains), which are proposed as the products after the hydrothermal degradation of HMT15. Chem. 2nd completely rev. Soc. Astron. This work is dedicated to the late Prof. Akira Shimoyama, a pioneer of organic cosmochemistry in meteorites. Hexamethylenetetramine | Uses, Dosage, Side Effects, FAQ - MedicinesFAQ Journal of the Iranian Chemical Society Soc. Bull. Hexamethylenetetramine is used as a formylation agent in the synthesis and as a precipitating agent. 3, 17921811 (2019). Technol. Glavin, D. P., Callahan, M. P., Dworkin, J. P. & Elsila, J. E. The effects of parent body processes on amino acids in carbonaceous chondrites. The available literature hexamethylenetetramine (hexamine) was reviewed with emphasis on its toxicology and epidemiology, its thermal decomposition and regulatory concerns related to its uses. Hexamethylenetetramine - Wikiwand Double Role of HMTA in ZnO Nanorods Grown by Chemical Bath Deposition Jacobsen, L. Deng, Y. Furukawa, L.E. The SAXS experiments were conducted at the second hutch of SPring-8 BL03XU (Frontier Softmaterial Beamline (FSBL)) constructed by the Consortium of Advanced Softmaterial Beamline with the proposal numbers 2017A7209 and 2017B7261. Safin, R.V. NMR and statistical structures of gels. Peer reviewer reports are available. Meyers, J.S. 2011;49:49417. Methenamine; methenaminum . Houwink R. The strength and modulus of elasticity of some amorphous materials, related to their internal structure. Astron. Muoz Caro, G. M. & Schutte, W. A. UV-photoprocessing of interstellar ice analogs: new infrared spectroscopic results. Furukawa, Y. et al. & Mazzeo, J. R. A study of ion suppression effects in electrospray ionization from mobile phase additives and solidphase extracts. Acta 58, 55795587 (1994). 2a. ADS Astrophys. Hexamethylenetetramine is a urinary tract antiseptic and antibacterial drug used for the prophylaxis and treatment of frequently recurring urinary tract infections requiring a long-term therapy. Hexamethylenetetramine is used in the synthesis of other chemical compounds such as plastics, pharmaceuticals, and rubber additives. We confirmed that no HMT was identified in this process. Hexamethylenetetramine-D12. wrote the paper. USA 108, 1917119176 (2011). CAS Chem. Biomol. (1) Formaldehyde is considered to be highly bactericidal. Downing, A.F. Although H2CO and NH3 are two significant components in interstellar ices3, which are mainly formed by the hydrogenation of CO and N atoms, respectively9, due to their low desorption temperatures from interstellar grains (<100K)41,42, unless transformed into other (non-volatile) species by chemical reactions, both molecules are likely to be lost from grains during warming up phases toward star formation if the temperature of the grains exceeds the desorption temperature of both molecules. 76, 1304 (2006), N. Blazevic, D. Kolbah, Synthesis, 3, 161 (1979), D.J. Boogert, A. C. A., Gerakines, P. A. Cody, G. D. et al. R. Astron. 2, 317323 (2018). J Polym Sci, Part B: Polym Phys. Chem. To remove inorganic salts and interfering organic matrix from the extracts, we isolated the HMT fraction using the cation exchange chromatography (AG50W-X8 resin, Bio-Rad Laboratories)46. PubMed Ber. It is also used in the production of phenolic resins and its moulding compounds, which finds application as binders in fire proof materials, brake and clutch linings. Corporate Engineering Center, Sumitomo Bakelite Co., Ltd., 2100 Takayanagi, Fujieda, Shizuoka, 426-0041, Japan, Neutron Science Laboratory, Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba, 277-8581, Japan, You can also search for this author in Note: the mass peak at the m/z of 68.9352 in the Murchison extract could not be successfully assigned to any ions under the assumption that the ion is composed of C, H, N, and O. Hexamethylenetetramine - 1,3 - MilliporeSigma Hexamethylentetraminum. 2, e1600285 (2016). Chem. Oba, Y., Takano, Y., Watanabe, N. & Kouchi, A. Deuterium fractionation during amino acid formation by photolysis of interstellar ice analogs containing deuterated methanol. Kebukawa, Y. et al. Shibayama M. Small-angle neutron scattering on polymer gels: phase behavior, inhomogeneities and deformation mechanisms. temperature, water/rock ratio, etc.) 354, 11331140 (2004). The reaction can be conducted in gas phase and in solution. In contrast, since solid HMT does not desorb from grains even at 330K (refs. We are using cookies to give you the best experience on our website. 100-97-0, and chemical formula C 6 H 12 N 4, is an odorless, white crystalline powder or colorless lustrous crystal. Unknown: aspirin, aspirin, duloxetine, duloxetine, apixaban, apixaban, polyethylene glycol 3350, polyethylene glycol 3350, mirabegron, mirabegron, levothyroxine, levothyroxine, acetaminophen, acetaminophen, cyanocobalamin, cyanocobalamin, ascorbic acid, ascorbic acid, cholecalciferol, cholecalciferol, After oral administration, rapid absorption of methenamine occurs. Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula (CH2)6N4. Google Scholar. J. Res. ADS 2012;8:80308. Rev. Rev. Astron. Hexamethylenetetramine, also known as methenamine, is one a preservative commonly used in various food, medical, and cosmetic applications. Callahan, M. P. et al. Its chemical formula is (CH2)6N4. 298, 131138 (1998). Methods of X-ray and neutron scattering in polymer science. Hexamethylenetetramine-d12 | C6H12N4 | CID 12224935 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological . Relationships between stoichiometry, microstructure and properties for amine-cured epoxies. Adv Polym Sci. 1 Toxic Effects and Modes of Action In man, hexamethylenetetramine is absorbed rapidly from the gastrointestinal tract. While in Murray, the concentration of HMT (299ppb) is lower than individual amino acid concentrations (512834ppb) in the same meteorite8. Am. The influence of van der Waals forces and primary bonds on binding energy, strength and orientation, with special reference to some artificial resins. 2, 28 (2012), A.N. 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. Institute of Low Temperature Science (ILTS), Hokkaido University, N19W8, Kita-ku, Sapporo, Hokkaido, 060-0189, Japan, Biogeochemistry Research Center (BGC), Japan Agency for Marine-Earth Science and Technology (JAMSTEC), 2-15 Natsushima, Yokosuka, Kanagawa, 237-0061, Japan, Department of Earth and Planetary Sciences, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, Fukuoka, 819-0395, Japan, Research Center for Planetary Trace Organic Compounds (PTOC), Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, Fukuoka, 819-0395, Japan, Department of Earth Science, Tohoku University, Sendai, 980-8578, Japan, Solar System Exploration Division, National Aeronautics and Space Administration (NASA), Goddard Space Flight Center (GSFC), Greenbelt, MD, 20771, USA, UTokyo Organization for Planetary and Space Science (UTOPS), University of Tokyo, 7-3-1 Hongo, Tokyo, 113-0033, Japan, Institute of Space and Astronautical Science (ISAS), Japan Aerospace Exploration Agency (JAXA), 3-1-1 Yoshinodai, Sagamihara, Kanagawa, 252-5210, Japan, You can also search for this author in We confirmed the weight of the sample tube did not change after heating, which indicated effectively no sample loss from the tube. 770 F mp 280 C (subl.) Soc. Kebukawa, Y., Kilcoyne, A. L. D. & Cody, G. D. Exploring the potential formation of organic solids in chondirtes and comets through polymerization of interstellar formaldehyde.