6, 239 (2009), R.M. Hexamethylenetetramine | Uses, Dosage, Side Effects, FAQ - MedicinesFAQ Becker, J. Prakt. Petersen, Org. Sci. Perry, S. Orenga, C. Dalbert, A. James, Org. Mon. Article CAS Google Scholar. In up to 7% of the patients who ingested these doses for weeks at a time, reversible side effects such as gastrointestinal symptoms (nausea, vomiting, abdominal cramp) and skin reactions (itching, urticaria . Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. Chem. For sample preparation, D.P.G. Soc. 49, 1160 (2008), A.T. Bottini, V. Dev, J. Org. The images or other third party material in this article are included in the articles Creative Commons license, unless indicated otherwise in a credit line to the material. In: Cohen Addad JP, editor. Properties vapor pressure <0.01 mmHg ( 20 C) Quality Level 200 product line ReagentPlus Assay 99% autoignition temp. Trans Faraday Soc. Schwoegler, H. Adkins, J. J. Gen. Chem. Rep. 10, 7755 (2020). Altwegg, K. et al. (1) Certain bacteria such as Proteus sp. Hexamine, also known as Hexamethylenetetramine, CAS No. Ehrenfreund, P. & Charnley, S. B. Organic molecules in the interstellar medium, comets, and meteorites: a voyage from dark clouds to the earth Earth. 10, 653 (1971), E. Fluck, P. Meiser, Chem. The concentrations of HMT in the three meteorites were 84637, 299, and 6719ppb (parts per billion; ng/g meteorite) for Murchison, Murray, and Tagish Lake, respectively (Table1). Insights into epoxy network nanostructural heterogeneity using AFM-IR. Warning! Chaudhuri, A. Modak, A. Bhaumik, S. Swarnakar, Int. J. 6, 1457 (2006), S.A. Chimatadar, S.V. Chem. Hexamethylenetetramine is cheap, nontoxic, rich in tertiary amine, and with a cage structure. It is possible that differences in the Murchison/Tagish Lake and Murray parent body conditions (e.g. Astrophys. 34, 48 (1972), M. Mihalic, F. Sunjic, P. Mildner, F. Kajfez, Croat. Space Res. Trans Faraday Soc. It is likely that desorption of HMT from asteroids could be induced either or both by external excitation energies (e.g., cosmic rays and ultraviolet photons) and by thermal processes, although these processes have not been studied experimentally so far. 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. Murashova, L.I. Katritzky, Y. Oba, Y., Takano, Y., Naraoka, H. et al. Jugosl. Solomon, H.B. Bull. Thermosetting polymers. This is the first time that the . 51B, 639 (2012), A. Javidan, M.B. Although the composition of products varies depending on the experimental conditions, HMT is generally abundant especially when methanol is used as an initial reactant16,18,20. Proc. Chem. Shibayama M. Spatial inhomogeneity and dynamic fluctuations of polymer gels. Am. 2a) and far above the blank detection level (Supplementary Fig. Chem. Gray, J. Reddy, Y.V.R. (1), You find simplified version here Hexamethylenetetramine, Download Bissoy App to talk Doctor online, Hexamethylenamine, Hexamethylene tetramine, Hexamethylenetetramine, Hexamethylentetramin, Hexamethylentetraminum, Hexamine, Hexaminum, HMTA, metenamina, mthnamine, Methenamine, methenaminum, amoxicillin, doxycycline, ciprofloxacin, cephalexin, ceftriaxone, levofloxacin, Augmentin, amoxicillin / clavulanate, nitrofurantoin, Keflex. 76, 4651 (1954), S.W. Hexamethylenetetramine, 99+%, Thermo Scientific Chemicals - Fisher Sci New York: John Wiley; 1996. pp. Bower, J. One-pot synthesis of amino acid precursors with insoluble organic matter in planetesimals with aqueous activity. 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. 2004;170:1113. Mijovi J, Koutsky JA. A laboratory survey of the thermal desorption of astrophysically relevant molecules. Annu. Ital. Health Hazard SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Meteor. PubMed Central Identifying hexamethylenetetramine in three carbonaceous meteorites, the authors propose formation from ammonia . PubChem Substance ID: 57654228 NACRES: NA.21 Pricing and availability is not currently available. 19, 1136 (2011), W.E. Google Scholar, I.M. Owing to its symmetric tetrahedral structure, HMT does not possess a permanent dipole moment, which precludes its remote observational detection by rotational spectroscopy. 1,2,3-Trihydroxybenzene: hexamethylenetetramine | C12H18N4O3 | CID For prophylactic or suppressive treatment of frequently recurring urinary tract infections when long-term therapy is considered necessary. Chem. Henaff, C.R. Shudo Y, Izumi A, Hagita K, Nakao T, Shibayama M. Large-scale molecular dynamics simulation of crosslinked phenolic resins using pseudo-reaction model. The injected samples were vaporized at 300C. 3, e1602093 (2017). Burke, M.J. Kolbezen, R.J. Reynolds, G.A. Hexamine; Hexaminum. Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula 6N4. Guss, Pharm. The Murchison extract was also analysed using the same HPLC/HRMS equipped with other separation columns: a Hypercarb separation column (2.1150mm, particle size of 5m, Thermo Fischer Scientific)19 at 30C or an InertSustain Amide column (3.0250mm, particle size of 3m, GL Science) at 40C in hydrophilic interaction (HILIC) chromatography mode to confirm that the detection of HMT does not depend on analytical columns (Supplementary Table2). Izumi A, Nakao T, Shibayama M. Synthesis and properties of a deuterated phenolic resin. 20, 56 (2012). Yasuhiro Oba. Chem. Schreiber, J. Liu, M.W. 100-97-0, and chemical formula C6H12N4, is an odorless, white crystalline powder or colorless lustrous crystal. 116, 96319663 (2016). Hexamethylenetetramine (HMTA or hexa) is by far the most important curing agent for novolac. Petersen, Org. Acta 73, 21502162 (2009). https://doi.org/10.1007/s13738-013-0260-2, DOI: https://doi.org/10.1007/s13738-013-0260-2. Chem. Asano A. NMR relaxation studies of elastomers. 143308. Here, we report on CBD of ZnO NRs using Zn nitrate salt and . However, despite extensive studies on the formation of organic molecules in various extraterrestrial environments such as molecular clouds9,10, protosolar nebula11,12, and asteroids13,14,15, it still remains under debate when, where, and how such extraterrestrial molecules were abiotically formed. & Whittet, D. C. B. Observations of the icy universe. Polymer. In the present study, we extracted relatively large portions (masses ranging from 0.5 to 2g) of interior samples of three carbonaceous chondrites, Murchison, Murray, and Tagish Lake, under mild conditions which utilized neither concentrated acidic solutions nor high temperatures for the extraction processes. to the dried substance) 797979 Hexamethylenetetramine, anhydrous, free-flowing, Redi-Dri, ACS reagent, 99.0% 55321 Hexamethylenetetramine The LXD was a minor structure having a cross-link fraction of 0.2, which was 56nm in size and comprised a few meshes. Nitrates, hexamethylenetetramine (HMT), and polyphosphates are the chemicals more commonly used against clostridia in cheese technology. The final fraction was dissolved in ~1mL of ultra-pure H2O and filtered by 0.20m PTFE cartridge filter just before the HRMS. Chem. 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. 1, 540550 (2017). Polym J. 6). 1990;23:224551. Chem. J. Chem. Hexamethylenetetramine, also known as methenamine, is one a preservative commonly used in various food, medical, and cosmetic applications. Hexamethylenetetramine, also known as methenamine, is a white crystalline heterocyclic organic compound that is highly solubi.in water and polar organic solvents. Rozenberg, G.V. 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. It has a cage-like structure similar to adamantane. 73, 4122 (1951), S. Liangwei, Y. Menglong, Z. Yazhu, Q. Guangming, L. Jian, Z. Liu, S.M. J. Ph. Annu Rep NMR Spectrosc. Bakhtiari, Chin. Soc. Astrophys. PubMed New York: John Wiley; 1996. pp. 321, 423 (1988), A.I. 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. (1), 70-90% of a single oral dose of methenamine is excreted unchanged in the urine within 24 hours. Deuterium fractionation upon the formation of hexamethylenetetramines through photochemical reactions of interstellar ice analogs containing deuterated methanol isotopologues. 106, 69 (1973), 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). The authors declare no competing interests. ISSN 1349-0540 (online) Methenamine: Uses, Interactions, Mechanism of Action | DrugBank Online temperature, water/rock ratio, etc.) Previous studies detected both molecules from carbonaceous meteorites after hydrothermal treatment and/or acid hydrolysis of meteorite powders at ~100C or above30,31,32, implying that both free ammonia and formaldehyde are released from their acid-labile precursors after these treatments. Meteor. The crystalline compound is also used as a reagent in organic chemistry, a food additive as a preservative, and as the base component in the manufacture of certain explosives. 54, 12831302 (2019). Am. 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). J Polym Sci, Part B: Polym Phys. Motsarev, V.J. Mass Spectrom. 3, 17921811 (2019). SAFETY DATA SHEET - Fisher Sci Cosmochim. CAS 73, 2777 (1951), V.I. Acta 48, 125 (1976), K. Ishizumi, K. Mori, Y. Komeno, J. Katsube, H. Yamamoto, Japanese Patent, (1977) 7739690, C.A. J Appl Polym Sci. 15,18), it should have more opportunity to be incorporated into inner solar system bodies. 5). Google Scholar. 77, 375 (1947), W.J. 1252, 7 (1975), A. Adejare, S. Sun, Curr. Natl Acad. 454, 327344 (1995). CAS the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Dzhagatspanyan, Zh. 2015;86:172. Urex (methenamine hippurate) is a urinary tract antiseptic drug used to treat and prevent urinary tract infections. Soc. Astrophys. Life Sci. 634, 5359 (2015). Muoz Caro, G. M. et al. Hexamethylenetetramine is also used to associated treatment for these conditions: Urinary Tract Infection, Hexamethylenetetramine does not have antibacterial properties in an alkaline environment (pH6); however, in a more acidic environment (pH<6), methenamine is hydrolyzed to formaldehyde. Dilley, Org. Am. 413, 209216 (2004). 47, 427480 (2009). Structure of gels as investigated by means of static scattering techniques. Hexamethylenetetramine - 1,3 - MilliporeSigma Groundwater, Y. Huang, J.D. The observed consistency in the fragmentation pattern of HMT by MS/MS experiments (see the Methods section) between the Murchison extract and the standard reagent further supports the above conclusion (Fig. Hexamethylenetetramine Electrochemical measurement 1. 74, 5524 (1952), P. Rajakumara, R. Padmanabhan, ARKIVOC, vi (2012) 155, P. Galimberti, C. Erba, Gazz. & Kobayashi, K. Molecular evolution during hydrothermal reactions from formaldehyde and ammonia simulating aqueous alteration in meteorite parent bodies. Khim. Pizzarello, S. & Holmes, W. Nitrogen-containing compounds in two CR2 meteorites: 15N composition, molecular distribution and precursor molecules. Meteor. Product name : Hexamethylenetetramine Product Number Brand Index-No. Planet. 27B, 218 (1949), W.J. This white crystalline compound is highly soluble in water and polar organic solvents. Google Scholar. Bracca, T.S. The pretreatment eliminates HPLC/ESI-Orbitrap-MS potential artefacts including a chromatographic retention shift27,47, ion suppression and ion-enhancement effect48,49. Soc. J. Zeng, J.Y. 2, 317323 (2018). 23, 411467 (2002). Note that monohydroxy-monomethyl-HMT possesses three structural isomers depending on the positions of the two functional groups. 11, 1085 (1974), H.E. We are using cookies to give you the best experience on our website. Thyagarajan, J. Heterocycl. Details of the supplier of the safety data sheet Company This study was conducted as part of the research activities of the Special Interest Group on Thermosetting Resins in the FSBL Consortium comprising the Asahi Kasei research group, the DENSO research group, and the Sumitomo Bakelite research group. The 67 digit numbers in the mass spectra indicate the exact masses of the parent molecule (C6H13N4: the protonated ion of HMT) and its fragments). Hexamethylenetetramine Write a review ACS reagent, 99.0% Synonym (s): 1,3,5,7-Tetraazatricyclo [3.3.1.13,7]decane, Hexamine, Methenamine, Urotropine Empirical Formula (Hill Notation): C6H12N4 CAS Number: 100-97- Molecular Weight: 140.19 Beilstein: 2018 EC Number: 202-905-8 MDL number: MFCD00006895 PubChem Substance ID: 24864723 Petrunin, M.T. 42, 2528 (1969), Department of Chemistry, Banasthali University, Banasthali, Jaipur, 304022, Rajasthan, India, You can also search for this author in Sci. Natl Acad. About 100L of the stock solution was transferred to a sample tube (~3cm in length, 6mm in diameter) made with pure Au whose one side had been tightly crimped by hand pliers. Fischer, E. Eibler, W. Wiegrebe, Arch. Mallet, C. R., Lu, Z. Sci. 338, 47 (1996), E. Kessler, Monatsh. Its chemical formula is (CH2)6N4. Antonova, Coord. The recovery of HMT was measured using its standard reagent to be >90%. The flow rate was 0.3mLmin1. Rev. Though the typical interstellar values (e.g., D/H ratio 0.01)33 are far higher than seen in any meteoritic compound. Kaufman, Org. CAS Bastide J, Candau SJ. Moreover, sample heterogeneity between different specimens of the same meteorite, which has been often invoked for explaining different quantitative results of some molecules including their different enantiomeric distributions in the same meteorites4, can also be invoked. Radwan, A.M.K. Houwink R. The strength and modulus of elasticity of some amorphous materials, related to their internal structure. ADS 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. Long, A.L. The fraction was then frozen and dried up by a vacuum freeze dryer (EYELA Co., Ltd) under ambient temperature. Environ. Supplementary Figs. The negligible amounts of HMT in the blank and control samples (see the Methods section) compared to the elevated concentrations of HMT measured in the meteorite extracts argue that HMT is indigenous to the meteorites. J. your institution. 24, 23172323 (2010). (1) Formaldehyde has nonspecific antibacterial activity and works by denaturing proteins and nucleic acid of bacteria. PubMed 49, 49 (2011), H.E. Tax calculation will be finalised during checkout. Chem. and JavaScript. Peer review information Nature Communications thanks Vassilissa Vinogradoff, David Bekaert and the other, anonymous, reviewer(s) for their contribution to the peer review of this work. Article SAFETY DATA SHEET Revision Date 05/24/2023 Version 6 - Sigma-Aldrich 1, Supplementary Fig. Khim. 70, 1555 (1948), J. Hartough, Am. 81 (1974) 120 788, D.J. Administration of 1 g twice daily produces continuous antibacterial activity in the urine. Chem. 1998;199:130. Majumdar, U. Das, U.K. Kundu, A. Bandyopadhyay, Tetrahedron 57, 7003 (2001), G. Kaupp, K.J. You can find out more about which cookies we are using or switch them off in settings. mthnamine. (S), 2, 154 (1998), M.M. 58, 544 (2011), K.C. 551, A128 (2013). Daigle, A.B. 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. 38, 261 (2004), L.H. Bills, J. Chem. 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. Soc. Extraterrestrial ribose and other sugars in primitive meteorites. Experimental evidence for glycolaldehyde and ethylene glycol formation by surface hydrogenation of CO molecules under dense molecular cloud conditions. Int. 81, 502 (1959), H. Fieser, J. Acta 269, 150166 (2020). Siele, M. Warman, E.E. 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. formula: C6H12N4. For Murchison and Murray, the presence of alkyl-imidazoles was strongly expected in their extracts; while, they were significantly depleted in Tagish Lake (Supplementary Figs. 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 Introduction Acid solutions are commonly used in industry, the most imported field of practice being acid pickling, acid cleaning, acid decaling and oil well acidizing [1], [2], [3]. According to the harmonised classification and labelling (ATP01) approved by the European Union, this substance is a flammable solid and may cause an allergic skin reaction. Chang, ARKIVOC xvi, 113 (2007), B. Cekavicus, B. Vigante, E. Liepinsh, R. Vilskersts, A. Sobolev, S. Belyakov, A. Plotniece, K. Mekss, G. Duburs, Tetrahedron 64, 9947 (2008), T.B. Accumulation is not observed. Baumgarten, F.A. CAS Chem. 859, 142 (12pp) (2018). volume10,pages 11931228 (2013)Cite this article. Hexamethylenetetramine, for synthesis 15614 Hexamethylenetetramine, meets analytical specification of Ph. Chem. Earth Planet. PubMedGoogle Scholar. Bowey, J. E., Adamson, A. J. 30, 524 (1965), K.K.C. 54, 220228 (2019). 354, 11331140 (2004). Correspondence to Large quantities of hexamine are used in the foundry, tire and rubber, and phenolformaldehyde resins industries and in other diverse applications. Planet. Very tiny amount of HMT was detected in the soil extract with the HMT concentration of 2ppb, which was <0.5% of the indigenous HMT concentration in the Murchison meteorite extract. Rapid Commun. 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. Astron. HMT was successfully detected from Murchison, Tagish Lake, and Murray meteorite extractsat parts-per-billion levels. Extraterrestrial hexamethylenetetramine in meteoritesa precursor of prebiotic chemistry in the inner solar system. Jpn 70, 520 (1950), B.P. 41, 82 (1961), E.J. Astron. It acts as an anti-infective agent which is most commonly used to treat urinary tract infections. Biomol. J. Chem. Hexamine, also known as Hexamethylenetetramine, CAS No. Book Chim. Sci. Under these experimental conditions, the mass precision is always better than 3ppm for each chromatogram (e.g., 141.11350.0004 for protonated HMT). Hexamethylenetetramine-d12 | C6H12N4 | CID 12224935 - PubChem
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hexamethylenetetramine uses