Compound: methenamine
SMILES: N12CN3CN(C1)CN(C2)C3
InChIKey: VKYKSIONXSXAKP-UHFFFAOYSA-N
Synonyms: methenamine, Hexamethylenetetramine, 100-97-0, Hexamine, Urotropine, Urotropin, 1,3,5,7-Tetraazaadamantane, Uritone, HMTA, Hexamethylenamine, Formamine, Hexamethylene tetramine, Methenamin, Ammoform, Cystamin, Cystogen, Ammonioformaldehyde, Formin, Aceto HMT, Hexamethylenetetraamine, Aminoformaldehyde, Preparation AF, Antihydral, Duirexol, Hexaform, Metenamina, Resotropin, Uratrine, Urodeine, Xametrin, Heterin, Uramin, Hexamethyleneamine, Hexilmethylenamine, Hexa-Flo-Pulver, Ekagom H, methenaminum, Hexaminum, Herax UTS, Hexamethylentetramin, Nocceler H, Sanceler H, Formin (heterocycle), Hexamine (heterocycle), Vulkacit H 30, Hexamethylentetraminum, 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane, S 4 (heterocycle), Hexamethylenetetraminum, Esametilentetramina, Methamin, DTXSID6020692, Hexa (vulcanization accelerator), Urisol, 1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane, J50OIX95QV, NSC-26346, INS NO.239, INS-239, NSC-403347, E239, DTXCID00692, CHEBI:6824, E-239, 1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decane, Silver, Hexamine, Methenamine, Silver, Silver, Methenamine, 1,3,5,7-Tetraazatricyclo(3.3.1.1(3,7))decane, 1,3,5,7-Tetraazatricyclo[3.3.1.1{3,7}]decane, Urasal, RefChem:6015, J01XX05, 202-905-8, 925-145-5, Aminoform, Hexaloids, Metramine, Hexasan, Hexamethylentetramine, Hexasan (VAN), Metenamine, Uro-phosphate, 1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decane, Vesaloin, HMT, 1,3,5,7-Tetraazatricyclo (3.3.1.1(3,7))decane, MFCD00006895, Hexamine (JAN), Hexamine (TN), 1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane, Hexamethylenetetramine (aliphatic), Silver Methenamine, Methenamine (USP/INN), 1,3,5,7-Tetraazatricyclo(3.3.1.1(sup 37))decane, H.M.T., Formin (the heterocyclic compound), 1,3,5,7-tetraazatricyclo[3.3.1.1?,?]decane, NSC26346, 1,3,5,7-Tetraazatricyclo(3.3.1.1(sup 3,7))decane, NCGC00094719-04, HEXAMINE [JAN], Hexamine Silver, Methenamine Silver, 1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane, Caswell No. 482, Methenamine [USAN:INN], Sanceler HT, Metenamina [INN-Spanish], Methenaminum [INN-Latin], Heksa K, Hexamine Superfine, Nocceler H-PO, Sanceler HT-PO, Hexa B, CAS-100-97-0, Esametilentetramina [Italian], Hexamethylentetramin [German], SMR000857139, Cohedur H 30, CCRIS 2297, HSDB 563, hexamethylene-tetramine, NSC403347, Rhenogran HEXA 80, Thixon 715B, SR-05000002024, Methenamine [USP:INN], 1,3,5,7-tetraazatricyclo[3.3.1.1<3,7>]decane, EINECS 202-905-8, NSC 26346, UN1328, UNII-J50OIX95QV, 1,3,5,7-Tetraazatricyclo[3.3.1.1(sup 3,7)]decane, EPA Pesticide Chemical Code 045501, NSC 403347, Naphthamine, Carin, EL 10 (corrosion inhibitor), AI3-09611, Methenamine CRS, HEXAMETHYLENETETRAMINE, ACS, EL 10, Prestwick_79, Vulkacit H30, 1,3,5,7-Tetraazatricyclo[3.3.1.13,7 ]decane, Grasselerator 102, Cystex (Salt/Mix), 37604-90-3, hexam-ethylenetetraamine, hexamethylene tetraamine, Spectrum_000991, METHENAMINE [MI], Spectrum2_000827, Spectrum3_001730, Spectrum4_000872, Spectrum5_001603, Methenamine (Mandelamine), METHENAMINE [INN], Formaldehyde-ammonia 6:4, [16]-Adamazane, INN, component of Uro-Phosphate, METHENAMINE [HSDB], Uro-phosphate (Salt/Mix), 1,5,7-Tetraazaadamantane, EC 202-905-8, Hexamethylentetramin(german), METHENAMINE [VANDF], Hexamethylenetetramine, 8CI, METHENAMINE [MART.], SCHEMBL33785, BSPBio_003380, Hexamethylenetetramine, tech., KBioGR_001563, KBioSS_001471, METHENAMINE [USP-RS], METHENAMINE [WHO-DD], Hexamethylenetetramine [UN1328] [Flammable solid], MLS001332361, MLS001332362, MLS002207085, DivK1c_000322, Hexamethylenetetramine (NIST), SPECTRUM1500394, SPBio_000753, Hexamethylenetetramine, BioXtra, CHEMBL1201270, 1,3,5,7-Tetraazatricyclodecane, GTPL10913, HMS501A04, KBio1_000322, KBio2_001471, KBio2_004039, KBio2_006607, KBio3_002600, NINDS_000322, HMS1920L13, HMS2091D08, HMS2233B09, HMS3371O15, HMS3652A05, HMS3715D17, METHENAMINE [EP MONOGRAPH], Pharmakon1600-01500394, METHENAMINE [USP MONOGRAPH], HY-B0514, STR00289, Tox21_113455, Tox21_201606, Tox21_300502, CCG-40289, EBC-03957, Hexamethylenetetramine, LR, >=99%, NSC757101, s3139, SBB008794, STL197471, AKOS000120003, AKOS005169648, Tox21_113455_1, Urotropine 100 microg/mL in Methanol, DB06799, FH23803, NSC-757101, IDI1_000322, NCGC00094719-01, NCGC00094719-02, NCGC00094719-03, NCGC00094719-05, NCGC00094719-06, NCGC00094719-08, NCGC00254463-01, NCGC00259155-01, SBI-0051439.P003, H0093, Hexamethylenetetramine, ReagentPlus(R), 99%, NS00006016, ST50823696, SW199604-2, EN300-16855, 1,5,7-Tetraazatricyclo[3.3.1.13,7]decane, D00393, Hexamethylenetetramine, ACS reagent, >=99.0%, Q71969, AB00052038_08, AB00052038_09, 1,3,5,7-tetraaza-tricyclo[3.3.1.13,7]decane, 1,3,5,7-tetraazatricyclo-[3.3.1.13,7]decane, 1,3,5,7-tetraazatricyclo[3,3,1,13,7]decane, 1,3,5,7-tetraazatricyclo[3.3.1.1,3,7]decane, AE-641/00560026, WLN: T66 B6 A B-C 1B I BN DN FN HNTJ, Hexamethylenetetramine [UN1328]  [Flammable solid], Hexamethylenetetramine, analytical reference material, Hexamethylenetetramine, p.a., ACS reagent, 99.0%, Hexamethylenetetramine, SAJ first grade, >=98.5%, SR-05000002024-1, SR-05000002024-3, 1,3,5,7-tetraaza-tricyclo[3.3.1.1*3,7*]decane, 1,3,5,7-Tetraazatricyclo-[3.3.1.1(3,7)]decane, BRD-K30114692-001-10-0, BRD-K30114692-001-15-9, BRD-K30114692-001-16-7, Hexamethylenetetramine, JIS special grade, >=99.0%, F2173-0429, Z362014242, Methenamine, European Pharmacopoeia (EP) Reference Standard, 1,3,5,7-TETRAAZATRICYCLO(3.3.1.1 SUP(3,7))DECANE, Methenamine, United States Pharmacopeia (USP) Reference Standard, InChI=1/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H, Hexamethylenetetramine, anhydrous, free-flowing, Redi-Dri(TM), ACS reagent, >=99.0%
Theoretical properties:
molecular_formula: C6H12N4
molecular_weight: 140.19 g/mol
exact_mass: 140.106196400 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 10
topological_polar_surface_area: 13 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystallizes from ethanol as colorless, hygroscopic rhombododecahedra.
color: Crystallizes from ethanol as colorless, hygroscopic rhombododecahedra.
odor: Odorless
boiling_point: Sublimes (NTP, 1992)
melting_point: 536 °F (sublimes) (NTP, 1992)
density: 1.35 at 68 °F (USCG, 1999) - Denser than water; will sink
solubility: greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)
flash_point: 482 °F (NTP, 1992)
vapor_pressure: 0.004 [mmHg]
Descriptions:
{"pubchem": "Hexamethylenetetramine is a polycyclic cage that is adamantane in which the carbon atoms at positions 1, 3, 5 and 7 are replaced by nitrogen atoms. It has a role as an antibacterial drug. It is a polycyclic cage, a tetramine and a polyazaalkane.", "chebi": "A polycyclic cage that is adamantane in which the carbon atoms at positions 1, 3, 5 and 7 are replaced by nitrogen atoms.", "chembl": "METHENAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Methenamine, also known as hexamine or hexamethylenetetramine and sold under the brand names Hiprex, Urex, and Urotropin among others, is a urinary tract antiseptic and antibacterial medication which is used in the prevention of recurrent urinary tract infections (UTIs). It is not an antibiotic, and unlike antibiotics, has no risk of bacterial resistance. Methenamine can reduce the risk of UTIs by 44 to 86% and has been found to be non-inferior to low-dose prophylactic antibiotics. It is taken by mouth. The drug is available both by prescription and at lower doses over the counter. Besides for UTI prevention, methenamine is also available in a topical form to treat hyperhidrosis.\nSide effects of methenamine are generally minor and include upset stomach, nausea, and headache, among others. Methenamine is a prodrug of formaldehyde in acidic urine. Formaldehyde is a non-specific antiseptic and bactericide which works via denaturation of bacterial proteins and nucleic acids. Conversion of methenamine into formaldehyde only occurs in acidic environments and hence its actions show selectivity for tissues like the bladder and stomach. Chemically, methenamine is a simple cyclized hydrocarbon and is similar in structure to adamantane.\nMethenamine was discovered in 1859 and was first introduced for medical use as a urinary antiseptic in 1895. It was formally approved for medical use in the United States in 1967. Though it became a \"forgotten drug\" following the discovery of antibiotics in 1928, there has been a resurgence in interest in methenamine since 2010 owing to increasing rates of bacterial resistance with antibiotics. Larger and higher-quality clinical trials of methenamine for UTI prevention have started to be published in the 2020s and it may soon be recommended by more medical guidelines. Methenamine has been found to be more cost-effective than low-dose prophylactic antibiotics for preventing UTIs."}