Methenamine
Title: Methenamine
CAS Registry Number: 100-97-0
CAS Name: 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane
Additional Names: hexamethylenetetramine; HMT; HMTA; hexamine; 1,3,5,7-tetraazaadamantane; hexamethylenamine
Molecular Formula: C6H12N4
Molecular Weight: 140.19
Percent Composition: C 51.40%, H 8.63%, N 39.96%
Literature References: Prepn: A. Butlerow, Ann. 115, 322 (1860); from formaldehyde and ammonia: F. Meissner, E. Schwiedessen, US 2762799; US 2762800 (both 1956); Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 445-448. Comprehensive reviews: J. F. Walker, Formaldehyde (Reinhold, New York, 3rd ed., 1964) pp 511-551; J. M. Dreyfors et al., Am. Ind. Hyg. Assoc. J. 50, 579-585 (1989). Review of therapeutic use: R. Gleckman et al., Am. J. Hosp. Pharm. 36, 1509-1512 (1979); of toxicology: H. J. Trochimowicz et al. in Patty's Industrial Hygiene and Toxicology vol. 2E, G. D. Clayton, F. E. Clayton, Eds. (John Wiley & Sons, New York, 1994) pp 3324-3327.
Properties: Colorless, odorless crystalline solid with sweet, metallic taste. Sublimes at about 263° without melting and with partial decompn; somewhat volatile at lower temp. Flammable. Specific heat: 36.4 cal/°C. d 1.331. Soly at 20° (g/100g): chloroform 13.4; methanol 7.25; abs ethanol 2.89; acetone 0.65; benzene 0.23; xylene 0.14; ether 0.06. Practically insol in petr ether. pH of 0.2 molar aq sol 8.4.
Density: d 1.331
 
Derivative Type: Anhydromethylenecitrate
CAS Registry Number: 6190-43-8
Trademarks: Helmitol (Bayer)
Molecular Formula: C6H12N4.C7H8O7
Molecular Weight: 344.32
Percent Composition: C 45.35%, H 5.85%, N 16.27%, O 32.53%
Properties: White, cryst powder. mp 175° with decompn. Sol in 10 parts water; very slightly sol in alcohol, ether.
Melting point: mp 175° with decompn
 
Derivative Type: Hippurate
CAS Registry Number: 5714-73-8
Trademarks: Hiprex (3M Pharma); Urex (3M Pharma); Urotractan (Klinge)
Molecular Formula: C6H12N4.C9H9NO3
Molecular Weight: 319.36
Percent Composition: C 56.41%, H 6.63%, N 21.93%, O 15.03%
Properties: Crystals, mp 105-110°. Freely sol in water, alcohol.
Melting point: mp 105-110°
 
Derivative Type: Mandelate
CAS Registry Number: 587-23-5
Trademarks: Mandelamine (Warner-Chilcott); Uronamin (Sumitomo)
Molecular Formula: C6H12N4.C8H8O3
Molecular Weight: 292.33
Percent Composition: C 57.52%, H 6.90%, N 19.17%, O 16.42%
Properties: Crystals or white, crystalline powder. mp 128-130°. Slightly sol in acetone, ether; sol in alcohol, chloroform; very sol in water.
Melting point: mp 128-130°
 
Derivative Type: Sulfosalicylate
CAS Registry Number: 20480-93-7
Molecular Formula: C6H12N4.C7H6O6S
Molecular Weight: 358.37
Percent Composition: C 43.57%, H 5.06%, N 15.63%, O 26.79%, S 8.95%
Properties: Occurs as the monohydrate. Odorless, cryst powder, mp ~190° with decompn. Sol in 8 parts water; slightly sol in alcohol.
Melting point: mp ~190° with decompn
 
Use: In adhesives, coatings, and sealing compounds; as cross-linking agent for hardening phenol-formaldehyde resin and vulcanizing rubber; as corrosion inhibitor for steel; as fuel tablets for camping stoves; as stabilizer for lubricating and insulating oils; for the manufacture of explosive compounds (see Cyclonite); antimicrobial food additive.
Therap-Cat: Antibacterial (urinary).
Therap-Cat-Vet: Antibacterial (urinary).
Keywords: Antibacterial (Synthetic).

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