5966. Methenamine

Nomenclature

CAS number: 100-97-0
1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane; hexamethylenetetramine; HMT; HMTA; hexamine; 1,3,5,7-tetraazaadamantane; hexamethylenamine.
C6H12N4; mol wt 140.19.
C 51.40%, H 8.63%, N 39.96%.

Description and 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. Crystal property studies: G. H. Heilmeier, Appl. Opt. 3, 1281 (1964). 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.

Chemical structure

Properties

Colorless, odorless crystalline solid with sweet, metallic taste. Sublimes at about 263° without melting and with partial decompn; somewhat volatile at lower temp. nD25 1.5911. 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.

Derivative

Anhydromethylenecitrate.

Nomenclature

CAS number: 6190-43-8
Helmitol (Bayer).
C6H12N4.C7H8O7; mol wt 344.32.
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.

Derivative

Hippurate.

Nomenclature

CAS number: 5714-73-8
Hiprex (3M Pharma); Urex (3M Pharma); Urotractan (Klinge).
C6H12N4.C9H9NO3; mol wt 319.36.
C 56.41%, H 6.63%, N 21.93%, O 15.03%.

Properties

Crystals, mp 105-110°. Freely sol in water, alcohol.

Derivative

Mandelate.

Nomenclature

CAS number: 587-23-5
Mandelamine (Warner-Chilcott); Uronamin (Sumitomo).
C6H12N4.C8H8O3; mol wt 292.33.
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.

Derivative

Sulfosalicylate.

Nomenclature

CAS number: 20480-93-7
C6H12N4.C7H6O6S; mol wt 358.37.
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.

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; detection of metals.

Therapeutic Category

Antibacterial (urinary).

Therapeutic Category (Veterinary)

Antibacterial (urinary).

Keywords

Antibacterial (Synthetic)