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Substance Name: Methenamine [USP:INN]
RN: 100-97-0
UNII: J50OIX95QV
InChIKey: VKYKSIONXSXAKP-UHFFFAOYSA-N

Note

  • An anti-infective agent most commonly used in the treatment of urinary tract infections. Its anti-infective action derives from the slow release of formaldehyde by hydrolysis at acidic pH. (From Martindale, The Extra Pharmacopoeia, 30th ed, p173).

Molecular Formula

  • C6-H12-N4

Molecular Weight

  • 140.1888
 

Classification Codes

  • Anti-Infective Agents
  • Anti-Infective Agents, Urinary
  • Antibacterial (Urinary)
  • Drug / Therapeutic Agent
  • Mutation Data
  • Renal Agents
  • Tumor Data

Names and Synonyms

Name of Substance

  • Hexamethylene tetramine
  • Hexamethyleneamine
  • Methenamine
  • Methenamine [USP:INN]

MeSH Heading

  • Methenamine

Synonyms

  • 1,3,5,7-Tetraazaadamantane
  • 1,3,5,7-Tetraazatricyclo (3.3.1.1(3,7))decane
  • 1,3,5,7-Tetraazatricyclo(3.3.1.1(sup 3,7))decane
  • 1,3,5,7-Tetraazatricyclo(3.3.1.1(sup 37))decane
  • Aceto HMT
  • AI3-09611
  • Aminoform
  • Aminoformaldehyde
  • Ammoform
  • Ammonioformaldehyde
  • Antihydral
  • Caswell No. 482
  • CCRIS 2297
  • Cohedur H 30
  • Cystamin
  • Cystogen
  • Duirexol
  • EC 202-905-8
  • EINECS 202-905-8
  • Ekagom H
  • EL 10
  • EL 10 (corrosion inhibitor)
  • EPA Pesticide Chemical Code 045501
  • Esametilentetramina
  • Esametilentetramina [Italian]
  • Formamine
  • Formin
  • Formin (heterocycle)
  • HA
  • Heksa K
  • Herax UTS
  • Heterin
  • Hexa
  • Hexa (vulcanization accelerator)
  • Hexa B
  • Hexa-Flo-Pulver
  • Hexaform
  • Hexaloids
  • Hexamethylenamine
  • Hexamethyleneamine
  • Hexamethylenetetraamine
  • Hexamethylenetetramine
  • Hexamethylenetetraminum
  • Hexamethylentetramin
  • Hexamethylentetramin [German]
  • Hexamethylentetramine
  • Hexamethylentetraminum
  • Hexamine
  • Hexamine (heterocycle)
  • Hexamine Superfine
  • Hexaminum
  • Hexasan
  • Hexasan (VAN)
  • Hexilmethylenamine
  • HMT
  • HMTA
  • HSDB 563
  • Metenamina
  • Metenamina [INN-Spanish]
  • Methenamide
  • Methenamin
  • Methenamine
  • Methenaminum
  • Methenaminum [INN-Latin]
  • Metramine
  • Nocceler H
  • Nocceler H-PO
  • NSC 26346
  • NSC 403347
  • Preparation AF
  • Resotropin
  • Rhenogran HEXA 80
  • S 4
  • S 4 (heterocycle)
  • Sanceler H
  • Sanceler HT
  • Sanceler HT-PO
  • Thixon 715B
  • UNII-J50OIX95QV
  • Uramin
  • Uratrine
  • Uritone
  • Urodeine
  • Urotropin
  • Urotropine
  • Vulkacit H 30
  • Xametrin

Systematic Names

  • 1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane
  • Hexamethylenetetramine
  • Methenamine

Superlist Names

  • 1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane
  • Hexamethylenetetramine
  • Hexamethylenetetramine solutions
  • Hexamethylenetetramine [UN1328] [Flammable solid]
  • Methenamine
  • UN1328

Mixture Names

  • Cystex
  • Uro-phosphate

Registry Numbers

CAS Registry Number

  • 100-97-0

FDA UNII

  • J50OIX95QV

Other Registry Numbers

  • 11103-67-6
  • 1556839-80-5
  • 15978-33-3
  • 187285-07-0
  • 56549-34-9
  • 74734-16-0
  • 91773-48-7

System Generated Number

  • 0000100970

Structure Descriptors

InChI

InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2

InChIKey

VKYKSIONXSXAKP-UHFFFAOYSA-N

Smiles

C1N2CN3CN(CN1C3)C2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo parenteral 200mg/kg (200mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
cat LDLo subcutaneous 200mg/kg (200mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 84, 1955.
guinea pig LDLo subcutaneous 300mg/kg (300mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 84, 1955.
mammal (species unspecified) LDLo parenteral 300mg/kg (300mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
mouse LD50 intravenous 17700uL/kg (17.7mL/kg)   Antibiotiki. Vol. 20, Pg. 891, 1975.
mouse LD50 oral 569mg/kg (569mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT		 Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 35(3), Pg. 115, 1970.
mouse LD50 subcutaneous 215mg/kg (215mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: TREMOR		 Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 225, Pg. 428, 1955.
mouse LDLo parenteral 450mg/kg (450mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
rat LD50 intravenous 9200mg/kg (9200mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 221, Pg. 166, 1954.
rat LDLo parenteral 200mg/kg (200mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.
rat LDLo subcutaneous 200mg/kg (200mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 84, 1955.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point >250 deg C   EXP
log P (octanol-water) -4.150 (none)   EST
Water Solubility 4.49E+05 mg/L 12 EXP
Vapor Pressure 0.004 mm Hg 25 EXP
Henry's Law Constant 1.64E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.09E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.