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Methenamine(CAS No. 100-97-0)

Methenamine C6H12N4 (cas 100-97-0) Molecular Structure

100-97-0 Structure

Identification and Related Records

【Name】
Methenamine
【CAS Registry number】
100-97-0
【Synonyms】
hexamethylene triamine
1,3,5,7-tetraazatricyclo[3.3.1.1(3,7)]decane
preparation af
resotropin
hexamethylenetetraamine
aceto hmt
ammonioformaldehyde
formamine
hexa
hexilmethylenamine
methamin
metheneamine
hexamine
hiprex
mandelamine
urex
uroqid
urotropin
hmta
hexaform
1,3,5,7-tetraazaadamantane
aminoform
ammoform
cystogen
formin
uritone
hmt
hexamethylenetetramine
hexamethylenetetramine (hexamine)
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane
1,3,5,7-tetraazatricyclo[3.3.1.13]decane
acetohmt
aminoformaldehyde
antihydral
carin
component of uro-phosphate
duirexol
ekagom h
ekagomh
esametilentetramina
formaldehyde-ammonia 6:4
formin[heterocycle]
grasselerator 102
herax uts
heraxuts
heterin
hexa-flo-pulver
【EINECS(EC#)】
202-905-8
【Molecular Formula】
C6H12N4 (Products with the same molecular formula)
【Molecular Weight】
140.19
【Inchi】
InChI=1/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
【InChIKey】
VKYKSIONXSXAKP-UHFFFAOYSA-N
【Canonical SMILES】
C1N2CN3CN1CN(C2)C3
【MOL File】
100-97-0.mol

Chemical and Physical Properties

【Appearance】
white crystalline powder
【Density】
1.331
【Melting Point】
280℃
【Boiling Point】
252.7°Cat760mmHg
【Vapour】
0.019mmHg at 25°C
【Flash Point】
250℃
【Water】
895 g/L (20℃)
【Solubilities】
895 g/L (20 oC)
【Color/Form】
RHOMBIC CRYSTALS FROM ALCOHOL
CRYSTALS OR GRANULES OR POWDER
COLORLESS, LUSTROUS CRYSTALS OR WHITE CRYSTALLINE POWDER
White, crystalline powder or colorless, lustrous crystals
【Stability】
Stable. Incompatible with strong acids, strong oxidizing agents.
【Storage temp】
Store at RT.
【Spectral properties】
SADTLER REFERENCE NUMBER: 2150 (IR, PRISM)
IR: 1633 (Coblentz Society Spectral Collection)
NMR: 6705 (Sadtler Research Laboratories Spectral Collection)
MASS: 744 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
Intense mass spectral peaks: 112 m/z, 140 m/z
【Computed Properties】
Molecular Weight:140.18628 [g/mol]
Molecular Formula:C6H12N4
XLogP3-AA:0.3
H-Bond Donor:0
H-Bond Acceptor:4
Rotatable Bond Count:0
Exact Mass:140.106196
MonoIsotopic Mass:140.106196
Topological Polar Surface Area:13
Heavy Atom Count:10
Formal Charge:0
Complexity:84.8
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Cation Count:4
Feature 3D Ring Count:4
Effective Rotor Count:1.2
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
F:Flammable
【Risk Statements】
R11;R42/43
【Safety Statements 】
S16;S22;S24;S37
【HazardClass】
4.1
【Safety】
Hazard Codes:F,Xn
Risk Statements:11-42/43
11:Highly Flammable
42/43:May cause sensitization by inhalation and skin contact
Safety Statements:16-22-24-37
16:Keep away from sources of ignition - No smoking
22:Do not breathe dust
24:Avoid contact with skin
37:Wear suitable gloves
RIDADR:UN 1328 4.1/PG 3
WGK Germany:1
HazardClass:4.1
PackingGroup:III
Hazardous Substances Data:100-97-0(Hazardous Substances Data)
【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
An irritant to skin, eyes, and mucous membranes.
【Cleanup Methods】
TOXIC COMPD CAN BE REMOVED BY REVERSE OSMOSIS. HEXAMETHYLENEAMINE TREATED WITH OXYGEN IN PRESENCE OF PYROLUSITE ORES TO FORM HCO2H & NANO3 WHICH CAN BE REMOVED BY BIOL TREATMENT.
【Transport】
UN 1325/1328
【Fire Fighting Procedures】
Solid streams of water may spread fire. Use water in flooding quantities as fog. Use dry chemical, graphite, or dry earth.
【Fire Potential】
Combustible when exposed to heat or flame.
【Formulations/Preparations】
METHENAMINE, METHENAMINE MANDELATE...METHENAMINE HIPPURATE...METHENAMINE SULFOSALICYLATE...
Technical, NF (as methenamine)
Hiprex tablets contain the dye tartrazine (FD&C yellow No. 5), which may cause allergic reactons including bronchial asthma in susceptible individuals.
【DOT Emergency Guidelines】
/GUIDE 133: FLAMMABLE SOLIDS/ Fire or Explosion: Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.
/GUIDE 133: FLAMMABLE SOLIDS/ Health: Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.
/GUIDE 133: FLAMMABLE SOLIDS/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 25 meters (75 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas.
/GUIDE 133: FLAMMABLE SOLIDS/ Protection Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.
/GUIDE 133: FLAMMABLE SOLIDS/ Evacuation: Large spill: Consider initial downwind evacuation for at least 100 meters (330 feet). Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 133: FLAMMABLE SOLIDS/ Fire: Small fires: Dry chemical, CO2, sand, earth, water spray or regular foam. Large fires: Water spray, fog or regular foam. Move containers from fire area if you can do it without risk. Fire involving tanks or car/trailer loads: Cool containers with flooding quantities of water until well after fire is out. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire.
/GUIDE 133: FLAMMABLE SOLIDS/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch or walk through spilled material. Small dry spills: With clean shovel place material into clean, dry container and cover loosely; move containers from spill area. Large spills: Wet down with water and dike for later disposal. Prevent entry into waterways, sewers, basements or confined areas.
/GUIDE 133: FLAMMABLE SOLIDS/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Removal of solidified molten material from skin requires medical assistance. Keep victim warm and quiet. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Reactivities and Incompatibilities】
Can react with oxidizing materials. Explosive reaction with acetic acid + acetic anhydride + ammonium nitrate + nitric acid; 1-bromopenta borane(9) (above 90 degrees C); iodoform (at 178 degrees C); iodine (at 138 degrees C). Reaction with nitric acid + acetic anhydride forms the military explosives RDX and HMX. Reacts violently with Na2O2.
【Other Preventative Measures】
Keep sparks, flames, and other sources of ignition away. Do not handle broken packages unless wearing appropriate personal protective equipment.
【Protective Equipment and Clothing】
An irritant to skin, eyes, and mucous membranes.
【Specification】

white crystalline powder
usageEng:Used in the treatment of urinary track infection.
Safety Statements:16-22-24-37
16:Keep away from sources of ignition - No smoking
22:Do not breathe dust
24:Avoid contact with skin
37:Wear suitable gloves
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Derivation: Action of ammonia on formaldehyde
U.S. Exports

(1972) NEGLIGIBLE
U.S. Imports

(1972) 5.9X10+7 G
U.S. Production

(1972) 4.32X10+10 G
Consumption Patterns

56% AS A CURING AGENT FOR PHENOLIC RESINS; 37% AS A CHEM INT FOR THE EXPLOSIVE, CYCLONITE; & 7% IN MISC APPLICATIONS (1974)
【Usage】
Used in the treatment of urinary track infection.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
【Therapeutic Uses】
Anti-Infective Agents, Urinary /SRP: Antibacterial/
Virtually all bacteria and fungi are susceptible to the nonspecific action of free formaldehyde produced by the hydrolysis of methenamine. /Included in US product labeling/
Methenamine is indicated in the treatment of uncomplicated lower urinary tract infections and in the suppressive treatment of urinary tract infections in patients with neurogenic bladder or in patients being catheterized intermittently. /Included in US product labeling/
Methenamine is indicated in the prophylaxis of urinary tract infections in patients with sterile urine after the eradication of urinary tract infections by other antibacterials. /Included in US product labeling/
METHENAMINE IS SOMETIMES EMPLOYED PROPHYLACTICALLY IN URINARY TRACT INSTRUMENTATION & CATHETERIZATION.
MEDICATION (VET): ...IT HAS BEEN USED OCCASIONALLY IN TETANUS & ENCEPHALITIS. DESPITE MORE SPECIFIC DRUGS, IT IS GIVEN TO SOWS TO CONTROL PIG SCOURS, OR IN MAMMITIS OF SOWS (& NOW RARELY IN COWS).
METHENAMINE IS NOT PRIMARY DRUG FOR TREATMENT OF ACUTE URINARY TRACT INFECTIONS, BUT IT IS OF VALUE FOR CHRONIC SUPPRESSIVE TREATMENT. AGENT IS MOST USEFUL WHEN CAUSATIVE ORGANISM IS E COLI, BUT IT CAN USUALLY SUPPRESS COMMON GRAM-NEGATIVE OFFENDERS & OFTEN STAPHYLOCOCCUS AUREUS...& EPIDERMIDIS AS WELL.
BECAUSE THIS AGENT IS ACTIVE ONLY IN ACID MEDIA, ITS EFFECTIVENESS IS MARKEDLY DIMINISHED IN INFECTIONS CAUSED BY UREA-SPLITTING ORGANISMS SUCH AS PROTEUS & SOME PSEUDOMONAS SPECIES.
WHEN URINE PH IS 6 & DAILY URINE VOL IS 1000-1500 ML, DAILY DOSE OF 2 G WILL YIELD CONCN OF 18-60 UG/ML OF FORMALDEHYDE; THIS IS MORE THAN THE MINIMAL INHIBITORY CONCN FOR MOST URINARY TRACT PATHOGENS.
...ACIDIFICATION OF URINE PROMOTES FORMALDEHYDE-DEPENDENT ANTIBACTERIAL ACTION. ... ACIDS COMMONLY USED ARE MANDELIC ACID, HIPPURIC ACID.
SALTS OF METHENAMINE HAVE RECEIVED SOME TRIAL AS TOPICAL ANTISEPTICS IN MANAGEMENT OF BURNS. /METHENAMINE SALTS/
MEDICATION (VET): METHENAMINE IN CONJUNCTION WITH ACID SODIUM PHOSPHATE HAS BEEN EMPLOYED AS URINARY ANTISEPTIC IN COMPANION ANIMAL PRACTICE. IT HAS BEEN RECOMMENDED FOR USE IN HERBIVOROUS ANIMALS BUT EVIDENCE IS INCONCLUSIVE.
MEDICATION (VET): PRIMARILY AS ORGANIC SOURCE OF IODINE IN ORAL TREATMENT OF ACTINOMYCOSIS, ACTINOBACILLOSIS, & TO AUGMENT OUTPUT OF RESP TRACT FLUIDS... /METHENAMINE TETRAIODIDE/
【Biomedical Effects and Toxicity】
Most of ingested HMTA has been reported to be excreted unchanged within 3 hr.
METHENAMINE IS ABSORBED ORALLY, BUT 10-30% DECOMP IN GASTRIC JUICE UNLESS DRUG IS PROTECTED BY ENTERIC COATING.
SOME FORMALDEHYDE /FORMED BY DECOMPOSITION OF METHENAMINE/ IS BOUND TO SUBSTANCES IN URINE AND IN SURROUNDING TISSUES...
Within 24 hours, 70-90% or more of a single oral dose of methenamine or one of its salts in excreted intact in the urine by glomerular filtration and tubular secretion.
Methenamine - Rapid, but 30 to 60% hydrolyzed by gastric acid if not enteric-covered. Methenamine hippurate - rapid, from the gastrointestinal tract. Methenamine mandelate (enteric-coated tablets) - Absorption slightly delayed; total absorption essentially unaffected.
Freely distributed to body tissues and fluids, but not clinically significant /SRP: in terms of formaldehyde and ammonia release/ because methenamine does not hydrolyze at pH greater than 6.8.
Elimination: renal; rapid. Almost completely (90%) excreted within 24 hours; of this amount at pH 5, approximately 20% is formaldehyde.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 55(SRC), determined from a structure estimation method(2), indicates that methenamine is expected to have high mobility in soil(SRC). Volatilization of methenamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-9 atm-cu m/mole(SRC), derived from experimental values for vapor pressure, 4.0X10-3 mm Hg(3), and water solubility, 4.49X10+5 mg/l(4). Methenamine is not expected to volatilize from dry soil surfaces based on its vapor pressure(3). Hydrolysis may be important in some soils(SRC). Methenamine hydrolyzes in water at pH 3 or 7, the half-life in each case is slightly over 1 day(5). In two biodegradation studies, 70 to 87% removal was observed after 28 days using an activated sludge inoculum(6,7). In a 5-day BOD test using a sewage seed, methenamine reached 2.02% of its theoretical BOD(8). In a semi-continuous activated sludge system, methenamine removal was 1.1, 18.2, 25.5, 33.6, 41.3, and 52.5% after 5, 10, 15, 20, 30, and 50 days, respectively; removal was attributed to acid hydrolysis of methenamine to formaldehyde and ammonia followed by biodegradation of these two compounds(9).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 55(SRC), determined from a structure estimation method(2), indicates that methenamine is expected to adsorb to suspended solids and sediment in water(SRC). Methenamine is not expected to volatilize from water surfaces(3,SRC) based upon an estimated Henry's Law constant of 1.6X10-9 atm-cu m/mole(SRC), derived from experimental values for vapor pressure, 4.0X10-3 mm Hg(4), and water solubility, 4.49X10+5 mg/l(5). According to a classification scheme(6), an estimated BCF of 0.40(3,SRC), from the water solubility(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Methenamine hydrolyzes in water at pH 3 or 7; the half-life in each case is slightly over 1 day(7). In two biodegradation studies, 70 to 87% removal was observed after 28 days using an activated sludge inoculum(8,9). In a 5-day BOD test using a sewage seed, methenamine reached 2.02% of its theoretical BOD(10). In a semi- continuous activated sludge system, methenamine removal was 1.1, 18.2, 25.5, 33.6, 41.3, and 52.5% after 5, 10, 15, 20, 30, and 50 days, respectively; removal was attributed to acid hydrolysis of methenamine to formaldehyde and ammonia followed by biodegradation of these two compounds(11).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methenamine, which has a vapor pressure of 4.0X10-3 mm Hg at 25 deg C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methenamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 15 minutes(3,SRC).

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