Triethylenemelamine
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Triethylenemelamine
structure -
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CAS No:
51-18-3
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Formula:
C9H12N6
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Chemical Name:
Triethylenemelamine
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Synonyms:
1,3,5-Triazine,2,4,6-tris(1-aziridinyl)-;s-Triazine,2,4,6-tris(1-aziridinyl)-;2,4,6-Tris(1-aziridinyl)-1,3,5-triazine;ENT 25296;Persistol Ho 1/193;Tretamine;Triaziridinyl triazine;Triethylenemelamine;2,4,6-Triethylenimino-s-triazine;2,4,6-Tris(1-aziridinyl)-s-triazine;2,4,6-Tris(ethylenimino)-s-triazine;Tris(ethyleneimino)triazine;2,4,6-Tris(ethyleneimino)-s-triazine;Trisaziridinyltriazine;TEM;Tretamin;Triamelin;NSC 9706;Persistol Hoe 1/193;SK 1133;Tem-Simes;TEM (cytostatic);DRP 859025;M 9500;R 246;TAT;TET;Triethanomelamine;Persistol;2,4,6-Tri(aziridin-1-yl)-1,3,5-triazine;39301-20-7
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CAS No:
Description
PHYSICAL DESCRIPTION: Odorless white crystalline powder. Melting point 160°C, then rapidly polymerizes to a white solid. Almost immediate degradation at pH 3.0; rapid degradation at pH 5.0; and very little degradation at pH 7.5. (NTP, 1992)
Triethylenemelamine is an odorless white crystalline powder. Melting point 160°C, then rapidly polymerizes to a white solid. Almost immediate degradation at pH 3.0; rapid degradation at pH 5.0; and very little degradation at pH 7.5. (NTP, 1992)
Triethylenemelamine is an odorless white crystalline powder. Melting point 160°C, then rapidly polymerizes to a white solid. Almost immediate degradation at pH 3.0; rapid degradation at pH 5.0; and very little degradation at pH 7.5. (NTP, 1992)|Tretamine is a member of 1,3,5-triazines. It has a role as an insect sterilant and an alkylating agent.|Toxic alkylating agent used in industry; also as antineoplastic and research tool to produce chromosome aberrations and cancers.|Triethylenemelamine is a trisaziridine alkylating agent with antineoplastic and carcinogenic properties. Used to induce cancer in experimental animal models, triethylenemelamine ethylates DNA, resulting in inhibition of DNA replication, unscheduled DNA synthesis, chromosomal aberrations, and sister chromatid exchanges. This agent also exhibits reproductive toxicities. (NCI04)
Triethylenemelamine Basic Attributes
204.23
204.23
200-083-5
F7IY6HZG9D
9706
2763
DTXSID3026225
C29858
MINUTE CRYSTALS FROM CHLOROFORM|WHITE, CRYSTALLINE POWDER
2933990090
Characteristics
47.7
-0.54
Triethylenemelamine is an odorless white crystalline powder. Melting point 160°C, then rapidly polymerizes to a white solid. Almost immediate degradation at pH 3.0; rapid degradation at pH 5.0; and very little degradation at pH 7.5. (NTP, 1992)
1.617g/cm3
39 °C (decomp)
430.2ºC at 760mmHg
214ºC
1.789
soluble in oxygenated and chlorinated solvents.
Refrigerator (+4°C) + Poison room
LD50 in mice, rats (mg/kg): 2.8, 1.0 i.p.; 15, 13 orally (Philips)
ODORLESS
DECOMP 139 °C; @ ROOM TEMP AQUEOUS SOLUTIONS POLYMERIZE|Polymerizes readily with heat or moisture
Soluble in water [Hawley]. Polymerizes readily with heat or moisture.
Amines, Phosphines, and Pyridines
Polymerizable
TRIETHYLENEMELAMINE polymerizes readily with heat or moisture. Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.
Safety Information
II
6.1(a)
3249
3
R28;R40
S24/25-S45
C
Stability Unstable - polymerizes at room temperature. Polymerizes more readily if heated and in the presence of moisture.
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.
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. 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. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it in a freezer. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)
Toxicity
LD50 Mouse oral 15.0 mg/kg /From table/|LD50 Mouse ip 2.8 mg/kg /From table/|LD50 Rat oral 13.0 mg/kg /From table/|LD50 Rat ip 1.0 mg/kg /From table/
TEM IS NOT KNOWN TO OCCUR IN NATURE.
Drug Information
Antineoplastic Agents, Alkylating|/FORMER USE:/ ONLY KNOWN COMMERCIAL USE...IN US WAS AS ANTINEOPLASTIC AGENT. ...MOST EFFECTIVE IN TREATMENT OF LEUKEMIAS, PARTICULARLY OF CHRONIC LYMPHOCYTIC LEUKEMIA & CHRONIC MYELOCYTIC LEUKEMIA, & OF MALIGNANT LYMPHOMAS, ESP HODGKIN'S DISEASE & LYMPHOSARCOMA. RECOMMENDED DOSAGE WAS 2.5-5 MG TWICE WEEKLY, INITIALLY FOR 4 WK.|/FORMER USE:/ IT MAY BE OCCASIONALLY EMPLOYED AS ADJUNCTIVE OR DESPERATION AGENT IN CHRONIC GRANULOCYTIC LEUKEMIA.
VOMITING OR LEUKOCYTE COUNT BELOW 4000 CELLS/CU MM IS SIGN THAT DOSE SHOULD BE REDUCED OR DISCONTINUED.|DRUG SHOULD NOT BE GIVEN IF THERE IS LIVER OR KIDNEY DAMAGE OR TO PREGNANT WOMEN IN FIRST TRIMESTER. BONE MARROW DEPRESSION FROM RADIATION OR PREVIOUS CHEMOTHERAPY IS CONTRAINDICATION.|ONSET OF ACTION OF TRIETHYLENEMELAMINE IS SLOW, & SEVERAL DAYS MAY BE SOMETIMES REQUIRED BEFORE RESPONSE IS SEEN.
A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)
IT IS LESS WELL ABSORBED FROM THE GI TRACT THAN FROM THE PERITONEAL CAVITY. ... BLOOD LEVELS OF TEM FALL RAPIDLY AFTER IV INJECTION IN MAN, THE CONCN BEING ONLY 10% OF THE EXPECTED VALUE 2 MIN AFTER ADMIN. THE IS NO PERSISTENT SELECTIVE UPTAKE BY ANY TISSUE.|FOLLOWING IP ADMIN TO MICE OF TEM LABELLED WITH (14)C IN TRIAZINE RING, MOST OF ACTIVITY WAS EXCRETED IN URINE WITHIN 24 HR... IN MICE INJECTED IP...IN WHICH AZIRIDINE RINGS WERE LABELLED WITH (14)C, ABOUT 70% OF ADMIN RADIOACTIVITY WAS EXCRETED IN URINE WITHIN FIRST 24 HR...|PATIENT WITH ACUTE LYMPHATIC LEUKEMIA WAS GIVEN TEM LABELLED WITH (14)C IN AZIRIDINE RING IV @ DOSE OF 2 MG ... OVER 90% OF RADIOACTIVITY DISAPPEARED FROM BLOOD WITHIN 5 MIN. ... PATIENT WITH METASTASIZING EPIDERMAL CARCINOMA, 3 MG OF DRUG ... ORALLY. IN BOTH CASES 25-30% OF ADMIN ACTIVITY ... EXCRETED IN URINE ... WITHIN FIRST 48 HR ... .|FOLLOWING ITS IV INJECTION IN MICE @...0.8 MG/KG BODY WT OR IN OSBORNE-MENDEL RATS @...0.11 & 0.13 MG/KG BODY WT, TEM DISAPPEARED RAPIDLY FROM BLOOD: WITHIN 10 MIN LEVEL HAD FALLEN TO LESS THAN 10% OF ORIGINAL ACTIVITY.
URINE FROM CANCER PT TREATED WITH LABELLED TEM CONTAINED 14 RADIOACTIVE METABOLITES. APPROX 8% OF RADIOACTIVITY EXCRETED IN URINE WAS IN UREA & CREATININE; NO UNCHANGED DRUG DETECTED.|IN MICE INJECTED IP WITH 9 MG/KG BODY WT TEM IN WHICH AZIRIDINE RINGS WERE LABELLED WITH (14)C...16 RADIOACTIVE METABOLITES WERE FOUND; ONLY ONE, CREATININE, WAS IDENTIFIED.
SYMPTOMS: Symptoms of exposure to this compound may include burning in the throat, vomiting, watery to bloody diarrhea, abdominal pain, oliguria, fall in blood pressure, anuria, cardiovascular collapse, delirium, convulsions, muscular weakness with respiratory failure, and lymphopenia. Other symptoms may include gastrointestinal disturbances and bone marrow depression. ACUTE/CHRONIC HAZARDS: This compound is highly toxic by ingestion. When heated to decomposition it emits toxic fumes of nitrogen oxides. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)
ANOREXIA & ABDOMINAL PAIN MAY...OCCUR. HEADACHE, EUPHORIA, HICCOUGHS, ASTHENIA, AMENORRHEA, OLIGOSPERMIA, & RETROSTERNAL BURNING SENSATIONS ARE LESS FREQUENT. MOST SERIOUS SIDE EFFECTS ARE BONE MARROW DEPRESSION...HEPATIC DAMAGE...& RENAL DAMAGE...HEMATURIA, ALBUMINURIA, & AZOTEMIA. HEPATIC & RENAL TOXICITY MAY BE DELAYED.|SUMMARY TOXICITY STATEMENT; ACUTE... VERY HIGH VIA ORAL, IP & IM ROUTES. HIGH= CAPABLE OF CAUSING DEATH OR PERMANENT INJURY DUE TO EXPOSURES OF NORMAL USE; INCAPACITATING & POISONOUS; REQUIRES SPECIAL HANDLING.|Oral doses of 1 to 5 mg/kg/day may produce gastrointestinal symptoms and depression of the formed elements in peripheral blood.
2,4,6-Triethylimino-1,3,5-Triazine
Triethylenemelamine Use and Manufacturing
PREPD FROM ETHYLENIMINE & CYANURIC CHLORIDE.
manufacture of resinous products, textile finishing agents.Insect sterilant.Research tool used as positive control for mutagenicity assays.
(1975) NOT PRODUCED COMMERCIALLY IN US|(1977) NOT PRODUCED COMMERCIALLY IN US
(1977) NO LONGER USED COMMERCIALLY IN US
TABLETS NF: 5 MG.|GRADE: NF.
LIKE OTHER POLYFUNCTIONAL ETHYLENEIMINE DERIVATIVES, TEM HAS BEEN CLASSIFIED AS A "RADIOMIMETIC" CMPD ... BECAUSE THE OBSERVED EFFECTS IN ANIMALS GROSSLY RESEMBLE THOSE PRODUCED BY ACUTE DOSES OF IONIZING RADIATION.
THIN-LAYER CHROMATOGRAPHY.
Computed Properties
Molecular Weight:204.23
XLogP3:0.7
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:204.11234441
Monoisotopic Mass:204.11234441
Topological Polar Surface Area:47.7
Heavy Atom Count:15
Complexity:205
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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