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Triethylenemelamine

HCID 5799
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
51-18-3
Standard SMILES
C1CN1c1nc(N2CC2)nc(N2CC2)n1
InChIKey
IUCJMVBFZDHPDX-UHFFFAOYSA-N
Molecular formula
C9H12N6
Average molar mass
204.23 g/mol
Monoisotopic mass
204.11234441

Overview

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)

Names & identifiers

Preferred name
Triethylenemelamine
IUPAC
2,4,6-tris(aziridin-1-yl)-1,3,5-triazine
English name
Triethylenemelamine
Molecular formula
C9H12N6
Molecular weight
204.23

Names & synonyms

TriethylenemelamineTretamine51-18-3TriamelinTrisaziridinyltriazineTretaminTriethanomelamineTem-SimesPersistolTriaziridinyl triazineTEM (cytostatic)2,4,6-Tris(1-aziridinyl)-s-triazine
Show more names
TEMTETRAMINER 246r-246M 9500m-9500sk1133nsc9706SK 1133
Persistol Ho 1/193Tretamina2,4,6-tris(aziridin-1-yl)-1,3,5-triazinePersistol Hoe 1/193Tris(ethyleneimino)triazineTriaethylenmelamintriethylene melamineTretaminum

Database identifiers

CAS
51-18-3
PubChem CID
5799
DTXSID
DTXSID3026225
ChEMBL
CHEMBL502384
ChEBI
CHEBI:27919
UNII
F7IY6HZG9D
EC Number
200-083-5
Nikkaji

Properties

Computed structural properties

XLogP
0.7
Topological polar surface area
47.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
3
Heavy atoms
15
Formal charge
0
Complexity
205

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
PesticidesPesticides -> Insect Sterilants
LogP · 2 items

Log P= -0.54

-0.2

OdorODORLESS
Color/Form · 2 items

MINUTE CRYSTALS FROM CHLOROFORM

WHITE, CRYSTALLINE POWDER

Solubility · 3 items

less than 1 mg/mL at 61 °F (NTP, 1992)

WT/WT @ 26 °C: WATER 40%, CHLOROFORM 28.1%, METHYLENE CHLORIDE 19.7%, DIOXANE 9.6%, ETHANOL 7.7%, DIMETHYL CELLOSOLVE 4.8%, ETHYL ACETATE 4.5%, CARBON TETRACHLORIDE 3.6%, ACETONE 10.6%, METHYL ETHYL KETONE 4.7%, METHANOL 12.5%, BENZENE 5.6%

Soluble in oxygenated and chlorinated solvents.

DecompositionWHEN HEATED TO DECOMP, EMITS HIGHLY TOXIC FUMES OF NO(X).
Melting Point · 2 items

282 °F (decomposes) (NTP, 1992)

@ 160 °C, IT INITIALLY MELTS, THEN RAPIDLY POLYMERIZES TO WHITE SOLID

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 item

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.

Hazards SummaryVery toxic by ingestion or parenteral routes; May cause liver, kidney, and bone marrow damage; [HSDB] Sensitive to moisture (may polymerize); An irritant; May cause bone marrow depression and damage to the liver and kidneys; [MSDSonline]
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity AlertsPolymerizable
Reactivity Profile · 1 item

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.

Air and Water ReactionsSoluble in water [Hawley]. Polymerizes readily with heat or moisture.

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

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.

MeSH Pharmacological Classification · 1 item

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)

Absorption, Distribution and Excretion · 4 items

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.

Uses & manufacturing

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
J4.112B
Vapor Pressure
0.0000361 [mmHg]
Physical Description · 2 items

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)

White, odorless solid; [Hawley] White to off-white crystalline powder; [MSDSonline]

Stability/Shelf Life · 4 items

AMPULED AQ SOLN STORED @ 4 DEG ARE STABLE FOR ABOUT 3 MO.

ALMOST IMMEDIATE DEGRADATION @ PH 3.0; EVEN @ PH 5.0, DEGRADATION WAS RAPID; BUT @ PH 7.5 THERE WAS VERY LITTLE DEGRADATION.

RECRYSTALLIZED FROM CHLOROFORM & STORED AS SOLID; STABLE IN AIR @ 5 DEG OR 25 DEG OR UNDER NITROGEN @ 5 °C FOR 48 DAYS.

STORAGE OF SOLID @ 75 °C LED TO POLYMERIZATION @ RATE OF APPROX 0.25%/DAY.

Other Experimental Properties · 2 items

DECOMP 139 °C; @ ROOM TEMP AQUEOUS SOLUTIONS POLYMERIZE

Polymerizes readily with heat or moisture

Physicochemical properties

Melting point
160 °C · 160 °C
Boiling point
332.73 °C · 332.73°C (rough estimate)
Density
1.2815 · 1.2815 (rough estimate)
refractive index
1.79 · 1.7900 (estimate)
storage temp.
Refrigerator (+4°C) + Poison room
pka
3.13 · 3.13±0.10(Predicted)
Stability
Unstable - polymerizes at room temperature. Polymerizes more readily if heated and in the presence of moisture.
EWG's Food Scores
1 · 1
FDA UNII
7 IY6HZG9D · F7IY6HZG9D
IARC
3 · 3 (Vol. 9, Sup 7) 1987
EPA Substance Registry System
Triethylenemelamine (51-18-3)
RIDADR
3249 · 3249
HazardClass
6.1 · 6.1(a)
PackingGroup
II
Hazardous Substances Data
51 · 51-18-3(Hazardous Substances Data)
Toxicity
50 in · LD50 in mice, rats (mg/kg): 2.8, 1.0 i.p.; 15, 13 orally (Philips)
First Aid · 1 item

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.

Nonfire Spill Response · 1 item

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.

Disposal Methods · 1 item

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.

Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Personal Protective Equipment (PPE) · 1 item

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)

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Natural Pollution SourcesTEM IS NOT KNOWN TO OCCUR IN NATURE.
Human Toxicity Excerpts · 3 items

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.

Carcinogen Classification · 5 items

2,4,6-Tris(1-aziridinyl)-s-triazine

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 9: (1975) Some Aziridines, N-, S- and O-Mustards and Selenium

1987

1987

Non-Human Toxicity Excerpts · 5 items

...113...FEMALE RF MICE...GIVEN 4 IP INJECTIONS OF 1.5 MG/KG BODY WT TEM IN SALINE @ 14-DAY INTERVALS. ... OF 99 TREATED MICE SURVIVING 30 DAYS OR MORE, 33% DEVELOPED THYMIC LYMPHOMAS, 53%, PULMONARY ADENOMAS & 52%, OVARIAN TUMORS...COMPARED WITH 10%, 15% & 20% IN 112 CONTROLS, RESPECTIVELY.

10 3-MO-OLD...A MICE RECEIVED 10 DOSES OF 0.0075 MG TEM BY IP INJECTION... ANIMALS WERE KILLED 100 DAYS AFTER 1ST INJECTION. PULMONARY ADENOMAS OCCURRED IN 8/10 TREATED MICE...AVG OF 2 TUMORS/MOUSE. OF 15 UNTREATED CONTROLS...1 HAD 3 LUNG TUMORS & ANOTHER, 1 LUNG TUMOR.

REPEATED SC INJECTIONS OF TEM IN ARACHIS OIL INTO...RATS (TOTAL...10 MG/KG BODY WT) PRODUCED LOCAL SARCOMAS IN 11/12...INDUCTION TIME OF 240-450 DAYS. ... USING INBRED WISTAR RATS, 5/12 DEVELOPED LOCAL SARCOMAS...INDUCTION TIME OF 438-506 DAYS; 2...ALSO DEVELOPED HEPATOMAS & 2, OVARIAN TUMORS.

TWO GROUPS OF 10 MALE STOCK ALBINO S MICE, 7-9 WK OLD WERE TREATED WITH EITHER SINGLE APPLICATION OF 0.24 MG TEM (AS 0.08% SOLN IN ACETONE) OR 15 WEEKLY APPLICATIONS OF 0.04% SOLN OF TEM (TOTAL DOSE 1.8 MG; NONE OF THE MICE DEVELOPED SKIN TUMORS DURING THIS TREATMENT. WHEN ANIMALS WERE TREATED WITH A SINGLE APPLICATION OF 0.24 MG TEM OR 0.5 MG TERM AND ALSO GIVEN WEEKLY APPLICATIONS OF 0.3 ML OF A 0.5% SOLN OF CROTON OIL IN ACETONE FOR 20 WK, STARTING 3 WK AFTER THE APPLICATION OF TEM, 5/10 AND 3/7 SURVIVING MICE DEVELOPED A TOTAL OF 18 AND 7 SKIN PAPILLOMAS.

For more Non-Human Toxicity Excerpts (Complete) data for S-TRIAZINE, 2,4,6-TRIS(1-AZIRIDINYL)- (25 total), please visit the HSDB record page.

Evidence for CarcinogenicityNo data are available in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.
Non-Human Toxicity Values · 4 items

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/

Safety data

ridadr
3249
Toxicity
LD50 in mice, rats (mg/kg): 2.8, 1.0 i.p.; 15, 13 orally (Philips)
hazard_class
6.1(a)
packing_group
II
Hazardous Substances Data
51-18-3(Hazardous Substances Data)
Uses · 6 items

Used as an alkylating agent in industry, cancer treatment, and research; [ChemIDplus] Used to make resins; Also used as a textile finishing agent, an insect sterilant, and a modifier of adhesives; [HSDB]

Working with Glues and Adhesives [Category: Other]

MFR OF RESINOUS PRODUCTS, TEXTILE FINISHING AGENTS, INSECT STERILANT, RESEARCH TOOL USED AS POSITIVE CONTROL FOR MUTAGENICITY ASSAYS; MEDICATION: ANTINEOPLASTIC

MODIFIER FOR CERTAIN ADHESIVES

MFR OF RESINOUS PRODUCTS & TEXTILE FINISHING AGENTS

Textile finishing agent.

U.S. Production · 2 items

(1975) NOT PRODUCED COMMERCIALLY IN US

(1977) NOT PRODUCED COMMERCIALLY IN US

Consumption Patterns(1977) NO LONGER USED COMMERCIALLY IN US
Methods of ManufacturingPREPD FROM ETHYLENIMINE & CYANURIC CHLORIDE.
Formulations/Preparations · 2 items

TABLETS NF: 5 MG.

GRADE: NF.

General Manufacturing InformationLIKE 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.
Applications · 4 items

UsesTretamine is an aziridine chemosterilant that functions as a fumigant.

Usesmanufacture of resinous products, textile finishing agents. Insect sterilant. Research tool used as positive control for mutagenicity assays.

UsesTriethylenemelamine (TEM) is a potent mutagen. It has little, if any, industrial application. TEM is mainly used in medicine as an antineoplastic agent and as a “positive control” in many in vitro and in vivo mutagenicity assays.

General DescriptionOdorless 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.

Upstream & downstream products

Upstream raw materials

Cyanuric chlorideEthyleneimine

Additional notes

DefinitionChEBI: Tretamine is a member of 1,3,5-triazines. It has a role as an insect sterilant and an alkylating agent.