Originator
Triethylene,Lederle,US,1954
Uses
Tretamine is an aziridine chemosterilant that functions as a fumigant.
Uses
Triethylenemelamine (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.
Uses
manufacture of resinous products, textile finishing agents. Insect sterilant. Research tool used as positive control for mutagenicity assays.
Definition
ChEBI: Tretamine is a member of 1,3,5-triazines. It has a role as an insect sterilant and an alkylating agent.
Manufacturing Process
Cyanuric chloride (which may or may not contain the usual commercial
impurities) is dispersed into ice water by stirring in a ratio of 18.8 g of
cyanuric chloride to a mixture of 100 g of ice and 100 g of water. The slurry
may conveniently be prepared directly in a 3-necked flask equipped with an
agitator, dropping funnel, and thermometer. The temperature of the flask and
contents is maintained within the range of 2°C to 5°C, with an ice-salt
mixture. A solution of ethylenimine in an aqueous solution of potassium carbonate prepared in the proportions of 14 g ethylenimine, 44.5 g potassium
carbonate, and 150 g of water, is added dropwise to the cyanuric chloride
slurry. The reaction solution is then clarified with a little activated charcoal,
filtered, and extracted with chloroform. Despite the fact that
triethylenemelamine is more soluble in water than in chloroform, in a two_x0002_phase system (water-chloroform) nearly 75% of the triethylenemelamine is
distributed in the chloroform, and hence a few extractions with that solvent
suffice to separate the material from the original reaction medium. Five
extractions with 50 ml portions of chloroform gave 19 g of product, and an
additional 3 extractions with 25 ml portions gave 0.5 g, a total yield of 95.7%.
The product obtained by evaporating such an extract is a white
microcrystalline powder.
Therapeutic Function
Antineoplastic
Synthesis Reference(s)
Journal of the American Chemical Society, 77, p. 5915, 1955
DOI: 10.1021/ja01627a040
General 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.
Air & Water Reactions
Soluble in water [Hawley]. Polymerizes readily with heat or moisture.
Reactivity Profile
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.
Fire Hazard
Flash point data for TRIETHYLENEMELAMINE are not available; however, TRIETHYLENEMELAMINE is probably combustible.
Safety Profile
Poison by ingestion,
intraperitoneal, intramuscular, intravenous,
and subcutaneous routes. Experimental
teratogenic and reproductive effects.
Questionable carcinogen with experimental
neoplastigenic and tumorigenic data. Human
mutation data reported. Can cause
gastrointestinal tract disturbances and bone
marrow depression. When heated to
decomposition it emits highly toxic fumes of
NOx. Used as an antineoplastic agent and as
an insect sterilant.
Carcinogenicity
In several older, limited studies,
triethylenemelamine reportedly produced tumors in mice by
the dermal and intraperitoneal routes and in rats by subcutaneous
and/or intramuscular administration. These data were
reviewed and evaluated by the IARC and judged as
“limited evidence of carcinogenicity in animals.” As a result
of this evaluation of the animal data and a lack of evidence of
carcinogenicity in humans, the IARC placed TEM in its
Group 3 category.
