9671. Triethylenemelamine

Nomenclature

CAS number: 51-18-3
2,4,6-Tris(1-aziridinyl)-1,3,5-triazine; 2,4,6-tris(ethylenimino)-s-triazine; 2,4,6-triethylenimino-1,3,5-triazine; triethanomelamine; tretamine; triamelin; TEM; NSC-9706; Persistol (Chevron).
C9H12N6; mol wt 204.23.
C 52.93%, H 5.92%, N 41.15%.

Description and references

Prepd from ethylenimine and cyanuric chloride: Bestian, Ann. 566, 210 (1950); Wystrach, Kaiser, US 2520619 (1950 to Am. Cyanamid); Kaiser, Schaefer, US 2653934 (1953); Wystrach et al., J. Am. Chem. Soc. 77, 5915 (1955). Toxicology: F. S. Philips, J. B. Thiersch, J. Pharmacol. Exp. Ther. 100, 398 (1950). Review of carcinogenic risk: IARC Monographs 9, 95-105 (1975); of comparative mutagenicity: C. Ramel, Environ. Sci. Res. 24, 943-976 (1981).

Chemical structure

Properties

Minute crystals from chloroform, dec 139°. Soly (w/w) at 26°: in water 40%, chloroform 28.1%, methylene chloride 19.7%, methanol 12.5%, acetone 10.6%, dioxane 9.6%, ethanol 7.7%, benzene 5.6%, dimethyl Cellosolve 4.8%, methyl ethyl ketone 4.7%, ethyl acetate 4.5%, carbon tetrachloride 3.6%. Stable at reduced temps; ampuled aq solns stored at 4° are stable for about 3 months. At room temp, aq solns polymerize. LD50 in mice, rats (mg/kg): 2.8, 1.0 i.p.; 15, 13 orally (Philips).

Use

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

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkylating Agents; Ethylenimines and Methylmelamines