Trichlormethine
Title: Trichlormethine
CAS Registry Number: 555-77-1
CAS Name: 2-Chloro-N,N-bis(2-chloroethyl)ethanamine
Additional Names: 2,2¢,2¢¢-trichlorotriethylamine; tris(b-chloroethyl)amine; trimustine
Manufacturers' Codes: HN-3
Molecular Formula: C6H12Cl3N
Molecular Weight: 204.53
Percent Composition: C 35.23%, H 5.91%, Cl 52.00%, N 6.85%
Line Formula: N(CH2CH2Cl)3
Literature References: Nitrogen mustard formerly used as a chemical warfare agent. Prepd by the action of thionyl chloride on triethanolamine: Ward, J. Am. Chem. Soc. 57, 914 (1935); US 2072348 (1937 to Hercules Powder). Improved procedure: Wilson, Tishler, J. Am. Chem. Soc. 73, 3635 (1951); Witten in Kirk-Othmer Encyclopedia of Chemical Technology vol. 7 (Interscience, New York, 1951) p 130. Clinical use in treatment of Hodgkin's disease and leukemias: L. S. Goodman et al., J. Am. Med. Assoc. 132, 126 (1946). Evaluation of carcinogenic risk: IARC Monographs 50, 143 (1990). GC determn in air: J. R. Stuff et al., J. Chromatogr. A 849, 529 (1999).
Properties: Mobile liquid. Faint odor of fish + soap. Vesicant, necrotizing irritant. Never use without appropriate gas mask. Volatility at 25° = 0.120 mg/l. d425 1.2347, mp -4°. bp15 144°. nD25 1.4925. Very slightly sol in water. Miscible with dimethylformamide, carbon disulfide, carbon tetrachloride, many other organic solvents and oils. The undiluted liq dec on standing and forms polymeric quaternary ammonium salts which are insol in the free base.
Melting point: mp -4°
Boiling point: bp15 144°
Index of refraction: nD25 1.4925
Density: d425 1.2347
 
Derivative Type: Hydrochloride
CAS Registry Number: 817-09-4
Trademarks: Trillekamin (Crookes)
Molecular Formula: C6H12Cl3N.HCl
Molecular Weight: 240.99
Percent Composition: C 29.90%, H 5.44%, Cl 58.85%, N 5.81%
Properties: Crystals, mp 130-131°. Freely sol in water, sol in alcohol.
Melting point: mp 130-131°
 
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkylating Agents; Nitrogen Mustards.

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