Mechlorethamine
Title: Mechlorethamine
CAS Registry Number: 51-75-2
CAS Name: 2-Chloro-N-(2-chloroethyl)-N-methylethanamine
Additional Names: 2,2¢-dichloro-N-methyldiethylamine; N-methyl-2,2¢-dichlorodiethylamine; di(chloroethyl)methylamine; methylbis(b-chloroethyl)amine; methyldi(2-chloroethyl)amine; chlormethine; nitrogen mustard; stickstofflost; MBA
Manufacturers' Codes: HN2
Molecular Formula: C5H11Cl2N
Molecular Weight: 156.05
Percent Composition: C 38.48%, H 7.10%, Cl 45.44%, N 8.98%
Literature References: A nitrogen mustard prepd by action of thionyl chloride on 2,2¢-(methylimino)diethanol in trichloroethylene: Prelog, Stepan, Collect. Czech. Chem. Commun. 7, 93 (1935); Hanby, Rydon, J. Chem. Soc. 1947, 513; Abrams et al., J. Soc. Chem. Ind. London 68, 280 (1949); T. W. Doyle, D. M. Vyas in Kirk-Othmer Encyclopedia of Chemical Technology vol. 5 (John Wiley & Sons, New York, 4th ed., 1993) pp 876-879, 900-901. Toxicity data: W. P. Anslow et al., J. Pharmacol. Exp. Ther. 91, 224 (1947).
Properties: Mobile liquid. Faint odor of herring. Vesicant, necrotizing irritant. Never use without appropriate gas mask. Volatility at 25° = 3.581 mg/l. d425 1.118. mp -60°. bp18 87°; bp10 75°; bp5 64°; bp2 59°. Very slightly sol in water. Miscible with DMF, CS2, CCl4, 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 -60°
Boiling point: bp18 87°; bp10 75°; bp5 64°; bp2 59°
Density: d425 1.118
 
Derivative Type: Hydrochloride
CAS Registry Number: 55-86-7
Trademarks: Caryolysine (Sanofi-Synthelabo); Mustargen (Merck & Co.); Mustine hydrochloride; Nitrogranulogen (Pliva)
Molecular Formula: C5H11Cl2N.HCl
Molecular Weight: 192.51
Percent Composition: C 31.20%, H 6.28%, Cl 55.25%, N 7.28%
Properties: Hygroscopic leaflets from acetone or chloroform, mp 109-111°. Very sol in water; sol in alcohol. Initial pH of a 2% aq soln: 3.0-4.0. Dry crystals are stable at temps up to 40°. LD50 in rats (mg/kg): 1.1 i.v.; 1.9 s.c. (Anslow).
Melting point: mp 109-111°
Toxicity data: LD50 in rats (mg/kg): 1.1 i.v.; 1.9 s.c. (Anslow)
 
Derivative Type: N-Oxide hydrochloride see Mechlorethamine Oxide Hydrochloride
 
CAUTION: Direct contact may cause severe skin and eye irritation; injury to deeper ocular structures, particularly the iris and lens. See Patty's Industrial Hygiene and Toxicology vol. 2E, G. D. Clayton, F. E. Clayton, Eds. (John Wiley & Sons, Inc., New York, 4th ed., 1994) pp 3297-3299. Mechlorethamine hydrochloride is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-192.
Use: Base as a gas warfare agent.
Therap-Cat: Hydrochloride as an antineoplastic.
Therap-Cat-Vet: Hydrochloride has been used as an antineoplastic.
Keywords: Antineoplastic; Alkylating Agents; Nitrogen Mustards.

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