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Substance Name: Mechlorethamine hydrochloride [USP]
RN: 55-86-7
UNII: L0MR697HHI
InChIKey: QZIQJVCYUQZDIR-UHFFFAOYSA-N

Note

  • A vesicant and necrotizing irritant destructive to mucous membranes. It was formerly used as a war gas. The hydrochloride is used as an antineoplastic in Hodgkin's disease and lymphomas. It causes severe gastrointestinal and bone marrow damage.

Molecular Formula

  • C5-H11-Cl2-N.Cl-H

Molecular Weight

  • 192.5158
 

Classification Codes

Classification Codes

  • Alkylating Agents
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 2A
  • Reasonably Anticipated to be a Carcinogen
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Names and Synonyms

Name of Substance

  • Mechlorethamine hydrochloride
  • Mechlorethamine hydrochloride [USP]

Synonyms

  • 1,5-Dichloro-3-methyl-3-azapentane hydrochloride
  • 2,2'-Dichloro-N-methyldiethylamine hydrochloride
  • 2-Chloro-N-(2-chloroethyl)-N-methylethanamine hydrochlroide
  • AI3-16195
  • Azotoyperite
  • beta,beta'-Dichlorodiethyl-N-methylamine hydrochloride
  • Bis(2-chloroethyl)methylamine hydrochloride
  • C 6866
  • Caryolysine
  • CCRIS 448
  • Chloramin
  • Chlorethamine
  • Chlormethine hydrochloride
  • Chlormethinum
  • Dema
  • Di(2-chloroethyl)methylamine hydrochloride
  • Dichloren
  • Dichloromethyldiethylamine hydrochloride
  • Dimitan
  • EINECS 200-246-0
  • Embichin
  • Embikhine
  • Embiquine
  • Erasol
  • Erasol-Ido
  • HN2 hydrochloride
  • HSDB 7176
  • Kloramin (VAN)
  • Mechlorethamine chloridrate
  • Mechlorethamine HCl
  • Mechlorethamine hydrochloride
  • Methyl-bis(beta-chloroethyl)amine hydrochloride
  • Methylbis(2-chloroethyl)amine hydrochloride
  • Methyldi(2-chloroethyl)amine hydrochloride
  • Methyldi(beta-chloroethyl)amine hydrochloride
  • Mitoxine
  • Mustargen
  • Mustin hydrochloride
  • Mustine hydrochloride
  • N,N-Bis(2-chloraethyl)methylamin-hydrochlorid
  • N,N-Bis(2-chloraethyl)methylamin-hydrochlorid [German]
  • N,N-Bis(2-chloroethyl)methylamine hydrochloride
  • N-Methyl-2,2'-dichlorodiethylamine hydrochloride
  • N-Methyl-bis-beta-chlorethylamine hydrochloride
  • N-Methyl-di-2-chloroethylamine hydrochloride
  • N-Methylbis(2-chloroethyl)amine hydrochloride
  • N-Mustard
  • N-Mustard [German]
  • NCI-C56382
  • Nitol
  • Nitol takeda
  • Nitrogen mustard (HN-2), hydrochloride
  • Nitrogen mustard hydrochloride
  • Nitrogranulogen hydrochloride
  • NSC 762
  • Pliva
  • SK 101
  • Stickstofflost
  • UNII-L0MR697HHI
  • Zagreb

Systematic Names

  • Chlormethine hydrochloride
  • Diethylamine, 2,2'-dichloro-N-methyl, hydrochloride
  • Ethanamine, 2-chloro-N-(2-chloroethyl)-N-methyl-, hydrochloride
  • Nitrogen mustard hydrochloride
  • Stickstofflost-ebewe

Superlist Names

  • Ethanamine, 2-chloro-N-(2-chloroethyl)-N-methyl-, hydrochloride
  • Mechlorethamine hydrochloride
  • Nitrogen mustard hydrochloride

Registry Numbers

CAS Registry Number

  • 55-86-7

FDA UNII

  • L0MR697HHI

Other Registry Numbers

  • 159923-90-7
  • 37244-63-6

Related Registry Number

  • 51-75-2 (Parent)

System Generated Number

  • 0000055867

Molecular Formulas

Molecular Formula

  • C5-H11-Cl2-N.Cl-H

Molecular Formula Fragments

  • C5-H11-Cl2-N
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C5H11Cl2N.ClH/c1-8(4-2-6)5-3-7;/h2-5H2,1H3;1H

InChIKey

QZIQJVCYUQZDIR-UHFFFAOYSA-N

Smiles

Cl.CN(CCCl)CCCl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 3850mg/kg (3850mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 131, 1949.
dog LD50 intravenous 1mg/kg (1mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 224, 1947.
human TDLo intravenous 400ug/kg (0.4mg/kg) BLOOD: LEUKOPENIA

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: THROMBOCYTOPENIA
Clinical Pharmacology and Therapeutics Vol. 6, Pg. 50, 1965.
monkey LDLo intravenous 340ug/kg (0.34mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: OTHER CHANGES

BLOOD: LEUKOPENIA
Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 201, 1965.
mouse LD50 intramuscular 2750ug/kg (2.75mg/kg)   Archiv der Pharmazie Vol. 306, Pg. 64, 1973.
mouse LD50 intraperitoneal 2900ug/kg (2.9mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 62, Pg. 96, 1966.
mouse LD50 intravenous 2mg/kg (2mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 224, 1947.
mouse LD50 oral 20mg/kg (20mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 224, 1947.
mouse LD50 subcutaneous 2600ug/kg (2.6mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 224, 1947.
rabbit LD50 intravenous 1600ug/kg (1.6mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 224, 1947.
rabbit LD50 oral 12500ug/kg (12.5mg/kg)   National Technical Information Service. Vol. PB158-507,
rat LD50 intramuscular 1100ug/kg (1.1mg/kg)   Archiv der Pharmazie Vol. 306, Pg. 64, 1973.
rat LD50 intraperitoneal 1500ug/kg (1.5mg/kg)   Toxicology and Applied Pharmacology. Vol. 5, Pg. 735, 1963.
rat LD50 intravenous 1100ug/kg (1.1mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 224, 1947.
rat LD50 oral 10mg/kg (10mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 224, 1947.
rat LD50 parenteral 1700ug/kg (1.7mg/kg)   Recent Results in Cancer Research. Vol. 52, Pg. 76, 1975.
rat LD50 subcutaneous 1900ug/kg (1.9mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 224, 1947.