Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Mechlorethamine
RN: 51-75-2
UNII: 50D9XSG0VR
InChIKey: HAWPXGHAZFHHAD-UHFFFAOYSA-N

Note

  • A biologic alkylating agent that exerts its cytotoxic effects by forming DNA ADDUCTS and DNA interstrand crosslinks, thereby inhibiting rapidly proliferating cells. The hydrochloride is an antineoplastic agent used to treat HODGKIN DISEASE and LYMPHOMA.

Molecular Formula

  • C5-H11-Cl2-N

Molecular Weight

  • 156.055
 

Classification Codes

Classification Codes

  • Alkylating Agents
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Blister Agent
  • Chemical Warfare Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Irritants
  • Mutation Data
  • Noxae
  • Poisons
  • Reproductive Effect
  • Riot Control Agents, Chemical
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 10 lb

Names and Synonyms

Results Name

  • Mechlorethamine

Name of Substance

  • Chlormethine [INN:BAN]
  • Mechlorethamine

MeSH Heading

  • Mechlorethamine

Synonyms

  • 2,2'-Dichloro-N-methyldiethylamine
  • 2,2'-Dichlorodiethyl-methylamine
  • 2-Chloro-N-(2-chloroethyl)-N-methylethanamine
  • 4-04-00-00446 (Beilstein Handbook Reference)
  • Antimit
  • beta,beta'-Dichlorodiethyl-N-methylamine
  • Bis(2-chloroethyl)methylamine
  • Bis(beta-chloroethyl)methylamine
  • BRN 0605323
  • C 6866
  • Caryolysine
  • CCRIS 447
  • Chloramine (the nitrogen mustard)
  • Chlorethazine
  • Chlormethine
  • Chlormethinum
  • Chlormethinum [INN-Latin]
  • Cloramin
  • Clormetina
  • Clormetina [INN-Spanish]
  • Di(2-chloroethyl)methylamine
  • Dichlor amine
  • Diethylamine, 2,2'-dichloro-N-methyl-
  • EINECS 200-120-5
  • Embichin
  • ENT-25294
  • Ethanamine, 2-chloro-N-(2-chloroethyl)-N-methyl-
  • HN-2
  • HN2
  • HSDB 5083
  • MBA
  • Mechlorethamine
  • Mecloretamina
  • Mecloretamina [Italian]
  • Methylbis(2-chloroethyl)amine
  • Methylbis(beta-chloroethyl)amine
  • Methyldi(2-chloroethyl)amine
  • N,N-Bis(2-chloroethyl)methylamine
  • N,N-Di(chloroethyl)methylamine
  • N-Methyl lost
  • N-Methyl-2,2'-dichlorodiethylamine
  • N-Methyl-bis(2-chloroethyl)amine
  • N-Methyl-bis(beta-chloroethyl)amine
  • N-Methyl-bis-chloraethylamin
  • N-Methyl-bis-chloraethylamin [German]
  • N-Methyl-lost
  • N-Methyl-lost [German]
  • Nitrogen mustard (HN-2)
  • NSC 762
  • NSC-10107
  • Stickstofflost (ebewe)
  • T 1024
  • T-1024
  • TL 146
  • UN 2927
  • UNII-50D9XSG0VR
  • Valchlor

Systematic Names

  • Chlormethine
  • Diethylamine, 2,2'-dichloro-N-methyl-
  • Ethanamine, 2-chloro-N-(2-chloroethyl)-N-methyl-

Superlist Names

  • 2-Chloro-N-(2-chloroethyl)-N-methylethanamine
  • Mechlorethamine
  • N-Methyl-bis(2-chloroethyl)amine
  • Nitrogen mustard

Registry Numbers

CAS Registry Number

  • 51-75-2

FDA UNII

  • 50D9XSG0VR

Related Registry Numbers

  • 126-85-2 (N-oxide)
  • 302-70-5 (N-oxide, hydrochloride)
  • 55-86-7 (hydrochloride)

System Generated Number

  • 0000051752

Structure Descriptors

InChI

1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3

InChIKey

HAWPXGHAZFHHAD-UHFFFAOYSA-N

Smiles

N(CCCl)(CCCl)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LCLo inhalation 290mg/m3/10M (290mg/m3) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: IRRITABILITY
National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. APR1942,
chicken LD50 intravenous 10mg/kg (10mg/kg)   National Technical Information Service. Vol. PB158-507,
dog LD65 intravenous 1mg/kg (1mg/kg)   National Technical Information Service. Vol. PB158-507,
domestic animals - goat/sheep LD50 skin 20mg/kg (20mg/kg)   National Technical Information Service. Vol. PB158-507,
domestic animals - goat/sheep LDLo oral 100mg/kg (100mg/kg)   National Technical Information Service. Vol. PB158-507,
guinea pig LD50 oral 12mg/kg (12mg/kg)   National Technical Information Service. Vol. PB158-507,
guinea pig LD50 subcutaneous 2mg/kg (2mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA National Technical Information Service. Vol. PB158-507,
monkey LDLo skin 50mg/kg (50mg/kg)   National Technical Information Service. Vol. PB158-507,
mouse LD50 intraperitoneal 2400ug/kg (2.4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1921, 1972.
mouse LD50 intravenous 2mg/kg (2mg/kg)   National Technical Information Service. Vol. PB158-507,
mouse LD50 oral 10mg/kg (10mg/kg)   National Technical Information Service. Vol. PB158-507,
mouse LD50 skin 29mg/kg (29mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 224, 1947.
mouse LD50 subcutaneous 2600ug/kg (2.6mg/kg)   National Technical Information Service. Vol. PB158-507,
pigeon LDLo intravenous 15mg/kg (15mg/kg)   National Technical Information Service. Vol. PB158-507,
rabbit LD50 intravenous 1600ug/kg (1.6mg/kg)   National Technical Information Service. Vol. PB158-507,
rabbit LD50 oral 5mg/kg (5mg/kg)   National Technical Information Service. Vol. PB158-507,
rabbit LD50 skin 12mg/kg (12mg/kg)   National Technical Information Service. Vol. PB158-507,
rabbit LD50 subcutaneous 3mg/kg (3mg/kg)   National Technical Information Service. Vol. PB158-507,
rat LD50 intracrebral 125ug/kg (0.125mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 18, Pg. 760, 1966.
rat LD50 intraperitoneal 860ug/kg (0.86mg/kg)   Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 1, Pg. 154, 1968.
rat LD50 intravenous 1100ug/kg (1.1mg/kg)   National Technical Information Service. Vol. PB158-507,
rat LD50 oral 10mg/kg (10mg/kg)   National Technical Information Service. Vol. PB158-507,
rat LD50 skin 12mg/kg (12mg/kg)   Fundamental and Applied Toxicology. Vol. 5, Pg. S160, 1985.
rat LD50 subcutaneous 1200ug/kg (1.2mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 83, Pg. 376, 1953.
rat LD50 unreported 1700ug/kg (1.7mg/kg)   Pharmaceutical Bulletin. Vol. 1, Pg. 297, 1953.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point -6.00E+01 deg C   EXP
Boiling Point 87 deg C   EXP
pKa Dissociation Constant 6.76 (none) 0 EXP
log P (octanol-water) 0.91 (none)   EXP
Water Solubility 1.20E+04 mg/L 25 EXP
Vapor Pressure 65.1 mm Hg 25 EST
Henry's Law Constant 8.48E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.39E-12 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.