SynCED: Mechlorethamine

Record Information

Version

1.0

Creation Date

2014-08-29 05:52:43 UTC

Update Date

2026-08-22 20:12:15 UTC

Accession Number

CHEM003164

Identification

Common Name

Mechlorethamine

Class

Small Molecule

Description

Mechlorethamine is only found in individuals that have used or taken this drug. It is 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. Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations. Mechlorethamine is cell cycle phase-nonspecific.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 2A
STOFF IDENT Compounds
T3DB toxins
Tobacco Smoke Compounds

Contaminant Type

Alkylating Agent
Amine
Antineoplastic Agent, Alkylating
Chemical Warfare Agent
Cigarette Toxin
Drug
Irritant
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,2'-Dichloro-N-methyldiethylamine	ChEBI
beta,Beta'-dichlorodiethyl-N-methylamine	ChEBI
Bis(2-chloroethyl)methylamine	ChEBI
Bis(beta-chloroethyl)methylamine	ChEBI
Chlormethine	ChEBI
Methylbis(2-chloroethyl)amine	ChEBI
Methylbis(beta-chloroethyl)amine	ChEBI
N-Methyl-bis(2-chloroethyl)amine	ChEBI
N-Methyl-bis(beta-chloroethyl)amine	ChEBI
Nitrogen mustard	ChEBI
b,Beta'-dichlorodiethyl-N-methylamine	Generator
Β,beta'-dichlorodiethyl-N-methylamine	Generator
Bis(b-chloroethyl)methylamine	Generator
Bis(β-chloroethyl)methylamine	Generator
Methylbis(b-chloroethyl)amine	Generator
Methylbis(β-chloroethyl)amine	Generator
N-Methyl-bis(b-chloroethyl)amine	Generator
N-Methyl-bis(β-chloroethyl)amine	Generator
Chlorethazine	HMDB
HN2	HMDB
MBA	HMDB
Mechloroethamine	HMDB
Mecloretamina	HMDB
Mustine	HMDB
Mechlorethamine hydrochloride N oxide	HMDB
Mechlorethamine hydrochloride N-oxide	HMDB
Merck frosst brand OF mechlorethamine hydrochloride	HMDB
NSC-762	HMDB
Embichin	HMDB
Hydrochloride N-oxide, mechlorethamine	HMDB
Mechlorethamine N oxide	HMDB
Mechlorethamine oxide	HMDB
Merck brand OF mechlorethamine hydrochloride	HMDB
Mitomen	HMDB
Nitrogen mustard N oxide	HMDB
Caryolysine	HMDB
Cloramin	HMDB
Hydrochloride, mechlorethamine	HMDB
Methylchlorethamine	HMDB
N-Oxide, mechlorethamine hydrochloride	HMDB
N-Oxide, nitrogen mustard	HMDB
Nitrogen mustard N-oxide	HMDB
Nitrogranulogen	HMDB
Nitromin	HMDB
Mechlorethamine hydrochloride	HMDB
Mechlorethamine N-oxide	HMDB
Mustargen	HMDB
NSC 762	HMDB

Chemical Formula

C₅H₁₁Cl₂N

Average Molecular Mass

156.054 g/mol

Monoisotopic Mass

155.027 g/mol

CAS Registry Number

51-75-2

IUPAC Name

bis(2-chloroethyl)(methyl)amine

Traditional Name

mechlorethamine

SMILES

CN(CCCl)CCCl

InChI Identifier

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

InChI Key

HAWPXGHAZFHHAD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Nitrogen mustard compounds

Direct Parent

Nitrogen mustard compounds

Alternative Parents

Substituents

Nitrogen mustard
Tertiary aliphatic amine
Tertiary amine
Organopnictogen compound
Hydrocarbon derivative
Organochloride
Organohalogen compound
Amine
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organochlorine compound (CHEBI:28925 )
nitrogen mustard (CHEBI:28925 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

alkylating agent

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	108 - 110°C
Boiling Point	87°C at 1.80E+01 mm Hg
Solubility	Very soluble

Predicted Properties

Property	Value	Source
Water Solubility	33.4 g/L	ALOGPS
logP	1.31	ALOGPS
logP	1.52	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Basic)	6.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	38.67 m³·mol⁻¹	ChemAxon
Polarizability	15.84 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Partially absorbed following intracavitary administration, most likely due to rapid deactivation by body fluids. When it is topically administered, systemic exposure was undetectable.

Mechanism of Toxicity

Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations. Mechlorethamine is cell cycle phase-nonspecific.

Metabolism

Undergoes rapid chemical transformation and combines with water or reactive compounds of cells, so that the drug is no longer present in active form a few minutes after administration. Half Life: 15 minutes

Toxicity Values

The oral LD50 for a rat is 10 mg/kg.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Chlormethine is probably carcinogenic to humans (Group 2A). Chlormethine is part of MOPP, a combination chemotherapy regimen that is carcinogenic to humans (Group 1). (1)

Uses/Sources

For the palliative treatment of Hodgkin's disease (Stages III and IV), lymphosarcoma, chronic myelocytic or chronic lymphocytic leukemia, polycythemia vera, mycosis fungoides, and bronchogenic carcinoma. Also for the palliative treatment of metastatic carcinoma resulting in effusion.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID