Tmic
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Record Information
Version2.0
Creation Date2014-08-29 05:52:43 UTC
Update Date2014-12-24 20:26:42 UTC
Accession NumberT3D4204
Identification
Common NameMechlorethamine
ClassSmall Molecule
DescriptionMechlorethamine 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.
Compound Type
  • Alkylating Agent
  • Amine
  • Antineoplastic Agent, Alkylating
  • Chemical Warfare Agent
  • Cigarette Toxin
  • Drug
  • Irritant
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
2,2'-dichloro-N-methyldiethylamine
beta,Beta'-dichlorodiethyl-N-methylamine
Bis(2-chloroethyl)methylamine
Bis(beta-chloroethyl)methylamine
Chlorethazine
Chlormethine
HN2
MBA
Mechloroethamine
Mecloretamina
Methylbis(2-chloroethyl)amine
Methylbis(beta-chloroethyl)amine
Mustargen
Mustine
N-methyl-bis(2-chloroethyl)amine
N-Methyl-bis(beta-chloroethyl)amine
Nitrogen mustard
Valchlor
β,β'-dichlorodiethyl-N-methylamine
Chemical FormulaC5H11Cl2N
Average Molecular Mass156.054 g/mol
Monoisotopic Mass155.027 g/mol
CAS Registry Number51-75-2
IUPAC Namebis(2-chloroethyl)(methyl)amine
Traditional Namemechlorethamine
SMILESCN(CCCl)CCCl
InChI IdentifierInChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3
InChI KeyInChIKey=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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassNitrogen mustard compounds
Direct ParentNitrogen 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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point108 - 110°C
Boiling Point87°C at 1.80E+01 mm Hg
SolubilityVery soluble
LogP0.91
Predicted Properties
PropertyValueSource
Water Solubility33.4 g/LALOGPS
logP1.31ALOGPS
logP1.52ChemAxon
logS-0.67ALOGPS
pKa (Strongest Basic)6.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.67 m³·mol⁻¹ChemAxon
Polarizability15.84 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9400000000-37f4081d8c3fd8e974c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2282bef263bfa8a41123View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-7900000000-b0b770790e86670fc2a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-5d96975a96ed8783c02eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-7801c92cb7dc490c200dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-4900000000-0df7677828ba3d2293adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08i3-9100000000-67d0e475a21ed8a44dcaView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-7900000000-66a0ef3007bd03bd9367View in MoNA
Toxicity Profile
Route of ExposurePartially absorbed following intracavitary administration, most likely due to rapid deactivation by body fluids. When it is topically administered, systemic exposure was undetectable.
Mechanism of ToxicityAlkylating 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.
MetabolismUndergoes 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 ValuesThe oral LD50 for a rat is 10 mg/kg.
Lethal DoseNot 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). (2)
Uses/SourcesFor 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 LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00888
HMDB IDHMDB15025
PubChem Compound ID4033
ChEMBL IDCHEMBL427
ChemSpider ID3893
KEGG IDC07115
UniProt IDNot Available
OMIM ID
ChEBI ID28925
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkMechlorethamine
References
Synthesis Reference

Paul Siedlecki, “Preparation of nitrogen mustard derivatives.” U.S. Patent US20030162990, issued August 28, 2003.

MSDSLink
General References
  1. FDA label
  2. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. De Alencar TA, Leitao AC, Lage C: Nitrogen mustard- and half-mustard-induced damage in Escherichia coli requires different DNA repair pathways. Mutat Res. 2005 Apr 4;582(1-2):105-15. [15781216 ]
  4. Loeber RL, Michaelson-Richie ED, Codreanu SG, Liebler DC, Campbell CR, Tretyakova NY: Proteomic analysis of DNA-protein cross-linking by antitumor nitrogen mustards. Chem Res Toxicol. 2009 Jun;22(6):1151-62. doi: 10.1021/tx900078y. [19480393 ]