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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:31:05 UTC
HMDB IDHMDB15025
Secondary Accession NumbersNone
Metabolite Identification
Common NameMechlorethamine
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. [PubChem]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.
Structure
Thumb
Synonyms
ValueSource
2,2'-dichloro-N-MethyldiethylamineChEBI
beta,Beta'-dichlorodiethyl-N-methylamineChEBI
Bis(2-chloroethyl)methylamineChEBI
Bis(beta-chloroethyl)methylamineChEBI
Methylbis(2-chloroethyl)amineChEBI
Methylbis(beta-chloroethyl)amineChEBI
N-Methyl-bis(2-chloroethyl)amineChEBI
N-Methyl-bis(beta-chloroethyl)amineChEBI
Nitrogen mustardChEBI
b,Beta'-dichlorodiethyl-N-methylamineGenerator
β,beta'-dichlorodiethyl-N-methylamineGenerator
Bis(b-chloroethyl)methylamineGenerator
Bis(β-chloroethyl)methylamineGenerator
Methylbis(b-chloroethyl)amineGenerator
Methylbis(β-chloroethyl)amineGenerator
N-Methyl-bis(b-chloroethyl)amineGenerator
N-Methyl-bis(β-chloroethyl)amineGenerator
ChlorethazineHMDB
HN2HMDB
MBAHMDB
MechloroethamineHMDB
MecloretaminaHMDB
MustineHMDB
Chemical FormulaC5H11Cl2N
Average Molecular Weight156.054
Monoisotopic Molecular Weight155.026854771
IUPAC Namebis(2-chloroethyl)(methyl)amine
Traditional Namemechlorethamine
CAS Registry Number51-75-2
SMILES
CN(CCCl)CCCl
InChI Identifier
InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3
InChI KeyInChIKey=HAWPXGHAZFHHAD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitrogen mustard compounds. These are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassNitrogen mustard compounds
Sub ClassNot Available
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Alkylating Agents
  • Antineoplastic Agents, Alkylating
  • Chemical Warfare Agents
  • Irritants
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point108 - 111 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.34e+01 g/LNot Available
LogP1.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility33.4 mg/mLALOGPS
logP1.31ALOGPS
logP1.52ChemAxon
logS-0.67ALOGPS
pKa (Strongest Basic)6.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.67 m3·mol-1ChemAxon
Polarizability15.84 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a4i-7900000000-66a0ef3007bd03bd9367View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00888
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00888
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-6 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00888
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3893
KEGG Compound IDC07115
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMechlorethamine
NuGOwiki LinkHMDB15025
Metagene LinkHMDB15025
METLIN IDNot Available
PubChem Compound4033
PDB IDNot Available
ChEBI ID28925
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available