| Common Name |
Mechlorethamine
| 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 Hodgkins 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, resliting 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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
2,2'-dichloro-N-MethyldiethylamineChEBI
beta,Beta'-dichlorodiethyl-N-methylamineChEBI
Bis(2-chloroethyl)methylamineChEBI
Bis(beta-chloroethyl)methylamineChEBI
ChlormethineChEBI
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
Mechlorethamine hydrochloride N oxideMeSH
Mechlorethamine hydrochloride N-oxideMeSH
Merck frosst brand OF mechlorethamine hydrochlorideMeSH
NSC-762MeSH
EmbichinMeSH
Hydrochloride N-oxide, mechlorethamineMeSH
Mechlorethamine N oxideMeSH
Mechlorethamine oxideMeSH
Merck brand OF mechlorethamine hydrochlorideMeSH
MitomenMeSH
Nitrogen mustard N oxideMeSH
CaryolysineMeSH
CloraminMeSH
Hydrochloride, mechlorethamineMeSH
MethylchlorethamineMeSH
N-Oxide, mechlorethamine hydrochlorideMeSH
N-Oxide, nitrogen mustardMeSH
Nitrogen mustard N-oxideMeSH
NitrogranliogenMeSH
NitrominMeSH
Mechlorethamine hydrochlorideMeSH
Mechlorethamine N-oxideMeSH
MustargenMeSH
NSC 762MeSH
| Chemical Formlia |
C5H11Cl2N
| Average Molecliar Weight |
156.054
| Monoisotopic Molecliar Weight |
155.026854771
| IUPAC Name |
bis(2-chloroethyl)(methyl)amine
| Traditional Name |
mechlorethamine
| CAS Registry Number |
51-75-2
| 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 |
This 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.
| Kingdom |
Organic compounds
| Super Class |
Organic nitrogen compounds
| Class |
Organonitrogen compounds
| Sub Class |
Nitrogen mustard compounds
| Direct Parent |
Nitrogen mustard compounds
| Alternative Parents |
Trialkylamines
Organopnictogen compounds
Organochlorides
Hydrocarbon derivatives
Alkyl chlorides
| Substituents |
Nitrogen mustard
Tertiary aliphatic amine
Tertiary amine
Organopnictogen compound
Hydrocarbon derivative
Organochloride
Organohalogen compound
Amine
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
organochlorine compound (CHEBI:28925 )
nitrogen mustard (CHEBI:28925 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Alkylating Agents
Antineoplastic Agents, Alkylating
Chemical Warfare Agents
Irritants
| Application |
Pharmaceutical
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point108 – 111 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.34e+01 g/LNot Available
LogP1.6Not Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| MS |
Mass Spectrum (Electron Ionization)splash10-0a4i-7900000000-66a0ef3007bd03bd9367View in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00888
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00888
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Predicted Concentrations |
|
| Biofluid |
Original age |
Original condition |
Blood0-6 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB00888
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
3893
| KEGG Compound ID |
C07115
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Mechlorethamine
| NuGOwiki Link |
HMDB15025
| Metagene Link |
HMDB15025
| METLIN ID |
Not Available
| PubChem Compound |
4033
| PDB ID |
Not Available
| ChEBI ID |
28925
Product: AMG 838
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not Available |
PMID: 18829454
