bis(2-chloroethyl)(methyl)amine

• ChemBase ID: 765
• Molecular Formular: C5H11Cl2N
• Molecular Mass: 156.05354
• Monoisotopic Mass: 155.02685472
• SMILES: ClCCN(CCCl)C
• Canonical SMILES: ClCCN(CCCl)C
• InChI: InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3
• InChIKey: HAWPXGHAZFHHAD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(2-chloroethyl)(methyl)amine
• IUPAC Traditional name: mechlorethamine
• Brand Name: Caryolysin; Caryolysine; Cloramin; Dichloren; Embichin; Mustargen; Mutagen
• Synonyms: MBA; Mechloroethamine; Mecloretamina; Nitrogen mustard; Chlormethine; Chlorethazine; Mustine; HN2; Mechlorethamine; 2-Chloro-N-(2-chloroethyl)-N-methylethanamine

Database IDs

• CAS Number: 51-75-2
• EC Number: 200-120-5
• MDL Number: MFCD00044509
• PubChem SID: 46505784; 160964228
• PubChem CID: 4033
• CHEBI ID: 28925
• ATC CODE: L01AA05; D08AX04
• CHEMBL: 427
• Chemspider ID: 3893
• DrugBank ID: DB00888
• KEGG ID: D0767
• MeSH Name: Mechlorethamine
• Unique Ingredient Identifier: 50D9XSG0VR
• Wikipedia Title: Mechlorethamine

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.84192747
• LogD (pH = 7.4): 1.4990624
• Log P: 1.5191492
• Molar Refractivity: 38.6747 cm^3
• Polarizability: 15.1456375 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.31
• LOG S: -0.67
• Solubility (Water): 3.34e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1.2E+004 mg/L
• Apperance: Colourless liquid
• Partition Coefficient: 0.91
• Hydrophobicity(logP): 1.6
• Odor: Ichtyal, ammoniacal

Pharmacology Properties

• Admin Routes: Intracavitary; Intrapericardial; Intravenous; Topical
• Excretion: 50% (renal)
• Half Life: <1 minute
• Legal Status: Rx
• Pregnancy Category: D (US)

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB00888

• Drug Groups: approved
• Description: 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]
• Indication: 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.
• Pharmacology: Mechlorethamine also known as mustine, nitrogen mustard, and HN2, is the prototype anticancer chemotherapeutic drug. Successful clinical use of mechlorethamine gave birth to the field of anticancer chemotherapy. The drug is an analogue of mustard gas and was derived from toxic gas warfare research. It belongs to the group of nitrogen mustard alkylating agents. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.
• Toxicity: Symptoms of overexposure include severe leukopenia, anemia, thrombocytopenia, and a hemorrhagic diathesis with subsequent delayed bleeding may develop. Death may follow. The intravenous LD₅₀ is 2 mg/kg and 1.6 mg/kg in mouse and rat, respectively.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: Partially absorbed following intracavitary administration, most likely due to rapid deactivation by body fluids.
• Half Life: 15 minutes
• External Links: Wikipedia; RxList; Drugs.com