Structure via PubChem · Public domain (PubChem)
mechlorethamine
Sign in to saveAlso known as Mustargen®, mustine, nitrogen mustard, nitrogen mustard N-oxide hydrochloride, methylbis(2-chloroethyl)amine, N-methyl-bis(2-chloroethyl)amine, 2,2'-dichloro-N-methyldiethylamine, N-methyl-bis(beta-chloroethyl)amine
Chlormethine (INN, BAN), also known as mechlorethamine (USAN, USP), mustine, HN2, and (in post-Soviet states) embikhin (эмбихин), is a nitrogen mustard sold under the brand name Mustargen among others. It is the prototype of alkylating agents, a group of anticancer chemotherapeutic drugs. It works by binding to DNA, crosslinking two strands and preventing cell duplication. It binds to the N7 nitrogen on the DNA base guanine. As the chemical is a blister agent, its use is strongly restricted within the Chemical Weapons Convention where it is classified as a Schedule 1 substance.
Chemical data
- Formula
- C5H11Cl2N
- Molecular weight
- 156.05 g/mol
- IUPAC name
- 2-chloro-N-(2-chloroethyl)-N-methylethanamine
- SMILES
- CN(CCCl)CCCl
- InChIKey
- HAWPXGHAZFHHAD-UHFFFAOYSA-N
- XLogP
- 0.9
- Polar surface area
- 3.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
6,025 papersvia PubMed
Wikidata facts
- Mass
- 155.026855
Show 7 more facts
- melting point
- -60
- chemical formula
- C₅H₁₁Cl₂N
- boiling point
- 75
- World Health Organisation international non-proprietary name
- chlormethine
- vapor pressure
- 0.427
- canonical SMILES
- CN(CCCl)CCCl
- Commons category
- Chlormethine
via Wikidata · CC0
~6 min read
Article
5 sectionsContents
- Uses
- Side effects and toxicity
- History
- Chemistry
- References
Chlormethine (INN, BAN), also known as mechlorethamine (USAN, USP), mustine, HN2, and (in post-Soviet states) embikhin (эмбихин), is a nitrogen mustard sold under the brand name Mustargen among others. It is the prototype of alkylating agents, a group of anticancer chemotherapeutic drugs. It works by binding to DNA, crosslinking two strands and preventing cell duplication. It binds to the N7 nitrogen on the DNA base guanine. As the chemical is a blister agent, its use is strongly restricted within the Chemical Weapons Convention where it is classified as a Schedule 1 substance.
Mechlorethamine belongs to the group of nitrogen mustard alkylating agents.