Chlormethine

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.

Chlormethine
Names
IUPAC name
2-Chloro-N-(2-chloroethyl)-N-methylethanamine
Other names
  • Bis(2-chloroethyl)(methyl)amine
  • mechlorethamine
  • mustine
  • HN-2
  • Ledaga
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.110
EC Number
  • 200-120-5
KEGG
MeSH Mechlorethamine
RTECS number
  • IA1750000
UNII
UN number 2810
  • InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3 Y
    Key: HAWPXGHAZFHHAD-UHFFFAOYSA-N Y
  • CN(CCCl)CCCl
Properties
C5H11Cl2N
Molar mass 156.05 g·mol−1
Appearance Colorless liquid
Odor Fishy, ammoniacal
log P 0.91
Pharmacology
D08AX04 (WHO) L01AA05 (WHO)
  • AU: B3
License data
  • Intracavitary
  • Intrapericardial
  • Intravenous
  • Topical
Pharmacokinetics:
<1 minute
50% (Kidney)
Legal status
  • AU: S4 (Prescription only)
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Related compounds
Related amines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Mechlorethamine belongs to the group of nitrogen mustard alkylating agents.

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