Chlormethine
Chemical compound / From Wikipedia, the free encyclopedia
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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.
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IUPAC name
2-Chloro-N-(2-chloroethyl)-N-methylethanamine | |
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Identifiers | |
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3D model (JSmol) |
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ChEBI | |
ChEMBL | |
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DrugBank |
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ECHA InfoCard | 100.000.110 |
EC Number |
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KEGG |
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MeSH | Mechlorethamine |
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RTECS number |
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UNII | |
UN number | 2810 |
CompTox Dashboard (EPA) |
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Properties | |
C5H11Cl2N | |
Molar mass | 156.05 g·mol−1 |
Appearance | Colorless liquid |
Odor | Fishy, ammoniacal |
log P | 0.91 |
Pharmacology | |
D08AX04 (WHO) L01AA05 (WHO) | |
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Pharmacokinetics: | |
<1 minute | |
50% (Kidney) | |
Legal status | |
Related compounds | |
Related amines |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Mechlorethamine belongs to the group of nitrogen mustard alkylating agents.[4][5][6]