Chlornaphazine

Chlornaphazine, a derivative of 2-naphthylamine, is a nitrogen mustard that was developed in the 1950s for the treatment of polycythemia and Hodgkin's disease.[1] However, a high incidence of bladder cancers in patients receiving treatment with chlornaphthazine led to use of the drug being discontinued.[2]

Chlornaphazine
Names
Preferred IUPAC name
N,N-Bis(2-chloroethyl)naphthalen-2-amine
Other names
Chlornapazine; 2-Naphthylbis(chloroethyl)amine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.078
KEGG
PubChem CID
UNII
InChI
  • InChI=1/C14H15Cl2N/c15-7-9-17(10-8-16)14-6-5-12-3-1-2-4-13(12)11-14/h1-6,11H,7-10H2
    Key: XCDXSSFOJZZGQC-UHFFFAOYAW
SMILES
  • ClCCN(c2ccc1c(cccc1)c2)CCCl
Properties
Chemical formula
 C14H15Cl2N
Molar mass 268.18 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The International Agency for Research on Cancer has listed chlornaphazine as a human carcinogen.[3]

References
  1. Videbaek, A.; Kaae, S. (1954). "2-Naphthylbis(chloroethyl)amine in the treatment of malignant diseases, particularly Hodgkin's disease". Acta Medica Scandinavica. 149 (5): 361–368. doi:10.1111/j.0954-6820.1954.tb11446.x. PMID 13180246.
  2. Benedicte Laursen (1970). "Cancer of the Bladder in Patients Treated with Chlornaphazine". Br Med J. 3 (5724): 684–685. doi:10.1136/bmj.3.5724.684. PMC 1701774. PMID 5470116.
  3. N,N-Bis(2-Chloroethyl)-2-Naphthylamine (Chlornaphazine), International Agency for Research on Cancer
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