Chlornaphazine

Chlornaphazine
IUPAC name N,N-Bis(2-chloroethyl)naphthalen-2-amine
Other names Chlornapazine; 2-Naphthylbis(chloroethyl)amine
Identifiers
CAS number	494-03-1
PubChem	10307
ChemSpider	9885
KEGG	C16446 Y
Jmol-3D images	Image 1
SMILES ClCCN(c2ccc1c(cccc1)c2)CCCl
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
Properties
Molecular formula	C14H15Cl2N
Molar mass	268.18 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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]

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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1701774. 
3. ^ N,N-Bis(2-Chloroethyl)-2-Naphthylamine (Chlornaphazine), International Agency for Research on Cancer