Chlornaphazine

Chlornaphazine
Names
	IUPAC name N,N-bis(2-Chloroethyl)naphthalen-2-amine
	Other names Chlornapazine; 2-Naphthylbis(chloroethyl)amine
Identifiers
CAS Number	494-03-1;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2107519;
ChemSpider	9885;
ECHA InfoCard	100.007.078
KEGG	C16446 ;
PubChem CID	10307;
UNII	U46E473275 ;
CompTox Dashboard (EPA)	DTXSID3060087 ;
	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

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

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.
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.
N,N-Bis(2-Chloroethyl)-2-Naphthylamine (Chlornaphazine), International Agency for Research on Cancer

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[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