Mechlorethamine

Chlormethine

Names
Preferred IUPAC name 2-Chloro-N-(2-chloroethyl)-N-methylethan-1-amine
Other names Bis(2-chloroethyl)(methyl)amine
Identifiers
CAS Number	51-75-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28925 Y
ChEMBL	ChEMBL427 Y
ChemSpider	3893 Y
DrugBank	DB00888 Y
ECHA InfoCard	100.000.110
EC Number	200-120-5
KEGG	D0767 N
MeSH	Mechlorethamine
PubChem	4033
RTECS number	IA1750000
UNII	50D9XSG0VR Y
UN number	2810
InChI InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3 Y Key: HAWPXGHAZFHHAD-UHFFFAOYSA-N Y
SMILES CN(CCCl)CCCl
Properties
Chemical formula	C5H11Cl2N
Molar mass	156.05 g·mol−1
Appearance	Colorless liquid
Odor	Fishy, ammoniacal
log P	0.91
Pharmacology
ATC code	D08AX04 (WHO) L01AA05 (WHO)
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Intracavitary Intrapericardial Intravenous Topical
Pharmacokinetics:
Biological half-life	<1 minute
Excretion	50% (renal)
Legal status	℞ (Prescription only)
Related compounds
Related amines	Dimethylamine Trimethylamine N-Nitrosodimethylamine Diethylamine Triethylamine Diisopropylamine Dimethylaminopropylamine Diethylenetriamine N,N-Diisopropylethylamine Triisopropylamine Tris(2-aminoethyl)amine HN1 (nitrogen mustard) HN3 (nitrogen mustard)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Chlormethine (INN, BAN), mechlorethamine (widely used in the US, not the USAN, however) also known as mustine and HN2 and in former USSR known as Embichin is a nitrogen mustard sold under the brand name Mustargen. 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.

Mechlorethamine belongs to the group of nitrogen mustard alkylating agents.

It has been derivatized into the estrogen analogue estramustine phosphate, used to treat prostate cancer. It can also be used in chemical warfare where it has the code-name HN2. This chemical is a form of nitrogen mustard gas and a powerful vesicant. Historically, some uses of mechlorethamine have included lymphoid malignancies such as Hodgkin’s disease, lymphosarcoma, chronic myelocytic leukemia, polycythemia vera, and bronchogenic carcinoma Mechlorethamine is often administered intravenously, but when compounded into a topical formulation it can also be used to treat skin diseases. There have been studies demonstrating that topical administration of mechlorethamine has efficacy in mycosis fungoides-type cutaneous T cell lymphoma.