Chlormethine

Chlormethine
Names
	IUPAC name 2-Chloro-N-(2-chloroethyl)-N-methylethanamine
	Other names Bis(2-chloroethyl)(methyl)amine; mechlorethamine; mustine; HN-2; Ledaga;
Identifiers
CAS Number	51-75-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28925 ;
ChEMBL	ChEMBL427 ;
ChemSpider	3893 ;
DrugBank	DB00888 ;
ECHA InfoCard	100.000.110
EC Number	200-120-5;
KEGG	D0767 ;
MeSH	Mechlorethamine
PubChem CID	4033;
RTECS number	IA1750000;
UNII	50D9XSG0VR ;
UN number	2810
CompTox Dashboard (EPA)	DTXSID2020975 ;
	InChI InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3 Key: HAWPXGHAZFHHAD-UHFFFAOYSA-N ;
	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	AU: B3;
Routes of; administration	Intracavitary; Intrapericardial; Intravenous; Topical;
	Pharmacokinetics:
Biological half-life	<1 minute
Excretion	50% (Kidney)
Legal status	AU: S4 (Prescription only); CA: ℞-only; EU: Rx-only; In general: ℞ (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). verify (what is ?) Infobox references

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.

Mechlorethamine belongs to the group of nitrogen mustard alkylating agents.^[4]^[5]^[6]

^ ^a ^b ^c "Ledaga". Therapeutic Goods Administration (TGA). 30 June 2021. Archived from the original on 5 September 2021. Retrieved 5 September 2021.
^ ^a ^b "Ledaga EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 5 September 2021. Retrieved 5 September 2021.
^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
^ Rappeneau S, Baeza-Squiban A, Jeulin C, Marano F (March 2000). "Protection from cytotoxic effects induced by the nitrogen mustard mechlorethamine on human bronchial epithelial cells in vitro". Toxicol. Sci. 54 (1): 212–21. doi:10.1093/toxsci/54.1.212. PMID 10746948.
^ "Chapter 3: Principles of Oncologic Pharmacotherapy". Cancer Management: A Multidisciplinary Approach. 2010. Archived from the original on 15 May 2009. Retrieved 8 October 2023.
^ "CDC - The Emergency Response Safety and Health Database: Blister Agent: NITROGEN MUSTARD HN-2 - NIOSH". U.S. Centers for Disease Control and Prevention (CDC). Archived from the original on 2019-06-28. Retrieved 2016-04-20.

[Ledaga_APM_summary-1] "Ledaga". Therapeutic Goods Administration (TGA). 30 June 2021. Archived from the original on 5 September 2021. Retrieved 5 September 2021.

[Ledaga_EPAR-2] "Ledaga EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 5 September 2021. Retrieved 5 September 2021.

[3] "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.

[pmid10746948-4] Rappeneau S, Baeza-Squiban A, Jeulin C, Marano F (March 2000). "Protection from cytotoxic effects induced by the nitrogen mustard mechlorethamine on human bronchial epithelial cells in vitro". Toxicol. Sci. 54 (1): 212–21. doi:10.1093/toxsci/54.1.212. PMID 10746948.

[5] "Chapter 3: Principles of Oncologic Pharmacotherapy". Cancer Management: A Multidisciplinary Approach. 2010. Archived from the original on 15 May 2009. Retrieved 8 October 2023.

[:0-6] "CDC - The Emergency Response Safety and Health Database: Blister Agent: NITROGEN MUSTARD HN-2 - NIOSH". U.S. Centers for Disease Control and Prevention (CDC). Archived from the original on 2019-06-28. Retrieved 2016-04-20.

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