LKT Labs

Biochemicals for Life Science Research

Mechlorethamine Hydrochloride

Product ID C2942
Cas No. 55-86-7
Purity ≥98%
Product Unit SizeCostQuantityStock
100 mg $45.80 In stock
1 g $82.10 In stock
5 g $153.80 In stock
10 g $272.10 In stock
25 g $473.40 In stock
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Description

Mechlorethamine is a nitrogen mustard DNA alkylator that binds and alkylates the N7 nitrogen on guanine and adenine bases in DNA. Mechlorethamine was initially developed as a blistering agent for use in chemical warfare but has since exhibited anticancer chemotherapeutic benefit. In vitro and in vivo, mechlorethamine forms a reactive aziridinium ion intermediate; it also can induce 5’-GNC-3’ DNA crosslinks. Additionally, this compound exhibits pro-oxidative activity, increasing levels of ROS and RNS in the treatment of B-cell chronic lymphocytic leukemia (CLL), inducing oxidative stress and apoptosis.

Product Info

Cas No.

55-86-7
Purity

≥98%
Formula

C5H11Cl2N • HCl
Formula Wt.

192.51
Chemical Name

2-Chloro-N-(2-chloroethyl)-N-methylethanamine, N-Methylbis(2-chloroethyl)amine hydrochloride
IUPAC Name

2-chloro-N-(2-chloroethyl)-N-methylethanamine;hydrochloride
Synonym

Nitrogen mustard, Bis(2-Chloroethyl)methylamine
Melting Point

108-111°C
Appearance

White Crystal Powder

Shipping and Storage

Store Temp

4°C
Ship Temp

Ambient

Downloads

MSDS

C2942 MSDS PDF
Info Sheet

C2942 Info Sheet PDF

References

Polavarapu A, Stillabower JA, Stubblefield SG, et al. The mechanism of guanine alkylation by nitrogen mustards: a computational study. J Org Chem. 2012 Jul 20;77(14):5914-21. PMID: 22681226.

Wang F, Li F, Ganguly M, et al. A bridging water anchors the tethered 5-(3-aminopropyl)-2'-deoxyuridine amine in the DNA major groove proximate to the N+2 C.G base pair: implications for formation of interstrand 5'-GNC-3' cross-links by nitrogen mustards. Biochemistry. 2008 Jul 8;47(27):7147-57. PMID: 18549246.

Crater J, Kannan S. Molecular mechanism of nitrogen mustard induced leukocyte(s) chemotaxis. Med Hypotheses. 2007;68(2):318-9. PMID: 16997491.

Eder JP Jr, Chan VT, Ng SW, et al. DNA topoisomerase II alpha expression is associated with alkylating agent resistance. Cancer Res. 1995 Dec 15;55(24):6109-16. PMID: 8521401.

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