3597-21-5

Basic information

• Product Name: 2-chloro-N-(2-chloroethyl)-N-(4-methylbenzyl)ethanamine
• Synonyms: 2-Chloro-N-(2-chloroethyl)-N-(4-methylbenzyl)ethanamine; benzenemethanamine, N,N-bis(2-chloroethyl)-4-methyl-
• CAS NO: 3597-21-5
• Molecular Formula: C₁₂H₁₇Cl₂N*ClH
• Molecular Weight: 246.1761
• Mol File: 3597-21-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 263.6°C at 760 mmHg
• Flash Point: 113.2°C
• Density: 1.128g/cm³
• Vapor Pressure: 0.0102mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: 2-chloro-N-(2-chloroethyl)-N-(4-methylbenzyl)ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-N-(2-chloroethyl)-N-(4-methylbenzyl)ethanamine(3597-21-5)
• EPA Substance Registry System: 2-chloro-N-(2-chloroethyl)-N-(4-methylbenzyl)ethanamine(3597-21-5)

Safety Data

• Hazardous Substances Data: 3597-21-5(Hazardous Substances Data)

Usage

General Description

2-chloro-N-(2-chloroethyl)-N-(4-methylbenzyl)ethanamine, also known as mechlorethamine, is a nitrogen mustard alkylating agent with potent cytotoxic and mutagenic properties. It is an antineoplastic and immunosuppressive agent that has historically been used in the treatment of Hodgkin's disease, non-Hodgkin's lymphomas, and other malignancies. Mechlorethamine works by damaging DNA, interrupting the growth and division of cancer cells. It is highly reactive and can cause severe skin and mucous membrane irritation upon contact, making it a hazardous and potentially toxic substance. Despite its toxicity, mechlorethamine has played a significant role in the development of cancer chemotherapy and continues to be used in certain chemotherapy regimens today.

Downstream Products

• 239797-71-8 [4-(4-chlorobenzyloxy)benzenesulfonyl]-1-(4-methylbenzyl)piperidine-4-carboxylic acid 
• 212770-65-5 4-(4-methoxy-benzenesulfonyl)-1-(4-methyl-benzyl)-piperidine-4-carboxylic acid 
• 239797-70-7 [4-(4-chlorobenzyloxy)benzenesulfonyl]-1-(4-methylbenzyl)piperidine-4-carboxylic acid ethyl ester 
• 212770-64-4 4-(4-methoxy-benzenesulfonyl)-1-(4-methyl-benzyl)-piperidine-4-carboxylic acid ethyl ester 

Relevant articles and documents

Synthesis and structure - Activity relationship of N-substituted 4-arylsulfonylpiperidine-4-hydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis

The matrix metalloproteinases (MMPs) are a family of zinc-containing endopeptidases that play a key role in both physiological and pathological tissue degradation. In our preceding paper, we have reported on a series of novel and orally active N-hydroxy-α-phenylsulfonylacetamide derivatives. However, these compounds had two drawbacks (moderate selectivity and chirality issues). To circumvent these two problems, a series of novel and orally active N-substituted 4-benzenesulfonylpiperidine-4-carboxylic acid hydroxyamide derivatives have been synthesized. The present paper deals with the synthesis and SAR of these compounds. Among the several compounds synthesized, derivative 55 turned out to be a potent, selective, and an orally active MMP inhibitor in the clinically relevant advanced rabbit osteoarthritis model. Detailed pharmacokinetics and metabolism data are described.