28920-67-4

Basic information

• Product Name: ethyl 2-(4-methylpiperazin-1-yl)acetate
• Synonyms: ethyl 2-(4-methylpiperazin-1-yl)acetate;4-Methyl piperazinyl acetate D'ethyle;4-Methyl piperazinyl acetate D'ethyle [french];Brn 0137991;Ethyl 4-methyl-1-piperazineacetate;Ethyl (4-Methyl-1-piperazinyl)acetate;2-(4-methyl-1-piperazinyl)acetic acid ethyl ester;2-(4-methylpiperazin-1-yl)acetic acid ethyl ester
• CAS NO: 28920-67-4
• Molecular Formula: C₉H₁₈N₂O₂
• Molecular Weight: 186.26
• Mol File: 28920-67-4.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 250.3°Cat760mmHg
• Flash Point: 105.2°C
• Appearance: /
• Density: 1.019g/cm³
• Vapor Pressure: 0.0218mmHg at 25°C
• Refractive Index: 1.466
• CAS DataBase Reference: ethyl 2-(4-methylpiperazin-1-yl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-(4-methylpiperazin-1-yl)acetate(28920-67-4)
• EPA Substance Registry System: ethyl 2-(4-methylpiperazin-1-yl)acetate(28920-67-4)

Safety Data

• Hazardous Substances Data: 28920-67-4(Hazardous Substances Data)

Usage

General Description

Ethyl 2-(4-methylpiperazin-1-yl)acetate is a chemical compound with the molecular formula C10H20N2O2. It is an ester, which means it is formed through the reaction of an alcohol with an acid. ethyl 2-(4-methylpiperazin-1-yl)acetate is commonly used in the pharmaceutical industry as a building block for the synthesis of various drugs and compounds. It is also known for its potential as a bioactive molecule, with studies showing its potential use in the treatment of various medical conditions. Furthermore, it has been identified as a key component in certain fragrance compounds due to its pleasant odor. Overall, ethyl 2-(4-methylpiperazin-1-yl)acetate is a versatile chemical with applications in various industries.

InChI:InChI=1/C9H18N2O2/c1-3-13-9(12)8-11-6-4-10(2)5-7-11/h3-8H2,1-2H3

Upstream product

• 109-01-3 1-methyl-piperazine 
• 623-73-4 diazoacetic acid ethyl ester 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 50398-09-9 N-methylpiperazine dihydrochloride 

Downstream Products

• 54699-92-2 (4-Methyl-piperazin-1-yl)-acetic acid 
• 50677-34-4 1-methyl-4-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]piperazine 
• 672285-91-5 2-(4-ethylpiperazin-1-yl)acetic acid 
• 24632-44-8 4-methyl-1-piperazinylacetic acid hydrazide 
• 1407510-24-0 C₂₆H₃₁FN₄O₃ 
• 1300731-02-5 2-(4-methylpiperazin-1-yl)-N-((R)-1-phenylethyl)acetamide 
• 1300731-08-1 (R)-N-2-((4-methylpiperazin-1-yl)ethyl)-1-phenylethanamine 
• 114584-89-3 1-(2-hydroxy-2,2-diphenyl-ethyl)-1,4,4-trimethyl-piperazinediium; bis-methyl sulfate 
• 121968-99-8 1-benzyl-4-(2-hydroxy-2,2-diphenyl-ethyl)-1-methyl-piperazinium; bromide 
• 21579-78-2 2-(4-methyl-piperazin-1-yl)-1,1-diphenyl-ethanol 

Relevant articles and documents

Synthesis and in vitro evaluation of novel morpholinyl- and methylpiperazinylacyloxyalkyl prodrugs of 2-(6-methoxy,2-naphthyl)propionic acid (naproxen) for topical drug delivery

Various novel morpholinyl- (3a,b) and methylpiperazinylacyloxyalkyl (3c- f) esters of 2-(6-methoxy-2-naphthyl)propionic acid were synthesized and evaluated in vitro for topical drug delivery as potential prodrugs of naproxen (1). Compounds 3a-f were prepared by coupling the corresponding naproxen hydroxyalkyl ester with the morpholinyl- or (4-methyl-1- piperazinyl)acyl acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)-pyridine (DMAP) and quantitatively hydrolyzed (t(1/2) = 1- 26 min) to naproxen in human serum. Compounds 3c-f showed higher aqueous solubility and similar lipophilicity, determined by their octanol-buffer partition coefficients (log P(app)), at pH 5.0 when compared to naproxen. At pH 7.4 they were significantly more lipophilic than naproxen. The best prodrug 3c led to a 4-and 1.5-fold enhancement of skin permeation when compared to naproxen at pH 7.4 and 5.0, respectively. The present study indicates using a methylpiperazinyl group yields prodrugs that are partially un-ionized under neutral and slightly acidic conditions, and thus, a desirable combination is achieved in terms of aqueous solubility and lipophilicity. Moreover, the resulting combination of biphasic solubility and fast enzymatic hydrolysis of the methylpiperazinylacyloxyalkyl derivatives gave improved topical delivery of naproxen.

MODIFIED DRUGS FOR USE IN LIPOSOMAL NANOPARTICLES

Drag derivatives are provided herein which are suitable for loading into liposomal nanoparticle carriers. In some preferred aspects, the derivatives comprise a poorly water-soluble drag derivatized with a weak-base moiety that facilitates active loading of the drag through a LN transmembrane pH or ion gradient into the aqueous interior of the LN. The weak-base moiety can optionally comprise a lipophilic domain that facilitates active loading of the drag to the inner monolayer of the liposomal membrane. Advantageously, LN formulations of the drag derivatives exhibit improved solubility, reduced toxicity, enhanced efficacy, and/or other benefits relative to the corresponding free drags.

Synthesis of a Gemcitabine Prodrug for Remote Loading into Liposomes and Improved Therapeutic Effect

The chemotherapeutic gemcitabine was actively and stably loaded into lipid nanoparticles through the formation of a prodrug. Gemcitabine was chemically modified to increase the lipophilicity and introduce a weak base moiety for remote loading. Several derivatives were synthesized and screened for their potential to be good liposomal drug candidates for remote loading by studying their solubility, stability, cytotoxicity, and loading efficiency. Two morpholino derivatives of GEM (22 and 23) were chosen as the preferred prodrugs for this purpose as they possessed the best loading efficiencies (100% for drug-to-lipid ratio of 0.36 w/w). This is a considerable improvement over a passive loading strategy where typical loading efficiencies are on the order of ～10-20% for a drug-to-lipid ratio of ～0.01. Liposomes loaded with these two prodrugs were studied in an s.c. tumor model in vivo and showed improved therapeutic effect over free GEM (～2-fold) and saline control (8- to 10-fold). This work demonstrates how chemical modification of a known hydrophilic drug can lead to improved loading, stability, and drug delivery in vivo.