7401-05-0

Basic information

• Product Name: 1-Piperazinecarboxamide,N-ethyl-4-methyl-(9CI)
• Synonyms: 1-Piperazinecarboxamide,N-ethyl-4-methyl-(9CI);N-ETHYL-4-METHYLPIPERAZINE-1-CARBOXAMIDE
• CAS NO: 7401-05-0
• Molecular Formula: C8 H17 N3 O
• Molecular Weight: 171.24
• Product Categories: PIPERIDINE
• Mol File: 7401-05-0.mol

Chemical Properties

• Boiling Point: 332.4 °C at 760 mmHg
• Flash Point: 154.8 °C
• Appearance: /
• Density: 1.036 g/cm³
• Vapor Pressure: 0.000147mmHg at 25°C
• Refractive Index: 1.489
• PKA: 14.20±0.20(Predicted)
• CAS DataBase Reference: 1-Piperazinecarboxamide,N-ethyl-4-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperazinecarboxamide,N-ethyl-4-methyl-(9CI)(7401-05-0)
• EPA Substance Registry System: 1-Piperazinecarboxamide,N-ethyl-4-methyl-(9CI)(7401-05-0)

Safety Data

• Hazardous Substances Data: 7401-05-0(Hazardous Substances Data)

Usage

Uses

1-Ethylcarbamyl-4-methylpiperazine is useful in the synthesis of antifilarial agents

InChI:InChI=1/C8H17N3O/c1-3-9-8(12)11-6-4-10(2)5-7-11/h3-7H2,1-2H3,(H,9,12)

Upstream product

• 109-01-3 1-methyl-piperazine 
• 41891-13-8 ethyl carbamoyl chloride 
• 109-90-0 ethyl isocyanate 
• 75-04-7 ethylamine 

Relevant articles and documents

Conformationally restrained carbamoylcholine homologues. Synthesis, pharmacology at neuronal nicotinic acetylcholine receptors and biostructural considerations

Exploration of small selective ligands for the nicotinic acetylcholine receptors (nAChRs) based on acetylcholine (ACh) has led to the development of potent agonists with clear preference for the α4β2 nAChR, the most prevalent nAChR subtype in the central nervous system. In this work we present the continuation of these efforts aimed at increasing this subtype selectivity by introduction of conformational restriction in the carbamoylcholine homologue, 3-(dimethylaminobutyl) dimethylcarbamate (DMABC). Our results highlight the importance of the N-carbamoyl substitution in α4β2-subtype selectivity. Moreover, we have confirmed the non-linear conformation of DMABC bound to nAChRs suggested by recent crystal structures of the compound in complex with the Lymnaea stagnalis ACh binding protein.

Macrofilaricidal activity of metabolites of diethylcarbamazine

The antifilarial compound diethylcarbamazine (N,N-diethyl-4-methyl-2-piperazine, DEC) is known rather for its micro- than macrofilaricidal activity. But in some human filariasis i.e. loaiasis, lymphatic filariasis, the spectrum of DEC activities extends to adult filaria. The potential role of the metabolites of DEC in the action of the parent drug once it had been metabolized in the body of infected animals was investigated. The metabolites were evaluated in a new experimental model on which DEC is active: Molinema dessetae in its natural host, the rodent Proechimys oris. Experimental studies were carried out in vivo and in vitro, on microfilariae, infective larvae and adult filaria. Several other nematodes were also used. The metabolites were DEC itself, N-ethyl-4-methyl-1-piperazine-carboxamide (MEC) and their N-oxides, 4-methyl-piperazine-carboxamide and N,N-diethyl-1-piperazine-carboxamide. In vivo most of the metabolites were found active on microfilariae and both N-oxides active on adults and infective larvae. In vitro, the activity of the metabolites was observed only with high concentrations; the in vitro test could not be used as a screening method for antifilarial chemotherapy with piperazine derivatives. Infective larvae were the most sensitive stage. In the rodent and in man, the antifilarial action of DEC is swift and of short duration. This action is prolonged by the activity of metabolites, especially the N-oxides.