104499-47-0

Basic information

• Product Name: N-(4-METHOXYBENZYL)-N'-METHYL-N-2-PYRIDINYL-1,2-ETHANEDIAMINE
• Synonyms: N-(4-METHOXYBENZYL)-N'-METHYL-N-2-PYRIDINYL-1,2-ETHANEDIAMINE;2-[[2-(MethylaMino)ethyl](4-Methoxybenzyl)aMino]pyridine;N-DesMethyl PyrilaMine
• CAS NO: 104499-47-0
• Molecular Formula: C₁₆H₂₁N₃O
• Molecular Weight: 271.36
• Product Categories: Aromatics;Intermediates;Amines;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 104499-47-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: N-(4-METHOXYBENZYL)-N'-METHYL-N-2-PYRIDINYL-1,2-ETHANEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-METHOXYBENZYL)-N'-METHYL-N-2-PYRIDINYL-1,2-ETHANEDIAMINE(104499-47-0)
• EPA Substance Registry System: N-(4-METHOXYBENZYL)-N'-METHYL-N-2-PYRIDINYL-1,2-ETHANEDIAMINE(104499-47-0)

Safety Data

• Hazardous Substances Data: 104499-47-0(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Oil

Uses

Metabolite of the antihistamine Pyrilamine.

Upstream product

• 109-04-6 2-bromo-pyridine 
• 541-41-3 chloroformic acid ethyl ester 
• 109912-28-9 N-(4-methoxybenzyl)-N-2-pyridinyl-1,2-ethanediamine 
• 91-84-9 pyrilamine 
• 74764-17-3 2-[(pyridin-2-yl)amino]ethylamine 
• 52818-63-0 2-(4-methoxybenzylamino)pyridine 
• 109912-29-0 N'-formyl-N-(4-methoxybenzyl)-N-2-pyridinyl-1,2-ethanediamine 

Downstream Products

• 109912-30-3 N-(4-methoxybenzyl)-N'-methyl-N'-(2-(N-phthalimido)ethyl)-N-2-pyridinyl-1,2-ethanediamine 
• 109912-31-4 2-[3-({2-[(4-Methoxy-benzyl)-pyridin-2-yl-amino]-ethyl}-methyl-amino)-propyl]-isoindole-1,3-dione 
• 109912-32-5 2-[4-({2-[(4-Methoxy-benzyl)-pyridin-2-yl-amino]-ethyl}-methyl-amino)-butyl]-isoindole-1,3-dione 
• 109912-34-7 N'-(4-cyanobutyl)-N-(4-methoxybenzyl)-N'-methyl-N-2-pyridinyl-1,2-ethanediamine 
• 109912-35-8 7-({2-[(4-Methoxy-benzyl)-pyridin-2-yl-amino]-ethyl}-methyl-amino)-heptanenitrile 
• 1345012-37-4 tert-butyl 4-(2-((2-((4-methoxybenzyl)(pyridin-2-yl)amino)ethyl)(methyl)amino)ethyl)piperazine-1-carboxylate 
• 1345012-41-0 (1H-indol-2-yl)(4-(2-((2-((4-methoxybenzyl)(pyridin-2-yl)amino)ethyl)(methyl)amino)ethyl)piperazin-1-yl)methanone 
• 1345012-42-1 (5-chloro-1H-indol-2-yl)(4-(2-((2-((4-methoxybenzyl)(pyridin-2-yl)amino)ethyl)(methyl)amino)ethyl)piperazin-1-yl)methanone 
• 1345012-51-2 (5-(1-((2-((4-methoxybenzyl)(pyridin-2-yl)amino)ethyl)(methyl)amino)propan-2-ylamino)-1H-indol-2-yl)(4-methylpiperazin-1-yl)methanone 
• 1345012-50-1 1-((2-((4-methoxybenzyl)(pyridin-2-yl)amino)ethyl)(methyl)amino)propan-2-one 
• 562847-59-0 ({2-[(4-methoxy-benzyl)-pyridin-2-yl-amino]-ethyl}-methyl-amino)-acetonitrile 
• 149841-54-3 N-cyano-N'-[2-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]ethyl]-N''-[3-[3-(piperidinomethyl)phenoxy]propyl]guanidine 
• 149841-55-4 N-cyano-N'-[3-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]propyl]-N''-[3-[3-(piperidinomethyl)phenoxy]propyl]guanidine 
• 149841-56-5 N-cyano-N'-[4-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]butyl]-N''-[3-[3-(piperidinomethyl)phenoxy]propyl]guanidine 

Relevant articles and documents

Synthesis and dual histamine H1 and H2 receptor antagonist activity of cyanoguanidine derivatives

Premedication with a combination of histamine H1 receptor (H1R) and H2 receptor (H2R) antagonists has been suggested as a prophylactic principle, for instance, in anaesthesia and surgery. Aiming at pharmacological hybrids combining H1R and H2R antagonistic activity, a series of cyanoguanidines 14-35 was synthesized by linking mepyramine-type H1R antagonist substructures with roxatidine-, tiotidine-, or ranitidine-type H2R antagonist moieties. N-desmethylmepyramine was connected via a poly-methylene spacer to a cyanoguanidine group as the "urea equivalent" of the H2R antagonist moiety. The title compounds were screened for histamine antagonistic activity at the isolated ileum (H1R) and the isolated spontaneously beating right atrium (H2R) of the guinea pig. The results indicate that, depending on the nature of the H2R antagonist partial structure, the highest H1R antagonist potency resided in roxatidine-type compounds with spacers of six methylene groups in length (compound 21), and tiotidine-type compounds irrespective of the alkyl chain length (compounds 28, 32, 33), N-cyano-N'-[2-[[(2- guanidino-4-thiazolyl)methyl] thio]ethyl]-N″-[2-[N-[2-[N-(4-methoxybenzyl)-N-(pyridyl)-amino] ethyl]-N-methylamino]ethyl] guanidine (25, pKB values: 8.05 (H1R, ileum) and 7.73 (H2R, atrium) and the homologue with the mepyramine moiety connected by a six-membered chain to the tiotidine-like partial structure (compound 32, pKB values: 8.61 (H1R) and 6.61 (H2R) were among the most potent hybrid compounds. With respect to the development of a potential pharmacotherapeutic agent, structural optimization seems possible through selection of other H1R and H2R pharmacophoric moieties with mutually affinity-enhancing properties.

Mepyramine-JNJ7777120-hybrid compounds show high affinity to hH 1R, but low affinity to hH4R

In literature, a synergism between histamine H1 and H 4 receptor is discussed. Furthermore, it was shown, that the combined application of mepyramine, a H1 antagonist and JNJ7777120, a H 4 receptor ligand leads to a synergistic effect in the acute murine asthma model. Thus, the aim of this study was to develop new hybrid ligands, containing one H1 and one H4 pharmacophor, connected by an appropriate spacer, in order to address both, H1R and H 4R. Within this study, we synthesized nine hybrid compounds, which were pharmacologically characterized at hH1R and hH4R. The new compounds revealed (high) affinity to hH1R, but showed only low affinity to hH4R. Additionally, we performed molecular dynamic studies for some selected compounds at hH1R, in order to obtain information about the binding mode of these compounds on molecular level.

Synthesis and pharmacological activity of fluorescent histamine H1 receptor antagonists related to mepyramine

Fluorescently labeled histamine H1 receptor antagonists were synthesized starting from N-demethylmepyramine by introduction of ω-aminoalkyl chains (2-8 methylene groups in length) followed by derivatization of the terminal NH2 group with various fluorophores (fluorescein, naphthofluorescein, rhodamine, tetramethylrhodamine, BODIPY, dansyl, and nitrobenzoxadiazole (NBD)). On the isolated guinea pig ileum and in a Ca2+ assay on U373MG human glioblastoma cells the highest H1 antagonistic activities were found in 5- and 6-carboxyfluorescein labeled compounds with hexa- and octamethylene spacers and in an analogous NBD-aminohexanoyl derivative (pA2 or pKB values in the range: 8.3-9.0; compared to 9.3-9.4 for mepyramine).

PYRIDYL ALKYLAMINE COMPOUNDS WHICH ARE USEFUL AGAINST HISTAMINE H1 AND H2 RECEPTORS

Arylalkylamine derivatives of the general formula STR1 are described which, owing to their anatagonistic action against histamine H. sub.1-and H 2-receptors, can be used for the prophylaxis and treatment of disorders in which histamine is involved. They are prepared in a manner known per se.

Iodobolpyramine and other iodinated derivatives as ligands for detecting histamine H1 receptors

The synthesis is described of potential I-labelled H1-receptor ligands.Receptor affinity is assessed in vitro from inhibition of histamine-stimulated contraction of guinea pig ileum and/or through binding to guinea pig cerebellar membranes.Dire