189192-18-5

Basic information

• Product Name: (R)-(+)-ALPHA-(3-HYDROXY-2-METHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL
• Synonyms: (R)-(+)-ALPHA-(3-HYDROXY-2-METHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL;4-PIPERIDINEMETHANOL, 1-[2-(4-FLUOROPHENYL)ETHYL]-ALPHA-(3-HYDROXY-2-METHOXYPHENYL)-, (ALPHAR);MDL 105725;DESMETHYL-MDL100907;(R)-(+)-(-(3-Hydroxy-2-methoxyphenyl)-1-[2-(4-fluoro-phenyl)ethyl]-4-piperidine methanol;4-Piperidinemethanol, 1-[2-(4-fluorophenyl)ethyl]-(-(3-hydroxy-2-methoxyphenyl)-, ((R)
• CAS NO: 189192-18-5
• Molecular Formula: C₂₁H₂₆FNO₃
• Molecular Weight: 359.43
• Product Categories: Serotonin 5-HT2a receptor antagonist.
• Mol File: 189192-18-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 484.628 °C at 760 mmHg
• Flash Point: 246.894 °C
• Appearance: colourless solid
• Density: 1.202 g/cm³
• CAS DataBase Reference: (R)-(+)-ALPHA-(3-HYDROXY-2-METHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-ALPHA-(3-HYDROXY-2-METHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL(189192-18-5)
• EPA Substance Registry System: (R)-(+)-ALPHA-(3-HYDROXY-2-METHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL(189192-18-5)

Safety Data

• Hazardous Substances Data: 189192-18-5(Hazardous Substances Data)

Usage

Chemical Properties

Colourless solid

Upstream product

• 311348-77-3 (R)-(-)-α-[2-methoxy-3-[(1,1-dimethylethyl)diphenylsilyl]oxyphenyl]-4-piperidinemethanol 
• 311348-75-1 (+/-)-α-[2-methoxy-3-[(1,1-dimethylethyl)diphenylsilyl]oxyphenyl]-4-piperidinemethanol 
• 311348-74-0 4-[2-methoxy-3-[(1,1-dimethylethyl)diphenylsilyl]oxybenzoyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 498-94-2 isonipecotic acid 
• 108534-61-8 (2-methoxyphenoxy)-(1,1-dimethylethyl)diphenylsilane 
• 139290-70-3 tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate 
• 90-05-1 2-methoxy-phenol 
• 252364-42-4 (+/-)-α-[2-methoxy-3-[(1,1-dimethylethyldiphenylsilyl)oxy]phenyl]-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanone 
• 332-42-3 (2-bromoethyl)-4-fluorobenzene 
• 311348-79-5 (R)-(-)-α-[2-methoxy-3-[(1,1-dimethylethyl)diphenylsilyl]oxyphenyl]-41-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol 

Downstream Products

• 1160522-53-1 (+)-MHMZ 
• 139290-65-6 R-(+)-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol 

Relevant articles and documents

Synthesis and activity of functionalizable derivatives of the serotonin (5-HT) 5-HT2A receptor (5-HT2AR) antagonist M100907

The approach of tethering together two known receptor ligands, to be used as molecular probes for the study of G protein-coupled receptor (GPCR) systems, has proven to be a valuable approach. Selective ligands that possess functionality that can be used to link to other ligands, are useful in the development of novel antagonists and agonists. Such molecules can also be attached to reporter molecules, such as fluorophores, for the study of GPCR dimerization and its role in signaling. The highly selective serotonin (5-HT) 5-HT2A receptor (5-HT2AR) antagonist M100907 (volinanserin) is of clinical interest in the treatment of neurological and mental health disorders. Here, we synthesized the most active (+)-M100907 enantiomer as well as a series of derivatives that possessed either an alkyne or an azide. The triazole resulting from the dipolar cycloaddition of these groups did not interfere with the ability of the bivalent ligand to act as an antagonist. Thus, we have synthesized a number of compounds which will prove useful in elucidating the role of the 5-HT2AR in the central nervous system.

A practical synthesis of the serotonin 5-HT(2a) receptor antagonist MDL 100907, its enantiomer and their 3-phenolic derivatives as precursors for [11C ]labeled PET ligands

A practical synthesis of the 3-phenolic precursor of MDL 100907, a selective 5-HT(2A) receptor antagonist, is described. The route was also applied to the enantiomeric series, thus affording the direct precursors of both 3-[11C]MDL 100907 and its enantiomer as ligands for positron emission tomography. Similar methodology was developed for the direct synthesis of MDL 100907 and its enantiomer, MDL 100009. The routes utilized classical optical resolution of the N-nor intermediates in at least 98% enantiomeric excess and easily afforded multigram amounts of the chiral precursors of a variety of N- and 3-O-substituted enantiomers. Copyright (C) 2000 Elsevier Science Ltd.