175673-57-1

Basic information

• Product Name: (-)-MDL 100907
• Synonyms: (S)-(2,3-DIMETHOXY-PHENYL)-(1-[2-(4-FLUORO-PHENYL)-ETHYL]-PIPERIDIN-4-YL)-METHANOL;(S)-MDL 100907;4-PIPERIDINEMETHANOL, A-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-, (AS)-;M 100009;MDL 100009
• CAS NO: 175673-57-1
• Molecular Formula: C₂₂H₂₈FNO₃
• Molecular Weight: 373.465
• Product Categories: Selective 5-HT2A antagonist.
• Mol File: 175673-57-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 499.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.150±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 13.93±0.20(Predicted)
• CAS DataBase Reference: (-)-MDL 100907(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-MDL 100907(175673-57-1)
• EPA Substance Registry System: (-)-MDL 100907(175673-57-1)

Safety Data

• Hazardous Substances Data: 175673-57-1(Hazardous Substances Data)

Usage

General Description

(-)-MDL 100907, also known as M100907, is a selective and potent antagonist of the serotonin 5-HT2A receptor. It is a chemical compound that has been extensively studied for its potential therapeutic applications, particularly in the treatment of a range of psychiatric and neurological disorders. Research has shown that (-)-MDL 100907 can effectively block the activity of the 5-HT2A receptor, which plays a key role in the regulation of mood, cognition, and perception. As a result, it has been investigated for its potential in treating conditions such as schizophrenia, depression, anxiety, and addiction. Additionally, (-)-MDL 100907 has been used in preclinical studies to investigate the role of the 5-HT2A receptor in various physiological and behavioral processes, shedding light on its broader functions in the central nervous system. Overall, (-)-MDL 100907 has shown promise as a valuable tool for understanding the role of the 5-HT2A receptor and as a potential therapeutic agent for a range of neuropsychiatric disorders.

Upstream product

• 869749-06-4 (S)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, (2S,3S)-(+)-di-(p-anisoyl)-tartaric acid salt 
• 139290-69-0 (2,3-dimethoxy-phenyl)-{1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-methanol 
• 139290-71-4 4-(2,3-Dimethoxybenzoyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester 
• 139290-72-5 (2,3-dimethoxyphenyl)(piperidin-4-yl)methanone 
• 140235-25-2 (+/-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol 
• 175553-32-9 1-[2-(4-fluorophenyl)ethyl]-4-piperidinecarboxylic acid N-methoxy N-methyl amide 
• 175553-31-8 1-[2-(4-fluorophenyl)-ethyl]-piperidine-4-carboxylic acid ethyl ester 
• 7589-27-7 2-(4-Fluorophenyl)ethanol 
• 332-42-3 (2-bromoethyl)-4-fluorobenzene 
• 252364-39-9 4-[1-oxo-1-(2,3-dimethoxyphenyl)methyl]-N-2-(4-fluorophenylethyl)piperidine 
• 311348-76-2 (S)-(-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol 
• 139290-76-9 (S,S)-(+)-α-[(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]-4-piperidinyl]methyl]-α-methoxybenzene acetate 
• 175553-30-7 (S)-(-)-α-(2-hydroxy-3-methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanone 
• 74-88-4 methyl iodide 

Downstream Products

• 139290-69-0 (2,3-dimethoxy-phenyl)-{1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-methanol 
• 175553-30-7 (S)-(-)-α-(2-hydroxy-3-methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanone 

Relevant articles and documents

Processes for the preparation of (R)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol"

The present invention provides various processes for the preparation of (R)-±-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol. These processes may be characterized by the following scheme:

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.

Synthesis and preliminary in vivo evaluation of [11C]MDL 100907: A potent and selective radioligand for the 5-HT2A receptor system

11C-Labeled MDL 100907 and MDL 100009 were prepared by the reaction of [11C]CH3I with the corresponding phenol precursors. In vivo studies conducted in rats and a baboon demonstrated that intravenously injected [2-O[11C]CH3]MDL 100907 was regionally distributed in the brain in a manner consistent with the known distribution of 5-HT2A receptors. Injection of [2-O[11C]CH3]MDL 100009 resulted in a uniform brain distribution of radioactivity without regional localization consistent with the lower affinity of MDL 100009 for 5-HT2A receptors.