311348-76-2

Basic information

• Product Name: (S)-(-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol
• Synonyms: (S)-(-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol
• CAS NO: 311348-76-2
• Molecular Weight: 251.326
• Mol File: 311348-76-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-(-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol(311348-76-2)
• EPA Substance Registry System: (S)-(-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol(311348-76-2)

Safety Data

• Hazardous Substances Data: 311348-76-2(Hazardous Substances Data)

Upstream product

• 140235-25-2 (+/-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol 
• 139290-70-3 tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate 
• 498-94-2 isonipecotic acid 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 139290-72-5 (2,3-dimethoxyphenyl)(piperidin-4-yl)methanone 
• 139290-71-4 4-(2,3-Dimethoxybenzoyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester 

Downstream Products

• 175673-57-1 (-)-MDL 100907 

Relevant articles and documents

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 in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET

Radiolabelled piperidine derivatives such as [11C]MDL 100907 and [18F]altanserin have played an important role in diagnosing malfunction in the serotonergic neurotransmission. A variety of novel piperidine MDL 100907 derivatives, possible to label with 18F-fluorine, were synthesized to improve molecular imaging properties of [11C]MDL 100907. Their in vitro affinities to a broad spectrum of neuroreceptors and their lipophilicities were determined and compared to the clinically used reference compounds MDL 100907 and altanserin. The novel compounds MA-1 (53) and (R)-MH.MZ (56) show Ki-values in the nanomolar range towards the 5-HT2A receptor and insignificant binding to other 5-HT receptor subtypes or receptors. Interestingly, compounds MA-1 (53), MH.MZ (55) and (R)-MH.MZ (56) provide a receptor selectivity profile similar to MDL 100907. These compounds could possibly be preferable antagonistic 18F-tracers for visualization of the 5-HT2A receptor status. Medium affine compounds (VK-1 (32), (51), (52), (54)) were synthesized and have Ki values between 30 and 120 nM. All promising compounds show log P values between 2 and 3, that is, within the range of those for the established radiotracers altanserin and MDL 100907. The novel compounds MA-1 (53) and (R)-MH.MZ (56) thus appear to be promising high affine and selective tracers of 18F-labelled analogues for 5-HT2A imaging with PET.