139290-65-6

Basic information

• Product Name: (R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL
• Synonyms: (+)-a-(2,3-Dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol;(aR)-a-(2,3-Dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol;M 100907;R-MDL 100907;(R)-(+)-(-(2,3-Dimethoxyphenyl)-1-[2-(4-fluoro-phenyl)ethyl]-4-piperidine methanol (R,R)-tartrate;4-Piperidinemethanol, 1-[2-(4-fluorophenyl)ethyl]-(-(2,3-dimethoxyphenyl)-, ((R), (R,R)-tartrate;MDL100907-L-tartrate;(R)-(+)-(-(2,3-Dimethoxyphenyl)-1-[2-(4-fluoro-phenyl)ethyl]-4-piperidine methanol
• CAS NO: 139290-65-6
• Molecular Formula: C₂₂H₂₈FNO₃
• Molecular Weight: 373.46
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 139290-65-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 89-91°C
• Boiling Point: 499.4°Cat760mmHg
• Flash Point: 255.8°C
• Appearance: off-white to light brown/
• Density: 1.15g/cm³
• Vapor Pressure: 8.6E-11mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: -20°C Freezer
• Solubility: DMSO: ≥20mg/mL
• CAS DataBase Reference: (R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL(139290-65-6)
• EPA Substance Registry System: (R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL(139290-65-6)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 139290-65-6(Hazardous Substances Data)

Usage

Description

(R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL is a complex organic compound with a unique molecular structure. It is characterized by its chiral center, which gives it the (R)-(+) configuration. (R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL features a 2,3-dimethoxyphenyl group attached to the alpha carbon, a 4-fluoro-phenylethyl group connected to the nitrogen of the piperidine ring, and a hydroxyl group at the end. Its specific arrangement of functional groups and stereochemistry may contribute to its potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
(R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique structure and stereochemistry make it a valuable intermediate in the development of new drugs, particularly those targeting specific receptors or enzymes.
Used in Chemical Research:
In the field of chemical research, (R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL can be used as a starting material or a reference compound for studying the effects of stereochemistry on biological activity. Its chirality and functional groups can provide insights into the interactions between molecules and their targets, leading to a better understanding of structure-activity relationships.
Used in Drug Development:
(R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL is used as a potential therapeutic agent for various medical conditions. Its specific molecular features may allow it to interact with specific targets in the body, such as receptors or enzymes, to produce desired pharmacological effects. Further research and development are necessary to explore its full potential in this area.
Used in Material Science:
The unique structure of (R)-(+)-ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUORO-PHENYL)ETHYL]-4-PIPERIDINE METHANOL may also find applications in material science, where its properties can be exploited to create new materials with specific characteristics. For example, its chirality and functional groups could be used to develop novel catalysts, sensors, or other advanced materials with tailored properties.

Biochem/physiol Actions

M100907 is a selective 5-HT2A Antagonist.

InChI:InChI=1/C22H28FNO3/c1-26-20-5-3-4-19(22(20)27-2)21(25)17-11-14-24(15-12-17)13-10-16-6-8-18(23)9-7-16/h3-9,17,21,25H,10-15H2,1-2H3

Upstream product

• 243640-22-4 α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, butyrate ester 
• 175553-29-4 (R)-(+)-α-(2-hydroxy-3-methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanone 
• 74-88-4 methyl iodide 
• 137756-90-2 4‐(2‐bromoethyl)phenylboronic acid 
• 243640-19-9 (2,3‐dimethoxyphenyl)(piperidine‐4‐yl)methanol 
• 243640-24-6 (R)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, butyrate ester 
• 243640-20-2 (R)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, (2S,3S)-(+)-di-(p-anisoyl)-tartaric acid salt 
• 243640-29-1 4-[1-oxo-1-(2,3-dimethoxyphenyl)methyl]-N-2-(4-fluorophen-1-oxo-ethyl)piperidine 
• 7589-27-7 2-(4-Fluorophenyl)ethanol 
• 252364-39-9 4-[1-oxo-1-(2,3-dimethoxyphenyl)methyl]-N-2-(4-fluorophenylethyl)piperidine 
• 139290-69-0 (2,3-dimethoxy-phenyl)-{1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-methanol 
• 311348-79-5 (R)-(-)-α-[2-methoxy-3-[(1,1-dimethylethyl)diphenylsilyl]oxyphenyl]-41-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol 
• 311348-74-0 4-[2-methoxy-3-[(1,1-dimethylethyl)diphenylsilyl]oxybenzoyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester 
• 311348-77-3 (R)-(-)-α-[2-methoxy-3-[(1,1-dimethylethyl)diphenylsilyl]oxyphenyl]-4-piperidinemethanol 

Downstream Products

• 175553-29-4 (R)-(+)-α-(2-hydroxy-3-methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanone 

Relevant articles and documents

Optimization of 18F-syntheses using 19F-reagents at tracer-level concentrations and liquid chromatography/tandem mass spectrometry analysis: Improved synthesis of [18F]MDL100907

Traditional radiosynthetic optimization faces the challenges of high radiation exposure, cost, and inability to perform serial reactions due to tracer decay. To accelerate tracer development, we have developed a strategy to simulate radioactive 18F-syntheses by using tracer-level (nanomolar) non-radioactive 19F-reagents and LC-MS/MS analysis. The methodology was validated with fallypride synthesis under tracer-level 19F-conditions, which showed reproducible and comparable results with radiosynthesis, and proved the feasibility of this process. Using this approach, the synthesis of [18F]MDL100907 was optimized under 19F-conditions with greatly improved yield. The best conditions were successfully transferred to radiosynthesis. A radiochemical yield of 19% to 22% was achieved with the radiochemical purity >99% and the molar activity 38.8 to 53.6?GBq/ μmol (n?=?3). The tracer-level 19F-approach provides a high-throughput and cost-effective process to optimize radiosynthesis with reduced radiation exposure. This new method allows medicinal and synthetic chemists to optimize radiolabeling conditions without the need to use radioactivity.

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.

Use of MDL-100,907 for treatment of allergic and eosinophil mediated diseases

Methods of modulating eosinophil migration, chemotaxis or generation, in vitro, ex vivo, and in vivo are provided. Methods include contacting eosinophils with an amount of 5-HT2A receptor agonist or antagonist sufficient to modulate eosinophil migration, chemotaxis or generation.