135729-78-1

Basic information

• Product Name: (S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide
• Synonyms: (S)-N-1-azabicyclo[2.2.0]oct-3-yl-5,6,7,8-tetrahydro-1-naphthalenecarboxamide;(S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide;Palonosetron Intermediate;(S)-N-(Quinuclidin-3-yl)-5,6,7,8-tetrahydronaphthalene-1-carboxaMide;N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-5,6,7,8-tetrahydro-1-naphthalenecarboxaMide;N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl] 5,6,7,8-tetrahydronaphthalene-1-carboxamide;Palonosetron Impurity 3
• CAS NO: 135729-78-1
• Molecular Formula: C₁₈H₂₄N₂O
• Molecular Weight: 284.4
• Product Categories: Intermediate of palonosetron hcl
• Mol File: 135729-78-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 439.2 °C at 760 mmHg
• Flash Point: 219.4 °C
• Appearance: /
• Density: 1.17
• Vapor Pressure: 6.48E-08mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide(135729-78-1)
• EPA Substance Registry System: (S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide(135729-78-1)

Safety Data

• Hazardous Substances Data: 135729-78-1(Hazardous Substances Data)

Usage

Description

(S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide is a complex organic compound with a unique molecular structure. It is characterized by its azabicyclo and naphthalene components, which contribute to its specific properties and potential applications.

Uses

Used in Pharmaceutical Industry:
(S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide is used as an impurity in the synthesis of Palonosetron HCl (P165800), a serotonin 5-HT3 receptor antagonist. (S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide plays a role in the development of antiemetic medications, specifically for the prevention and treatment of chemotherapy-induced nausea and vomiting (CINV). Its presence in the synthesis process is crucial for the effectiveness of the final product, as it contributes to the overall pharmacological action of Palonosetron HCl.

InChI:InChI=1/C18H24N2O/c21-18(19-17-12-20-10-8-14(17)9-11-20)16-7-3-5-13-4-1-2-6-15(13)16/h3,5,7,14,17H,1-2,4,6,8-12H2,(H,19,21)/t17-/m1/s1

Upstream product

• 110808-69-0 5,6,7,8-tetrahydronaphthylene-1-carboxylic acid chloride 
• 120570-05-0 (S)-3-aminoquinuclidine 
• 4242-18-6 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid 
• 79-37-8 oxalyl dichloride 
• 6530-09-2 (S)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride 

Downstream Products

• 135729-56-5 (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one 
• 135729-60-1 palonosetron 
• 135729-60-1 palonosetron 
• 135755-51-0 palonosetron hydrochloride 
• 135755-51-0 palonosetron hydrochloride 
• 135755-51-0 RS 25233-198 

Relevant articles and documents

Synthesis and Pharmacological Evaluation of [11C]Granisetron and [18F]Fluoropalonosetron as PET Probes for 5-HT3 Receptor Imaging

Serotonin-gated ionotropic 5-HT3 receptors are the major pharmacological targets for antiemetic compounds. Furthermore, they have become a focus for the treatment of irritable bowel syndrome (IBS) and there is some evidence that pharmacological modulation of 5-HT3 receptors might alleviate symptoms of other neurological disorders. Highly selective, high-affinity antagonists, such as granisetron (Kytril) and palonosetron (Aloxi), belong to a family of drugs (the "setrons") that are well established for clinical use. To enable us to better understand the actions of these drugs in vivo, we report the synthesis of 8-fluoropalonosetron (15) that has a binding affinity (Ki = 0.26 ± 0.05 nM) similar to the parent drug (Ki = 0.21 ± 0.03 nM). We radiolabeled 15 by nucleophilic 18F-fluorination of an unsymmetrical diaryliodonium palonosetron precursor and achieved the radiosynthesis of 1-(methyl-11C)-N-granisetron ([11C]2) through N-alkylation with [11C]CH3I, respectively. Both compounds [18F]15 (chemical and radiochemical purity >95%, specific activity 41 GBq/μmol) and [11C]2 (chemical and radiochemical purity ≥99%, specific activity 170 GBq/μmol) were evaluated for their utility as positron emission tomography (PET) probes. Using mouse and rat brain slices, in vitro autoradiography with both [18F]15 and [11C]2 revealed a heterogeneous and displaceable binding in cortical and hippocampal regions that are known to express 5-HT3 receptors at significant levels. Subsequent PET experiments suggested that [18F]15 and [11C]2 are of limited utility for the PET imaging of brain 5-HT3 receptors in vivo.

PREPARATION OF CRYSTALLINE PALONOSETRON HYDROCHLORIDE

Processes for the preparation of palonosetron hydrochloride and its crystalline forms.

2-(Quinuclidin-3-yl)pyrido[4,3-b]indol-1-ones and isoquinolin-1-ones. Potent conformationally restricted 5-HT3 receptor antagonists

Several series of N-(quinuclidin-3-yl)aryl and heteroaryl-fused pyridones were synthesized and evaluated for 5-HT3 receptor affinity. In the heteroaryl series,2-(quinuclidin-3-yl)tetrahydropyrido[4,3-b]indol-1-one (8a) and the 4,5-alkano-bridge