135755-51-0

Basic information

• Product Name: (R,S)-Palonosetron Hydrochloride
• Synonyms: (R,S)-Palonosetron Hydrochloride;(3aR)-2-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-1H-benz[de]isoquinolin-1-one Hydrochloride;3aR-2S-Palonosetron hydrochloride;(R,S)-Palonosetron;(R)-2-((S)-quinuclidin-3-yl)-2,3,3a,4,5,6-hexahydro-1H-benzo[de]isoquinolin-1-
• CAS NO: 135755-51-0
• Molecular Formula: C19H25ClN2O
• Molecular Weight: 332.8676
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 135755-51-0.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Sparingly)
• Stability: Hygroscopic
• CAS DataBase Reference: (R,S)-Palonosetron Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S)-Palonosetron Hydrochloride(135755-51-0)
• EPA Substance Registry System: (R,S)-Palonosetron Hydrochloride(135755-51-0)

Safety Data

• Hazardous Substances Data: 135755-51-0(Hazardous Substances Data)

Usage

Description

(R,S)-Palonosetron Hydrochloride, also known as P165800, is a potent and selective antagonist of the 5-HT3 receptor. It is an enantiomer of Palonosetron, which is a medication used to prevent nausea and vomiting caused by certain types of chemotherapy, radiation therapy, and surgery. The compound exhibits high affinity and selectivity for the 5-HT3 receptor, making it a valuable pharmaceutical candidate for various applications.

Uses

Used in Pharmaceutical Industry:
(R,S)-Palonosetron Hydrochloride is used as an active pharmaceutical ingredient for the treatment of nausea and vomiting associated with chemotherapy, radiation therapy, and surgery. It works by blocking the 5-HT3 receptors in the brain, which are responsible for the sensation of nausea and vomiting.
Used in Research and Development:
(R,S)-Palonosetron Hydrochloride is used as a research compound in the development of new drugs targeting the 5-HT3 receptor. It serves as a valuable tool for studying the mechanisms of action and potential therapeutic applications of 5-HT3 receptor antagonists.
Used in Quality Control:
(R,S)-Palonosetron Hydrochloride is used as an impurity in the quality control of Palonosetron and its formulations. It helps ensure the purity, potency, and safety of the final drug product by providing a reference standard for comparison and analysis.

Upstream product

• 177793-80-5 (1-azabicyclo[2.2.2]oct-3-yl)-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)amine 
• 503-38-8 trichloromethyl chloroformate 
• 138752-28-0 (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione 
• 81-84-5 1,8-Naphthalic anhydride 
• 1193337-96-0 2-[(S)-1-aza-bicyclo[2.2.2]oct-3-yl]-2,3,3a,4,5,6-hexahydro-1H-benz[de]isoquinolin-1-one hydrochloride 
• 135729-55-4 (S)-2-<1-azabicyclo<2.2.2>oct-3-yl>-2,4,5,6-tetrahydro-1-oxo-1H-benzisoquinoline hydrochloride 
• 135729-60-1 palonosetron 
• 110808-69-0 5,6,7,8-tetrahydronaphthylene-1-carboxylic acid chloride 
• 135729-78-1 N-<(S)-1-azabicyclo<2.2.2>oct-3-yl>-5,6,7,8-tetrahydronaphthalene-1-carboxamide 
• 4242-18-6 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid 
• 135729-56-5 (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one 
• 18278-24-5 (S)-(-)-1,2,3,4-tetrahydro-1-naphthaldehyde 
• 1193-65-3 3-quinuclidinone hydrochloride 
• 80096-46-4 (1,2-dihydronaphthalen-4-yl)methanamine hydrochloride 

Downstream Products

• 135729-60-1 palonosetron 

Relevant articles and documents

A short total synthesis of palonosetron using catalytic hydrogenation

The 5-HT3 receptor antagonists (1) and (2) (palonosetron) were synthesized by an efficient new route. The critical hydrogenation of imide (4) was carried out with either Pd/C catalyst or PtO2 catalyst.

Preparation method of high-purity palonosetron hydrochloride

The invention discloses a preparation method of high-purity palonosetron hydrochloride. A synthesis method is as follows: taking 1,2,3,4-tetrahedro-naphthoic acid as a starting raw material, taking quinine as a resolving agent to obtain chiral(S)-1,2,3,4-tetrahedro-naphthoic acid, acylating the chiral(S)-1,2,3,4-tetrahedro-naphthoic acid by using oxalyl chloride, and then reacting with (S)-3-aminoquinuclidine ammonia salt to obtain amide compound; concentrating, adding water to dilute, adding alkali to adjust pH value to obtain (R)-N-((S)-3-quinine)-1,2,3,4-tetralyl-1-formamide; performing reduction reaction on an intermediate under the existence of the sodium borohydride and boron trifluoride diethyl etherate so as to obtain (R)-N-(1-((S)-1,2,3,4-tetralyl)methyl)-3-quinine amine, continuously reacting with the triphosgene and boron trifluoride diethyl etherate, salting, extracting and regulating the pH value to obtain a crude product of the Palonosetron after the reaction is completed; and salting and refining the crude product in isopropanol so as to obtain the Palonosetron Hydrochloride with high purity. The preparation method not only solves the problem that the palonosetron hydrochloride is low in yield and unstable in process for a long time, but also adopts class-three solvent ethyl acetate to extract in the synthesis of each step, the invention is in favor of the environmental protection, and convenient for solvent recycling and cost saving, and is suitable for industrial production.

A hydrochloric acid palonosetron synthesis method

The invention relates to a new synthetic method of palonosetron hydrochloride, and belongs to the field of pharmaceutical organic synthesis. The synthetic method adopts racemized tetrahydro naphthoic acid as a raw material; a reaction is carried out with thionyl chloride and (S)-3-aminoquinuclidine; after repeated washing, (S,S)-quinuclidine tetrahydronaphthalene carboxamide is obtained; the amide is reacted with sodium borohydride and boron trifluoride diethyl etherate; the product is added into a hydrochloric acid aqueous solution to obtain the palonosetron hydrochloride. According to the method, in the amide synthetic process, ethyl acetate is used as a solvent, which reduces the generation of by-products. In addition, according to the method, in the post-treatment process, impurities are removed by phase transfer, which increases product optical purity; through repeated washing, other impurities generated in the reaction are removed, and high-purity product is obtained.