99291-24-4

Basic information

• Product Name: Levodropropizine
• Synonyms: (S)-Dropropizine;(S)-3-(4-Phenyl-1-piperazinyl)-1,2-propanediol;Levodropropizine;(R)-3-(4-Phenyl-1-piperazinyl)-1,2-propanediol;1,2-Propanediol, 3-(4-phenyl-1-piperazinyl)-, (R)-;Brn 3592398;Dropropizine S-form;Levdropropizina
• CAS NO: 99291-24-4
• Molecular Formula: C13H20N2O2
• Molecular Weight: 236.31
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API
• Mol File: 99291-24-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 98-100°
• Boiling Point: 412.7 °C at 760 mmHg
• Flash Point: 220.9 °C
• Appearance: White or off white crystalline powder
• Density: 1.168 g/cm³
• Vapor Pressure: 1.5E-07mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), Methanol (Slightly)
• PKA: 14.21±0.20(Predicted)
• CAS DataBase Reference: Levodropropizine(CAS DataBase Reference)
• NIST Chemistry Reference: Levodropropizine(99291-24-4)
• EPA Substance Registry System: Levodropropizine(99291-24-4)

Safety Data

• Hazardous Substances Data: 99291-24-4(Hazardous Substances Data)

Usage

Description

Levodropropizine is an antitussive with antiinflammatory activity, the L-isomer of dropropizine. Compared with the racemate, levodropropizine is reported to have less sedative potential and better therapeutic index, while maintaining the the same efficacy levels as an antitussive and antiinflammatory.

Originator

Dompe (Italy)

Uses

Different sources of media describe the Uses of 99291-24-4 differently. You can refer to the following data:
1. R-Form of Dropropizine (D681495). (R)-(+)-Dropropizine is a cough suppressive phenylpiperazine derivative. (R)-(+)-Dropropizine is an antitussive and central sedative therapeutic agent.
2. receptor agonist, treatment of colds and allergic rhinitis

Brand name

Levotus

InChI:InChI=1/C13H20N2O2/c16-11-13(17)10-14-6-8-15(9-7-14)12-4-2-1-3-5-12/h1-5,13,16-17H,6-11H2/t13-/m0/s1

Upstream product

• 92-54-6 4-phenyl-1-piperazine 
• 51704-66-6 (+/-)-2,3-dihydroxypropyl tosylate 
• 41274-09-3 (R)-3-tosyloxy-1,2-propanediol 
• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 113826-06-5 (R)-glycidyl tosylate 
• 50765-70-3 (S)-1-tosyloxy-2,3-propanediol 
• 72566-27-9 1-(1-phenyl-4-piperazino)-2,3-epoxypropane 
• 142730-57-2 (R,S)-3-(4-phenyl-1-piperazinyl)-1,2-propanediol diacetate 

Downstream Products

• 152237-41-7 C₁₃H₂₀N₂O₄ 
• 142730-59-4 Acetic acid 2-hydroxy-3-(4-phenyl-piperazin-1-yl)-propyl ester 
• 142794-17-0 Acetic acid (S)-1-acetoxymethyl-2-(4-phenyl-piperazin-1-yl)-ethyl ester 

Relevant articles and documents

Catalytic, Kinetic, and Mechanistic Insights into the Fixation of CO2 with Epoxides Catalyzed by Phenol-Functionalized Phosphonium Salts

A series of hydroxy-functionalized phosphonium salts were studied as bifunctional catalysts for the conversion of CO2 with epoxides under mild and solvent-free conditions. The reaction in the presence of a phenol-based phosphonium iodide proceeded via a first order rection kinetic with respect to the substrate. Notably, in contrast to the aliphatic analogue, the phenol-based catalyst showed no product inhibition. The temperature dependence of the reaction rate was investigated, and the activation energy for the model reaction was determined from an Arrhenius-plot (Ea=39.6 kJ mol?1). The substrate scope was also evaluated. Under the optimized reaction conditions, 20 terminal epoxides were converted at room temperature to the corresponding cyclic carbonates, which were isolated in yields up to 99 %. The reaction is easily scalable and was performed on a scale up to 50 g substrate. Moreover, this method was applied in the synthesis of the antitussive agent dropropizine starting from epichlorohydrin and phenylpiperazine. Furthermore, DFT calculations were performed to rationalize the mechanism and the high efficiency of the phenol-based phosphonium iodide catalyst. The calculation confirmed the activation of the epoxide via hydrogen bonding for the iodide salt, which facilitates the ring-opening step. Notably, the effective Gibbs energy barrier regarding this step is 97 kJ mol?1 for the bromide and 72 kJ mol?1 for the iodide salt, which explains the difference in activity.

1,3-dioxolanes with antitussive activity

(S)-3-(4-Phenyl-1-piperazinyl)-1,2-propanediol cyclic acetals useful as antitussive agents and as intermediates for the preparation of levodropropizine and the salts thereof, as well as a process for the preparation of said acetals, are disclosed.

2,2-disubstituted 1,3-dioxolanes as antitussive agents

(±) 3-(4-Phenyl-1-piperazinyl)-1,2-propanediol cyclic acetals, a process for the optical resolution thereof and their use as intermediates for the preparation of (?) 3-(4-phenyl-1-piperazinyl)-1,2-propanediol (levodropropizine) and salts thereof.