7640-51-9

Basic information

• Product Name: PROMETHAZINE SULFOXIDE
• Synonyms: PROMETHAZINE SULFOXIDE; N-[2-(Dimethylamino)propyl]phenothiazine S-Oxide; Promethazine 5-Sulfoxide;N,N,a-Trimethyl-10H-phenothiazine-10-ethanamine 5-Oxide;Promethazine 5-Oxide;Romergan Sulfoxide;N,N,α-TriMethyl-10H-phenothiazine-10-ethanaMine 5-Oxide;ProMethazine EP IMpurity D
• CAS NO: 7640-51-9
• Molecular Formula: C₁₇H₂₀N₂OS
• Molecular Weight: 300.42
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 7640-51-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 461.6°C at 760 mmHg
• Flash Point: 233°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.06E-08mmHg at 25°C
• Refractive Index: 1.678
• Storage Temp.: Refrigerator
• PKA: 8.90±0.50(Predicted)
• CAS DataBase Reference: PROMETHAZINE SULFOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PROMETHAZINE SULFOXIDE(7640-51-9)
• EPA Substance Registry System: PROMETHAZINE SULFOXIDE(7640-51-9)

Safety Data

• Hazardous Substances Data: 7640-51-9(Hazardous Substances Data)

Usage

Uses

A metabolite of Promethazine (P757000).

InChI:InChI=1/C17H20N2OS/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)21(20)17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3

Upstream product

• 60-87-7 promethazine cation radical 

Relevant articles and documents

A mechanistic study on the disproportionation and oxidative degradation of phenothiazine derivatives by manganese(III) complexes in phosphate acidic media

The oxidative degradation of phenothiazine derivatives (PTZ) by manganese(III) was studied in the presence of a large excess of manganese(III)-pyrophosphate (P2O7 2-), phosphate (PO4 3-), and H+ ions using UV-vis. spectroscopy. The first irreversible step is a fast reaction between phenothiazine and manganese pyrophosphate leading to the complete conversion to a stable phenothiazine radical. In the second step, the cation radical is oxidized by manganese to a dication, which subsequently hydrolyzes to phenothiazine 5-oxide. The reaction rate is controlled by the coordination and stability of manganese(III) ion influenced by the reduction potential of these ions and their strong ability to oxidize many reducing agents. The cation radical might also be transformed to the final product in another competing reaction. The final product, phenothiazine 5-oxide, is also formed via a disproportionation reaction. The kinetics of the second step of the oxidative degradation could be studied in acidic phosphate media due to the large difference in the rates of the first and further processes. Linear dependences of the pseudo-first-order rate constants (k obs) on [Mn III] with a significant non-zero intercept were established for the degradation of phenothiazine radicals. The rate is dependent on [H+] and independent of [PTZ] within the excess concentration range of the manganese(III) complexes used in the isolation method. The kinetics of the disproportionation of the phenothiazine radical have been studied independently from the further oxidative degradation process in acidic sulphate media. The rate is inversely dependent on [PTZ+.], dependent on [H+], and increases slightly with decreasing H+ concentration. Mechanistic consequences of all these results are discussed.