125-24-6

Basic information

• Product Name: Pseudomorphine (Morphine Impurity)
• Synonyms: Pseudomorphine (Morphine Impurity);4,5α:4',5'α-Bisoxy-17,17'-dimethyl[2,2'-bi(7,8-didehydromorphinan)]-3,3',6α,6'α-tetrol;Pseudomorpine;(2,2'-Bimorphinan)-3,3',6,6'-tetrol, 7,7',8,8'-tetradehydro-4,5:4',5'-diepoxy-17,17'-dimethyl-, (5alpha,6alpha)-(5'alpha,6'alpha)-;Pseudomorphine (free base);Morphine Sulfate Related Compound B CII (20 mg) (Pseudomorphine);Morphine Sulfate Related CoMpound B CII;FOJYFDFNGPRXDR-NMGDDHEWSA-N
• CAS NO: 125-24-6
• Molecular Formula: C34H36N2O6
• Molecular Weight: 568.666
• Product Categories: Chiral Reagents;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 125-24-6.mol
• Article Data: 26

Chemical Properties

• Melting Point: >225°C (dec.)
• Boiling Point: 632.54°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.1922 (rough estimate)
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Controlled Substance, -20?C Freezer
• CAS DataBase Reference: Pseudomorphine (Morphine Impurity)(CAS DataBase Reference)
• NIST Chemistry Reference: Pseudomorphine (Morphine Impurity)(125-24-6)
• EPA Substance Registry System: Pseudomorphine (Morphine Impurity)(125-24-6)

Safety Data

• Hazardous Substances Data: 125-24-6(Hazardous Substances Data)

Usage

Description

Pseudomorphine (Morphine Impurity) is a degradation product of Morphine, which can be formed as a dimolecular base through the gentle oxidation of Morphine in an alkaline solution. It is also known as the C17 alkaloid base and appears as a beige solid.

Uses

Used in Pharmaceutical Industry:
Pseudomorphine (Morphine Impurity) is used as an impurity in the production and analysis of Morphine for various pharmaceutical applications. As a degradation product, it is essential to monitor and control its presence in Morphine to ensure the quality, safety, and efficacy of the final drug product.
Used in Research and Development:
In the field of research and development, Pseudomorphine (Morphine Impurity) serves as a valuable compound for studying the chemical properties, degradation pathways, and potential interactions of Morphine. This knowledge can be applied to improve the stability, formulation, and overall performance of Morphine-based medications.
Used in Quality Control and Regulatory Compliance:
Pseudomorphine (Morphine Impurity) is used as a reference material in quality control processes and regulatory compliance assessments for Morphine-containing products. By analyzing the presence and concentration of Pseudomorphine, manufacturers can ensure that their products meet the required standards and guidelines, maintaining the integrity and reliability of Morphine-based medications.

InChI:InChI=1/C34H36N2O6/c1-35-9-7-33-19-3-5-23(37)31(33)41-29-25(33)15(13-21(19)35)11-17(27(29)39)18-12-16-14-22-20-4-6-24(38)32-34(20,8-10-36(22)2)26(16)30(42-32)28(18)40/h3-6,11-12,19-24,31-32,37-40H,7-10,13-14H2,1-2H3/t19-,20-,21+,22+,23-,24-,31-,32-,33-,34-/m0/s1

Upstream product

• 57-27-2 MORPHIN 
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• 120-83-2 2,4-dichlorophenol 
• 66423-06-1 (R)-2-(2,4-Dichlorphenoxy)propionsaeure-ethylester 
• 1356837-79-0 (R,S)-2-(2,4-dichlorophenoxy)propionyl 3-(2-pyridine)pyrazolide 
• 120-36-5 2-(2,4-dichlorophenoxy)propionic acid 
• 58048-37-6 2-(2,4-dichloro-phenoxy)-propionyl chloride 
• 122674-95-7 (S)-(-)-Methyl 2-(2,4-dichlorophenoxy)propionate 
• 130-95-0 Quinine 
• 118-10-5 Cinchonin 
• 1912-23-8 (S)-2-phenoxypropanoic acid 
• 156-34-3 l-amphetamine 
• 122674-96-8 (R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate 
• 62784-66-1 bis(1-naphthyl)methanol 

Relevant articles and documents

Stability of morphine solutions in plastic syringes determined by reversed-phase ion-pair liquid chromatography

A reversed-phase ion-pair HPLC assay has been developed for quantitating morphine, codeine, apomorphine, and pseudomorphine in aqueous solutions. Using two types of plastic syringes, the effect of light (25 W) and temperature (22 and 3°C) on the stability of morphine, over a 12-week period, has been investigated in the presence and absence of preservative and antioxidant. The leaching of contaminants from the plastic syringes to water stored in them, for a period of up to 12 weeks, has also been investigated. The results indicate that 1 year. Some unidentified leached contaminants have been detected in water stored in both brands of syringes.

ENZYMATIC TRANSFORMATIONS OF MORPHINANE ALKALOIDS

Horseradish peroxidase transforms morphinane alkaloids into N-oxides and morphine to pseudomorphine in the presence of hydrogen peroxide.The crude poppy enzyme fraction shows the same activities.The rates of reactions were influenced by phenolic compounds and their relation controlled by the concentration of hydrogen peroxide and the presence of ascorbic acid. - Key Word Index: Papaver somniferum; Papaveraceae; morphine; codeine; thebaine; morphinane N-oxides; pseudomorphine; peroxidase; poppy enzyme fraction; phenolcarboxylic acids; ascorbic acid.

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Structural insights into the differences among lactisole derivatives in inhibitory mechanisms against the human sweet taste receptor

Lactisole, an inhibitor of the human sweet taste receptor, has a 2-phenoxypropionic acid skeleton and has been shown to interact with the transmembrane domain of the T1R3 subunit (T1R3-TMD) of the receptor. Another inhibitor, 2,4-DP, which shares the same molecular skeleton as lactisole, was confirmed to be approximately 10-fold more potent in its inhibitory activity than lactisole; however the structural basis of their inhibitory mechanisms against the receptor remains to be elucidated. Crystal structures of the TMD of metabotropic glutamate receptors, which along with T1Rs are categorized as class C G-protein coupled receptors, have recently been reported and made it possible to create an accurate structural model for T1R3-TMD. In this study, the detailed structural mechanism underlying sweet taste inhibition was characterized by comparing the action of lactisole on T1R3-TMD with that of 2,4-DP. We first performed a series of experiments using cultured cells expressing the sweet taste receptor with mutations and examined the interactions with these inhibitors. Based on the results, we next performed docking simulations and then applied molecular dynamics-based energy minimization. Our analyses clearly revealed that the (S)-isomers of both lactisole and 2,4-DP, interacted with the same seven residues in T1R3-TMD and that the inhibitory potencies of those inhibitors were mainly due to stabilizing interactions mediated via their carboxyl groups in the vertical dimension of the ligand pocket of T1R3-TMD. In addition, 2,4-DP engaged in a hydrophobic interaction mediated by its o-Cl group, and this interaction may be chiefly responsible for the higher inhibitory potency of 2,4-DP.

Synthesis and structure-activity relationships of novel phenoxyacetamide inhibitors of the Pseudomonas aeruginosa type III secretion system (T3SS)

The increasing prevalence of drug-resistant bacterial infections is driving the discovery and development not only of new antibiotics, but also of inhibitors of virulence factors that are crucial for in vivo pathogenicity. One such virulence factor is the type III secretion system (T3SS), which plays a critical role in the establishment and dissemination of Pseudomonas aeruginosa infections. We have recently described the discovery and characterization of a series of inhibitors of P. aeruginosa T3SS based on a phenoxyacetamide scaffold. To better characterize the factors involved in potent T3SS inhibition, we have conducted a systematic exploration of this structure, revealing several highly responsive structure-activity relationships indicative of interaction with a specific target. Most of the structural features contributing to potency were additive, and combination of those features produced optimized inhibitors with IC50 values 1 μM.