66164-06-5

Basic information

• Product Name: N-Didesmethyl Loperamide
• Synonyms: 4-(4-Chlorophenyl)-4-hydroxy-a,a-diphenyl-1-piperidinebutanamide;N-Didesmethyl Loperamide;R 21345;4-(4-Chlorophenyl)-4-hydroxy-α,α-diphenyl-1-piperidinebutanaMide;Di desmethylloperamide D5
• CAS NO: 66164-06-5
• Molecular Formula: C₂₇H₂₉ClN₂O₂
• Molecular Weight: 448.98436
• Product Categories: Amines;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 66164-06-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 210-212?C
• Boiling Point: 677.8°C at 760 mmHg
• Flash Point: 363.7°C
• Appearance: /
• Density: 1.229g/cm³
• Vapor Pressure: 2.67E-19mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: -20°C Freezer
• PKA: 13.85±0.20(Predicted)
• CAS DataBase Reference: N-Didesmethyl Loperamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Didesmethyl Loperamide(66164-06-5)
• EPA Substance Registry System: N-Didesmethyl Loperamide(66164-06-5)

Safety Data

• Hazardous Substances Data: 66164-06-5(Hazardous Substances Data)

Usage

Description

N-Didesmethyl Loperamide is a metabolite of Loperamide, an off-white solid with unique chemical properties. It has gained significant attention due to its potential applications in various fields, particularly in the medical and pharmaceutical industries.

Uses

Used in Pharmaceutical Industry:
N-Didesmethyl Loperamide is used as a new and improved PET (Positron Emission Tomography) radiotracer for imaging P-gp (P-glycoprotein) function. P-glycoprotein is a membrane protein that acts as an efflux pump, playing a crucial role in multidrug resistance in cancer cells. The use of N-Didesmethyl Loperamide as a PET radiotracer allows for better visualization and understanding of P-gp function, which can lead to the development of more effective cancer treatments.
Used in Medical Imaging:
In the field of medical imaging, N-Didesmethyl Loperamide serves as a valuable tool for researchers and clinicians. Its role as a PET radiotracer enables the assessment of P-gp function in various tissues and organs, providing insights into the mechanisms of drug resistance and the potential for personalized treatment strategies. This application can significantly impact the diagnosis and management of various diseases, particularly cancer.
Used in Drug Development:
N-Didesmethyl Loperamide's unique properties also make it a promising candidate for drug development. Its ability to target and image P-gp function can be leveraged to design and develop novel therapeutic agents that can overcome multidrug resistance in cancer cells. This can lead to the creation of more effective drugs with fewer side effects, ultimately improving patient outcomes and quality of life.

InChI:InChI=1/C27H29ClN2O2/c28-24-13-11-21(12-14-24)26(32)15-18-30(19-16-26)20-17-27(25(29)31,22-7-3-1-4-8-22)23-9-5-2-6-10-23/h1-14,32H,15-20H2,(H2,29,31)

Upstream product

• 63959-33-1 VUF 5742 
• 39512-49-7 4-(4-chlorophenyl)-4-hydroxypiperidine 
• 39186-58-8 4-bromo-2,2-diphenylbutyronitrile 

Downstream Products

• 1067642-12-9 [¹¹C]N-desmethylloperamide 
• 66164-07-6 Desmethylloperamide 
• 1424272-65-0 4-(4-(4-chlorophenyl)-4-hydroxypiperidine-1-yl)-N-(3-fluoropropyl)-2,2-diphenylbutanamide 
• 1424272-64-9 4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-N-(2-fluoroethyl)-2,2-diphenylbutanamide 
• 1424272-67-2 11-(4-chlorophenyl)-4,4-diphenyl-10-oxa-1,6-diazabicyclo[9.2.2]pentadecan-5-one 
• 1424272-68-3 [N-ethyl-¹⁸F]-N-desmethylloperamide 

Relevant articles and documents

Overcoming chloroquine resistance in malaria: Design, synthesis and structure-activity relationships of novel chemoreversal agents

Malaria remains a significant infectious disease with even artemisinin-based therapies now facing resistance in the field. Development of new therapies is urgently needed, either by finding new compounds with unique modes of action, or by reversing resistance towards known drugs with 'chemosensitizers' or 'chemoreversal' agents (CRA). Concerning the latter, we have focused on the resistance mechanisms developed against chloroquine (CQ). We have synthesized a series of compounds related to previously identified CRAs, and found promising novel compounds. These compounds show encouraging results in a coumarin labeled chloroquine uptake assay, exhibiting a dose response in resensitising parasites to the antimalarial effects of chloroquine. Selected compounds show consistent potency across a panel of chloroquine and artemisinin sensitive and resistant parasites, and a wide therapeutic window. This data supports further study of CRAs in the treatment of malaria and, ultimately, their use in chloroquine-based combination therapies.

Radiosynthesis of 18F-labeled N-desmethyl-loperamide analogues for prospective molecular imaging radiotracers

A simple procedure for preparing fluoroethyl-N-desmethyl-loperamide 4 and its analogue 5 was developed. Standard compound 4 was synthesized in useful yields for radiolabeling analysis. [N-Ethyl-18F]N-desmethyl-loperamide, 3, was rapidly and efficiently labeled with no-carrier added fluorine-18 (t 1/2 = 109.7 min) by treatment of readily prepared [ 18F]1-bromo-2-fluoro ethane with a N-desmethyl-loperamide precursor at a consistent 7% radiochemical yield. This procedure was also adapted to the radiosynthesis of 3 by [18F]ethylene tosylate, but at a lower 3% radiochemical yield. Copyright

RADIOTRACERS FOR IMAGING P-GLYCOPROTEIN FUNCTION

P-glycoprotein transporter (P-gp) acts as a pump at the blood-brain barrier to exclude a wide range of xenobiotics (e.g., toxins, drugs, etc.) from the brain and is also expressed in a tumor in response to exposure to established or prospective chemothera