51116-23-5

Basic information

• Product Name: 2-(1,3-benzodioxol-5-yl)-4-(3,4-dimethoxyphenyl)-4-oxobutanenitrile
• CAS NO: 51116-23-5
• Molecular Formula: C₁₉H₁₇NO₅
• Molecular Weight: 339.342
• Mol File: 51116-23-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 547°C at 760 mmHg
• Flash Point: 235.7°C
• Density: 1.266g/cm³
• Vapor Pressure: 5.09E-12mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 2-(1,3-benzodioxol-5-yl)-4-(3,4-dimethoxyphenyl)-4-oxobutanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,3-benzodioxol-5-yl)-4-(3,4-dimethoxyphenyl)-4-oxobutanenitrile(51116-23-5)
• EPA Substance Registry System: 2-(1,3-benzodioxol-5-yl)-4-(3,4-dimethoxyphenyl)-4-oxobutanenitrile(51116-23-5)

Safety Data

• Hazardous Substances Data: 51116-23-5(Hazardous Substances Data)

Usage

Chemical Structure

C20H21NO4

Classification

Synthetic opioid and derivative of tramadol

Function

Prodrug to the active metabolite desmethyltramadol

Analgesic Properties

Yes, used for treating moderate to severe pain

Mechanism of Action

Norepinephrine and serotonin reuptake inhibitor, activates opioid receptors in the central nervous system

Potential for Abuse and Dependence

High, classified as a controlled substance in many countries

Side Effects

Respiratory depression, sedation, and other opioid-related side effects

Upstream product

• 51116-22-4 (E)-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxyphenyl)-prop-2-en-1-one 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 120-57-0 piperonal 
• 151-50-8 potassium cyanide 

Relevant articles and documents

Structure-activity relationships in a series of orally active γ- hydroxy butenolide endothelin antagonists

The design of potent and selective non-peptide antagonists of endothelin-1 (ET-1) and its related isopeptides are important tools defining the role of ET in human diseases. In this report we will describe the detailed structure-activity relationship (SAR) studies that led to the discovery of a potent series of butenolide ET(A) selective antagonists. Starting from a micromolar screening hit, PD012527, use of Topliss decision tree analysis led to the discovery of the nanomolar ET(A) selective antagonist PD155080. Further structural modifications around the butenolide ring led directly to the subnanomolar ET(A) selective antagonist PD156707, IC50's = 0.3 (ET(A)) and 780 nM (ET(B)). This series of compounds exhibited functional activity exemplified by PD156707. This derivative inhibited the ET(A) receptor mediated release of arachidonic acid from rabbit renal artery vascular smooth muscle cells with an IC50 = 1.1 nM and also inhibited the ET-1 induced contraction of rabbit femoral artery rings (ET(A) mediated) with a pA2 = 7.6. PD156707 also displayed in vivo functional activity inhibiting the hemodynamic responses due to exogenous administration of ET-1 in rats in a dose dependent fashion. Evidence for the pH dependence of the open and closed tautomerization forms of PD156707 was demonstrated by an NMR study. X- ray crystallographic analysis of the closed butenolide form of PD156707 shows the benzylic group located on the same side of the butenolide ring as the γ- hydroxyl and the remaining two phenyl groups on the butenolide ring essentially orthogonal to the butenolide ring. Pharmacokinetic parameters for PD156707 in dogs are also presented.

Synthesis of allonitidine and related compounds

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