4697-67-0

Basic information

• Product Name: (16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester
• Synonyms: (16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester;Speciogynine
• CAS NO: 4697-67-0
• Molecular Formula: C₂₃H₃₀N₂O₄
• Molecular Weight: 398.4953
• Mol File: 4697-67-0.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester(4697-67-0)
• EPA Substance Registry System: (16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester(4697-67-0)

Safety Data

• Hazardous Substances Data: 4697-67-0(Hazardous Substances Data)

Usage

Description

(16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester is a complex chemical compound derived from corynantheine alkaloids, which are naturally occurring alkaloids found in various plant species. (16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester features a carboxylic acid group, two methoxy groups, and a methyl ester, which contribute to its unique properties and potential applications in medicinal chemistry and pharmacology. Its structure suggests that it may possess biological activity and could serve as a starting point for developing new pharmaceutical compounds. Further research is required to explore its full potential and effects.

Uses

Used in Pharmaceutical Industry:
(16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester is used as a potential starting compound for the development of new pharmaceuticals due to its unique structure and the presence of functional groups that may confer biological activity. Its potential applications in medicinal chemistry could lead to the discovery of novel therapeutic agents.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (16E)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester is used as a subject of study to understand its biological activity and explore its potential as a precursor for synthesizing new compounds with therapeutic properties. This research could contribute to the advancement of drug discovery and the development of innovative treatments for various diseases and conditions.

Upstream product

• 173102-63-1 (E)-2-[(2S,12bS)-3-Eth-(Z)-ylidene-8-methoxy-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl]-3-methoxy-acrylic acid methyl ester 
• 918430-83-8 C₂₅H₃₄N₂O₆ 
• 951327-94-9 (2R,3S,12bS)-tert-butyl 3-ethyl-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7-hexahydroindolo[2,3-a]quinolizine-12(12bH)-carboxylate 
• 107-31-3 Methyl formate 
• 149-73-5 trimethyl orthoformate 
• 951327-89-2 4-methoxy-D-tryptophan benzyl ester 
• 951327-85-8 (R,Z)-benzyl 2-(2-iodobut-2-enylamino)-3-(4-methoxy-1H-indol-3-yl)propanoate 
• 951327-90-5 (1S,3R,Z)-benzyl 2-(2-iodobut-2-enyl)-5-methoxy-1-(4-methoxy-4-oxo-3,3-bis(phenylthio)butyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 951327-86-9 (1S,3R)-benzyl 2-((Z)-2-iodobut-2-enyl)-5-methoxy-1-((E)-4-methoxy-4-oxobut-2-enyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 951327-91-6 (2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate 
• 951327-87-0 methyl 2-((2R,12bS,E)-3-ethylidene-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quino-lizin-2-yl)acetate 
• 951327-93-8 methyl 2-((2R,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate 
• 951327-81-4 3-(((2R,5S)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazin-2-yl)methyl)-4-methoxy-2-(trimethylsilyl)-1H-indole 
• 951327-83-6 tert-butyl 3-(((2R,5S)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazin-2-yl)methyl)-4-methoxy-2-(tri-methylsilyl)-1H-indole-1-carboxylate 

Downstream Products

• 174418-82-7 Mitragynine hydroxyindolenine 
• 174418-81-6 O-Acetylmitragynine hydroxyindolenine 
• 23407-35-4 methyl (E)-2-((2S,3S,12bS)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate 
• 29472-77-3 gambirine 

Relevant articles and documents

MITRAGYNINE ANALOGS FOR THE TREATMENT OF PAIN, MOOD DISORDERS AND SUBSTANCE USE DISORDERS

The present invention provides a compound having the structure (I): or a pharmaceutically acceptable salt or ester thereof, and a method of treating a subject afflicted with pain a depressive disorder, a mood disorder or an anxiety disorder by administering the compound to the subject.

Synthetic and Receptor Signaling Explorations of the Mitragyna Alkaloids: Mitragynine as an Atypical Molecular Framework for Opioid Receptor Modulators

Mu-opioid receptor agonists represent mainstays of pain management. However, the therapeutic use of these agents is associated with serious side effects, including potentially lethal respiratory depression. Accordingly, there is a longstanding interest in the development of new opioid analgesics with improved therapeutic profiles. The alkaloids of the Southeast Asian plant Mitragyna speciosa, represented by the prototypical member mitragynine, are an unusual class of opioid receptor modulators with distinct pharmacological properties. Here we describe the first receptor-level functional characterization of mitragynine and related natural alkaloids at the human mu-, kappa-, and delta-opioid receptors. These results show that mitragynine and the oxidized analogue 7-hydroxymitragynine, are partial agonists of the human mu-opioid receptor and competitive antagonists at the kappa- and delta-opioid receptors. We also show that mitragynine and 7-hydroxymitragynine are G-protein-biased agonists of the mu-opioid receptor, which do not recruit β-arrestin following receptor activation. Therefore, the Mitragyna alkaloid scaffold represents a novel framework for the development of functionally biased opioid modulators, which may exhibit improved therapeutic profiles. Also presented is an enantioselective total synthesis of both (-)-mitragynine and its unnatural enantiomer, (+)-mitragynine, employing a proline-catalyzed Mannich-Michael reaction sequence as the key transformation. Pharmacological evaluation of (+)-mitragynine revealed its much weaker opioid activity. Likewise, the intermediates and chemical transformations developed in the total synthesis allowed the elucidation of previously unexplored structure-activity relationships (SAR) within the Mitragyna scaffold. Molecular docking studies, in combination with the observed chemical SAR, suggest that Mitragyna alkaloids adopt a binding pose at the mu-opioid receptor that is distinct from that of classical opioids.

Indole Alkaloid Derivatives Having Opioid Receptor Agonistic Effect, and Therapeutic Compositions and Methods Relating to Same

Indole alkaloid derivatives having an opioid receptor agonistic effect, their synthesis, and therapeutic compositions containing these derivatives, and methods of treating conditions with these compounds and therapeutic compositions, are provided.